WO2025103939A1 - Sulfonimidoyl benzamides with herbicidal action - Google Patents

Sulfonimidoyl benzamides with herbicidal action Download PDF

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WO2025103939A1
WO2025103939A1 PCT/EP2024/081863 EP2024081863W WO2025103939A1 WO 2025103939 A1 WO2025103939 A1 WO 2025103939A1 EP 2024081863 W EP2024081863 W EP 2024081863W WO 2025103939 A1 WO2025103939 A1 WO 2025103939A1
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methyl
alkyl
compounds
acid
halogen
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German (de)
French (fr)
Inventor
Hartmut Ahrens
Harald Jakobi
Arnim Köhn
Christian Waldraff
Elisabeth ASMUS
Birgit BOLLENBACH-WAHL
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • A01P13/02—Herbicides; Algicides selective

Definitions

  • BCS231028 Ausland Mak/lep 2024-08-30 - 1 - Herbicidally active sulfonimidoylbenzamides
  • the invention relates to the technical field of herbicides, in particular to herbicides for the selective control of weeds and grass weeds in crops.
  • WO 2011/035874 A1 discloses herbicidally active N-(1,2,5-oxadiazol-3-yl)benzamides.
  • EP10174893 discloses certain N-(tetrazol-5-yl)- and N-(triazol-5-yl)benzamides and -nicotinamides as herbicides.
  • WO 2013/124228 discloses herbicidal 3-(sulfin- and sulfonimidoyl)-benzamides.
  • the herbicidal efficacy and/or crop tolerance of the compounds mentioned in these documents is not always sufficient.
  • the object of the present invention was to provide herbicidally active compounds with improved properties compared to those known from the prior art. It has now been found that certain sulfonimidoylbenzamides bearing an unsubstituted 1,3,4-oxadiazole on the amide nitrogen are particularly suitable as herbicides.
  • the present invention therefore provides sulfonimidoylbenzamides of the formula (I) or salts thereof.
  • Z means halogen, cyano, (C1-C6)-alkyl, halogen-(C1-C6)-alkyl, (C2-C6)-alkenyl, halogen-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halogen-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, Halogen-(C3-C6)-cycloalkyl, halogen-(C1-C6)-alkoxy, (C1-C6)-alkylsulfonyl, W means hydrogen, halogen, R means (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, R' means hydrogen, cyano
  • 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, and hexyls, such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl.
  • alkenyl denotes, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl.
  • Alkynyl means, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • the multiple bond can be located in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic, saturated ring system with three to six C atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
  • perhaloalkyl also includes
  • Alkoxy means an alkyl radical bonded via an oxygen atom, e.g. B. (but not limited to) (C1-C6) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-ethylbutoxy
  • Alkoxyalkyl means an alkoxy radical bonded via an alkyl group.
  • Haloalkoxy means a haloalkyl radical bonded via an oxygen atom, e.g. (but not limited to) OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, and OCH2CH2Cl.
  • alkylthio stands for straight-chain or branched S-alkyl, for example (C1-C6)-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 1,1-Dimethylpropylthio, 1,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1-Ethylpropylthio, Hexylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, 1,1-dimethylbuty
  • the number of C atoms refers to the alkyl radical in the alkylcarbonyl group.
  • halogen means, for example, fluorine, chlorine, bromine, or iodine. When used for a radical, "halogen” means, for example, a fluorine, chlorine, bromine, or iodine atom.
  • the compounds can form tautomers by hydrogen shift which would not be structurally covered by formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of formula (I) according to the invention, unless a specific tautomer is the subject of consideration.
  • many carbonyl compounds can exist in both the keto form and the enol form, both forms being encompassed by the definition of the compound of formula (I).
  • the compounds of general formula (I) can exist as stereoisomers depending on the nature and linkage of the substituents. If, for example, one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained during production 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 which are encompassed by the general formula (I) but are not specifically defined.
  • the invention also relates to all E-/Z-isomers and mixtures thereof which are encompassed by the general formula (I) but are not specifically defined.
  • the compounds of the formula (I) can form salts.
  • Salt formation can take place by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom, e.g. in the case of R''.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and also ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate.
  • salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRR*R**R***] + where R, R*, R** and R*** are independently BCS231028 Foreign countries - 4 - each represent an organic radical, in particular alkyl, aryl, aralkyl, or alkylaryl.
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRR*R**R***] + where R, R*, R** and R*** are independently BCS231028 Foreign countries - 4 - each represent an organic radical
  • Alkylsulfonium and alkylsulfoxonium salts are also suitable.
  • the compounds of formula (I) can be prepared by addition of a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H2SO4, H3PO4, or HNO 3 , or organic acids, e.g. carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid, with a basic group such as e.g.
  • Preferred compounds of the general formula (I) are those in which X is halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, (C3-C6)-cycloalkyl, Z is halogen, (C1-C3)-alkyl, halo-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, halo-(C1-C3)-alkoxy, W is hydrogen, fluorine, R is (C 1 -C 3 )-alkyl, R' is hydrogen, R'' is hydrogen.
  • the compounds according to the invention can be prepared by following the processes described in WO 2013/124228.
  • the compounds according to the invention can be prepared stepwise, first at the thioether stage of the formula (I-thioether) according to the method shown in Scheme 1 by base-catalyzed BCS231028 Foreign countries - 5 - reaction of a benzoic acid chloride (II) with a 2-amino-1,3,4-oxadiazole (VII).
  • the thioether intermediates can then be prepared according to Scheme a 4 are converted into the sulfonimidoylbenzamides of formula (I) according to the invention.
  • Step of formula (I-thioether) can be prepared according to the method shown in Scheme 2 by reacting a benzoic acid of formula (IV) with a 2-amino-1,3,4-oxadiazole (VII).
  • the thioether intermediates can then be converted into the inventive sulfonimidoylbenzamides of formula (I) can be converted.
  • F for Amidation reactions such as 1,1'-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide 3P) can be used.
  • BCS231028 Abroad - 6 - Invention corresponding compounds in which the substituent R’’ is ni Which represents hydrogen, can be prepared, for example, according to the method shown in Scheme 3 by reacting an N-(1,3,4-oxadiazol-2-yl)-arylcarboxamide (I-NH) with a compound of the general formula (VIII), where L represents a leaving group such as chlorine, bromine, iodine, mesyloxy, tosyloxy, trifluorosulfonyloxy, etc.: known in the literature described methods.
