Substituted isophthalic acid diamides and use thereof as herbicides

Abstract

The invention relates to isophthalic acid diamides of formula (I) as herbicides. In formula (I), X, Y, Z1, Z2 and Rx represent radicals such as alkyl, cycloalkyl, haloalkyl and halogen.

Description

[0001] Substituted isophthalic acid diamides and their use as herbicides

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

[0003] WO2021204665, WO2021204669, WO2021204666 and WO2021204667 describe herbicidally active isophthalic acid diamides which differ essentially in the type of substituents on the two amide functions but also on the phenyl part.

[0004] The isophthalic acid diamides specifically disclosed therein do not always exhibit sufficient herbicidal activity and / or tolerance to crop plants. The object of the present invention is to provide alternative herbicidally active ingredients. This object is achieved by the isophthalic acid diamides according to the invention described below, which carry a haloalkoxy radical in the 4-position.

[0005] The present invention thus relates to isophthalic acid diamides of the formula (I) or salts thereof where the symbols and indices have the following meanings:

[0006] R x means (C1-C6)-alkyl,

[0007] X is halogen, (C1-C6)alkyl or (C3-C6)cycloalkyl,

[0008] Y means halogen-(C1-C6)-alkoxy,

[0009] Z 1 and Z 2 each independently denote hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, halogen-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-C(O)-(C1-C6)-alkyl or R 2 R 3 NC(O)-(C1-C6)-alkyl, where (Cg-C6)-cycloalkyl each has m substituents R 1 carries,

[0010] R 1means halogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C1-C6)-alkoxy, halogen-(C1-C6)-alkyl, (C1-C6)-alkyloxy-C(O), (C1-C6)-alkyloxy-C(O)-(C1-C6)-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals,

[0011] R 2 and R 3 independently of one another each represent hydrogen, (C1-C6)alkyl or (C3-C6)cycloalkyl, and m represents 0, 1, 2 or 3.

[0012] 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 refers to a carbocyclic, saturated ring system with three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0013] Halogen stands for fluorine, chlorine, bromine or iodine.

[0014] The compounds of formula (I) or (II) may 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 may 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) or (II) but not specifically defined.

[0015] Preferred compounds are those of formula (I) in which the symbols and indices have the following meanings:

[0016] R x means (C1-C6)-alkyl,

[0017] X is halogen, (C1-C6)alkyl or (C3-C6)cycloalkyl,

[0018] Y means OCF3, OCHF2, OCH2CHF2 or OCF2Me,

[0019] Z 1 and Z 2 each independently denote hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, halogen-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-C(O)-(C1-C6)-alkyl or R 2 R 3 NC(O)-(C1-C6)-alkyl, where (C3-C6)-cycloalkyl each has m substituents R 1 carries,

[0020] R 1 means halogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C1-C6)-alkoxy, halogen-(C1-C6)-alkyl, (C1-C6)-alkyloxy-C(O), (C1-C6)-alkyloxy-C(O)-(C1-C6)-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals,

[0021] R 2 and R 3independently represent hydrogen, Me, Et or c-Pr, and m represents 0, 1, 2 or 3.

[0022] Particularly preferred compounds of formula (I) are those in which the symbols and indices have the following meanings:

[0023] R x means Me or Et,

[0024] X is chlorine, bromine, methyl, ethyl or cyclopropyl,

[0025] Y means OCF3, OCHF2or OCH2CHF2, and

[0026] Z 1 and Z 2 independently of one another each represent hydrogen, Me, Et, Pr, i-Pr, c-Pr-CH2, c-Pr, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-isobutylcyclopropyl, 1-cyclobutylcyclopropyl, 1-ethynylcyclopropyl, 1-methoxymethylcyclopropyl, 1-ethoxymethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluoromethylcyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 1-methoxycyclopropyl, 1-ethoxycyclopropyl, 1-

[0027] Ethoxycarbonylcyclopropyl, 1-Etoxycarbonylmethylcyclopropyl, 1-cyanocyclopropyl, 1-phenylcyclopropyl, l-(2-chlorophenyl)-cyclopropyl, l-(3-chlorophenyl)-cyclopropyl, l-(2-furyl)-cyclopropyl, l-(3-furyl)-cyclopropyl, MeC(O)CH2, EtC(O)CH2, c-PrC(O)CH2, MeNHC(O)CH2, EtNHC(O)CH2 or c-PrNHC(O)CH2.

[0028] In all formulas mentioned below, the substituents and symbols, unless otherwise defined, have the same meaning as described under formula (I).

[0029] Compounds of formula (II) are novel and are very suitable as intermediates for the preparation of the compounds of formula (I) according to the invention. The present invention thus further relates to compounds of formula (II), where the symbols and indices have the following meanings:

[0030] L means halogen or R 4 O,

[0031] X is halogen or (C1-C6)alkyl or (C3-C6)cycloalkyl,

[0032] Y means halogen-(C1-C6)-alkoxy, Z 1 and Z 2 each independently denote hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, halogen-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-C(O)-(C1-C6)-alkyl or R 2 R 3 NC(O)-(C1-C6)-alkyl, where (C3-C6)-cycloalkyl each has m substituents R 1 carries,

[0033] R 1 means halogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C1-C6)-alkoxy, halogen-(C1-C6)-alkyl, (C1-C6)-alkyloxy-C(O), (C1-C6)-alkyloxy-C(O)-(C1-C6)-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals,

[0034] R 2 and R 3 independently of one another each represent hydrogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl,

[0035] R 4means hydrogen or (C1-C6)alkyl, and m means 0, 1, 2 or 3.

[0036] Preferred compounds (II) are those in which

[0037] L means chlorine, methoxy or hydroxy,

[0038] X is chlorine, bromine, methyl, ethyl or cyclopropyl,

[0039] Y means OCF3, OCHF2or OCH2CHF2and

[0040] Z 1 and Z 2 independently of one another each represent hydrogen, Me, Et, Pr, i-Pr, c-Pr-CH2, c-Pr, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-isobutylcyclopropyl, 1-cyclobutylcyclopropyl, 1-ethynylcyclopropyl, 1-methoxymethylcyclopropyl, 1-ethoxymethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluoromethylcyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 1-methoxycyclopropyl, 1-ethoxycyclopropyl, 1-

[0041] Ethoxycarbonylcyclopropyl, 1-Etoxycarbonylmethylcyclopropyl, 1-cyanocyclopropyl, 1-phenylcyclopropyl, l-(2-chlorophenyl)-cyclopropyl, l-(3-chlorophenyl)-cyclopropyl, l-(2-furyl)-cyclopropyl, l-(3-furyl)-cyclopropyl, MeC(O)CH2, EtC(O)CH2, c-PrC(O)CH2, MeNHC(O)CH2, EtNHC(O)CH2 or c-PrNHC(O)CH2.

[0042] In all formulas mentioned below, the substituents and symbols, unless otherwise defined, have the same meaning as described under formula (I).

[0043] Compounds of the general formula (I) according to the invention can be prepared, for example, as also described in WO2012 / 028579, by reacting the compounds of the general formula (IIb: compounds II, where L=hydroxy) according to the invention with substituted aminotetrazoles:

[0044] The synthesis of the compounds of general formula (IIb) can be carried out, for example, according to the following scheme and methods known to the person skilled in the art:

[0045] 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.

[0046] 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.

[0047] The equipment listed leads to a modular approach in which the individual work steps are automated, but manual operations must be performed between the work steps. This can be avoided 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 obtained, 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 specialist literature, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

[0048] 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.

[0049] 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.

[0050] 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.

[0051] The compounds of 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.

[0052] 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.

[0053] 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.

[0054] Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, C6ntaurea, 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.

[0055] 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.

[0056] 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.

[0057] 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 well suited for the selective control of undesirable plant growth in plant crops such as agricultural crops or ornamental plantings.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] Preferably, the compounds according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or which have been made resistant by genetic engineering.

[0062] 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).

[0063] 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”).

[0064] 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.

[0065] 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 substitutions can be performed, partial sequences removed, or natural or synthetic sequences 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.

[0066] 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. 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] When the active compounds 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.

[0072] The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crops.

[0073] The compounds according to the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in conventional 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 required.Possible formulation options include: 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 micro-, spray-, lift- and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

[0074] These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology",

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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

[0079] Ca-dodecylbenzenesulfonate or non-ionic emulsifiers such as fatty acid polyglycol esters,

[0080] Alkylaryl polyglycol ether, fatty alcohol polyglycol ether,

[0081] Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as

[0082] Sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

[0083] 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.

[0084] 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.

[0085] Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and, if appropriate, surfactants, such as those already listed above for the other formulation types.

[0086] Granules can be produced either by spraying the active ingredient onto adsorbent, 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 such as polyvinyl alcohol, sodium polyacrylate, or mineral oils. Suitable active ingredients can also be granulated in the usual way for the production of fertilizer granules—if desired, mixed with fertilizers.

[0087] 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.

[0088] 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.

[0089] 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.

[0090] The agrochemical preparations generally contain 0.1 to 99 wt.%, in particular 0.1 to 95

[0091] % by weight of compounds according to the invention. In wettable powders, the active ingredient concentration is, for example, about 10 to 90 wt. %, the remainder to 100 wt. % consists of conventional formulation ingredients. In emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80 wt. %. Dust-like formulations contain

[0092] 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.%.

[0093] In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH value and viscosity.

[0094] 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.

[0095] 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 before use.

[0096] 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.

[0097] 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 literature cited therein. Known herbicides or plant growth regulators which can be combined with compounds of formula (I) are, for example:The following active ingredients are listed (the compounds are designated either by their common name according to the International Organization for Standardization (ISO), their chemical name, or their 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 listed as examples:

[0098] Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim sodium, Ametryn, Amicarbazone, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor,

[0099] 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, 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. (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, 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,

[0100] Endothal-Dinatrium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethamet- sulfuron-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-lH-tetrazol-l-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-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, E- 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-l-yl (2S)-2- {3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoat, HW-02, d.h. l-(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-Lithium, -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, 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-(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, Prop- isochlor, Propoxycarbazone, Propoxycarbazone-Natrium, Propyrisulfuron, Propyzamid, Prosulfocarb,Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-Ethyl, Pyrasulfotol, Pyrazolynat (Pyrazolat), Pyrazo- sulfuron, 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. l-{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, Sulfo- meturon, 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, Thien- carbazone, 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- 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- 1 H-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] - 1 H-pyrazol-5-yl propan- 1 -sulfonat, 4- { 2-Chlor-3- [(3 ,5-dimethyl- 1 H- pyrazol- 1 -yl)methyl] -4-(methylsulfonyl)benzoyl} - 1 -methyl- 1 H-pyrazol-5 -yl- 1 ,3 -dimethyl- 1 H-pyrazol- 4-carboxylat; Cyanomethyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Prop-2-yn-l-yl 4-amino-3-chlor-5-fluor-6-(7-fluor-lH-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-lH-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-( 1 -acetyl-7 - fluor-lH-indol-6-yl)-4-amino-3-chlor-5-fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-6-[l-(2,2- dimethylpropanoyl)-7-fluor-lH-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- l,2-oxazol-3-yl)-4-hydroxy-l-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-(trifluormethyl)pyridin-2- yl]imidazolidin-2-on, 6-[(2-Hydroxy-6-oxocyclohex-l-en-l-yl)carbonyl]-l,5-dimethyl-3-(2- methylphenyl)chinazolin-2,4(lH,3H)-dion, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-l-en- 1 -yl)carbonyl] - 1 -methylchinazolin-2,4( 1 H,3H)-dion, 2- [2-chlor-4-(methylsulfonyl)-3-(morpholin-4- ylmethyl)benzoyl] -3-hydroxycyclohex-2-en- 1 -on, 1 -(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin- 1 - iumsalz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat),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), l-(2-Carboxyethyl)-4-(l,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-l(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2S)- 2- { [(E)-( { 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate,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)-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-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.,

[0101] 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- 1 -yl] -3-methylpenta-2,4-dienoat, (2Z,4E)-3-ethyl-5-( 1 -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 -ylcarbonsäure N-Methyl- 1-aminocyclopropyl-l -carbonsäure, 1 -Aminocyclopropyl- 1 -carbonsäureamid, substituierte 1-.

[0102] Aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxamic acid, 5-aminoethyl vulinic 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 through which I can distinguish it from chitin molecules [(C8H 13 NO5) n CAS No. 1398-61-4] and chitosan molecules [(C5H 11 NO4) n, CAS No. 9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 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 called symbiotic nodulation signals (Nod or Nod factors) or Myc factors, consist of an oligosaccharide backbone of ß-l,4-linked IV-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, 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-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-l-yl)propanoate, Sodium 3-(cycloprop-l-en-l-yl)propanoate, sidefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-Fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine.,

[0103] 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.

[0104] Safeners which can be used 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:

[0105] SI) Compounds of the formula (SI), where the symbols and indices have the following meanings: n A is a natural number from 0 to 5, preferably 0 to 3;

[0106] R A 1 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl;

[0107] W Ais an unsubstituted or substituted divalent heterocyclic radical from the group of the 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 ;

[0108] R A 2 is OR A 3 , SR A 3 or NR A 3 R A 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 (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 ;

[0109] R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms;

[0110] R A 4 is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl;

[0111] R A 5 is H, (C1-C3)alkyl, (C1-C3)haloalkyl, (C1-C4)alkoxy(C1-C3)alkyl, cyano or COOR A 9 , wherein

[0112] R A 9 Hydrogen, (C1-C3)alkyl, (C1-C3)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-C3)alkyl, (C1-C3)haloalkyl, (C3- C 12)Cycloalkyl or substituted or unsubstituted phenyl;

[0113] 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 (Sl a ), preferably

[0114] Compounds such as l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid ethyl ester (S 1 - 1)

[0115] ("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 ethyl l-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (Sl-5), methyl l-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (Sl-6) and related compounds as described, for example, in EP-A-268554; d) compounds of the triazolecarboxylic acid type (Sl 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 ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (Sl-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (Sl-9) and related compounds as described in WO-A-91 / 08202, or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (Sl-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (Sl-11) ("Isoxadifen-ethyl") or -n-propyl ester (Sl-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (Sl-13) as described in patent application WO-A-95 / 07897. f) Compounds of the triazolyloxyacetic acid derivative type (Slf ), 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 (Sl-19), as described in patent application W02021105101

[0116] S2) quinoline derivatives of the formula (S2), where the symbols and indices have the following meanings:

[0117] R B 1 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl; n Bis a natural number from 0 to 5, preferably 0 to 3;

[0118] R B 2 is OR B 3 , SR B 3 or NR B 3 R B 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 OR B 3 , NHR B 4 or N(CH3)2, in particular of the formula OR B 3 ;

[0119] R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms;

[0120] R B4 is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl;

[0121] T B is 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 (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy)acetic acid (l,3-dimethyl-but-l-yl) ester (S2-2),

[0122] (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)-l-ethyl ester (S2-8), (5-chloro-8-quinolinoxy)acetic acid 2-oxo-prop-l-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), its hydrates and salts, for example its 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 of (5-chloro-8-quinolinoxy)malonic acid (S2 b ), preferably compounds such as (5-chloro-8-quinolinoxy)malonic acid diethyl ester,

[0123] 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.

[0124] S3) Compounds of formula (S3) where the symbols and indices have the following meanings:

[0125] R C 1 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C3-C7)cycloalkyl, preferably dichloromethyl;

[0126] R C 2 , R C 3 are identical or different hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl,

[0127] (C2-C4)alkynyl, (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, substituted or unsubstituted phenyl, or R C 2 and R C3together 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-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 orMonsanto (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).

[0128] S4) N-acylsulfonamides of formula (S4) and their salts, where the symbols and indices have the following meanings:

[0129] X D is CH or N;

[0130] R D 1 is CO-NR D 5 R D 6 or NHCO-R D 7 ;

[0131] R D 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;

[0132] R D 3is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl;

[0133] R D 4 is 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;

[0134] R D 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 substituted by VD substituents from the group 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;

[0135] R D 6 is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl, where the last three radicals are substituted by VD radicals from the group halogen, hydroxy, (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkylthio, or

[0136] R D 5 and R D 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;

[0137] R D 7 is hydrogen, (C1-C4)alkylamino, di-(C1-C4)alkylamino, (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; n D is 0, 1 or 2; m D is 1 or 2; v Dis 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 wherein

[0138] R D 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;

[0139] R D 4 Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF 3; m D 1 or 2; v D 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

[0140] R D 5 = Cyclopropyl and (R D 4 ) = 2-OMe ("Cyprosulfamide", S4-1),

[0141] RD 5 = Cyclopropyl and (R D 4 ) = 5-Cl-2-OMe is (S4-2),

[0142] R D 5 = Ethyl and (R D 4 ) = 2-OMe is (S4-3),

[0143] R D 5 = Isopropyl and (R D 4 ) = 5-Cl-2-OMe is (S4-4) and

[0144] R D 5 = Isopropyl and (R D 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

[0145] R D 8 and R D 9 independently of one another hydrogen, (C1-C3)alkyl, (C3-C3)cycloalkyl, (C3-C6)alkenyl,

[0146] (C3-C6)alkynyl,

[0147] R D 4 Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3m D1 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.

[0148] 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.