  • the compounds of formula (I) according to the invention can be prepared, for example, from the corresponding thioethers of formula (I-thioether) (Scheme 4).
  • the thioether is converted, for example, with cyanamide and an oxidizing agent (iodosobenzene diacetate, sodium hypochlorite, or N-bromosuccinimide) into the corresponding sulfilimine, which can then be further oxidized to the sulfoximine.
  • Oxidizing agents such as meta-chloroperbenzoic acid, sodium permanganate, or a mixture of sodium periodate and ruthenium trichloride are suitable for the oxidation to the sulfoximine.
  • NH-sulfoximines are accessible, for example, from sulfoxides with sodium azide and sulfuric acid and can be functionalized at the nitrogen atom with reagents such as cyanogen bromide, acid chlorides or acid anhydrides, chloroformate, nitric acid, or other compounds.
  • reagents such as cyanogen bromide, acid chlorides or acid anhydrides, chloroformate, nitric acid, or other compounds.
  • the oxidation of N-sulfonated sulfilimines to the corresponding sulfoximines is achieved, for example, with hydrogen peroxide.
  • sulfoxides can be converted to N-acylated or N-sulfonated sulfoximines.
  • the carboxamide or sulfonamide can then be cleaved to the NH-sulfoximine.
  • Such synthetic methods for the generation of sulfilimines and sulfoximines from thioethers or for the generation of sulfoximines from sulfoxides or for the derivatization of sulfilimines and sulfoximines, including NH-sulfoximines can be found, for example, in Bolm, C. Org. Lett. 2004, 6, 1305; Bolm, C. Org. Lett. 2007, 9, 3809; Bolm, C. Synthesis 2010, 17, 2922; Bolm, C. Adv. Synth. Catal. 2010, 352, 309; WO 2007/095229, WO 2008/141843, US 2008/0207910, US 2008/0194634 and US 2010/0056534.
  • esters such as methyl or ethyl esters are suitable.
  • Tert-butyl esters often provide steric protection against nucleophilic reagents and are easily cleavable in acidic media (T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd Edition, John Wiley & Sons, Inc. 1991, p. 227 ff.).
  • residues that are significantly more stable than carboxyl groups, yet are readily accessible from carboxylic acids and can also be easily converted back into the free carboxylic acids.
  • residues include, for example, oxazolines.
  • BCS231028 Abroad - 8 - (T.W. Greene, P.G.M. . Wuts, Protective Groups in Organic Synthesis, 2nd Edition , John Wiley & Sons, Inc.1991, p. 265 ff.; Z . Hell et al, Tetrahedron Letters 43 (2002), 3985 - 3987).
  • the inventive NH-sulfoximes of formula (I) in one step from the corresponding thioethers of formula (I-thioether) (Scheme 5).
  • the thioether is, for example, is converted directly into the corresponding NH-sulfoximines with ammonium carbamate and iodosobenzene diacetate (J. A. Bull et al. Synlett 2017, 28, 2525-2538).
  • the compounds of formula (I) are obtained as racemic mixtures.
  • the pure enantiomers can be obtained therefrom by methods known to those skilled in the art. Chiral separation methods, such as chromatographic enantiomer separation on chiral supports, can be used.
  • the respective reaction mixtures are generally processed using known methods, for example, by crystallization, aqueous extractive processing, chromatographic methods, or a combination of these methods. Collections of compounds of formula (I) and/or their salts, which can be synthesized by the above-mentioned reactions, can also be prepared in parallel, which can be done manually, partially automated, or fully automated. For example, it is possible to automate the reaction procedure, the workup, or the purification of the products or intermediates. 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.
  • a range of commercially available devices can be used for parallelized reaction execution and workup, for example, Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA; reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 113AZ, England; or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA.
  • Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA
  • reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 113AZ, England
  • MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA.
  • BCS231028 Foreign countries - 9 - Chromatography equipment is available, for example, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
  • 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 circumvented by using partially or fully integrated automation systems, in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be 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).
  • the preparation of compounds of general formula (I) and their salts can be carried out completely or partially by solid-phase-assisted methods.
  • individual intermediates or all intermediates of the synthesis, or of a synthesis adapted for the respective procedure are bound to a synthesis 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, CA 92064, USA.
  • the implementation of individual or multiple synthesis steps in both the solid and liquid phases can be supported by the use of microwave technology.
  • a number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (editors C. O. Kappe and A. Stadler), Wiley Publishers, 2005.
  • Preparation according to the processes described here yields compounds of formula (I) and their salts in the form of collections of substances called libraries.
  • the present invention also relates to libraries containing at least two compounds of formula (I) and their salts.
  • the compounds of formula (I) according to the invention (and/or their salts), hereinafter collectively referred to as “compounds according to the invention”, have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual weeds.
  • BCS231028 Foreign countries - 10 - Even difficult-to-control perennial weeds that sprout from rhizomes, rootstocks, or other permanent organs are effectively controlled by the active ingredients.
  • 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., weeds such as monocotyledonous 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.
  • Monocotyledonous weeds 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.
  • 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 cease growth and finally die completely after three to four weeks.
  • the active ingredients are applied post-emergence to the green parts of the plant, growth stops after treatment, and the weeds remain in the growth stage present at the time of application or die completely after a certain period of time, thus eliminating weed competition harmful to the crop plants very early and sustainably.
  • the compounds according to the invention exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, e.g., dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus,Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, are only slightly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate.
  • crops of economically important crops e.g., dicotyledonous crops of the genera Arachis, Beta
  • the present compounds are very suitable for the selective control of undesirable plant growth in plant crops, such as agricultural crops or ornamental plants.
  • the compounds according to the invention (depending on their respective structure and the application rate) exhibit excellent growth-regulating properties in crops. They regulate the plant's own metabolism and can therefore be used to specifically influence plant substances and to facilitate harvesting, for example by triggering desiccation and stunting.
  • they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as it can, for example, reduce or completely prevent lodging.
  • the active ingredients can also be used to control weeds in crops of plants modified genetically or by conventional mutagenesis.
  • the transgenic plants are generally characterized by particularly advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens that cause plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to, for example, B. the harvest in terms of quantity, quality, storability, composition, and specific ingredients.
  • transgenic crops 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 corn, or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetables.