[0149] S6) Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g. l-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, l-methyl-3-(2-thienyl)-l,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1 ,2-dihydro-quinoxalin-2-one hydrochloride, 1 -(2-

[0150] Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydroquinoxa-lin-2-one, as described in WO-A-2005 / 112630.

[0151] S7) Compounds of formula (S7) as described in WO-A-1998 / 38856 where the symbols and indices have the following meanings: R E 1 , R E 2 are independently halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl, (C1-C4)alkylamino, di-(C1-C4)alkylamino, nitro;

[0152] A E is COOR E 3 or COSR E 4

[0153] 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 n E 2 , n E 3are independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, diphenylmethoxyacetic acid ethyl ester, diphenylmethoxyacetic acid methyl ester (CAS Reg. No. 41858-19-9) (S7-1).

[0154] S8) Compounds of formula (S8) as described in WO-A-98 / 27049

[0155] Wherein

[0156] 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 ,

[0157] 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,

[0158] R F 2 Hydrogen or (C1-C4)alkyl

[0159] R F 3hydrogen, (C1-C3)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

[0160] X F CH, n F an integer from 0 to 2 ,

[0161] R F 1 Halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy,

[0162] R F 2 hydrogen or (C1-C4)alkyl,

[0163] R F 3Hydrogen, (C1-C3)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.

[0164] 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.

[0165] S10) Compounds of the formulas (S10 a ) or (S10 b ) as described in WO-A-2007 / 023719 and WO-A-2007 / 023764 wherein

[0166] R G 1 Halogen, (C1-C4)alkyl, methoxy, nitro, cyano, CF3, OCF3

[0167] Y G , ZG independently O or S, n G an integer from 0 to 4,

[0168] R G 2 (C1-C 16 ) alkyl, (C2-C6)alkenyl, (C3-C6)cycloalkyl, aryl; benzyl, halobenzyl,

[0169] R G 3 hydrogen or (C1-C6)alkyl.

[0170] Si l) Active substances of the oxyimino compound type (Sil), 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.

[0171] 12) 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.

[0172] 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]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia, "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), "Dietholate" (O,O-Diethyl-O- phenylphosphorothioat) (S13-8), "Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9).

[0173] 514) Active substances which, in addition to a herbicidal effect against harmful plants, also have a safener effect on cultivated plants such as rice, such as: B. "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-l-carbothioate), which is known as a safener for rice against damage from the herbicide Molinate, "Daimuron" or "SK 23" (l-(l-methyl-l-phenylethyl)-3-p-tolylurea), which is 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), which is known as a safener for rice against damage from some herbicides, "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is 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 damage from some herbicides in rice.

[0174] S15) Compounds of formula (S15) or their tautomers as described in WO-A-2008 / 131861 and WG-A-2008 / 131860 where R H 1 a (C1-C6)haloalkyl radical and

[0175] R H 2 hydrogen or halogen and

[0176] 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)C cycloalkyl, which is side of the ring is condensed with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)cycloalkoxy which is condensed with a 4 to 6-membered saturated or unsaturated carbocyclic ring on one side of the 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, (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,

[0177] R H 3 (C1-C4)alkoxy, (C2-C4)alkenyloxy, (C2-C6)alkynyloxy or (C2-C4)haloalkoxy means and

[0178] R H 4 hydrogen or (C1-C4)-alkyl or

[0179] 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.

[0180] 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).

[0181] Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocetmexyl, benoxacor, dichlormid, and metcamifen. The following examples illustrate the invention.

[0182] A. Chemical Examples

[0183] Synthesis of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1):

[0184] Step 1: Preparation of l-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4): 20.35 ml (145.2 mmol) of diisopropylamine were placed in 250 ml of tetrahydrofuran under argon, and 79.4 ml (127.1 mmol) of n-butyllithium (1.6 M solution in hexane) were added dropwise at -60°C. The solution was then briefly warmed to -40°C, and a solution of 25 g (90.8 mmol) of l-bromo-2-chloro-4-(trifluoromethoxy)benzene (3) in 60 ml of tetrahydrofuran was added dropwise at -60°C. The solution was stirred for 1 h. Then, 11.5 ml (181.5 mmol) of iodomethane were added dropwise, and the mixture was stirred 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%) l-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4). 1 H NMR (400 MHz, DMSO-d6): δ = 7.79 (d, 1H); 7.35 (d, 1H); 2.39 (s, 3H).

[0185] Step 2: Preparation of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5):

[0186] 18.91 g (65.33 mmol) of l-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4) were dissolved in 150 mL of dimethylformamide, and 11.7 g (130.65 mmol) of copper(I) cyanide were 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 gave 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).

[0187] Step 3: Preparation of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6):

[0188] 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. This gave 11.07 g (94%) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6). 1 H NMR (400 MHz, DMSO-d6): δ = 13.59 (br s, 1H); 7.72 (d, 1H); 7.45 (br d, 1H); 2.35 (s, 3H).

[0189] 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 charged in 400 ml of dichloromethane and 3 ml of dimethylformamide, and 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. The solution was stirred for 3 h at room temperature and 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). 21.26 g (91%) of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7) were obtained. 1 H NMR (400 MHz, DMSO-d6): δ = 7.75 (d, 1H); 7.49 (br d, 1H); 3.88 (s, 3H); 2.36 (s, 3H).

[0190] Step 5: Preparation of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (8): 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 at 120°C for 8 h. 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). 13.25 g (98%) of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (8) were obtained. 1 H NMR (400 MHz, DMSO-d6): δ = 7.92 (d, 1H); 7.57 (br d, 1H); 4.75 (s, 2H); 3.89 (s, 3H).

[0191] Step 6: Preparation of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1): 26.20 g (75 mmol) of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (8) were initially charged in 300 ml of acetonitrile, and 26.50 g (226 mmol) of N-methylmorpholine N-oxide were added portionwise at 10°C. After the exothermic reaction had subsided, the reaction mixture was stirred at room temperature for 12 h. The mixture was then evaporated, the residue was taken up in water, and extracted several times with ethyl acetate. The organic phases were combined, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→80 / 20). 16.39 g (77%) of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1) were obtained. 1 H NMR (400 MHz, DMSO-d6): δ = 10.37 (s, 1H); 8.12 (d, 1H); 7.66 (br d, 1H); 3.91 (s, 3H).

[0192] Synthesis of methyl 2-chloro-4-(difluoromethoxy)-3-formylbenzoate (2):

[0193] Step 1: Preparation of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10): 10 g (47.35 mmol) of commercially available methyl 2-chloro-4-hydroxy-3-methylbenzoate (9) were added portionwise to a solution of 19.93 g of potassium hydroxide in 75 ml of acetonitrile and 75 ml of water at 0°C. Then, 17.52 ml (94.71 mmol) of diethyl [bromo(difluoro)methyl]phosphonate were added, and the mixture was stirred at 0°C for 1 h. 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). 9.80 g (82%) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10) were obtained. 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 (11): 20.65 g (82.39 mmol) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10) was dissolved in 200 ml 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 at 120°C for 8 h. 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 yielded 26.47 g (97%) of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (11). 1 H NMR (400 MHz, DMSO-d6): 5 = 7.89 (d, 1H); 7.48 (t, 1H); 7.36 (d, 1H); 4.73 (s, 2H); 3.88 (s, 3H).

[0194] Step 3: Preparation of methyl 2-chloro-4-(difluoromethoxy)-3-formylbenzoate (2): 5.96 g (18 mmol) of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (11) were initially charged in 200 ml of acetonitrile, and 6.36 g (54 mmol) of N-methylmorpholine N-oxide were added portionwise at 10°C. After the exothermic reaction had subsided, the reaction mixture was stirred at room temperature for 12 h. The mixture was then evaporated, the residue was taken up in water, and extracted several times with ethyl acetate. The organic phases were combined, dried, and evaporated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). 4.33 g (90%) of methyl 2-chloro-4-(difluoromethoxy)-3-formylbenzoate (1) were obtained. 1 H NMR (400 MHz, DMSO-d6): δ = 10.34 (s, 1H); 8.06 (d, 1H); 7.44 (d, 1H); 7.39 (t, 1H); 3.89 (s, 3H).

[0195] Examples of the preparation of the compounds (II) and (I) according to the invention:

[0196] Production of 2-chloro-N 3 -cyclopropyl-N 1 -(l-ethyl-lH-tetrazol-5-yl)-4-(trifluoromethoxy)isophthalamide (2-24):

[0197] Step 1: Preparation of 2-chloro-3-(methoxycarbonyl)-6-(trifluoromethoxy)benzoic acid: 6.70 g (23.71 mmol) of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1) were initially dissolved in 200 mL of acetone, and a 2.5M solution of chromium(VI) oxide (11.38 mL, 28.45 mmol) in a 3:1 mixture of water and sulfuric acid was slowly added dropwise at 0°C. The reaction mixture was then stirred at room temperature for 12 h. After adding isopropanol to remove excess oxidant, the reaction mixture was evaporated. The residue was taken up with water and extracted with ethyl acetate; the organic phase was separated, dried, and evaporated. 6.85 g (92%) of 2-chloro-3-(methoxycarbonyl)-6-(trifluoromethoxy)benzoic acid were obtained. 1H-NMR (400 MHz, DMSO-d6): δ = 14.50 (br s, 1H); 8.01 (d, 1H); 7.63 (br d, 1H); 3.89 (s, 3H).

[0198] Step 2: Preparation of methyl 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoate (3-24): 1.04 g (3.48 mmol) of 2-chloro-3-(methoxycarbonyl)-6-(trifluoromethoxy)benzoic acid were initially charged in 50 ml of dichloromethane, and one drop of dimethylformamide was added, followed by 0.47 ml (5.22 mmol) of oxalyl chloride. The reaction solution was stirred at room temperature for 1 h, then evaporated, and the residue was taken up in toluene and re-evaporated. This residue was dissolved in 10 ml of dry dichloromethane and added dropwise at 0°C to a solution of 0.36 ml (5.22 mmol) of cyclopropylamine and 1.2 ml (6.96 mmol) of Hünig's base in 40 ml of dry dichloromethane. The mixture was then stirred at room temperature for 4 h. After dilution with dichloromethane, the mixture was washed with 2M hydrochloric acid, and the organic phase was separated, dried, and evaporated. 1.13 g (96%) of methyl 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoate (3-24) was obtained.

[0199] Step 3: Preparation of 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoic acid (4-24): 1.25 g (3.70 mmol) of methyl 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoate (3-24) were initially charged in 50 ml of methanol, and 2.8 ml (5.55 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. 1.12 g (89%) of 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoic acid (4-24) was obtained.

[0200] Step 4: Production of 2-chloro-N 3 -cyclopropyl-N 1 -(l-ethyl-lH-tetrazol-5-yl)-4-

[0201] (trifluoromethoxy)isophthalamide (2-24): 200 mg (0.61 mmol) of 2-chloro-3-(cyclopropylcarbamoyl)-4-(trifluoromethoxy)benzoic acid (4-24) and 110.4 mg (0.92 mmol) of 5-amino-1-ethyl-1H-tetrazole were initially charged in 3 ml of pyridine, and 0.085 ml (0.92 mmol) of oxalyl chloride was added dropwise at room temperature. The reaction solution was stirred for 12 h at room temperature. After addition of 10 ml of water, the mixture was stirred for a further 10 min and then extracted with dichloromethane. The organic phase was separated, dried, and evaporated. The residue was purified by chromatography (HPLC, CI 8, gradient: acetonitrile / water (+0.05% trifluoroacetic acid) 10 / 90→400 / 0). 85 mg (31%) of 2-chloro-N was obtained 3 -cyclopropyl-N 1 -(l-ethyl-lH-tetrazol-5-yl)-4-(trifluoromethoxy)isophthalamide (2-24).

[0202] The examples listed in the following tables were prepared analogously to the methods described above or are available analogously to the methods described above. These compounds are particularly preferred.

[0203] The abbreviations used mean:

[0204] Me = Methyl Et = Ethyl Pr = Propyl i-Pr = iso-Propyl c-Pr = cyclo-Propyl Bu = Butyl i-Bu = iso-Butyl Ph = Phenyl c-Bu = cyclo-Butyl

[0205] Table 1: Compounds of formula (I) according to the invention, wherein R x represents a methyl group and the other substituents have the meanings given below.

[0206]

[0207]

[0208] 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.

[0209]

[0210] Table 3: Compounds of formula (II) according to the invention, wherein L is methoxy and the other substituents have the meanings given below,

[0211]

[0212]

[0213] Table 4: Compounds of the formula (II) according to the invention, wherein L is hydroxy and the other substituents have the meanings given below,

[0214]

[0215]

[0216] Table 5: Compounds of formula (II) according to the invention, wherein L is chlorine and the other substituents have the meanings given below

[0217]

[0218] For numerous compounds of the formula (I) and

[0219] (II) NMR data are disclosed below for further characterization:

[0220] Example No. 1-1: 1 H NMR (400 MHz, DMSO-d6): δ = 11.66 (br s, 1H); 8.51 (q, 1H); 7.78 (d, 1H); 7.42 (br d, 1H); 3.98 (s, 3H); 2.79 (d, 3H); 2.34 (s, 3H);

[0221] Example No. 1-2: 1 H NMR (400 MHz, DMSO-d6): δ = 11.65 (br s, 1H); 8.60 (t, 1H); 7.78 (d, 1H); 7.41 (br d, 1H); 3.98 (s, 3H); 3.28 (m, 2H); 2.35 (s, 3H); 1.11 (t, 3H);

[0222] Example No. 1-6: 1 H NMR (400 MHz, DMS O-d6): δ = 11.66 (br s, 1H); 8.67 (d, 1H); 7.41 (br d, 1H); 3.98 (s, 3H); 2.82 (m, 1H);2.34 (s, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

[0223] Example No. 1-10: 1 H NMR (400 MHz, DMSO-d6): δ = 11.71 (br s, 1H); 8.52 (br q, 1H); 7.79 (d, 1H); 7.43 (br d, 1H); 3.99 (s, 3H); 2.79 (d, 3H); 2.73 (q, 2H); 1.15 (t, 3H);

[0224] Beispiel-Nr. 1-11: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.71 (br s, 1H); 8.62 (br t, 1H); 7.79 (d, 1H); 7.43 (br d, 1H); 3.99 (s, 3H); 3.29 (m, 2H); 2.75 (q, 2H); 1.17 (t, 3H); 1.11 (t, 3H);

[0225] Beispiel-Nr. 1-15: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.68 (br s, 1H); 8.67 (br d, 1H); 7.79 (d, 1H); 7.40 (br d, 1H); 3.99 (s, 3H); 3.82 (m, 1H); 2.74 (q, 2H); 1.16 (t, 3H); 0.72 (m, 2H); 0.48 (m, 2H);

[0226] Beispiel-Nr. 1-19: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 8.70 (q, 1H); 7.91 (d, 1H); 7.62 (d, 1H); 4.00 (s, 3H); 2.80 (d, 3H);

[0227] Beispiel-Nr. 1-20: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 8.77 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.00 (s, 3H); 3.28 (m, 2H); 1.11 (t, 3H);

[0228] Beispiel-Nr. 1-21: 1H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.77 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.00 (s, 3H); 3.23 (m, 2H); 1.52 (m, 2H); 0.92 (t, 3H);

[0229] Beispiel-Nr. 1-22: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.67 (d, 1H); 7.89 (d, 1H); 7.60 (d, 1H); 4.06 (m, 1H); 4.00 (s, 3H); 1.14 (d, 6H);

[0230] Beispiel-Nr. 1-23: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 8.85 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.00 (s, 3H); 3.17 (m, 2H); 0.99 (m, 1H); 0.44 (m, 2H); 0.24 (m, 2H);

[0231] Beispiel-Nr. 1-24: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.84 (d, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.00 (s, 3H); 2.82 (m, 1H); 0.73 (m, 2H); 0.49 (m, 2H);

[0232] Beispiel-Nr. 1-25: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.97 (s, 1H); 7.89 (d, 1H); 7.59 (d, 1H); 3.99 (s, 3H); 1.39 (s, 3H); 0.70 (m, 2H); 0.62 (m, 2H); Beispiel-Nr. 1-26: 1H-NMR (400 MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.93 (br s, 1H); 7.88 (d, 1H); 7.59 (br d, 1H); 3.99 (s, 3H); 1.62 (q, 2H); 0.97 (t, 3H); 0.68 (m, 2H); 0.64 (m, 2H);

[0233] Beispiel-Nr. 1-27: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.89 (br s, 1H); 8.93 (s, 1H); 7.88 (d, 1H); 7.59 (br d, 1H); 3.99 (s, 3H); 1.58 (m, 2H); 1.48 (m, 2H); 0.90 (t, 3H); 0.68 (m, 2H); 0.63 (m, 2H);

[0234] Beispiel-Nr. 1-29: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.89 (br s, 1H); 9.08 (s, 1H); 7.89 (d, 1H); 7.58 (br d, 1H); 3.99 (s, 3H); 3.53 (s, 2H); 3.48 (q, 2H); 1.11 (t, 3H); 0.78 (m, 2H); 0.72 (m, 2H);

[0235] Beispiel-Nr. 1-32: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 7.91 (d, 1H); 7.61 (br d, 1H); 4.50 (d, 2H); 4.00 (s, 3H); 0.95 (m, 2H); 0.83 (m, 2H);