  • the compounds according to the invention can preferably be used as herbicides in crops that are resistant to the phytotoxic effects of the herbicides or have been genetically engineered to be resistant.
  • Conventional methods for producing new plants that have modified properties compared to previously existing plants include, for example, classical breeding methods and the generation of mutants.
  • new plants with modified properties can be produced using BCS231028
  • Foreign countries - 12 - produced by genetic engineering techniques (see, for example, EP-A-0221044, EP-A-0131624).
  • genetic engineering techniques see, for example, EP-A-0221044, EP-A-0131624.
  • the following have been described in several cases: - genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806), - transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf. e.g.
  • Bt toxins Bacillus thuringiensis toxins
  • EP-A-0193259 Bacillus thuringiensis toxins
  • - Transgenic crops with modified fatty acid composition WO 91/13972.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence modification by recombination of DNA sequences. Using standard procedures, base exchanges can be performed, partial sequences can be removed, or natural or synthetic sequences can be added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments, see e.g. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Genes and Clones", VCH Weinheim, 2nd ed. 1996.
  • 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, ⁇ BCS231028 Foreign countries - 13 - of a sense RNA to achieve a cosuppression effect or the expression of at least one correspondingly constructed ribozyme that specifically cleaves transcripts of the aforementioned gene product.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences present, as well as DNA molecules that comprise only parts of the coding sequence, whereby these parts must be long enough to produce an antisense effect in the cells.
  • DNA sequences that exhibit a high degree of homology to the coding sequences of a gene product can be localized in any compartment of the plant cell.
  • a specific compartment can be used.
  • the coding region can be linked to DNA sequences that ensure localization in a specific compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850, Sonnewald et al., Plant J.
  • the compounds according to the invention can preferably be used in transgenic crops that are resistant to growth promoters, such as dicamba, or to herbicides that inhibit essential plant enzymes, e.g., acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS), or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates, or benzoyl isoxazoles and analogous active ingredients.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the use according to the invention for controlling weeds or for regulating plant growth also includes the case in which the active ingredient of formula (I) or its salt is formed from a precursor substance ("prodrug") only after application to the plant, in the plant, or in the soil.
  • the invention also relates to the use of one or more compounds of the formula (I) or salts thereof or of an agent according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the formula (I) or salts thereof is applied to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in or on which the plants grow, or the area under cultivation.
  • the invention also relates to a herbicidal and/or plant growth regulating agent, characterized in that the agent contains (a) one or more compounds of the formula (I) and/or salts thereof as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas I-1 to I-33 and/or salts thereof, in each case as defined above, and (b) one or more further substances selected from groups (i) and/or (ii): (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e.
  • component (i) of a composition according to the invention are preferably selected from the group of substances listed in "The Pesticide Manual", 19 th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021.
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, BCS231028 Foreign countries - 15 - inorganic salts, dusts, carriers that are solid at 25°C and 1013 mbar, preferably adsorbent, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents that are miscible with water in any ratio at 25°C and 1013 mbar.
  • formulation auxiliaries selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, BCS231028
  • Foreign countries - 15 - inorganic salts, dusts, carriers that are solid at 25°C and 1013 mbar preferably adsorbent
  • the compounds according to the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in the usual preparations.
  • the invention therefore also relates to herbicidal and plant growth-regulating compositions containing the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on the biological and/or chemical-physical parameters specified.
  • Possible formulation options include: 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.
  • WP wettable powders
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • CS oil- or water-based dispersions
  • DP
  • a diluent or inert substance as well as 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.
  • ionic and/or non-ionic surfactants e.g., polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulf
  • the herbicidal 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.
  • 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 these organic solvents, with the addition of one or more ionic and/or non-ionic surfactants (emulsifiers).
  • emulsifiers examples include calcium salts of alkylarylsulfonic acid, such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.
  • alkylarylsulfonic acid such as calcium dodecylbenzenesulfonate
  • non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, such as sorbitan fatty
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g., talc, natural clays such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, with the addition of surfactants, such as those listed above for the other formulation types.
  • Emulsions e.g., oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • 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, e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oils.
  • Suitable active ingredients can also be granulated in the usual manner for the production of fertilizer granules—if desired, mixed with fertilizers.
  • Water-dispersible granules are generally produced using conventional processes such as spray drying, fluidized-bed granulation, disc granulation, mixing with high-speed mixers, and ⁇ BCS231028 Foreign countries - 17 - Extrusion without solid inert material.
  • spray drying fluidized-bed granulation
  • disc granulation mixing with high-speed mixers
  • ⁇ BCS231028 Foreign countries - 17 - Extrusion without solid inert material.
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention.
  • the active ingredient concentration is about 10 to 90% by weight, with the remainder (to 100% by weight) consisting of conventional formulation components.
  • the active ingredient concentration can be about 1 to 90% by weight, preferably 5 to 80% by weight.
  • Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably 5 to 20% by weight of active ingredient, while sprayable solutions contain about 0.05 to 80% by weight, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends partly on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.
  • the active ingredient content for example, is between 1 and 95 wt.%, preferably between 10 and 80 wt.%.
  • the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents, solvents, fillers, carriers, dyes, defoamers, evaporation inhibitors, and pH and viscosity modifiers. Examples of formulation aids are described, among others, in “Chemistry and Technology of Agrochemical Formulations,” ed. D. A. Knowles, Kluwer Academic Publishers (1998).
  • the compounds of formula (I) or their salts can be used as such or in the form of their preparations (formulations) in combination with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and/or growth regulators, e.g., as a ready-to-use formulation or as tank mixes.
  • pesticidally active substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and/or growth regulators, e.g., as a ready-to-use formulation or as tank mixes.
  • the combination formulations can be prepared based on the above-mentioned formulations, taking into account the physical properties and stability of the active ingredients to be combined.
  • BCS231028 Foreign countries - 18 - Of particular interest is the selective control of weeds in crops of useful and ornamental plants.
  • the compounds (I) according to the invention already exhibit very good to sufficient selectivity in many crops, phytotoxicity can in principle occur in some crops, especially in the case of mixtures with other herbicides that are less selective.
  • combinations of compounds (I) according to the invention that contain the compounds (I) or their combinations with other herbicides or pesticides and safeners are of particular interest.