[0236] Beispiel-Nr. 1-35: 1H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 9.41 (s, 1H); 7.92 (d, 1H); 7.62 (d, 1H); 4.11 (q, 2H); 4.00 (s, 3H); 1.48 (m, 2H); 1.19 (t, 3H); 1.10 (m, 2H);

[0237] Beispiel-Nr. 1-37: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.93 (br s, 1H); 9.82 (s, 1H); 7.97 (d, 1H); 7.67 (br d, 1H); 4.00 (s, 3H); 1.65 (m, 2H); 1.20 (m, 2H);

[0238] Beispiel-Nr. 1-38: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 9.38 (s, 1H); 7.91 (d, 1H); 7.61 (br d, 1H); 3.99 (s, 3H); 3.06 (s, 1H); 1.21 (m, 2H); 1.03 (m, 2H);

[0239] Beispiel-Nr. 1-42: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 9.54 (s, 1H); 7.93 (d, 1H); 7.63 (br d, 1H); 7.49 (m, 1H); 6.40 (m, 1H); 4.00 (s, 1H); 1.33 (m, 2H); 1.16 (m, 2H);

[0240] Beispiel-Nr. 1-45: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 9.16 (t, 1H); 7.92 (d, 1H); 7.63 (d, 1H); 4.12 (d, 2H); 4.00 (s, 3H); 2.15 (s, 3H);

[0241] Beispiel-Nr. 1-46: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 9.15 (t, 1H); 7.93 (d, 1H); 7.63 (d, 1H); 4.13 (d, 2H); 4.00 (s, 3H); 2.50 (q, 2H); 0.97 (t, 3H);

[0242] Beispiel-Nr. 1-48: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 9.04 (t, 1H); 7.91 (d, 1H); 7.76 (m, 1H); 7.60 (d, 1H); 4.00 (s, 3H); 3.89 (d, 2H); 2.64 (d, 3H);

[0243] Beispiel-Nr. 1-49: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 9.02 (t, 1H); 7.91 (d, 1H); 7.79 (br t, 1H); 7.60 (d, 1H); 4.00 (s, 3H); 3.88 (d, 2H); 3.13 (m, 2H); 1.04 (t, 3H);

[0244] Beispiel-Nr. 1-50: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.99 (t, 1H); 7.95 (br d, 1H); 7.90 (d, 1H); 7.60 (d, 1H); 4.00 (s, 3H); 3.85 (d, 2H); 2.65 (m, 1H); 0.64 (m, 2H); 0.41 (m, 2H);

[0245] Beispiel-Nr. 1-51: 1H-NMR (400 MHz, DMSO-d6): δ = 11.93 (br s, 1H); 7.94 (d, 1H); 7.67 (d, 1H); 4.01 (s, 3H); 3.05 (s, 3H); 2.82 (s, 3H);

[0246] Beispiel-Nr. 1-52: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.93 (br s, 1H); 7.94 (d, 1H); 7.67 (d, 1H); 4.01 (s, 3H); 3.62 and 3.45 and 3.14 (3x m, 2H); 3.02 and 2.80 (2x s, 3H); 1.14 and 1.07 (2x t, 3H); Beispiel-Nr. 1-53: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.93 (br s, 1H); 7.94 (m, 1H); 7.66 (m, 1H); 4.01 (s, 3H); 3.01 (s, 3H); 2.90 (m, 1H); 0.90-0.50 (m, 4H);

[0247] Beispiel-Nr. 1-63: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.40 (q, 1H); 7.74 (d, 1H); 7.24 (t, 1H); 7.22 (d, 1H); 3.97 (s, 3H); 2.77 (d. 3H); 2.31 (s, 3H);

[0248] Beispiel-Nr. 1-64: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.47 (t, 1H); 7.74 (d, 1H); 7.23 (t, 1H); 7.21 (d, 1H); 3.97 (s, 3H); 3.26 (m, 2H); 2.33 (s, 3H); 1.11 (t, 3H);

[0249] Beispiel-Nr. 1-68: 1H-NMR (400 MHz, DMSO-d6): δ = 11.57 (br s, 1H); 8.54 (d, 1H); 7.73 (d, 1H); 7.22 (t, 1H); 7.21 (d, 1H); 3.97 (s, 3H); 2.81 (m, 1H); 2.31 (s, 3H); 0.70 (m, 2H); 0.49 (m, 2H);

[0250] Beispiel-Nr. 1-72: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.61 (br s, 1H); 8.39 (br q, 1H); 7.74 (d, 1H); 7.24 (t, 1H); 7.22 (d, 1H); 3.98 (s, 3H); 2.78 (d, 3H); 2.72 (q, 2H); 1.14 (t, 3H);

[0251] Beispiel-Nr. 1-73: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.60 (br s, 1H); 8.48 (br t, 1H); 7.74 (d, 1H); 7.23 (t, 1H); 7.20 (d, 1H); 3.98 (s, 3H); 3.27 (m, 1H); 2.74 (q, 2H); 1.16 (t, 3H); 1.11 (t, 3H);

[0252] Beispiel-Nr. 1-77: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.60 (br s, 1H); 8.55 (br d, 1H); 7.74 (d, 1H); 7.22 (t, 1H); 7.20 (d, 1H); 3.98 (s, 3H); 2.82 (m, 1H); 2.72 (q, 2H); 1.14 (t, 3H); 0.70 (m, 2H); 0.48 (m, 2H);

[0253] Beispiel-Nr. 1-81: 1H-NMR (400 MHz, DMSO-d6): δ = 11.84 (br s, 1H); 8.57 (q, 1H); 7.84 (d, 1H); 7.39 (d, 1H); 7.32 (t, 1H); 3.99 (s, 3H); 2.78 (d, 3H);

[0254] Beispiel-Nr. 1-82: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.84 (br s, 1H); 8.63 (t, 1H); 7.84 (d, 1H); 7.38 (d, 1H); 7.30 (t, 1H); 3.99 (s, 3H); 3.27 (m, 2H); 1.11 (t, 3H);

[0255] Beispiel-Nr. 1-83: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.84 (br s, 1H); 8.63 (t, 1H); 7.84 (d, 1H); 7.38 (d, 1H); 7.31 (t, 1H); 3.99 (s, 3H); 3.21 (m, 2H); 1.52 (m, 2H); 0.92 (t, 3H);

[0256] Beispiel-Nr. 1-84: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 8.52 (d, 1H); 7.83 (d, 1H); 7.37 (d, 1H); 7.27 (t, 1H); 4.05 (m, 1H); 3.99 (s, 3H); 1.14 (d, 6H);

[0257] Beispiel-Nr. 1-86: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 8.69 (d, 1H); 7.37 (d, 1H); 7.30 (t, 1H); 3.99 (s, 3H); 2.80 (m, 1H); 0.71 (m, 2H); 0.49 (m, 2H);

[0258] Beispiel-Nr. 1-87:1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 8.82 (s, 1H); 7.82 (d, 1H); 7.36 (d, 1H); 7.25 (t, 1H); 3.98 (s, 3H); 1.39 (s, 3H); 0.71 (m, 2H); 0.61 (m, 2H);

[0259] Beispiel-Nr. 1-88: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 8.78 (s, 1H); 7.82 (d, 1H); 7.35 (d, 1H); 7.27 (t, 1H); 3.98 (s, 3H); 1.62 (q, 2H); 0.97 (t, 3H); 0.69 (m, 2H); 0.61 (m, 2H); Beispiel-Nr. 1-89: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 8.76 (br s, 1H); 7.78 (d, 1H); 7.31 (d, 1H); 7.24 (t, 1H); 3.94 (s, 3H); 1.58 (m, 2H); 1.49 (m, 2H); 0.90 (t, 3H); 0.69 (m, 2H); 0.60 (m, 2H);

[0260] Beispiel-Nr. 1-90: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 8.78 (br s, 1H); 7.81 (d, 1H); 7.35 (d, 1H); 7.27 (t, 1H); 3.98 (s, 3H); 1.97 (m, 1H); 1.50 (d, 2H); 0.93 (d, 6H); 0.72 (m, 2H); 0.60 (m, 2H);

[0261] Beispiel-Nr. 1-91: 1H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 8.94 (br s, 1H); 7.82 (d, 1H); 7.35 (d, 1H); 7.24 (t, 1H); 3.98 (s, 3H); 3.53 (s, 2H); 3.49 (q, 2H); 1.11 (t, 3H); 0.77 (m, 2H); 0.72 (m, 2H);

[0262] Beispiel-Nr. 1-92: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 8.82 (s, 1H); 7.82 (d, 1H); 7.36 (d, 1H); 7.29 (t, 1H); 3.98 (s, 3H); 3.51 (t, 2H); 3.22 (s, 3H); 1.86 (t, 2H); 0.69 (m, 4H);

[0263] Beispiel-Nr. 1-94: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.84 (br s, 1H); 9.09 (s, 1H); 7.84 (d, 1H); 7.37 (d, 1H); 7.26 (t, 1H); 4.49 (d, 2H); 3.99 (s, 3H); 0.93 (m, 2H); 0.84 (m, 2H);

[0264] Beispiel-Nr. 1-95: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.85 (br s, 1H); 9.51 (s, 1H); 7.86 (d, 1H); 7.39 (d, 1H); 7.31 (t, 1H); 3.99 (s, 3H); 3.31 (s, 3H); 1.05 (m, 2H); 0.87 (m, 2H);

[0265] Beispiel-Nr. 1-96: 1H-NMR (400 MHz, DMSO-d6): δ = 11.84 (br s, 1H); 9.50 (br s, 1H); 7.85 (d, 1H); 7.38 (d, 1H); 7.31 (t, 1H); 3.99 (s, 3H); 3.64 (q, 2H); 1.10 (t, 3H); 1.06 (m, 2H); 0.87 (m, 2H);

[0266] Beispiel-Nr. 1-97: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.85 (br s, 1H); 9.28 (s, 1H); 7.86 (d, 1H); 7.39 (d, 1H); 7.29 (t, 1H); 4.11 (q, 2H); 3.99 (s, 3H); 1.46 (m, 2H); 1.20 (t, 3H); 1.11 (m, 2H);

[0267] Beispiel-Nr. 1-98: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 8.99 (s, 1H); 7.82 (d, 1H); 7.33 (d, 1H); 7.19 (t, 1H); 4.06 (q, 2H); 3.98 (s, 3H); 2.73 (s, 2H); 1.18 (t, 3H); 0.80 (m, 2H); 0.76 (m, 2H);

[0268] Beispiel-Nr. 1-99: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 9.65 (s, 1H); 7.90 (d, 1H); 7.43 (d, 1H); 7.34 (t, 1H); 3.99 (s, 3H); 1.63 (m, 2H); 1.20 (m, 2H);

[0269] Beispiel-Nr. 1-100: 1H-NMR (400 MHz, DMSO-d6): δ = 11.88 (br s, 1H); 9.20 (br s, 1H); 7.80 (d, 1H); 7.33 (d, 1H); 7.24 (t, 1H); 3.93 (s, 3H); 3.03 (s, 1H); 1.19 (m, 2H); 1.04 (m, 2H);

[0270] Beispiel-Nr. 1-101: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.87 (br s, 1H); 9.37 (s, 1H); 7.87 (d, 1H); 7.42 (d, 1H); 7.40 (t, 1H); 7.30 (m, 3H); 7.19 (m, 2H); 4.00 (s, 3H); 1.29 (m, 4H);

[0271] Beispiel-Nr. 1-102: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.79 (br s, 1H); 9.31 (s, 1H); 7.80 (d, 1H); 7.79 (m, 1H); 7.40 (m, 1H); 7.30 (m, 3H); 7.15 (t, 1H); 3.96 (s, 3H); 1.17 (m, 4H); Beispiel-Nr. 1-103: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 9.44 (s, 1H); 7.88 (d, 1H); 7.42 (m, 1H); 7.40 (t, 1H); 7.31 (d, 1H); 7.20 (m, 3H); 4.00 (s, 3H); 1.35 (m, 2H); 1.30 (m, 2H);

[0272] Beispiel-Nr. 1-104: 1H-NMR (400 MHz, DMSO-d6): δ = 11.85 (br s, 1H); 9.41 (s, 1H); 7.86 (d, 1H); 7.48 (m, 1H); 7.40 (d, 1H); 7.36 (t, 1H); 6.39 (m, 1H); 6.30 (m, 1H); 3.99 (s, 3H); 1.32 (m, 2H); 1.17 (m, 2H);

[0273] Beispiel-Nr. 1-105: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.85 (br s, 1H); 9.30 (br s, 1H); 7.85 (d, 1H); 7.56 (m, 1H); 7.49 (s, 1H); 7.40 (d, 1H); 7.37 (t, 1H); 6.33 (m, 1H); 3.99 (s, 3H); 1.14 (m, 2H); 1.12 (m, 2H);

[0274] Beispiel-Nr. 1-107: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.85 (br s, 1H); 9.07 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.09 (d, 2H); 3.99 (s, 3H); 2.16 (s, 3H);

[0275] Beispiel-Nr. 1-108: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.85 (br s, 1H); 9.06 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.10 (d, 2H); 3.99 (s, 3H); 2.55 (q, 2H); 0.96 (t, 3H);

[0276] Beispiel-Nr. 1-110: 1H-NMR (400 MHz, DMSO-d6): δ = 11.84 (br s, 1H); 8.93 (t, 1H); 7.85 (d, 1H); 7.65 (m, 1H); 7.38 (d, 1H); 7.32 (t, 1H); 3.99 (s, 3H); 3.88 (d, 2H); 2.64 (d, 3H);

[0277] Beispiel-Nr. 1-111: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.84 (br s, 1H); 8.92 (t, 1H); 7.85 (d, 1H); 7.67 (b t, 1H); 7.38 (d, 1H); 7.32 (t, 1H); 3.99 (s, 3H); 3.88 (d, 2H); 3.13 (m, 2H); 1.04 (t, 3H);

[0278] Beispiel-Nr. 1-113: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.87 (d, 1H); 7.46 (d, 1H); 7.42 (t, 1H); 4.00 (s, 3H); 3.04 (s, 3H); 2.81 (s, 3H);

[0279] Beispiel-Nr. 1-114: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.86 (d, 1H); 7.44 (m, 2H); 3.99 (s, 3H); 3.52 and 3.13 (2x m, 2H); 3.01 and 2.78 (2x s, 3H); 1.14 and 1.04 (2x t, 3H);

[0280] Beispiel-Nr. 1-115: 1H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.86 (d, 1H); 7.46 (t, 1H); 7.43 (d, 1H); 4.00 (s, 3H); 3.00 and 2.71 (2x s, 3H); 2.90 and 2.62 (2x m, 1H); 0.82-0.46 (m, 4H);

[0281] Beispiel-Nr. 1-125: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.90 (br s, 1H); 8.97 (br s, 1H); 7.89 (d, 1H); 7.60 (br d, 1H); 3.99 (s, 3H); 2.57 (m, 1H); 1.88-1.62 (m, 6H); 0.68 (m, 4H);

[0282] Beispiel-Nr. 1-126: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 8.83 (br s, 1H); 7.82 (d, 1H); 7.36 (d, 1H); 7.28 (t, 1H); 3.99 (s, 3H); 2.57 (m, 1H); 1.87-1.63 (m, 6H); 0.67 (m, 4H);

[0283] Beispiel-Nr. 1-127: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.61 (br s, 1H); 8.43 (q, 1H); 7.69 (d, 1H); 7.43 (d, 1H); 4.02 (s, 3H); 2.79 (d, 3H); 2.14 (m, 1H); 8.83 (m, 2H); 0.60 (m, 2H);

[0284] Beispiel-Nr. 1-128: 1H-NMR (400 MHz, DMSO-d6): δ = 11.61 (br s, 1H); 8.52 (t, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 4-02 (s, 3H); 3.30 (m, 2H); 2.17 (m, 1H); 1.12 (t, 3H); 0.84 (m, 2H); 0.63 (m, 2H); Beispiel-Nr. 1-129: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.61 (br s, 1H); 8.59 (d, 1H); 7.68 (d, 1H); 7.42 (d, 1H); 4.02 (s, 3H); 2.80 (m, 1H); 2.15 (m, 1H); 0.84 (m, 2H); 0.71 (m, 2H); 0.61 (m, 2H); 0.51 (m, 2H);

[0285] Beispiel-Nr. 1-130: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.54 (br s, 1H); 8.33 (br q, 1H); 7.63 (d, 1H); 7.23 (d, 1H); 7.20 (t, 1H); 4.01 (s, 3H); 2.78 (d, 3H); 2.12 (m, 1H); 0.82 (m, 2H); 0.58 (m, 2H);

[0286] Beispiel-Nr. 1-131: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.54 (br s, 1H); 8.40 (br t, 1H); 7.62 (d, 1H); 7.23 (d, 1H); 7.18 (t, 1H); 4.01 (s, 3H); 3.28 (m, 2H); 2.15 (m, 1H); 1.13 (t, 3H); 0.82 (m, 2H); 0.61 (m, 2H);

[0287] Beispiel-Nr. 1-132: 1H-NMR (400 MHz, DMSO-d6): δ = 11.53 (br s, 1H); 8.47 (d, 1H); 7.62 (d, 1H); 7.22 (d, 1H); 7.18 (t, 1H); 4.01 (s, 3H); 2.79 (m, 1H); 2.13 (m, 1H); 0.82 (m, 2H); 0.70 (m, 2H); 0.59 (m, 2H); 0.51 (m, 2H);

[0288] Beispiel-Nr. 1-133: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.70 (br s, 1H); 8.35 (q, 1H); 7.75 (d, 1H); 7.29 (d, 1H); 6.34 (tt, 1H); 4.45 (td, 2H); 3.97 (s, 3H); 2.75 (d, 3H);

[0289] Beispiel-Nr. 1-134: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.69 (br s, 1H); 8.42 (t, 1H); 7.75 (d, 1H); 7.28 (d, 1H); 6.34 (tt, 1H); 4.44 (td, 2H); 3.97 (s, 3H); 3.24 (m, 2H); 1.10 (t, 3H);

[0290] Beispiel-Nr. 1-135: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.69 (br s, 1H); 8.49 (d, 1H); 7.75 (d, 1H); 7.26 (d, 1H); 6.34 (tt, 1H); 4.42 (td, 2H); 3.97 (s, 3H); 2.75 (m, 1H); 0.68 (m, 2H); 0.49 (m, 2H);

[0291] Beispiel-Nr. 2-1: 1H-NMR (400 MHz, DMSO-d6): δ = 11.55 (br s, 1H); 8.51 (q, 1H); 7.78 (d, 1H); 7.42 (br d, 1H); 4.33 (q, 2H); 2.79 (d, 3H); 2.33 (s, 3H); 1.46 (t, 3H);

[0292] Beispiel-Nr. 2-2: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.56 (br s, 1H); 8.59 (t, 1H); 7.77 (d, 1H); 7.40 (br d, 1H); 4.32 (q, 2H); 3.27 (m, 2H); 2.35 (s, 3H); 1.45 (t, 3H); 1.11 (t, 3H);

[0293] Beispiel-Nr. 2-6: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.54 (br s, 1H); 8.66 (d, 1H); 7.77 (d, 1H); 7.41 (br d, 1H); 4.33 (q, 2H); 2.82 (m, 1H); 2.34 (s, 3H); 1.46 (t, 3H); 0.72 (m, 2H); 0.48 (m, 2H);

[0294] Beispiel-Nr. 2-10: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.51 (br q, 1H); 7.78 (d, 1H); 7.43 (br d, 1H); 4.34 (q, 2H); 2.79 (d, 3H); 2.73 (q, 2H); 1.47 (t, 3H); 1.16 (t, 3H);

[0295] Beispiel-Nr. 2-11: 1H-NMR (400 MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.60 (br t, 1H); 7.78 (d, 1H); 7.42 (br d, 1H); 4.34 (q, 2H); 2.29 (m, 2H); 2.75 (q, 2H); 1.47 (t, 3H); 1.17 (t, 3H); 1.11 (t, 3H);

[0296] Beispiel-Nr. 2-15: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.57 (br s, 1H); 8.67 (br d, 1H); 7.77 (d, 1H); 7.42 (br d, 1H); 4.34 (q, 2H); 2.83 (m, 1H); 2.74 (m, 2H); 1.46 (t, 3H); 1.16 (t, 3H); 0.72 (m, 2H); 0.48 (m, 2H); Beispiel-Nr. 2-19: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 8.70 (q, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.36 (q, 2H); 2.80 (d, 3H); 1.47 (t, 3H);

[0297] Beispiel-Nr. 2-20: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 8.77 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.36 (q, 2H); 3.29 (m, 2H); 1.46 (t, 3H); 1.11 (t, 3H);

[0298] Beispiel-Nr. 2-21: 1H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 8.77 (t, 1H); 7.89 (d, 1H); 7.61 (d, 1H); 4.36 (q, 2H); 3.23 (m, 2H); 1.53 (m, 2H); 1.47 (t, 3H); 0.92 (t, 3H);

[0299] Beispiel-Nr. 2-22: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.79 (br s, 1H); 8.67 (d, 1H); 7.89 (d, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 4.06 (m, 1H); 1.47 (t, 3H); 1.15 (d, 6H);

[0300] Beispiel-Nr. 2-23: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 8.85 (t, 1H); 7.90 (d, 1H); 7.61 (d, 1H); 4.36 (q, 2H); 3.17 (m, 2H); 1.47 (t, 3H); 1.00 (m, 1H); 0.44 (m, 2H); 0.25 (m, 2H);

[0301] Beispiel-Nr. 2-24: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 8.84 (d, 1H); 7.89 (d, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 2.82 (m, 1H); 1.46 (t, 3H); 0.74 (m, 2H); 0.49 (m, 2H);

[0302] Beispiel-Nr. 2-25: 1H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 8.97 (s, 1H); 7.88 (d, 1H); 7.59 (d, 1H); 4.36 (q, 2H); 1.46 (t, 3H); 1.39 (s, 3H); 0.70 (m, 2H); 0.63 (m, 2H);

[0303] Beispiel-Nr. 2-27: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.79 (br s, 1H); 8.93 (s, 1H); 7.87 (d, 1H); 7.59 (br d, 1H); 4.35 (q, 2H); 1.57 (m, 2H); 1.48 (m, 2H); 1.46 (t, 3H); 0.90 (t, 3H); 0.70 (m, 2H); 0.63 (m, 2H);

[0304] Beispiel-Nr. 2-27: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 9.38 (s, 1H); 7.91 (d, 1H); 7.61 (br d, 1H); 4.36 (q, 2H); 3.06 (s, 1H); 1.46 (t, 3H); 1.21 (m, 2H); 1.03 (m, 2H);

[0305] Beispiel-Nr. 2-29: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.79 (br s, 1H); 9.08 (s, 1H); 7.88 (d, 1H); 7.58 (d, 1H); 4.36 (q, 2H); 3.53 (s, 2H); 3.48 (q, 2H); 1.46 (t, 3H); 1.11 (t, 3H); 0.79 (m, 2H); 0.72 (m, 2H);

[0306] Beispiel-Nr. 2-32: 1H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 9.23 (s, 1H); 7.90 (d, 1H); 7.61 (br d, 1H); 4.50 (d, 2H); 4.36 (q, 2H); 1.46 (t, 3H); 0.96 (m, 2H); 0.83 (m, 2H);

[0307] Beispiel-Nr. 2-35: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 9.41 (s, 1H); 7.92 (d, 1H); 7.62 (d, 1H); 4.36 (q, 2H); 4.11 (q, 2H); 1.47 (m, 5H); 1.19 (t, 3H); 1.10 (m, 2H);

[0308] Beispiel-Nr. 2-37: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 9.82 (s, 1H); 7.97 (d, 1H); 7.67 (br d, 1H); 4.36 (q, 2H); 1.65 (m, 2H); 1.46 (t, 3H), 1.20 (m, 2H);

[0309] Beispiel-Nr. 2-42: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 9.54 (s, 1H); 7.92 (d, 1H); 7.63 (br d, 1H); 7.49 (m, 1H); 6.40 (m, 1H); 6.25 (m, 1H); 4.36 (q, 2H); 1.47 (t, 3H); 1.33 (m, 2H); 1.16 (m, 2H); Beispiel-Nr. 2-45: 1H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 9.16 (t, 1H); 7.92 (d, 1H); 7.63 (d, 1H); 4.36 (q, 2H); 4.13 (d, 2H); 2.16 (s, 3H); 1.47 (t, 3H);

[0310] Beispiel-Nr. 2-46: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.81 (br s, 1H); 9.15 (t, 1H); 7.92 (d, 1H); 7.62 (d, 1H); 4.36 (q, 2H); 4.13 (d, 2H); 2.51 (q, 2H); 1.47 (t, 3H); 0.97 (t, 3H);

[0311] Beispiel-Nr. 2-48: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.79 (br s, 1H); 9.04 (t, 1H); 7.90 (d, 1H); 7.77 (m, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 3.89 (d, 2H); 2.64 (d, 3H); 1.46 (t, 3H);

[0312] Beispiel-Nr. 2-49: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 9.02 (t, 1H); 7.90 (d, 1H); 7.79 (br t, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 3.88 (d, 2H); 3.13 (m, 2H); 1.46 (t, 3H); 1.04 (t, 3H);

[0313] Beispiel-Nr. 2-50: 1H-NMR (400 MHz, DMSO-d6): δ = 11.80 (br s, 1H); 9.00 (t, 1H); 7.96 (br d, 1H); 7.60 (d, 1H); 4.36 (q, 2H); 3.85 (d, 2H); 2.65 (m, 1H); 1.47 (t, 3H); 0.64 (m, 2H); 0.41 (m, 2H);

[0314] Beispiel-Nr. 2-51: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 7.94 (d, 1H); 7.67 (d, 1H); 4.37 (d, 2H); 3.05 (s, 3H); 2.83 (s, 3H); 1.47 (t, 3H);

[0315] Beispiel-Nr. 2-52: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 7.93 (d, 1H); 7.67 (d, 1H); 4.37 (q, 2H); 3.62 and 3.46 and 3.14 (3x m, 2H); 3.02 and 2.80 (2x s, 3H); 1.47 (t, 3H); 1.14 and 1.07 (2x t, 3H);

[0316] Beispiel-Nr. 2-53: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 7.93 (m, 1H); 7.65 (m, 1H); 4.37 (q, 2H); 3.02 (s, 3H); 2.91 (m, 1H); 1.47 (t, 3H); 0.88-0.51 (m, 4H);

[0317] Beispiel-Nr. 2-63: 1H-NMR (400 MHz, DMSO-d6): δ = 11.47 (br s, 1H); 8.40 (q, 1H); 7.73 (d, 1H); 7.24 (t, 1H); 7.22 (d, 1H); 4.32 (q, 2H); 2.78 (d, 3H); 2.31 (s, 3H); 1.46 (t, 3H);

[0318] Beispiel-Nr. 2-64: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.46 (br s, 1H); 8.47 (t, 1H); 7.73 (d, 1H); 7.23 (t, 1H); 7.22 (d, 1H); 4.32 (q, 2H); 3.27 (m, 2H); 2.33 (s, 3H); 1.46 (t, 3H); 1.11 (t, 3H);

[0319] Beispiel-Nr. 2-68: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.46 (br s, 1H); 8.53 (d, 1H); 7.72 (d, 1H); 7.22 (t, 1H); 7.21 (d, 1H); 4.32 (q, 2H); 2.81 (m, 1H); 2.31 (s, 3H); 1.46 (t, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

[0320] Beispiel-Nr. 2-72: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.49 (br s, 1H); 8.39 (br q, 1H); 7.73 (d, 1H); 7.24 (t, 1H); 7.22 (d, 1H); 4.33 (q, 2H); 2.78 (d, 3H); 2.71 (q, 2H); 1.46 (t, 3H); 1.14 (t, 3H);

[0321] Beispiel-Nr. 2-73: 1H-NMR (400 MHz, DMSO-d6): δ = 11.49 (br s, 1H); 8.48 (br t, 1H); 7.73 (d, 1H); 7.23 (t, 1H); 7.22 (d, 1H); 4.33 (q, 2H); 3.27 (m, 2H); 2.74 (q, 2H); 1.46 (t, 3H); 1.16 (t, 3H); 1.11 (t, 3H);

[0322] Beispiel-Nr. 2-77: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.48 (br s, 1H); 8.55 (br d, 1H); 7.73 (d, 1H); 7.22 (t, 1H); 7.21 (d, 1H); 4.32 (q, 2H); 2.82 (m, 1H); 2.72 (m, 2H); 1.46 (t, 3H); 1.14 (t, 3H); 0.71 (m, 2H); 0.48 (m, 2H); Beispiel-Nr. 2-81: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.84 (br s, 1H); 8.57 (q, 1H); 7.84 (d, 1H); 7.39 (d, 1H); 7.32 (t, 1H); 3.99 (s, 3H); 2.78 (d, 3H);

[0323] Beispiel-Nr. 2-82: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.73 (br s, 1H); 8.63 (t, 1H); 7.83 (d, 1H); 7.38 (d, 1H); 7.30 (t, 1H); 4.35 (q, 2H); 3.27 (m, 2H); 1.46 (t, 3H); 1.11 (t, 3H);

[0324] Beispiel-Nr. 2-83: 1H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.63 (t, 1H); 7.83 (d, 1H); 7.38 (d, 1H); 7.31 (t, 1H); 4.35 (q, 2H); 3.21 (m, 2H); 1.52 (m, 2H); 1.46 (t, 3H); 0.92 (t, 3H);

[0325] Beispiel-Nr. 2-84: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.52 (d, 1H); 7.82 (d, 1H); 7.37 (d, 1H); 7.27 (t, 1H); 4.35 (q, 2H); 4.05 (m, 1H); 1.46 (t, 3H); 1.14 (d, 6H);

[0326] Beispiel-Nr. 2-86: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.69 (d, 1H); 7.83 (d, 1H); 7.38 (d, 1H); 7.30 (t, 1H); 4.35 (q, 2H); 2.81 (m, 1H); 1.47 (t, 3H); 0.72 (m, 2H); 0.50 (m, 2H);

[0327] Beispiel-Nr. 2-87: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.71 (br s, 1H); 8.82 (s, 1H); 7.81 (d, 1H); 7.36 (d, 1H); 7.25 (t, 1H); 4.35 (q, 2H); 1.46 (t, 3H); 1.39 (s, 3H); 0.72 (m, 2H; 0.62 (m, 2H);

[0328] Beispiel-Nr. 2-88: 1H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.78 (s, 1H); 7.81 (d, 1H); 7.36 (d, 1H); 7.27 (t, 1H); 4.35 (q, 2H); 1.62 (q, 2H); 1.46 (t, 3H); 0.97 (t, 3H); 0.69 (m, 2H); 0.61 (m, 2H);

[0329] Beispiel-Nr. 2-89: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.78 (br s, 1H); 7.80 (d, 1H);

[0330] 7.35 (d, 1H); 7.26 (t, 1H); 4.34 (q, 2H); 3.32 (s, 3H); 1.58 (m, 2H); 1.50 (m, 2H); 1.46 (t, 3H); 0.90 (t,

[0331] 3H); 0.70 (m, 2H); 0.61 (m, 2H);

[0332] Beispiel-Nr. 2-90: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.78 (br s, 1H); 7.80 (d, 1H);

[0333] 7.34 (d, 1H); 7.27 (t, 1H); 4.34 (q, 2H); 1.96 (m, 1H); 1.49 (d, 2H); 1.46 (t, 3H); 0.93 (d, 6H); 0.73 (m,

[0334] 2H); 0.60 (m, 2H);

[0335] Beispiel-Nr. 2-91: 1H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.94 (s, 1H); 7.81 (d, 1H); 7.35 (d, 1H); 7.24 (t, 1H); 4.35 (q, 2H); 3.53 (s, 2H); 3.49 (q, 2H); 1.46 (t, 3H); 1.11 (t, 3H); 0.77 (m, 2H); 0.72 (m, 2H);

[0336] Beispiel-Nr. 2-92: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.82 (br s, 1H); 7.81 (d, 1H);

[0337] 7.36 (d, 1H); 7.29 (t, 1H); 4.35 (q, 2H); 3.51 (t, 2H); 3.22 (s, 3H); 1.86 (t, 3H); 1.46 (t, 3H); 0.69 (m, 4H);

[0338] Beispiel-Nr. 2-94: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.73 (br s, 1H); 9.09 (s, 1H); 7.83 (d, 1H); 7.37 (d, 1H); 7.26 (t, 1H); 4.49 (d, 2H); 4.35 (q, 2H); 1.46 (t, 3H); 0.94 (m, 2H); 0.83 (m, 2H);

[0339] Beispiel-Nr. 2-95: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.74 (br s, 1H); 9.50 (br s, 1H); 7.85 (d, 1H); 7.39 (d, 1H); 7.31 (t, 1H); 4.35 (q, 2H); 3.31 (s, 3H); 1.46 (t, 3H); 1.05 (m, 2H); 0.87 (m, 2H); Beispiel-Nr. 2-96: 1H-NMR (400 MHz, DMSO-d6): δ = 11.73 (br s, 1H); 7.84 (d, 1H); 7.38 (d, 1H); 7.31 (t, 1H); 4.35 (q, 2H); 3.65 (q, 2H); 1.46 (t, 3H); 1.10 (t, 3H); 1.04 (m, 2H); 0.87 (m, 2H);

[0340] Beispiel-Nr. 2-97: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.74 (br s, 1H); 9.28 (s, 1H); 7.85 (d, 1H); 7.39 (d, 1H); 7.29 (t, 1H); 4.35 (q, 2H); 4.11 (q, 2H); 1.46 (m, 5H); 1.20 (t, 3H); 1.11 (m, 2H);

[0341] Beispiel-Nr. 2-98: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.71 (br s, 1H); 8.99 (s, 1H); 7.81 (d, 1H); 7.33 (d, 1H); 7.19 (t, 1H); 4.34 (q, 2H); 4.06 (q, 2H); 2.73 (s, 2H); 1.45 (t, 3H); 1.18 (t, 3H); 0.80 (m, 2H); 0.77 (m, 2H);

[0342] Beispiel-Nr. 2-99: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.76 (br s, 1H); 9.65 ( s, 1H); 7.89 (d, 1H); 7.43 (d, 1H); 7.34 (t, 1H); 4.35 (q, 2H); 1.63 (m, 2H); 1.46 (t, 3H); 1.20 (m, 2H);