  • the safeners which are used in an antidote-effective concentration, reduce the phytotoxic side effects of the herbicides/pesticides used, e.g., in economically important crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton, and soybeans, preferably cereals.
  • the weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the respective safener and can vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20.
  • the safeners can be formulated analogously to the compounds (I) or mixtures thereof with other herbicides/pesticides and supplied and applied as a ready-to-use formulation or tank mix with the herbicides.
  • the herbicide or herbicide-safener formulations available in commercial form are diluted, if appropriate, in the customary manner, e.g., with water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, soil-applied or broadcast granules, and sprayable solutions are not normally diluted with other inert substances before use. External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of formula (I) and/or their salts. The application rate can vary within wide limits.
  • the total amount of compounds of formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, more preferably in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, particularly preferably in the range from 0.05 to 1 kg/ha. This applies to both pre-emergence and post-emergence application.
  • the total application rate is preferably in the range from 0.001 to 2 kg/ha, preferably in the range from 0.005 to 1 kg/ha, in particular in the range from 10 to 500 g/ha, very particularly preferably in the range from 20 to 250 g/ha.
  • BCS231028 Foreign countries - 19 - Application as a stem shortener can occur at various stages of plant growth. For example, application after tillering, at the beginning of longitudinal growth, is preferred.
  • application as a plant growth regulator can also be applied to the seeds, which includes various seed dressing and coating techniques.
  • the application rate depends on the individual techniques and can be determined in preliminary trials.
  • known active ingredients that are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase or that act as plant growth regulators can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 19th edition, The British Crop Protection Council and the Royal Soc.
  • herbicides or plant growth regulators that can be combined with compounds of general formula (I) include, for example, the following active ingredients (the compounds are designated either by the "common name” according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • Acetochlor Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammonium sulfamate, Anilofos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azafenidine, Azimsul
  • Dicamba and its salts (e.g., Dicamba biproamine, Dicamba N,N-bis(3-aminopropyl)methylamine, Dicamba butotyl, Dicamba choline, Dicamba diglycolamine, Dicamba dimethylammonium, Dicamba diethanolamine ammonium, Dicamba diethylammonium, Dicamba isopropylammonium, Dicamba methyl, Dicamba monoethanolamine, Dicamba o
  • COs (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chitooligosaccharides (CO; COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs.
  • COs sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(C 8 H 13 NO 5 ) n , CAS No.1398-61-4] and chitosan molecules [(C 5 H 11 NO 4 ) n , CAS No.9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet sodium, n-decanol,
  • LCOs differ in the number of GlcNAc units in the backbone structure, the length and degree of saturation of the fatty acid chain, and the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, Methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-( ⁇ [(2R)-4-methyl-5-oxo-2,5-di
  • nA is a natural number from 0 to 5, preferably 0 to 3
  • RA 1 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl
  • WA is an unsubstituted or substituted divalent heterocyclic radical from the group of partially saturated or aromatic five-membered ring heterocycles with 1 to 3 hetero ring atoms from the group BCS231028 Foreign countries - 26 - 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 ), R 2 is ORA 3 , SRA of the NRA 3 R is a saturated or unsatur
  • RD3 O (R O D 4 )mD BCS231028 Foreign - 30 - RD 1 is CO-NRD 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl;
  • RD 3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl;
  • RD 4 is halogen, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C3-C6)-cycloalkyl,
  • 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.
  • S6 Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.
  • BCS231028 Foreign countries - 34 - S9)
  • Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones e.g., 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.
  • S11 Active ingredients of the oxyimino compound type (S11), which are known as seed dressings, such as B.
  • “Oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet against metolachlor damage
  • "Fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), which is known as a seed dressing safener for millet against metolachlor damage
  • “Cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet against metolachlor damage.
  • S12 Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.
  • S12 isothiochromanones
  • S13 One or more compounds from group (S13): "Naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as BCS231028 Foreign countries - 35 - Safener for pretilachlor in sown rice, "Flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415” (CAS Reg.
  • the reaction mixture was then stirred at room temperature for 20 hours. For workup, a little water and then sodium bisulfite were added. The mixture was largely freed of solvent using a rotary evaporator. The residue was taken up with dichloromethane and a little water. After phase separation, the organic phase was freed from solvent using a rotary evaporator. The residue was purified by chromatography, yielding 25.2 mg of pure product.
  • the ⁇ value in ppm is listed first, followed by the signal intensity in parentheses.
  • the ⁇ value – signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ 1 (Intensity 1 ) ; ⁇ 2 (Intensity 2 );........; ⁇ i (Intensity i ) ; hence; ⁇ n (Intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
  • tetramethylsilane For calibration of the chemical shift of 1
  • tetramethylsilane and/or the chemical shift of the solvent especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not appear in NMR peak lists.
  • 1 H-NMR peaks are similar to the classical 1 H-NMR printouts and thus usually contain all peaks that are recorded in a classical NMR interpretation. In addition, they can be interpreted like classical 1 H-NMR printouts show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and/or peaks from impurities.
  • a wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurine as wetting and dispersing agent and milling the mixture in a pin mill.
  • a dispersion concentrate readily dispersible in water is obtained by mixing 20 parts by weight of a compound of formula (I) and/or its salts with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO), and 71 parts by weight of paraffinic mineral oil (boiling range, e.g., approximately 255 to over 277°C) and grinding in a ball mill to a fineness of less than 5 microns.
  • 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.
  • Water-dispersible granules are obtained by mixing 75 parts by weight of a compound of formula (I) and/or its salts, 10 parts by weight of calcium ligninsulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol, and 7 parts by weight of kaolin, grinding the mixture in a pin mill, and granulating the powder in a fluidized bed by spraying water as the granulation liquid.
  • Water-dispersible granules are also obtained by BCS231028 Foreign countries - 43 - 25 parts by weight of a compound of formula (I) and/or its salts, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurine, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate, and 50 parts by weight of water were homogenized and pre-comminuted in a colloid mill, then ground in a bead mill, and the resulting suspension was atomized and dried in a spray tower using a single-component nozzle.
  • Table A1a Postemergence effect at 20 g/ha against ALOMY in %
  • Foreign countries - 44 - Table A1b Post-emergence effect at 80 g/ha against ALOMY in %
  • Table A2a Post-emergence effect at 5 g/ha against AMARE in %
  • Table A2b Post-emergence effect at 20 g/ha against AMARE in %
  • Table A15a Post-emergence effect at 5g/ha against ZEAMX in %
  • Table A15b Post-emergence effect at 20g/ha against ZEAMX in %
  • Table A16a Post-emergence effect at 5g/ha against TRZAS in %
  • ABUTH Abutilon theophrasti
  • Alopecurus myosuroides Alopecurus myosuroides
  • AZAS Amaranthus retroflexus
  • Avena fatua AVEFA
  • Digitaria sanguinalis DIGSA
  • Echinochloa crus-galli EHCG
  • Kochia scoparia KCHSC
  • Lolium rigidum LLOLRI
  • Matricaria inodora MATIN
  • Pharbitis purpurea Pharbitis purpurea
  • POLCO Polygonum convolvulus
  • Setaria viridis SETVI
  • Veronica persica VERPE
  • Viola tricolor Viola tricolor
  • BCS231028 Foreign countries - 56 - 2.
  • Herbicidal Activity and Crop Compatibility in Pre-Emergence Seeds of monocotyledonous and dicotyledonous weeds and cultivated plants were sown in plastic or organic plant pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or emulsion concentrates (EC), were then applied to the surface of the covering soil as an aqueous suspension or emulsion with the addition of 0.5% additive at a water application rate of the equivalent of 600 l/ha. After treatment, the pots were placed in the greenhouse and maintained under good growth conditions for the test plants.
  • WP wettable powders
  • EC emulsion concentrates
  • Table B1a Pre-emergence effect at 80 g/ha against ALOMY in %
  • Table B2a Pre-emergence effect at 20 g/ha against AMARE in %
  • Table B3a Pre-emergence effect at 20 g/ha against AVEFA in %
  • BCS231028 Foreign countries - 58 - Table B4a: Pre-emergence effect at 20 g/ha against DIGSA in %
  • Table B4b Pre-emergence effect at 80 g/ha against DIGSA in %
  • Table B5a Pre-emergence effect at 20 g/ha against ECHCG in %
  • BCS231028 Foreign countries - 59 -
  • Table B15a Pre-emergence effect at 20g/ha against ZEAMX in %
  • Foreign countries - 65 - Table B15b Pre-emergence effect at 80/ha against ZEAMX in %
  • Table B16a Pre-emergence effect at 20g/ha against TRZAS in %
  • ABUTH Abutilon theophrasti
  • Alopecurus myosuroides Alopecurus myosuroides
  • AZAS Amaranthus retroflexus
  • Avena fatua AVEFA
  • Digitaria sanguinalis DIGSA
  • Echinochloa crus-galli EHCG
  • Kochia scoparia KCHSC
  • Lolium rigidum LLOLRI
  • Matricaria inodora MATIN
  • Pharbitis purpurea Pharbitis purpurea
  • POLCO Polygonum convolvulus
  • Setaria viridis SETVI
  • Veronica persica VERPE
  • Viola tricolor Viola tricolor
  • Table C1 Compound according to the invention Structurally close compound from WO2013/124228 1-1 (according to the invention) * 7-18 (WO2013 /124228) * 1-2 (according to the invention) * 7-6 (WO2013/124228) * 1-7 (according to the invention) * 7-17 (WO2013/124228) * 1-11 (according to the invention) * 7-12 (WO2013/124228) * 1-13 (according to the invention) * 7-29 (WO2013/124228) *
  • Table C2-C11 the post-emergence effects on various weeds of compounds according to the invention and literature-known structurally close compound from BCS231028 Foreign countries - 68 - WO2013/124228 at an application rate corresponding to 20 g/ha and lower, which were obtained according to the aforementioned test procedure.
  • Tables C12-C16 below show the post-emergence crop tolerance of compounds according to the invention and the structurally similar compound from WO2013/124228, which are known from the literature, at an application rate corresponding to 20 g/ha and lower, obtained according to the aforementioned test procedure.
  • Tables C17-C28 below show the preemergence effects on various weeds of compounds according to the invention and the structurally similar compound from WO2013/124228 obtained according to the aforementioned test procedure at an application rate corresponding to 80 g/ha and lower.
  • Tables C29-C32 below show the pre-emergence crop tolerances of compounds according to the invention and the structurally similar compound from WO2013/124228, which are known from the literature, at an application rate corresponding to 80 g/ha and lower, obtained according to the aforementioned test procedure.

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Abstract

The invention relates to sulfonimidoyl benzamides of formula (I) as herbicides. In formula (I), X, W, Z, R, R' and R'' represent radicals such as alkyl, cycloalkyl, haloalkyl and halogen.

Description

BCS231028 Ausland Mak/lep 2024-08-30 - 1 - Herbizid wirksame Sulfonimidoylbenzamide Die Erfindung betrifft das technische Gebiet der Herbizide, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsern in Nutzpflanzenkulturen. Aus WO 2011/035874 A1 sind herbizid wirksame N-(1,2,5-Oxadiazol-3-yl)benzamide bekannt. Aus der prioritätsälteren, nicht vorveröffentlichten europäischen Patentanmeldung EP10174893 sind bestimmte N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)benzamide und -nicotinamide als Herbizide bekannt. Aus WO 2013/124228 sind herbizide 3-(Sulfin- und Sulfonimidoyl)-benzamide bekannt. Die herbizide Wirksamkeit und/oder die Kulturpflanzenverträglichkeit der in diesen Schriften genannten Verbindungen ist jedoch nicht immer ausreichend.