[0343] Beispiel-Nr. 2-100: 1H-NMR (400 MHz, DMSO-d6): δ = 11.73 (br s, 1H); 9.22 (br s, 1H); 7.83 (d, 1H); 7.37 (d, 1H); 7.28 (t, 1H); 4.34 (q, 2H); 3.04 (s, 1H); 1.46 (t, 3H); 1.19 (m, 2H); 1.04 (m, 2H);

[0344] Beispiel-Nr. 2-101: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.75 (br s, 1H); 9.37 (s, 1H); 7.86 (d, 1H); 7.42 (d, 1H); 7.40 (t, 1H); 7.30 (m, 3H); 7.19 (m, 2H); 4.36 (q, 2H); 1.47 (t, 3H); 1.29 (m, 4H);

[0345] Beispiel-Nr. 2-102: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.68 (br s, 1H); 9.31 (br s, 1H); 7.79 (d, 1H); 7.70 (m, 1H); 7.41 (m, 1H); 7.31 (m, 3H); 7.15 (t, 1H); 4.32 (q, 2H); 1.44 (t, 3H); 1.19 (m, 2H); 1.16 (m, 2H);

[0346] Beispiel-Nr. 2-103: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.76 (br s, 1H); 9.44 (br s, 1H); 7.87 (d, 1H); 7.43 (d, 1H); 7.40 (m, 2H); 7.31 (d, 1H); 7.21 (m, 3H); 4.36 (q, 2H); 1.47 (t, 3H); 1.36 (m, 2H); 1.30 (m, 2H);

[0347] Beispiel-Nr. 2-104: 1H-NMR (400 MHz, DMSO-d6): δ = 11.74 (br s, 1H); 9.41 (s, 1H); 7.85 (d, 1H); 7.48 (m, 1H); 7.40 (d, 1H); 7.36 (t, 1H); 6.39 (m, 1H); 6.31 (m, 1H); 4.35 (q, 2H); 1.47 (t, 3H); 1.32 (m, 2H); 1.17 (m, 2H);

[0348] Beispiel-Nr. 2-105: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.74 (br s, 1H); 9.30 (br s, 1H); 7.84 (d, 1H); 7.56 (m, 1H); 7.49 (s, 1H); 7.40 (d, 1H); 7.37 (t, 1H); 6.33 (m, 1H); 4.35 (q, 2H); 1.47 (t, 3H); 1.14 (m, 2H); 1.12 (m, 2H);

[0349] Beispiel-Nr. 2-107: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.74 (br s, 1H); 9.07 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.36 (q, 2H); 4.09 (d, 2H); 2.16 (s, 3H); 1.47 (t, 3H);

[0350] Beispiel-Nr. 2-108: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.74 (br s, 1H); 9.07 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.36 (q, 2H); 4.09 (d, 2H); 2.16 (s, 3H); 1.47 (t, 3H);

[0351] Beispiel-Nr. 2-110: 1H-NMR (400 MHz, DMSO-d6): δ = 11.74 (br s, 1H); 9.06 (t, 1H); 7.86 (d, 1H); 7.40 (d, 1H); 7.34 (t, 1H); 4.36 (q, 2H); 4.10 (d, 2H); 2.55 (q, 2H); 1.47 (t, 3H); 0.96 (t, 3H); Beispiel-Nr. 2-111: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.74 (br s, 1H); 8.92 (t, 1H); 7.84 (d, 1H); 7.68 (br t, 1H); 7.38 (d, 1H); 7.32 (t, 1H); 4.35 (q, 2H); 3.88 (d, 2H); 3.14 (m, 2H); 1.46 (t, 3H); 1.04 (t, 3H);

[0352] Beispiel-Nr. 2-112: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.73 (br s, 1H); 8.88 (t, 1H); 7.87 (m, 1H); 7.84 (d, 1H); 7.38 (d, 1H); 7.30 (t, 1H); 4.36 (q, 2H); 3.85 (d, 2H); 2.65 (m, 1H); 1.46 (t, 3H); 0.65 (m, 2H); 0.41 (m, 2H);

[0353] Beispiel-Nr. 2-113: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.76 (br s, 1H); 7.86 (d, 1H); 7.46 (d, 1H); 7.42 (t, 1H); 4.36 (q, 2H); 3.04 (s, 3H); 2.81 (s, 3H); 1.47 (t, 3H);

[0354] Beispiel-Nr. 2-114: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.76 (br s, 1H); 7.86 (d, 1H); 7.44 (m, 2H);

[0355] 4.36 (q, 2H); 3.52 and 3.13 (2x m, 2H); 3-01 and 2.78 (2x, 3H); 1.47 (t, 3H); 1.14 and 1.06 (2x t, 3H);

[0356] Beispiel-Nr. 2-115: 1 H-NMR (400 MHz, DMSO-d6): δ = 11. 76 (br s, 1H); 7.85 (d, 1H); 7.46 (t, 1H); 7.43 (m, 1H); 7.36 (q, 2H); 3.00 and 2.71 (2s, 3H); 2.90 and 2.62 (2x m, 1H); 1.47 (t, 3H); 0.83-0.46 (m, 4H);

[0357] Beispiel-Nr. 2-125: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.79 (br s, 1H); 8.97 (br s, 1H); 7.88 (d, 1H); 7.60 (br d, 1H); 4.36 (q, 2H); 2.58 (m, 1H); 1.88-1.62 (m, 6H); 1.46 (t, 3H); 0.68 (m, 4H);

[0358] Beispiel-Nr. 2-126: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 8.83 (br s, 1H); 7.81 (d, 1H);

[0359] 7.36 (d, 1H); 7.28 (t, 1H); 4.35 (q, 2H); 2.57 (m, 1H); 1.87-1.63 (m, 6H); 1.46 (t, 3H); 0.67 (m, 4H);

[0360] Beispiel-Nr. 2-127: 1H-NMR (400 MHz, DMSO-d6): δ = 11.50 (br s, 1H); 8.44 (q, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 4.36 (q, 2H); 2.80 (d, 3H); 2.14 (m, 1H); 1.48 (t, 3H); 0.83 (m, 2H); 0.60 (m, 2H);

[0361] Beispiel-Nr. 2-128: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.50 (br s, 1H); 8.52 (t, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 4.37 (q, 2H); 3.29 (m, 2H); 2.17 (m, 1H); 1.48 (t, 3H); 1.13 (t, 3H); 0.83 (m, 2H); 0.63 (m, 2H);

[0362] Beispiel-Nr. 2-129: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.50 (br s, 1H); 8.59 (d, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 4.36 (q, 2H); 2.80 (m, 1H); 2.15 (m, 1H); 1.48 (t, 3H); 0.84 (m, 2H); 0.71 (m, 2H); 0.62 (m, 2H); 0.51 (m, 2H);

[0363] Beispiel-Nr. 2-130: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.42 (br s, 1H); 8.33 (br q, 1H); 7.62 (d, 1H); 7.24 (d, 1); 7.20 (t, 1H); 4.36 (q, 2H); 2.78 (d, 3H); 1.48 (t, 3H); 0.81 (2H); 0.58 (m, 2H);

[0364] Beispiel-Nr. 2-131: 1H-NMR (400 MHz, DMSO-d6): δ = 11.42 (br s, 1H); 8.40 (t, 1H); 7.61 (d, 1H); 7.23 (d, 1H); 7.18 (t, 1H); 4.36 (q, 2H); 3.28 (m, 2H); 2.14 (m, 2H); 1.48 (t, 3H); 1.12 (t, 3H); 0.82 (m, 2H); 0.60 (m, 2H);

[0365] Beispiel-Nr. 2-132: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.42 (br s, 1H); 8.47 (d, 1H); 7.61 (d, 1H); 7.22 (d, 1H); 7.18 (t, 1H); 4.35 (q, 2H); 2.80 (m, 1H); 2.13 (m, 1H); 1.47 (s, 3H); 0.82 (m, 2H); 0.70 (m, 2H); 0.59 (m, 2H); 0.51 (m, 2H); Beispiel-Nr. 2-133: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.59 (br s, 1H); 8.35 (br q, 1H); 7.74 (d, 1H);

[0366] 7.29 (d, 1H); 6.34 (it, 1H); 4.45 (td, 2H); 4.34 (q, 2H); 2.75 (d, 3H); 1.46 (t, 3H);

[0367] Beispiel-Nr. 2-134: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.58 (br s, 1H); 8.42 (br t, 1H); 7.74 (d, 1H); 7.28 (d, 1H); 6.34 (tt, 1H); 4.44 (td, 2H); 4.34 (q, 2H); 3.25 (m, 2H); 1.46 (t, 3H); 1.10 (t, 3H);

[0368] Beispiel-Nr. 2-135: 1H-NMR (400 MHz, DMSO-d6): δ = 11.60 (br s, 1H); 8.49 (d, 1H); 7.74 (d, 1H); 7.27 (d, 1H); 6.34 (tt, 1H); 4.42 (td, 2H); 4.33 (q, 2H); 2.76 (m, 1H); 1.46 (t, 3H); 0.69 (m, 2H); 0.49 (m, 2H);

[0369] Beispiel-Nr. 3-1: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.49 (br q, 1H); 7.89 (d, 1H); 7.37 (br d, 1H); 3.85 (s, 3H); 2.77 (d, 3H); 2.39 (s, 3H);

[0370] Beispiel-Nr. 3-2: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.57 (br t, 1H); 7.89 (d, 1H); 7.37 (br d, 1H); 3.85 (s, 3H); 3.27 (m, 2H); 2.41 (s, 3H); 1.10 (t, 3H);

[0371] Beispiel-Nr. 3-6: 1 H-NMR (400 MHz, CDC 13 ): δ = 7.91 (d, 1H); 7.16 (br d, 1H); 5.83 (br s, 1H); 3.90 (s, 3H); 2.92 (m, 1H); 2.57 (s, 3H); 0.90 (m, 2H); 0.64 (m, 2H);

[0372] Beispiel-Nr. 3-10: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.49 (m, 1H); 7.88 (d, 1H); 7.37 (br d, 1H); 3.85 (s, 3H); 2.80 (q, 2H); 2.77 (d, 3H); 1.12 (t, 3H);

[0373] Beispiel-Nr. 3-11:1 H-NMR (400 MHz, DMSO-d6): δ = 8.58 (br t, 1H); 7.88 (d, 1H); 7.37 (br d, 1H); 3.86 (s, 3H); 3.27 (m, 2H); 2.83 (q, 2H); 1.13 (t, 3H); 1.09 (t, 3H);

[0374] Beispiel-Nr. 3-15: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.62 (br d, 1H); 7.87 (d, 1H); 7.36 (br d, 1H); 3.85 (s, 3H); 2.81 (m, 3H); 1.12 (t, 3H); 0.71 (m, 2H); 0.46 (m, 2H);

[0375] Beispiel-Nr. 3-19: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.66 (br q, 1H); 7.94 (d, 1H); 7.56 (d, 1H); 3.89 (s, 3H); 2.78 (d, 3H);

[0376] Beispiel-Nr. 3-20: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.73 (br t, 1H); 7.93 (d, 1H); 7.56 (d, 1H); 3.89 (s, 3H); 3.27 (m, 2H); 1.10 (t, 3H);

[0377] Beispiel-Nr. 3-22: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.61 (br d, 1H); 7.92 (d, 1H); 7.55 (br d, 1H); 4.05 (m, 1H); 3.89 (s, 3H); 1.13 (d, 6H);

[0378] Beispiel-Nr. 3-23: 1H-NMR (400 MHz, DMSO-d6): δ = 8.80 (br t, 1H); 7.93 (d, 1H); 7.56 (br d, 1H); 3.89 (s, 3H); 3.15 (m, 2H); 0.98 (m, 1H); 0.43 (m, 2H); 0.23 (m, 2H);

[0379] Beispiel-Nr. 3-24: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.78 (d, 1H); 7.93 (d, 1H); 7.56 (d, 1H); 3.88 (s, 3H); 2.80 (m, 1H); 0.72 (m, 2H); 0.48 (m, 2H);

[0380] Beispiel-Nr. 3-25: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.92 (s, 1H); 7.92 (d, 1H); 7.54 (d, 1H); 3.89 (s, 3H); 1.38 (s, 3H); 0.69 (m, 2H); 0.63 (m, 2H); Beispiel-Nr. 3-26: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.87 (br s, 1H); 7.92 (d, 1H); 7.54 (br d, 1H); 3.88 (s, 3H); 1.61 (q, 2H); 0.95 (t, 3H); 0.66 (m, 2H); 0.63 (m, 2H);

[0381] Beispiel-Nr. 3-27: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.87 (br s, 1H); 7.91 (d, 1H); 7.54 (br d, 1H); 3.88 (s, 3H); 1.47 (m, 2H); 1.48 (m, 2H); 0.89 (t, 3H); 0.67 (m, 2H); 0.62 (m, 2H);

[0382] Beispiel-Nr. 3-29: 1H-NMR (400 MHz, DMSO-d6): δ = 9.01 (br s, 1H); 7.92 (d, 1H); 7.53 (br s, 1H); 3.88 (s, 3H); 3.52 (s, 2H); 3.47 (q, 2H); 1.11 (t, 3H); 0.78 (m, 2H); 0.70 (m, 2H);

[0383] Beispiel-Nr. 3-31: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.72 (br t, 1H); 7.93 (d, 1H); 7.56 (m, 1H); 3.89 (s, 3H); 3.21 (m, 2H); 1.51 (m, 2H); 0.91 (t, 3H);

[0384] Beispiel-Nr. 3-32: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.17 (br s, 1H); 7.94 (d, 1H); 7.56 (br d, 1H); 4.48 (d, 2H); 3.89 (s, 3H); 0.94 (m, 2H); 0.82 (m, 2H);

[0385] Beispiel-Nr. 3-35: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.35 (br s, 1H); 7.95 (d, 1H); 7.57 (br d, 1H); 4.11 (q, 2H); 3.89 (s, 3H); 1.47 (m, 2H); 1.18 (t, 3H); 1.09 (m, 2H);

[0386] Beispiel-Nr. 3-37: 1 H-NMR (400 MHz, DMSO-d6): δ = 14.84 (br s, 1H); 9.74 (s, 1H); 7.97 (d, 1H); 7.57 (br d, 1H); 3.08 (s, 1H); 1.63 (m, 2H); 1.18 (m, 2H);

[0387] Beispiel-Nr. 3-38: 1H-NMR (400 MHz, DMSO-d6): δ = 9.32 (br s, 1H); 7.94 (d, 1H); 7.56 (br d, 1H); 3.88 (s, 3H); 3.05 (s, 1H); 1.20 (m, 2H); 1.02 (m, 2H);

[0388] Beispiel-Nr. 3-42: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.48 (br s, 1H); 7.96 (d, 1H); 7.58 (br d, 1H); 7.48 M, 1H); 6.39 (m, 1H); 6.24 (m, 1H); 3.89 (s, 3H); 1.31 (m, 2H); 1.15 (m, 2H);

[0389] Beispiel-Nr. 3-45: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.12 (br t, 1H); 7.95 (d, 1H); 7.57 (br d, 1H); 4.11 (d, 1H); 3.89 (s, 3H); 2.14 (s, 3H);

[0390] Beispiel-Nr. 3-46: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.11 (br t, 1H); 7.95 (d, 1H); 7.57 (br d, 1H); 4.12 (d, 2H); 3.89 (s, 3H); 2.52 (m, 2H); 0.96 (t, 3H);

[0391] Beispiel-Nr. 3-48: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.00 (br t, 1H); 7.94 (d, 1H); 7.75 (br m, 1H); 7.55 (br d, 1H); 3.89 (s, 3H); 3.87 (d, 2H); 2.63 (d, 3H);

[0392] Beispiel-Nr. 3-49: 1H-NMR (400 MHz, DMSO-d6): δ = 8.99 (br t, 1H); 7.94 (d, 1H); 7.78 (br r, 1H); 7.55 (br d, 1H); 3.89 (s, 3H); 3.87 (d, 2H); 3.12 (m, 2H); 1.03 (t, 3H);

[0393] Beispiel-Nr. 3-50: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.96 (br t, 1H); 7.94 (br s, 1H); 7.93 (d, 1H); 7.54 (br d, 1H); 3.89 (s, 3H); 3.84 (d, 2H); 2.64 (m, 1H); 0.64 (m, 2H); 0.40 (m, 2H);

[0394] Beispiel-Nr. 3-51: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.00 (d, 1H); 7.62 (d, 1H); 3.89 (s, 3H); 3.03 (s, 3H); 2.73 (s, 3H); Beispiel-Nr. 3-52: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.99 (d, 1H); 7.62 (br d, 1H); 3.89 (s, 3H); 3.60, 3.43 and 3.09 (3x m, 2H); 3.01 and 2.76 (2x s, 3H); 1.13 and 1.04 (2x t, 3H);

[0395] Beispiel-Nr. 3-53: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.00 (m, 1H); 7.61 (m, 1H); 3.89 (s, 3H); 3.00 and 2.69 (2x s, 3H); 2.48 and 2.59 (2x m, 1H); 0.83 and 0.70 and 0.60 and 0.48 (4x m, 4H);