Figure imgf000002_0003
Aufgabe der vorliegenden Erfindung war die Bereitstellung von herbizid wirksamen Verbindungen mit gegenüber den aus dem Stand der Technik bekannten Verbindungen verbesserten Eigenschaften. Es wurde nun gefunden, dass bestimmte Sulfonimidoylbenzamide, die am Amidstickstoff ein unsubstituiertes 1,3,4-Oxadiazol tragen, als Herbizide besonders gut geeignet sind. Ein Gegenstand der vorliegenden Erfindung sind somit Sulfonimidoylbenzamide der Formel (I) oder deren Salze
Figure imgf000002_0002
Figure imgf000002_0001
worin die X bedeutet Halogen, Cyano, (C1-C6)-Alkyl, (C1-C6)-Alkoxy, (C1-C6)-Alkylthio, Halogen-(C1-C6)- alkyl, (C1-C6)-Alkoxy-(C1-C6)-alkyl, (C2-C6)-Alke yl, (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl, Z bedeutet Halogen, Cyano, (C1-C6)-Alkyl, Halogen-(C1-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2- C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)- cycloalkyl, Halogen-(C1-C6)-alkoxy, (C1-C6)-Alkylsulfonyl, W bedeutet Wasserstoff, Halogen, R bedeutet (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(C1-C6)-alkyl, (C1-C6)-Alkoxy- (C1-C6)-alkyl, R’ bedeutet Wasserstoff, Cyano, (C1-C6)-Alkyl, BCS231028 Ausland - 2 - R’’ bedeutet Wasserstoff, (C1-C6)-Alkylcarbonyl. In der Formel (I) und allen nachfolgenden Formeln können Alkylreste mit mehr als zwei Kohlenstoffatomen geradkettig oder verzweigt sein. Alkylreste bedeuten z.B. Methyl, Ethyl, n oder -i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1,3-Dimethylbutyl. Analog bedeutet Alkenyl z.B. Allyl, 1-Methylprop-2-en-1-yl, 2-Methyl-prop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, 1-Methyl-but-3-en-1-yl und 1-Methyl-but-2-en-1-yl. Alkinyl bedeutet z.B. Propargyl, But-2-in-1-yl, But-3-in-1-yl, 1-Methyl-but-3-in-1-yl. Die Mehrfachbindung kann sich jeweils in beliebiger Position des ungesättigten Rests befinden. „Cycloalkyl” bedeutet ein carbocyclisches, gesättigtes Ringsystem mit drei bis sechs C--Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. „Halogenalkyl“, „Halogenalkenyl-“ und „Halogenalkinyl“ bedeuten durch gleiche oder verschiedene Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Monohalogenalkyl) wie z. B. CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F; Dihaloalkyl (= Dihalogenalkyl) wie z. B. CH2CHF2, CH2CHCl2, CH2CHBr2, CF2CH3, CHCl2, CHF2; Perhaloalkyl wie z. B. CCl3, CFCl2, CClF2, CF3, CF2CClF2, CF2CClFCF3; Polyhaloalkyl wie z. B. CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. „Alkoxy“ bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B. (aber nicht beschränkt auf) (C1-C6)-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1-Methylethoxy, Butoxy, 1-Methylpropoxy, 2- Methylpropoxy, 1,1-Dimethylethoxy, Pentoxy, 1-Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1,1- Dimethylpropoxy, 1,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1-Ethylpropoxy, Hexoxy, 1- Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1,1-Dimethylbutoxy, 1,2-Di- methylbutoxy, 1,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1- Ethylbutoxy, 2-Ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-Ethyl-1-methyl- propoxy und 1-Ethyl-2-methylpropoxy. „Alkoxyalkyl“ steht für einen über eine Alkylgruppe gebundenen Alkoxyrest. „Halogenalkoxy“ bedeutet über ein Sauerstoffatom gebundenen Halogenalkylrest, z.B. (aber nicht beschränkt auf) OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2Cl. Erfindungsgemäß steht "Alkylthio" für geradkettiges oder verzweigtes S-Alkyl, z.B. (C1-C6)-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2- Methylpropylthio, 1,1-Dimethylethylthio, Pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3- Methylbutylthio, 1,1-Dimethylpropylthio, 1,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1- Ethylpropylthio, Hexylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutylthio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Tri- BCS231028 Ausland - 3 - methylpropylthio, 1,2,2-Trimethylpropylthio, 1-Ethyl-1-methylpropylthio und 1-Ethyl-2-methyl- propylthio. „Alkylcarbonyl“ (Alkyl-C(=O)-), soweit nicht an anderer Stelle anders definiert, steht erfindungsgemäß für Alkylreste, die über -C(=O)- an das Gerüst gebunden sind, wie (C1-C6)-Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonylgruppe. Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder Iod. Wird die Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder Iodatom. Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die Formel (I) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der Formel (I) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der Betrachtung ist. So können beispielsweise viele Carbonylverbindungen sowohl in der Ketoform wie auch in der Enolform vorliegen, wobei beide Formen durch die Definition der Verbindung der Formel (I) umfasst werden. Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Sind beispielsweise ein oder mehrere asymmetrisch substituierte Kohlenstoff- atome vorhanden, so können Enantiomere und Diastereomere auftreten. Außerdem liegt das Schwefelatom in der Sulfoximinogruppe als chirales Zentrum vor. Stereoisomere lassen sich aus den bei der Herstellung anfallenden Gemischen nach üblichen Trennmethoden, beispielsweise durch chromatographische Trennverfahren, erhalten. Ebenso können Stereoisomere durch Einsatz stereo- selektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft auch alle Stereoisomeren und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Die Erfindung betrifft auch alle E- /Z-Isomere und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Die Verbindungen der Formel (I) können Salze bilden. Salzbildung kann durch Einwirkung einer Base auf solche Verbindungen der Formel (I) erfolgen, die ein acides Wasserstoffatom tragen, z.B. im Falle von R´´. Geeignete Basen sind beispielsweise organische Amine , wie Trialkylamine, Morpholin, Piperidin oder Pyridin sowie Ammonium-, Alkali- oder Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quaternäre) Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRR*R**R***]+, worin R, R*, R** und R*** unabhängig BCS231028 Ausland - 4 - voneinander jeweils einen organischen Rest, insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkylsulfoxoniumsalze, wie (C1-C4)-Trialkylsulfonium- und (C1-C4)-Trialkylsulfoxoniumsalze. Die Verbindungen der Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, H3PO4 oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p-Toluolsulfonsäure, an eine basische Gruppe, wie z.B. Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. Bevorzugt sind Verbindungen der allgemeinen Formel (I), worin X bedeutet Halogen, (C1-C3)-Alkyl, (C1-C3)-Alkoxy, (C3-C6)-Cycloalkyl, Z bedeutet Halogen, (C1-C3)-Alkyl, Halogen-(C1-C3)-alkyl, (C3-C6)-Cycloalkyl, Halogen-(C1-C3)- alkoxy, W bedeutet Wasserstoff, Fluor, R bedeutet (C1-C3)-Alkyl, R’ bedeutet Wasserstoff, R’’ bedeutet Wasserstoff. Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin X bedeutet Chlor, Methyl, Ethyl, Methoxy, Cyclopropyl, Z bedeutet Chlor, Methyl, Difluormethyl, Trifluormethyl, Cyclopropyl, Trifluormethoxy, W bedeutet Wasserstoff, R bedeutet Methyl, Ethyl, R’ bedeutet Wasserstoff, R’’ bedeutet Wasserstoff. Die erfindungsgemäßen Verbindungen können in Anlehnung an die in WO 2013/124228 beschriebenen Verfahren hergestellt werden. So können die erfindungsgemäßen Verbindungen beispielsweise schrittweise zunächst auf der Thioether- Stufe der Formel (I-Thioether) nach der in Schema 1 angegebenen Methode durch basenkatalysierte
Figure imgf000006_0001
Figure imgf000006_0011
Figure imgf000006_0002
Figure imgf000006_0005
Figure imgf000006_0006
Figure imgf000006_0007
BCS231028 Ausland - 5 - Umsetzung eines Benzoesäurechlorids (II) mit einem 2-Amino-1,3,4-oxadiazol (VII) hergestellt werden. Die Thioether-Zwischenprodukte können dann gemäß Schem
Figure imgf000006_0008
a
Figure imgf000006_0010
Figure imgf000006_0012
4 in die erfindungsgemäßen Sulfonimidoylbenzamide der Formel (I) übergeführt werden.
Figure imgf000006_0003
Figure imgf000006_0004
Figure imgf000006_0009
E
Figure imgf000006_0015
Stufe der Formel (I- Thioether) nach der in Schema 2 angegebenen Methode durch Umsetzung einer Benzoesäure der Formel (IV) mit einem 2-Amino-1,3,4-oxadiazol (VII) hergestellt werden. Die Thioether-Zwischenprodukte können dann gemäß Schema 4 in die erfindungsgemä
Figure imgf000006_0014
ßen Sulfonimidoylbenzamide der Formel (I) übergeführt werden.
Figure imgf000006_0017
Figure imgf000006_0013
F für
Figure imgf000006_0016
Amidierungsreaktionen, wie z. B. 1,1`-Carbonyldiimidazol (CDI), Dicyclohexyl-carbodiimid (DCC), 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide 3P) eingesetzt werden.
Figure imgf000007_0004
Figure imgf000007_0026
Figure imgf000007_0007
Figure imgf000007_0015
Figure imgf000007_0017
Figure imgf000007_0006
BCS231028 Ausland
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- 6
Figure imgf000007_0029
Figure imgf000007_0003
-
Figure imgf000007_0024
Erfindungsg
Figure imgf000007_0002
emäße Verbindungen, in denen der Substituent R’’ ni
Figure imgf000007_0022
cht Wasserstoff bedeutet, können beispielsweise nach der in Schema 3 angegebenen Methode durch Umsetzung eines N-(1,3,4-Oxadiazol- 2-yl)-arylcarbonsäureamids (I-NH) mit einer Verbindung der allgemeinen Formel (VIII), wobei L für eine Abgangsgruppe wie z. B. Chlor, Brom, Jod, Mesyloxy, Tosyloxy, Trifluorsulfonyloxy etc. steht, hergestellt werden:
Figure imgf000007_0001
Figure imgf000007_0020
Figure imgf000007_0025
Figure imgf000007_0012
Figure imgf000007_0031
Figure imgf000007_0032
Figure imgf000007_0013
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Figure imgf000007_0027
Figure imgf000007_0010
Figure imgf000007_0030
Figure imgf000007_0018
Figure imgf000007_0028
Figure imgf000007_0008
annten in der Literatur
Figure imgf000007_0023
beschriebenen Methoden hergestellt werden.
Figure imgf000007_0009
Figure imgf000007_0021
Die erfindungsgemäßen Verbindungen der Formel (I) können beispielsweise aus den entsprechenden Thioethern der Formel (I-Thioether) hergestellt werden (Schema 4). Dazu wird der Thioether beispielsweise mit Cyanamid und einem Oxidationsmittel (Iodosobenzoldiacetat, Natriumhypochlorit oder N-Bromsuccinimid) in das entsprechende Sulfilimin übergeführt, welches weiter zum Sulfoximin oxidiert werden kann. Für die Oxidation zum Sulfoximin sind Oxidationsmittel wie beispielsweise meta- Chlorperbenzoesäure, Natriumpermanagant oder ein Gemisch aus Natriumperiodat und Rutheniumtrichlorid geeignet. NH-Sulfoximine sind beispielsweise aus Sulfoxiden mit Natriumazid und Schwefelsäure zugänglich und können am Stickstoffatom mit Reagenzien wie beispielswesie Bromcyan, Säurechloriden oder Säureanhydriden, Chlorameisensäureester, Salpetersäure oder anderen Verbindungen funktionalisiert werden. Die Oxidation von N-sulfonierten Sulfiliminen zu den entsprechenden Sulfoximinen gelingt beispielsweise mit Wasserstoffperoxid. Alternativ können Sulfoxide zu N-acylierten oder N-sulfonierten Sulfoximinen umgesetzt werden. Das Carboxamid bzw. Sulfonamid kann anschließend zum NH-Sulfoximin gespalten werden. Solche Synthesemethoden für die Generierung von Sulfiliminen und Sulfoximinen aus Thioethern oder für die Generierung von Sulfoximinen aus Sulfoxiden bzw. für die Derivatisierung von Sulfiliminen und Sulfoximinen, unter anderem auch von NH-Sulfoximinen, sind beispielsweise in Bolm, C. Org. Lett.2004, 6, 1305; Bolm, C. Org. Lett.2007, 9, 3809; Bolm, C. Synthesis 2010, 17, 2922; Bolm, C. Adv. Synth. Catal.2010, 352, 309; WO 2007/095229, WO 2008/141843, US 2008/0207910, US 2008/0194634 und US 2010/0056534 beschrieben.