[0396] Beispiel-Nr. 3-63: 1H-NMR (400 MHz, DMSO-d6): δ = 8.38 (br q, 1H); 7.86 (d, 1H); 7.25 (t, 1H); 7.17 (br d, 1H); 3.83 (s, 3H); 2.76 (d, 3H); 2.38 (s, 3H);

[0397] Beispiel-Nr. 3-64: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.45 (br, t, 1H); 7.86 (d, 1H); 7.23 (t, 1H); 7.17 (d, 1H); 3.83 (s, 3H); 3.26 (m, 2H); 2.40 (s, 3H); 1.10 (t, 3H);

[0398] Beispiel-Nr. 3-68: 1 H-NMR (400 MHz, CDC 13 ): δ = 7.89 (d, 1H); 7.04 (br d, 1H); 6.55 (t, 1H); 5.85 (br s, 1H); 3.89 (s, 3H); 2.92 (m, 1H); 2.55 (s, 3H); 0.88 (m, 4H);

[0399] Beispiel-Nr. 3-72: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.38 (m, 1H); 7.85 (d, 1H); 7.26 (t, 1H); 7.17 (d, 1H); 3.84 (s, 3H); 2.80 (q, 2H); 2.76 (d, 3H); 1.11 (t, 3H);

[0400] Beispiel-Nr. 3-73: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.45 (br t, 1H); 7.85 (d, 1H); 7.23 (t, 1H); 7.17 (d, 1H); 3.84 (s, 3H); 3.27 (m, 2H); 2.82 (q, 2H); 1.12 (t, 3H); 1.09 (t, 3H);

[0401] Beispiel-Nr. 3-77: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.50 (br d, 1H); 7.85 (d, 1H); 7.23 (t, 1H); 7.16 (d, 1H); 3.83 (s, 3H); 2.80 (m, 3H); 1.11 (t, 3H); 0.70 (m, 2H); 0.47 (m, 2H);

[0402] Beispiel-Nr. 3-81: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.53 (br q, 1H); 7.90 (d, 1H); 7.34 (d, 1H); 7.33 (t, 1H); 3.87 (s, 3H); 2.77 (d, 3H);

[0403] Beispiel-Nr. 3-82: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.59 (br t, 1H); 7.89 (d, 1H); 7.34 (d, 1H); 7.31 (t, 1H); 3.87 (s, 3H); 3.26 (m, 2H); 1.10 (t, 3H);

[0404] Beispiel-Nr. 3-83: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.58 (br t, 1H); 7.89 (d, 1H); 7.34 (d, 1H); 7.32 (t, 1H); 3.87 (s, 3H); 3.19 (m, 2H); 1.51 (m, 2H); 0.91 (t, 3H);

[0405] Beispiel-Nr. 3-84: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.47 (d, 1H); 7.88 (d, 1H); 7.32 (d, 1H); 7.28 (t, 1H); 4.02 (m, 1H); 3.87 (s, 3H); 1.13 (d, 6H);

[0406] Beispiel-Nr. 3-86: 1H-NMR (400 MHz, DMSO-d6): δ = 8.64 (br d, 1H); 7.89 (d, 1H); 7.33 (d, 1H); 7.31 (t, 1H); 3.86 (s, 3H); 2.79 (m, 1H); 0.71 (m, 2H); 0.48 (m, 2H);

[0407] Beispiel-Nr. 3-87: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.77 (s, 1H); 7.87 (d, 1H); 7.31 (d, 1H); 7.26 (t, 1H); 3.86 (s, 3H); 1.38 (s, 3H); 0.70 (m, 2H); 0.60 (m, 2H);

[0408] Beispiel-Nr. 3-88: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.73 (br s, 1H); 7.88 (d, 1H); 7.31 (d, 1H); 7.28 (t, 1H); 3.86 (s, 3H); 1.61 (q, 2H); 0.96 (t, 3H); 0.67 (m, 2H); 0.60 (m, 2H); Beispiel-Nr. 3-89: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.73 (br s, 1H); 7.87 (d, 1H); 7.31 (d, 1H); 7.28

[0409] (t, 1H); 3.86 (s, 3H); 1.56 (m, 2H); 1.48 (m, 2H); 0.89 (t, 3H); 0.68 (m, 2H); 0.60 (m, 2H);

[0410] Beispiel-Nr. 3-90: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.73 (br s, 1H); 7.87 (d, 1H); 7.31 (d, 1H); 7.28

[0411] (t, 1H); 3.86 (s, 3H); 1.95 (m, 1H); 1.49 (d, 2H); 0.92 (d, 6H); 0.71 (m, 2H); 0.59 (m, 2H);

[0412] Beispiel-Nr. 3-91: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.88 (br s, 1H); 7.88 (d, 1H); 7.30 (br d, 1H); 7.25 (t, 1H); 3.86 (s, 3H); 3.52 (s, 2H); 3.48 (q, 2H); 1.11 (t, 3H); 0.76 (m, 2H); 0.71 (m, 2H);

[0413] Beispiel-Nr. 3-92: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.77 (br s, 1H); 7.88 (d, 1H); 7.31 (d, 1H); 7.30 (t, 1H); 3.86 (s, 3H); 3.50 (t, 2H); 3.22 (s, 3H); 1.85 (t, 3H); 0.67 (m, 4H);

[0414] Beispiel-Nr. 3-94: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.03 (br s, 1H); 7.90 (d, 1H); 7.33 (d, 1H); 7.27 (t, 1H); 4.48 (d, 2H); 3.86 (s, 3H); 0.93 (m, 2H); 0.83 (m, 2H);

[0415] Beispiel-Nr. 3-95: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.45 (br s, 1H); 7.91 (d, 1H); 7.35 (d, 1H); 7.32 (t, 1H); 3.87 (s, 3H); 3.30 (s, 3H); 1.04 (m, 2H); 0.86 (m, 2H);

[0416] Beispiel-Nr. 3-96: 1H-NMR (400 MHz, DMSO-d6): δ = 9.44 (br s, 1H); 7.91 (d, 1H); 7.34 (d, 1H); 7.32 (t, 1H); 3.86 (s, 3H); 3.63 (q, 2H); 1.09 (t, 3H); 1.04 (m, 2H); 0.85 (m, 2H);

[0417] Beispiel-Nr. 3-97: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.22 (br s, 1H); 7.91 (d, 1H); 7.34 (d, 1H); 7.30 (t, 1H); 4.10 (q, 2H); 3.87 (s, 3H); 1.44 (m, 2H); 1.19 (t, 3H); 1.09 (m, 2H);

[0418] Beispiel-Nr. 3-98: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.93 (br s, 1H); 7.87 (d, 1H); 7.29 (d, 1H); 7.20 (t, 1H); 4.05 (q, 2H); 3.86 (s, 3H); 2.72 (s, 2H); 1.19 (t, 3H); 0.78 (m, 2H); 0.76 (m, 2H);

[0419] Beispiel-Nr. 3-99: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.59 (s, 1H); 7.96 (d, 1H); 7.38 (d, 1H); 7.34 (t, 1H); 3.87 (s, 3H); 1.61 (m, 2H); 1.19 (m, 2H);

[0420] Beispiel-Nr. 3-100: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.17 (br s, 1H); 7.90 (d, 1H); 7.33 (d, 1H); 7.29 (t, 1H); 3.86 (s, 3H); 3.03 (s, 1H); 1.18 (m, 2H); 1.03 (m, 2H);

[0421] Beispiel-Nr. 3-101: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.31 (br s, 1H); 7.93 (d, 1H); 7.41 (t, 1H); 7.37 (d, 1H); 7.31-7.12 (m, 5H); 3.87 (s, 3H); 0.95 (m, 2H); 0.89 (m, 2H);

[0422] Beispiel-Nr. 3-102: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.25 (br s, 1H); 7.86 (d, 1H); 7.69 (m, 1H); 7.40 (m, 1H); 7.27 (m, 2H); 7.26 (d, 1H); 7.16 (t, 1H); 3.84 (s, 3H); 1.16 (m, 4H);

[0423] Beispiel-Nr. 3-103: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.38 (br s, 1H); 7.94 (d, 1H); 7.39 (m, 2H); 7.37 (t, 1H); 7.30 (d, 1H); 7.25 (m, 1H); 7.22 (m, 1H); 3.88 (s, 3H); 1.32 (m, 4H);

[0424] Beispiel-Nr. 3-104: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.35 (br s, 1H); 7.92 (d, 1H); 7.48 (m, 1H); 7.37 (t, 1H); 7.36 (d, 1H); 6.39 (m, 1H); 6.30 (m, 1H); 3.87 (s, 3H); 1.31 (m, 2H); 1.16 (m, 2H); Beispiel-Nr. 3-105: 1H-NMR (400 MHz, DMSO-d6): δ = 9.24 (br s, 1H); 7.91 (d, 1H); 7.56 (m, 1H); 7.48 (m, 1H); 7.38 (t, 1H); 7.35 (d, 1H); 6.32 (m, 1H); 3.87 (s, 3H); 1.13 (m, 2H); 1.11 (m, 2H);

[0425] Beispiel-Nr. 3-107: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.05 (br t, 1H); 7.92 (d, 1H); 7.35 (d, 1H); 7.34 (t, 1H); 4.07 (d, 2H); 3.88 (s, 3H); 2.15 (s, 3H);

[0426] Beispiel-Nr. 3-108: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.03 (br t, 1H); 7.92 (d, 1H); 7.35 (d, 1H); 7.34 (t, 1H); 4.09 (d, 2H); 3.87 (s, 3H); 2.54 (m, 2H); 0.95 (t, 3H);

[0427] Beispiel-Nr. 3-110: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.90 (br t, 1H); 7.91 (d, 1H); 7.62 (br q, 1H);

[0428] 7.33 (d, 1H); 7.32 (t, 1H); 3.87 (s, 3H); 2.64 (d, 2H);

[0429] Beispiel-Nr. 3-111: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.90 (br t, 1H); 7.91 (d, 1H); 7.64 (br t, 1H);

[0430] 7.34 (d, 1H); 7.33 (t, 1H); 3.87 (s, 3H); 3.87 (d, 2H); 3.13 (m, 2H); 1.04 (t, 3H);

[0431] Beispiel-Nr. 3-112: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.84 (br t, 1H); 7.90 (d, 1H); 7.84 (br d, 1H); 7.33 (d, 1H); 7.30 (t, 1H); 3.87 (s, 3H); 3.83 (d, 2H); 2.65 (m, 1H); 0.64 (m, 2H); 0.41 (m, 2H);

[0432] Beispiel-Nr. 3-113: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.95 (d, 1H); 7.42 (t, 1H); 7.41 (d, 1H); 3.78 (s, 3H); 3.02 (s, 3H); 2.77 (s, 3H);

[0433] Beispiel-Nr. 3-114: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.94 (d, 1H); 7.45 and 7.42 (2x t, 1H); 7.40 (d, 1H); 3.87 (s, 3H); 3.51 and 3.08 (2x m, 2H); 3.32 and 2.74 (2x s, 3H); 1.13 and 1.03 (2x t, 3H);

[0434] Beispiel-Nr. 3-115: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.95 (d, 1H); 7.47 (t, 1H); 7.39 (d, 1H); 3.87 (s, 3H); 2.98 and 2.67 (2x s, 3H); 2.89 and 2.58 (2x m, 1H); 0.81 and 0.72 and 0.57 and 0.45 (4x m, 4H);

[0435] Beispiel-Nr. 3-125: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.91 (br s, 1H); 7.92 (d, 1H); 7.55 (br d, 1H); 3.88 (s, 3H); 2.55 (m, 1H); 1.80 (m, 5H); 1.63 (m, 1H); 0.67 (m, 4H);

[0436] Beispiel-Nr. 3-126: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.77 (br s, 1H); 7.88 (d, 1H); 7.32 (d, 1H); 7.29 (t, 1H); 3.86 (s, 3H); 2.56 (m, 1H); 1.62-1.88 (m, 6H); 0.66 (m, 4H);

[0437] Beispiel-Nr. 3-127: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.44 (br q, 1H); 7.65 (d, 1H); 7.38 (br d, 1H); 3.87 (s, 3H); 2.78 (d, 3H); 2.09 (m, 1H); 0.82 (m, 2H); 0.45 (m, 2H);

[0438] Beispiel-Nr. 3-128: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.49 (br t, 1H); 7.64 (d, 1H); 7.37 (br d, 1H); 3.86 (s, 3H); 3.28 (m, 2H); 2.10 (m, 1H); 1.11 (t, 3H); 0.82 (m, 2H); 0.47 (m, 2H);

[0439] Beispiel-Nr. 3-129: 1H-NMR (400 MHz, DMSO-d6): δ = 8.57 (br d, 1H); 7.64 (d, 1H); 7.37 (br d, 1H); 3.86 (s, 3H); 2.79 (m, 1H); 2.08 (m, 1H); 0.82 (m, 2H); 0.70 (m, 2H); 0.48 (m, 4H);

[0440] Beispiel-Nr. 3-130: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.32 (br d, 1H); 7.60 (d, 1H); 7.19 (t, 1H); 7.18 (d, 1H); 3.84 (s, 3H); 2.77 (d, 3H); 2.09 (m, 1H); 0.79 (m, 2H); 0.42 (m, 2H); Beispiel-Nr. 3-131: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.39 (br t, 1H); 7.59 (d, 1H); 7.17 (t, 1H); 7.17 (d, 1H); 3.85 (s, 3H); 3.28 (m, 2H); 2.10 (m, 1H); 1.10 (t, 3H); 0.80 (m, 2H); 0.46 (m, 2H);

[0441] Beispiel-Nr. 3-132: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.44 (br d, 1H); 7.59 (d, 1H); 7.16 (t, 1H); 7.16 (d, 1H); 3.84 (s, 3H); 2.79 (m, 1H); 2.05 (m, 1H); 0.79 (m, 2H); 0.68 (m, 2H); 0.50 (m, 2H); 0.43 (m, 2H);

[0442] Beispiel-Nr. 3-133: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.32 (br s, 1H); 7.84 (br d, 1H); 7.25 (br d, 1H);

[0443] 6.32 (br t, 1H); 4.43 (br t, 2H); 3.83 (s, 3H); 2.73 (br d, 3H);

[0444] Beispiel-Nr. 3-134: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.39 (br t, 1H); 7.84 (d, 1H); 7.23 (d, 1H); 6.32 (tt, 1H); 4.43 (td, 2H); 3.83 (s, 3H); 3.23 (m, 2H); 1.08 (t, 3H);

[0445] Beispiel-Nr. 3-135: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.45 (br d, 1H); 7.84 (d, 1H); 7.22 (d, 1H); 6.32 (tt, 1H); 4.42 (td, 2H); 3.83 (s, 3H); 2.74 (m, 1H); 0.66 (m, 2H); 0.48 (m, 2H);

[0446] Beispiel-Nr. 4-1: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.25 (br s, 1H); 8.47 (q, 1H); 7.89 (d, 1H); 7.33 (br d, 1H); 2.77 (d, 3H); 2.41 (s, 3H);

[0447] Beispiel-Nr. 4-2: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.23 (br s, 1H); 8.55 (t, 1H); 7.89 (d, 1H); 7.33 (br d, 1H); 3.27 (m, 2H); 2.43 (s, 3H); 1.10 (t, 3H);

[0448] Beispiel-Nr. 4-6: 1H-NMR (400 MHz, DMSO-d6): δ = 13.25 (br s, 1H); 8.61 (d, 1H); 7.89 (d, 1H); 7.32 (br d, 1H); 2.81 (m, 1H); 2.41 (s, 3H); 0.71 (m, 2H); 0.46 (m, 2H);

[0449] Beispiel-Nr. 4-10: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.27 (br s, 1H); 8.47 (br q, 1H); 7.88 (d, 1H); 7.34 (br d, 1H); 2.85 (q, 2H); 2.77 (d, 3H); 1.13 (t, 3H);

[0450] Beispiel-Nr. 4-11: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.27 (br s, 1H); 8.56 (br t, 1H); 7.88 (br d, 1H); 7.34 (br d, 1H); 3.27 (m, 2H); 2.87 (q, 2H); 1.14 (t, 3H); 1.09 (t, 3H);

[0451] Beispiel-Nr. 4-15: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.26 (br s, 1H); 8.60 (br d, 1H); 7.88 (d, 1H);

[0452] 7.32 (br d, 1H); 2.86 (q, 2H); 2.80 (m, 1H); 1.13 (t, 3H); 0.71 (m, 2H); 0.46 (m, 2H);

[0453] Beispiel-Nr. 4-19: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.75 (br s, 1H); 8.63 (m, 1H); 7.91 (d, 1H); 7.51 (m, 2H); 2.78 (d, 3H);

[0454] Beispiel-Nr. 4-20: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.74 (br s, 1H); 8.71 (br t, 1H); 7.90 (d, 1H); 7.51 (d, 1H); 3.27 (m, 2H); 1.10 (t, 3H);

[0455] Beispiel-Nr. 4-21: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.73 (br s, 1H); 8.70 (t, 1H); 7.90 (d, 1H); 7.51 (m, 1H); 3.21 (m, 2H); 1.50 (m, 2H); 0.91 (t, 3H);

[0456] Beispiel-Nr. 4-22: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.71 (br s, 1H); 7.89 (d, 1H); 7.50 (m, 1H); 4.05 (m, 1H); 1.13 (d, 6H); Beispiel-Nr. 4-23: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.76 (br s, 1H); 8.78 (t, 1H); 7.90 (d, 1H); 7.51 (m, 1H); 3.15 (m, 2H); 0.98 (m, 1H); 0.43 (m, 2H); 0.23 (m, 2H);

[0457] Beispiel-Nr. 4-24: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.75 (br s, 1H); 8.75 (d, 1H); 7.90 (d, 1H); 7.50 (m, 1H); 2.80 (m, 1H); 0.72 (m, 2H); 0.47 (m, 2H);

[0458] Beispiel-Nr. 4-25: 1H-NMR (400 MHz, DMSO-d6): δ = 13.76 (br s, 1H); 8.90 (s, 1H); 7.88 (d, 1H); 7.48 (m, 1H); 1.38 (s, 3H); 0.68 (m, 2H); 0.62 (m, 2H);

[0459] Beispiel-Nr. 4-26: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.83 (br s, 1H); 7.77 (d, 1H); 7.43 (br d, 1H); 1.61 (q, 2H); 0.95 (t, 3H); 0.66 (m, 2H); 0.62 (m, 2H);

[0460] Beispiel-Nr. 4-27: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.73 (br s, 1H); 8.85 (br s, 1H); 7.88 (d, 1H);

[0461] 7.49 (br, d, 1H); 1.56 (m, 2H); 1.47 (m, 2H); 0.89 (t, 3H); 0.67 (m, 2H); 0.62 (m, 2H);

[0462] Beispiel-Nr. 4-29: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.73 (br s, 1H); 8.99 (br s, 1H); 7.88 (d, 1H); 7.48 (br d, 1H); 3.52 (s, 2H); 3.47 (q, 2H); 1.11 (t, 3H); 0.77 (m, 2H); 0.70 (m, 2H);

[0463] Beispiel-Nr. 4-32: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.76 (br s, 1H); 9.15 (br s, 1H); 7.90 (d, 1H);

[0464] 7.50 (br d, 1H); 4.48 (d, 2H); 0.94 (m, 2H); 0.81 (m, 2H);

[0465] Beispiel-Nr. 4-35: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.79 (br s, 1H); 7.92 (d, 1H); 7.53 (br d, 1H); 4.11 (q, 2H); 1.46 (m, 2H); 1.19 (t, 3H); 1.09 (m, 2H);

[0466] Beispiel-Nr. 4-37: 1 H-NMR (400 MHz, DMSO-d6): δ = 9.76 (s, 1H); 8.00 (d, 1H); 7.61 (br d, 1H); 3.89 (s, 3H); 1.64 (m, 2H); 1.19 (m, 2H);

[0467] Beispiel-Nr. 4-38: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.77 (br s, 1H); 9.29 (br s, 1H); 7.91 (d, 1H);

[0468] 7.51 (br s, 1H); 3.04 (s, 1H); 1.19 (m, 2H); 1.02 (m, 2H);

[0469] Beispiel-Nr. 4-42: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.78 (br s, 1H); 9.46 (br s, 1H); 7.92 (d, 1H); 7.54 (br d, 1H); 7.48 (m, 1H); 6.39 (m, 1H); 6.24 (m, 1H); 1.32 (m, 2H); 1.16 (m, 2H);

[0470] Beispiel-Nr. 4-45: 1H-NMR (400 MHz, DMSO-d6): δ = 13.79 (br s, 1H); 9.10 (t, 1H); 7.92 (d, 1H); 7.53 (m, 1H); 4.10 (d, 2H); 2.14 (s, 3H);

[0471] Beispiel-Nr. 4-46: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.78 (br s, 1H); 9.10 (t, 1H); 7.92 (d, 1H); 7.53 (m, 1H); 4.11 (d, 2H); 2.54 (q, 2H); 0.96 (t, 3H);

[0472] Beispiel-Nr. 4-48: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.80 (br s, 1H); 8.98 (t, 1H); 7.91 (d, 1H); 7.73 (br q, 1H); 7.50 (m, 1H); 3.87 (d, 2H); 2.63 (d, 3H);

[0473] Beispiel-Nr. 4-49: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.90 (br s, 1H); 8.97 (t, 1H); 7.91 (d, 1H); 7.75 (t, 1H); 7.50 (m, 1H); 3.86 (d, 2H); 3.12 (m, 2H); 1.03 (t, 3H); Beispiel-Nr. 4-50: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.94 (t, 1H); 7.91 (m, 1H); 7.90 (d, 1H); 7.50 (m, 1H); 3.83 (d, 2H); 2.64 (m, 1H); 0.64 (m, 2H); 0.40 (m, 2H);

[0474] Beispiel-Nr. 4-51: 1H-NMR (400 MHz, DMSO-d6): δ = 13.80 (br s, 1H); 7.96 (d, 1H); 7.58 (m, 1H); 3.03 (s, 3H); 2.78 (s, 3H);

[0475] Beispiel-Nr. 4-52: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.85 (br s, 1H); 7.96 (m, 1H); 7.57 (m, 1H); 3.61, 3,42, 3.09 (3x m, 2H); 3.00, 2.76 (2x s, 3H); 1.17, 1.15 (2x t, 3H);

[0476] Beispiel-Nr. 4-53: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.80 (br s, 1H); 7.96 (m, 1H); 7.57 (m, 1H); 3.00, 2.69 (2x s, 3H); 2.89, 2.59 (2x m, 1H); 0.82, 071, 0.61, 0.48 (4x m, 4H);

[0477] Beispiel-Nr. 4-63: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.04 (br s, 1H); 8.36 (q, 1H); 7.86 (d, 1H); 7.22 (t, 1H); 7.14 (d, 1H); 2.75 (d, 3H); 2.39 (s, 3H);

[0478] Beispiel-Nr. 4-64: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.04 (br s, 1H); 8.42 (t, 1H); 7.86 (d, 1H); 7.21 (t, 1H); 7.13 (d, 1H); 3.25 (m, 2H); 2.41 (s, 3H); 1.09 (t, 3H);

[0479] Beispiel-Nr. 4-68: 1H-NMR (400 MHz, DMSO-d6): δ = 13.04 (br s, 1H); 8.48 (br d, 1H); 7.86 (d, 1H);

[0480] 7.20 (t, 1H); 7.13 (d, 1H); 2.80 (m, 1H); 2.40 (s, 3H); 0.69 (m, 2H); 0.47 (m, 2H);

[0481] Beispiel-Nr. 4-72: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.07 (br q, 1H); 8.36 (br q, 1H); 7.86 (d, 1H); 7.23 (t, 1H); 7.14 (d, 1H); 2.85 (q, 2H); 2.76 (d, 3H); 1.11 (t, 3H);

[0482] Beispiel-Nr. 4-73: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.02 (br s, 1H); 8.43 (br t, 1H); 7.86 (d, 1H);

[0483] 7.21 (t, 1H); 7.13 (d, 1H); 3.26 (m, 2H); 2.88 (q, 2H); 1.13 (t, 3H); 1.09 (t, 3H);

[0484] Beispiel-Nr. 4-77: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.04 (br s, 1H); 8.48 (br d, 1H); 7.85 (d, 1H); 7.20 (t, 1H); 7.12 (d, 1H); 2.83 (q, 2H); 2.80 (m, 1H); 1.12 (t, 3H); 0.69 (m, 2H); 0.47 (m, 2H);

[0485] Beispiel-Nr. 4-81: 1H-NMR (400 MHz, DMSO-d6): δ = 13.50 (br s, 1H); 8.51 (q, 1H); 7.87 (d, 1H); 7.30 (d, 1H); 7.30 (t, 1H); 2.76 (d, 2H);

[0486] Beispiel-Nr. 4-82: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.55 (br s, 1H); 8.56 (t, 1H); 7.87 (d, 1H); 7.30 (d, 1H); 7.28 (t, 1H); 3.25 (m, 2H); 1.10 (t, 3H);

[0487] Beispiel-Nr. 4-83: 1 H-NMR (400 MHz, DMSO-d6): δ = 12.80 (br s, 1H); 8.56 (t, 1H); 7.86 (d, 1H); 7.30 (d, 1H); 7.29 (t, 1H); 3.19 (m, 2H); 1.51 (m, 2H); 0.91 (t, 3H);

[0488] Beispiel-Nr. 4-84: 1 H-NMR (400 MHz, DMSO-d6): δ = 12.50 (br s, 1H); 8.45 (d, 1H); 7.86 (d, 1H); 7.29 (d, 1H); 7.25 (t, 1H); 4.04 (m, 1H); 1.13 (d, 6H);

[0489] Beispiel-Nr. 4-86: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.51 (br s, 1H); 8.62 (d, 1H); 7.86 (d, 1H); 7.29 (d, 1H); 7.27 (t, 1H); 2.79 (m, 1H); 0.70 (m, 2H); 0.48 (m, 2H); Beispiel-Nr. 4-87: 1H-NMR (400 MHz, DMSO-d6): δ = 13.40 (br s, 1H); 8.75 (s, 1H); 7.85 (d, 1H); 7.27 (d, 1H); 7.23 (t, 1H); 1.38 (s, 3H); 0.69 (m, 2H); 0.60 (m, 2H);

[0490] Beispiel-Nr. 4-88: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.40 (br s, 1H); 8.75 (s, 1H); 7.85 (d, 1H); 7.27 (d, 1H); 7.23 (t, 1H); 1.38 (s, 3H); 0.69 (m, 2H); 0.60 (m, 2H);

[0491] Beispiel-Nr. 4-89: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.55 (br s, 1H); 8.71 (br s, 1H); 7.85 (d, 1H);

[0492] 7.27 (d, 1); 7.25 (t, 1H); 1.61 (q, 2H); 0.96 (t, 3H); 0.68 (m, 2H); 0.60 (m, 2H);

[0493] Beispiel-Nr. 4-90: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.52 (br s, 1H); 8.71 (br s, 1H); 7.85 (d, 1H);

[0494] 7.27 (d, 1H); 7.25 (t, 1H); 1.96 (m, 1H); 1.49 (d, 2H); 0.92 (d, 6H); 0.71 (m, 2H); 0.59 (m, 2H);

[0495] Beispiel-Nr. 4-91: 1H-NMR (400 MHz, DMSO-d6): δ = 13.52 (br s, 1H); 8.86 (s, 1H); 7.85 (d, 1H); 7.26 (d, 1H); 7.22 (t, 1H); 3.52 (s, 2H); 3.48 (q, 2H); 1.11 (t, 3H); 0.76 (m, 2H); 0.71 (m, 2H);

[0496] Beispiel-Nr. 4-92: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.54 (br s, 1H); 8.74 (br s, 1H); 7.85 (d, 1H);

[0497] 7.27 (d, 1H); 7.26 (t, 1H); 3.50 (t, 2H); 3.22 (s, 3H); 1.85 (t, 2H); 0.66 (m, 4H);

[0498] Beispiel-Nr. 4-94: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.55 (br s, 1H); 9.01 (br s, 1H); 7.87 (d, 1H);

[0499] 7.29 (d, 1H); 7.24 (t, 1H); 4.48 (d, 2H); 0.92 (m, 2H); 0.83 (m, 2H);

[0500] Beispiel-Nr. 4-95: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.65 (br s, 1H); 9.42 (br s, 1H); 7.86 (d, 1H);

[0501] 7.30 (d, 1H); 7.28 (t, 1H); 3.30 (s, 3H); 1.04 (m, 2H); 0.85 (m, 2H);

[0502] Beispiel-Nr. 4-96: 1H-NMR (400 MHz, DMSO-d6): δ = 13.58 (br s, 1H); 9.42 (br s, 1H); 7.88 (d, 1H);

[0503] 7.30 (d, 1H); 7.29 (t, 1H); 3.63 (q, 2H); 1.09 (t, 3H); 1.04 (m, 2H); 0.85 (m, 2H);

[0504] Beispiel-Nr. 4-97: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.55 (br s, 1H); 9.20 (s, 1H); 7.88 (d, 1H); 7.30 (d, 1H); 7.27 (t, 1H); 4.10 (q, 2H); 1.44 (m, 2H); 1.19 (t, 3H); 1.09 (m, 2H);

[0505] Beispiel-Nr. 4-98: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.52 (br s, 1H); 8.91 (s, 1H); 7.85 (d, 1H); 7.25 (d, 1H); 7.17 (t, 1H); 4.05 (q, 2H); 3.72 (s, 2H); 1.19 (t, 3H); 0.78 (m, 2H); 0.75 (m, 2H);

[0506] Beispiel-Nr. 4-99: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.61 (br s, 1H); 9.57 (s, 1H); 7.93 (d, 1H); 7.34 (d, 1H); 7.30 (t, 1H); 1.61 (m, 2H); 1.19 (m, 2H);

[0507] Beispiel-Nr. 4-100: 1H-NMR (400 MHz, DMSO-d6): δ = 13.57 (br s, 1H); 9.14 (br s, 1H); 7.88 (d, 1H); 7.29 (d, 1H); 7.26 (t, 1H); 3.02 (s, 1H); 1.18 (m, 2H); 1.03 (m, 2H);

[0508] Beispiel-Nr. 4-101: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.56 (br s, 1H); 9.29 (br s, 1H); 7.90 (d, 1H); 7.38 (t, 1H); 7.34 (d, 1H); 7.29 (m, 4H); 7.18 (m, 1H); 1.28 (br s, 4H);

[0509] Beispiel-Nr. 4-102: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.43 (br s, 1H); 9.23 (br s, 1H); 7.83 (d, 1H);

[0510] 7.69 (m, 1H); 7.40 (m, 1H); 7.29 (m, 2H); 7.23 (d, 1H); 7.12 (t, 1H); 1.16 (m, 4H); Beispiel-Nr. 4-103: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.59 (br s, 1H); 9.36 (br s, 1H); 7.92 (d, 1H);

[0511] 7.40-7.16 (m, 6H); 7.36-1.27 (m, 4H);

[0512] Beispiel-Nr. 4-104: 1H-NMR (400 MHz, DMSO-d6): δ = 13.56 (br s, 1H); 9.33 (br s, 1H); 7.89 (d, 1H); 7.48 (m, 1H); 7.34 (d, 1H); 7.31 (t, 1H); 6.39 (m, 1H); 6.30 (m, 1H); 1.29 (m, 2H); 1.15 (m, 2H);

[0513] Beispiel-Nr. 4-105: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.55 (br s, 1H); 9.22 (br s, 1H); 7.88 (d, 1H); 7.56 (m, 1H); 7.47 (m, 1H); 7.35 (t, 1H); 7.33 (d, 1H); 6.32 (m, 1H); 1.13 (m, 2H); 1.09 (m, 2H);

[0514] Beispiel-Nr. 4-107: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.51 (br s, 1H); 9.03 (br t, 1H); 7.89 (d, 1H);

[0515] 7.31 (d, 1H), 7.31 (t, 1H); 4.06 (d, 2H); 2.15 (s, 3H);

[0516] Beispiel-Nr. 4-108: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.50 (br s, 1H); 9.01 (br t, 1H); 7.89 (d, 1H);

[0517] 7.32 (t, 1H); 7.31 (d, 1H); 4-07 (d, 2H); 2.55 (m, 2H); 0.95 (t, 3H);

[0518] Beispiel-Nr. 4-110: 1H-NMR (400 MHz, DMSO-d6): δ = 13.40 (br s, 1H); 8.89 (t, 1H); 7.88 (d, 1H); 7.60 (br q, 1H); 7.31 (d, 1H); 7.31 (t, 1H); 3.87 (d, 2H); 2.64 (d, 3H);

[0519] Beispiel-Nr. 4-111: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.88 (br t, 1H); 7.89 (d, 1H); 7.62 (br t, 1H);

[0520] 7.31 (t, 1H); 7.30 (d, 1H); 3.86 (d, 2H); 3.12 (m, 2H); 1.04 (t, 3H);

[0521] Beispiel-Nr. 4-112: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.60 (br s, 1H); 8.83 (t, 1H); 7.88 (d, 1H); 7.82 (br d, 1H); 7.33 (d, 1H); 7.30 (t, 1H); 3.83 (d, 2H); 2.65 (m, 1H); 0.65 (m, 2H); 0.49 (m, 2H);

[0522] Beispiel-Nr. 4-113: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.50 (br s, 1H); 7.92 (d, 1H); 7.40 (t, 1H); 7.37 (d, 1H); 3.02 (s, 3H); 2.77 (s, 3H);

[0523] Beispiel-Nr. 4-114: 1H-NMR (400 MHz, DMSO-d6): δ = 13.40 (br s, 1H); 7.92 (d, 1H); 7.39, 7.37 (2x t, 1H); 7.35 (d, 1H); 3.50, 3.09 (2x m, 2H); 2.99, 2.74 (2x s, 3H); 117, 113 (2x t, 3H);

[0524] Beispiel-Nr. 4-115: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.59 (br s, 1H); 7.93 (d, 1H); 7.44 (t, 1H); 7.35 (d, 1H); 2.98 (s, 3H); 2.59 (m, 1H); 0.52-0.41 (m, 4H);

[0525] Beispiel-Nr. 4-125: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.74 (br s, 1H); 8.89 (br s, 1H); 7.88 (d, 1H); 7.50 (br d, 1H); 2.56 (m, 1H); 1.69-1.89 (m, 5H); 1.64 (m, 1H); 0.67 (m, 4H);

[0526] Beispiel-Nr. 4-126: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.52 (br s, 1H); 8.75 (br s, 1H); 7.85 (d, 1H);

[0527] 7.28 (d, 1H); 7.25 (t, 1H); 2.56 (m, 1H); 1.62-1.88 (m, 6H); 0.66 (m, 4H);

[0528] Beispiel-Nr. 4-127: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.22 (br s, 1H); 8.42 (br q, 1H); 7.63 (d, 1H);

[0529] 7.34 (br d, 1H); 2.78 (d, 3H); 2.10 (m, 1H); 0.82 (m, 2H); 0.50 (m, 2H);

[0530] Beispiel-Nr. 4-128: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.22 (br s, 1H); 7.62 (d, 1H); 7.34 (br d, 1H);

[0531] 3.27 (m, 2H); 2.12 (m, 1H); 1.11 (t, 3H); 0.82 (m, 2H); 0.53 (m, 2H); Beispiel-Nr. 4-129: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.23 (br s, 1H); 8.55 (br d, 1H); 7.62 (d, 1H);

[0532] 7.33 (br d, 1H); 2.78 (m, 1H); 2.10 (m, 1H); 0.82 (m, 2H); 0.70 (m, 2H); 0.51 (m, 4H);

[0533] Beispiel-Nr. 4-130: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.05 (br s, 1H); 8.31 (br q, 1H); 7.59 (d, 1H);

[0534] 7.16 (t, 1H); 7.14 (d, 1H); 2.76 (d, 3H); 2.08 (m, 1H); 0.80 (m, 2H); 0.48 (m, 2H); Beispiel-Nr. 4-131: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.08 (br s, 1H); 8.38 (br t, 1H); 7.58 (d, 1H);

[0535] 7.14 (t, 1H); 7.13 (d, 1H); 3.27 (m, 2H); 1.11 (t, 3H); 0.80 (m, 2H); 0.51 (m, 2H);

[0536] Beispiel-Nr. 4-132: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.04 (br s, 1H); 8.43 (br d, 1H); 7.58 (d, 1H);

[0537] 7.14 (t, 1H); 7.13 (d, 1H); 2.78 (m, 1H); 2.07 (m, 1H); 0.80 (m, 2H); 0.68 (m, 2H); 0.50 (m, 4H);

[0538] Beispiel-Nr. 4-133: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.20 (br s, 1H); 8.30 (br q, 1H); 7.83 (d, 1H); 7.21 (d, 1H); 6.32 (tt, 1H); 4.42 (td, 2H); 2.73 (d, 3H);

[0539] Beispiel-Nr. 4-134: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.20 (br s, 1H); 8.36 (br t, 1H); 7.83 (d, 1H);

[0540] 7.20 (d, 1H); 6.32 (tt, 1H); 4.45 (td, 2H); 3.22 (m, 2H); 1.08 (t, 3H);

[0541] Beispiel-Nr. 4-135: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.20 (br s, 1H); 8.43 (br d, 1H); 7.83 (d, 1H);

[0542] 7.19 (d, 1H); 6.32 (tt, 1H); 4.40 (td, 2H); 2.74 (m, 1H); 0.67 (m, 2H); 0.46 (m, 2H);

[0543] 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 grinding the mixture in a hammer mill. b) A wettable powder 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 wetting and dispersing agents, and grinding the mixture 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

[0544] 75 parts by weight of a compound of formula (I) and / or salts thereof,

[0545] 10 parts by weight of calcium ligninsulfonate,

[0546] 5 parts by weight of sodium lauryl sulfate,

[0547] 3 parts by weight of polyvinyl alcohol and

[0548] 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

[0549] 25 parts by weight of a compound of formula (I) and / or salts thereof,

[0550] 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium

[0551] 2 parts by weight of oleoylmethyltaurine sodium,

[0552] 1 part by weight of polyvinyl alcohol,

[0553] 17 parts by weight of calcium carbonate and

[0554] 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.

[0555] C. Biological examples

[0556] The abbreviations used here mean:

[0557] ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides

[0558] AVEFA Avena fatua AMARE Amaranthus retroflexus

[0559] CYPES Cyperus esculentus DIGSA Digitaria sanguinalis

[0560] ECHCG Echinochloa crus-galli HORMU Hordeum murinum

[0561] KCHSC Kochia scoparia LOLMU Lolium multiflorum

[0562] LOLRI Lolium rigidum MATIN Matricaria inodora

[0563] PHBPU Pharbitis purpurea POLCO Polygonum convolvulus

[0564] SETVI Setaria green STEAM Stellaria medium

[0565] VERPE Veronica persica V IOTR Viola tricolor

[0566] 1. Herbizide Wirkung gegen Schadpflanzen im Vorauflauf

[0567] 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 as 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.

[0568] Table Cl: Pre-emergence effect at 20g / ha against ZEAMX in %

[0569] Table C-2: Pre-emergence effect at 80g / ha against ZEAMX in %

[0570] Table C-3: Pre-emergence effect at 20g / ha against TRZAS in %

[0571] Table C-4: Pre-emergence effect at 80g / ha against TRZAS in %

[0572] Table C-5: Pre-emergence effect at 20g / ha against GLXMA in %

[0573] Table C-6: Pre-emergence effect at 80g / ha against GLXMA in %

[0574] Table C-7: Pre-emergence effect at 20g / ha against BRSNW in %

[0575] Table C-8: Pre-emergence effect at 80g / ha against BRSNW in %

[0576] Table C-9: Pre-emergence effect at 20g / ha against ABUTH in %

[0577] Table C-10: Pre-emergence effect at 80g / ha against ABUTH in %

[0578] Table Cl l: Pre-emergence effect at 20g / ha against ALOMY in %

[0579] Table C-12: Pre-emergence effect at 80g / ha against ALOMY in %

[0580]

[0581] Table C-13: Pre-emergence effect at 20g / ha against AM ARE in %

[0582] Table C-14: Pre-emergence effect at 80g / ha against AMARE in %

[0583] Table C-15: Pre-emergence effect at 20g / ha against AVEFA in %

[0584] Table C-16: Pre-emergence effect at 80g / ha against AVEFA in %

[0585] Table C-17: Pre-emergence effect at 20g / ha against DIGS A in %

[0586] Table C-18: Pre-emergence effect at 80g / ha against DIGSA in % Table C-19: Pre-emergence efficacy at 20g / ha against ECHCG in %

[0587] Table C-20: Pre-emergence efficacy at 80g / ha against ECHCG in %

[0588] Table C-21: Pre-emergence effect at 80g / ha against LOLRI in %

[0589]

[0590] Table C-22: Pre-emergence effect at 20g / ha against MATIN in %

[0591] Table C-23: Pre-emergence effect at 80g / ha against MATIN in % Table C-24: Pre-emergence effect at 20g / ha against PHBPU in %

[0592] Table C-25: Pre-emergence effect at 80g / ha against PHBPU in % Table C-26: Pre-emergence effect at 20g / ha against POLCO in %

[0593] Table C-27: Pre-emergence effect at 80g / ha against POLCO in %

[0594] Table C-28: Pre-emergence effect at 20g / ha against SETVI in %

[0595] Table C-29: Pre-emergence effect at 80g / ha against SETVI in %

[0596] Table C-30: Pre-emergence effect at 20g / ha against VERPE in % Table C-31: Pre-emergence effect at 80g / ha against VERPE in %

[0597] Table C-32: Pre-emergence effect at 20g / ha against VIOTR in %

[0598] Table C-33: Pre-emergence effect at 80g / ha against VIOTR in %

[0599]

[0600] Table C-34: Pre-emergence effect at 20g / ha against KCHSC in % Table C-35: Pre-emergence effect at 80g / ha against KCHSC in %

[0601] 2. Herbicidal effect against post-emergence weeds

[0602] 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 growing conditions. Two to three weeks after sowing, the test plants are treated at the single-leaf stage.

[0603] The compounds according to the invention, formulated in the form of 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 600 to 800 l / ha with the addition of 0.2% wetting agent. After approximately 3 weeks of the test plants being kept in the greenhouse under optimal growth conditions, the effect of the preparations is visually compared to untreated

[0604] Controls were assessed (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 variety 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.

[0605] Table C-36: Post-emergence effect at 20g / ha against ZEAMX in %

[0606] Table C-37: Post-emergence effect at 80g / ha against ZEAMX in %

[0607] Table C-38: Post-emergence effect at 20g / ha against TRZAS in %

[0608] Table C-39: Post-emergence effect at 80g / ha against TRZAS in %

[0609] Table C-40: Post-emergence effect at 20g / ha against GLXMA in %

[0610] Table C-41: Post-emergence effect at 80g / ha against GLXMA in %

[0611] Table C-42: Post-emergence effect at 20g / ha against BRSNW in %

[0612] Table C-43: Post-emergence effect at 80g / ha against BRSNW in %

[0613] Table C-44: Post-emergence effect at 20g / ha against ABUTH in %

[0614] Table C-45: Post-emergence effect at 80g / ha against ABUTH in %

[0615] Table C-46: Post-emergence effect at 20g / ha against ALOMY in %

[0616] Table C-47: Post-emergence effect at 80g / ha against ALOMY in % Table C-48: Post-emergence effect at 20g / ha against AMARE in %

[0617] Table C-49: Post-emergence effect at 80g / ha against AMARE in %

[0618] Table C-50: Post-emergence effect at 20g / ha against AVEFA in %

[0619] Table C-51: Post-emergence effect at 80g / ha against AVEFA in %

[0620]

[0621] Table C-52: Post-emergence effect at 20g / ha against DIGSA in %

[0622] Table C-53: Post-emergence effect at 80g / ha against DIGS A in %

[0623] Table C-54: Post-emergence effect at 20g / ha against ECHCG in %

[0624] Table C-55: Post-emergence effect at 80g / ha against ECHCG in %

[0625] Table C-56: Post-emergence effect at 20g / ha against LOLRI in %

[0626] Table C-57: Post-emergence effect at 80g / ha against LOLRI in %

[0627]

[0628] Table C-58: Post-emergence effect at 20g / ha against MATIN in %

[0629] Table C-59: Post-emergence effect at 80g / ha against MATIN in %

[0630] Table C-60: Post-emergence effect at 20g / ha against PHBPU in %

[0631] Table C-61: Post-emergence effect at 80g / ha against PHBPU in %

[0632]

[0633] Table C-62: Post-emergence effect at 80g / ha against POLCO in % Table C-63: Post-emergence effect at 20g / ha against SETVI in %

[0634] Table C-64: Post-emergence effect at 80g / ha against SETVI in % Table C-65: Post-emergence effect at 20g / ha against VERPE in %

[0635] Table C-66: Post-emergence effect at 80g / ha against VERPE in % Table C-67: Post-emergence effect at 20g / ha against VIOTR in %

[0636] Table C-68: Post-emergence effect at 80g / ha against VIOTR in %

[0637] Table C-69: Post-emergence effect at 20g / ha against KCHSC in % Table C-70: Post-emergence effect at 80g / ha against KCHSC in %

[0638] Comparison attempts

[0639] In the following experiments, the herbicidal activity of numerous compounds according to the invention and that of the structurally closest compounds known from WO2021 / 204665 (DI) 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 or to those of the respective comparison compounds from DI.

[0640] Herbicidal activity in pre-emergence: efg. = according to invention

[0641] Post-emergence herbicidal activity: efg. = according to invention

Claims

Patent claims:

1. Isophthalic acid diamides of formula (I) or their salts where the symbols and indices have the following meanings: R x means (C 1 -C 6 )-alkyl, X means halogen, (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, Y means halogen-(C 1 -C 6 )-alkoxy, Z 1 and Z 2 independently of each other each represent hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )- cycloalkyl, halogen-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-Cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-C(O)- (C 1 -C 6 )-alkyl or R 2 R 3 NC(O)-(C 1 -C 6 )-alkyl, where (C 3 -C 6 )-cycloalkyl each with m substituents R 1 carries, R 1 means halogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, (C 1 -C 6 )- alkoxy, halogen-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-Alkyloxy- C(O), (C 1 -C 6 )-alkyloxy-C(O)-(C 1 -C 6 )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals, R 2 and R 3 independently of each other each represent hydrogen, (C 1 -C 6 )-alkyl or (C 3 -C 6 )- cycloalkyl, and m is 0, 1, 2 or 3.

2. Isophthalic acid diamides according to claim 1, wherein the symbols have the following meanings: R x means (C1 -C 6 )-alkyl, X means halogen, (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, Y means OCF 3 , OCHF 2 , OCH 2 CHF 2 or OCF 2 Me, Z 1 and Z 2 independently of each other each represent hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )- cycloalkyl, halogen-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-Cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-C(O)- (C 1 -C 6 )-alkyl or R 2 R 3 NC(O)-(C 1 -C 6 )-alkyl, where (C 3 -C 6 )-cycloalkyl each m Substituents R 1 carries, R 1 means halogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2-C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, (C 1 -C 6 )- alkoxy, halogen-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-Alkyloxy- C(O), (C 1 -C 6 )-alkyloxy-C(O)-(C 1 -C 6 )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals, R 2 and R 3 independently represent hydrogen, Me, Et or c-Pr, and m represents 0, 1, 2 or 3.

3. Isophthalic acid diamides according to claim 1 or, where the symbols have the following meanings: R x means Me or Et, X is chlorine, bromine, methyl, ethyl or cyclopropyl, Y means OCF 3 , OCHF 2 or OCH 2 CHF 2 , Z 1 and Z2 independently represent hydrogen, Me, Et, Pr, i-Pr, c-Pr-CH 2 , c-Pr, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-isobutylcyclopropyl, 1-cyclobutycyclopropyl, 1-ethynylcyclopropyl, 1-methoxymethylcyclopropyl, 1-ethoxymethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluoromethylcyclopropyl, 2,2-difluoro-l-methylcyclopropyl, 1-Methoxycyclopropyl, 1-Ethoxycyclopropyl, 1- Ethoxycarbonylcyclopropyl, 1-Etoxycarbonylmethylcyclopropyl, 1-cyanocyclopropyl, 1-phenylcyclopropyl, l-(2-chlorophenyl)-cyclopropyl, l-(3-chlorophenyl)-cyclopropyl, l-(2-furyl)-cyclopropyl, l-(3-furyl)-cyclopropyl, MeC(O)CH 2 , EtC(O)CH 2 , c-PrC(O)CH 2 , MeNHC(O)CH 2 , EtNHC(O)CH 2 or c-PrNHC(O)CH 2 .

4. Herbicidal compositions comprising at least one isophthalic acid diamide 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 isophthalic acid diamide according to one of claims 1 to 3 or of herbicidal compositions according to claim 4 or 5 is applied to the plants or to the site of undesirable plant growth.

7. Use of isophthalic acid diamides 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 isophthalic acid diamides of the formula (I) are used to combat undesirable plants in crops of useful plants.

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

10. Compounds of formula (II), where the symbols and indices have the following meanings: L means halogen or R 4 O, X means halogen, (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, Y means halogen-(C 1 -C 6 )-alkoxy, Z 1 and Z 2 independently of each other each represent hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )- Cycloalkyl, halogen-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-CycIoalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-C(O)-(C 1 - C 6 )-alkyl or R 2 R 3 NC(O)-(C 1 -C 6 )-alkyl, where (C 3 -C 6)-cycloalkyl each with m substituents R 1 carries, R 1 means halogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-Alkyl-O-(C 1 -C 6 )-alkyl, (C 1 -C 6 )- Alkoxy, Halogen-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-Alkyloxy- C(O), (C 1 -C 6 )-Alkyloxy-C(O)-(C 1 -C 6 )-alkyl, cyano, phenyl or heterocyclyl, where the last two radicals may be substituted by up to two halogen radicals, R 2 and R 3 independently of each other each represent hydrogen, (C 1 -C 6 )-alkyl or (C 3 -C 6 )- Cycloalkyl, R 4 means hydrogen or (C 1 -C 6)-alkyl, and m is 0, 1, 2 or 3.

11. Compounds of formula (II) according to claim 10, wherein L means chlorine, methoxy or hydroxy, X is chlorine, bromine, methyl, ethyl or cyclopropyl, Y means OCF 3 , OCHF 2 or OCH 2 CHF 2 and Z 1 and Z 2 independently represent hydrogen, Me, Et, Pr, i-Pr, c-Pr-CH 2 , c-Pr, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-isobutylcyclopropyl, 1-cyclobutycyclopropyl, 1-ethynylcyclopropyl, 1-methoxymethylcyclopropyl, 1-ethoxymethylcyclopropyl, 1-trifluoromethylcyclopropyl, 1-fluoromethylcyclopropyl, 2,2- Difluoro-l-methylcyclopropyl, 1-Methoxycyclopropyl, 1-Ethoxycyclopropyl, 1- Ethoxycarbonylcyclopropyl, 1-Etoxycarbonylmethylyclopropyl, 1-Cyanocyclopropyl, 1- Phenylcyclopropyl, l-(2-Chlorphenyl)-cyclopropyl, l-(3-Chlorphenyl)-cyclopropyl, l-(2- Furyl)-cyclopropyl, l-(3-Furyl)-cyclopropyl, MeC(O)CH 2 , EtC(O)CH 2 , c-PrC(O)CH 2 , MeNHC(O)CH 2 , EtNHC(O)CH 2 oder c-PrNHC(O)CH 2 .

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