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Gegebenenfalls n für solche Synthese uen en Schutzgruppen einge werden, um eine hinreichende Selektivität zu erreichen. Insbesondere die Funktionalisierung am NH-Sulfoximin steht prinzipiell in Konkurrenz zur analogen Funktionalisierung am Amid-Stickstoffatom. Es kann zweckmäßig sein, Reaktionsschritte in ihrer Reihenfolge zu ändern. sind Benzoesäuren, die ein Sulfoxid tragen, nicht ohne weiteres in ihre Säurechloride zu überführen. Hier bietet sich an, zunächst auf Thioether-Stufe das Amid herzustellen und danach den Thioether zum Sulfoxid zu oxidieren. Sulfoximine und insbesondere Sulfilimine sind unter manchen Bedingungen nicht hinreichend stabil (Bolm, C. Adv. Synth. Catal. 2010, 352, 309), so dass es von Vorteil sein kann, wie in den obigen Schemata gezeigt, zuerst auf Thioether-Stufe das Benzamid zu synthetisieren und erst am Ende der Synthesesequenz das Sulfilimin bzw. das Sulfoximin aus dem Thioether zu generieren. Bei hinreichender Stabilität kann es aber je nach Substitutionsmuster auch sinnvoll sein, zuerst auf der Benzoesäure-Stufe (oder in einem noch früheren Schritt) das Sulfilimin bzw. das Sulfoximin aus dem Thioether zu generieren und erst danach die Benzoesäure in ihr Amid zu überführen. Gegebenenfalls ist es von Vorteil, für die Umsetzungen nicht die freie Benzoesäure sondern Derivate hiervon zu verwenden. Manchmal ist es für die Stabilität einer funktionellen Gruppe schon ausreichend, sich nur im sauren oder nur im basischen Medium zu bewegen, das heißt, nur mit der freien Benzoesäure oder nur mit ihrem Salz zu arbeiten. In vielen Fällen sind Ester wie Methyl- oder Ethylester geeignet. Tert.-Butylester schirmen die Carboxylgruppe oftmals sterisch wirksam gegen nucleophile Reagentien ab und sind im sauren Medium leicht spaltbar (T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd Edition, John Wiley & Sons, Inc. 1991, S. 227 ff.). Ferner sind Reste geeignet, die wesentlich stabiler als Carboxylgruppen sind, jedoch einfach aus Carbonsäuren zugänglich sind und sich auch einfach wieder in die freien Carbonsäuren überführen lassen. Hierzu zählen beispielsweise Oxazoline
Figure imgf000009_0008
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BCS231028 Ausland
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- 8 -
Figure imgf000009_0041
(T. W. Greene, P. G. M
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. Wuts, Protective Groups in Organic Synthesis, 2nd Edition
Figure imgf000009_0039
, John Wiley & Sons,
Figure imgf000009_0006
Inc.1991, S.
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265 ff.; Z
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. Hell et al, Tetrahedron Letters 43 (2002), 3985 - 3987).
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Darüber hinaus ist es auch möglich, die erfindungsgemäßen NH-Sulfoxime der Formel (I) in einem Schritt aus den entsprechenden Thioethern der Formel (I-Thioether) zu erhalten (Schema 5). Dazu wird der Thioether beispielswe
Figure imgf000009_0010
ise mit Ammoniumcarbamat und Iodosobenzoldiacetat (J. A. Bull et al. Synlett 2017, 28, 2525-2538) direkt in die entsprechenden NH-Sulfoximine übergeführt.
Figure imgf000009_0001
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B i de oben n sy Verfahren fallen die du m ulf e der Formel (I) als racemische Gemische an. Die reinen Enantiomere können daraus durch dem Fachmann bekannte
Figure imgf000009_0026
Figure imgf000009_0028
Figure imgf000009_0030
Figure imgf000009_0034
chirale Trennmethoden, wie beispielsweise durch chromatographische Enantiomerentrennung an chiralen Trägermaterialien, erhalten werden. Die Aufarbeitung der jeweiligen Reaktionsmischungen erfolgt in der Regel nach bekannten Verfahren, beispielsweise durch Kristallisation, wässrig-extraktive Aufarbeitung, durch chromatographische Methoden oder durch Kombination dieser Methoden. Kollektionen aus Verbindungen der Formel (I) und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in parallelisierter Weise hergestellt werden, wobei dies in manueller, teilweise automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es beispielsweise möglich, die Reaktionsdurchführung, die Aufarbeitung oder die Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch D. Tiebes in Combinatorial Chemistry – Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley 1999, auf den Seiten 1 bis 34 beschrieben ist. Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden, beispielsweise Calpyso-Reaktionsblöcke (Caylpso reaction blocks) der Firma Barnstead International, Dubuque, Iowa 52004-0797, USA oder Reaktionsstationen (reaction stations) der Firma Radleys, Shirehill, Saffron Walden, Essex, CB 113AZ, England oder MultiPROBE Automated Workstations der Firma Perkin Elmar, Waltham, Massachusetts 02451, USA. Für die parallelisierte Aufreinigung von Verbindungen der allgemeinen Formel (I) und deren Salzen beziehungsweise von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem BCS231028 Ausland - 9 - Chromatographieapparaturen zur Verfügung, beispielsweise der Firma ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. Die aufgeführten Apparaturen führen zu einer modularen Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise durch Roboter bedient werden. Derartige Automationssysteme können zum Beispiel von der Firma Caliper, Hopkinton, MA 01748, USA bezogen werden. Die Durchführung einzelner oder mehrerer Syntheseschritte kann durch den Einsatz von Polymer- supported reagents/Scavanger-Harze unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich). Neben den hier beschriebenen Methoden kann die Herstellung von Verbindungen der allgemeinen Formel (I) und deren Salzen vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende Vorgehensweise angepassten Synthese an ein Syntheseharz gebunden. Festphasen- unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z.B. Barry A. Bunin in “The Combinatorial Index”, Verlag Academic Press, 1998 und Combinatorial Chemistry – Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley, 1999. Die Verwendung von Festphasen- unterstützten Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Die Reaktionen können beispielsweise mittels IRORI-Technologie in Mikroreaktoren (microreactors) der Firma Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA durchgeführt werden. Sowohl an fester als auch in flüssiger Phase kann die Durchführung einzelner oder mehrerer Syntheseschritte durch den Einsatz der Mikrowellen-Technologie unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in Microwaves in Organic and Medicinal Chemistry (Herausgeber C. O. Kappe und a. Stadler), Verlag Wiley, 2005. Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen der Formel (I) und deren Salze in Form von Substanzkollektionen, die Bibliotheken genannt werden. Gegenstand der vorliegenden Erfindung sind auch Bibliotheken, die mindestens zwei Verbindungen der Formel (I) und deren Salzen enthalten. Die erfindungsgemäßen Verbindungen der Formel (I) (und/oder deren Salze), im folgenden zusammen als „erfindungsgemäße Verbindungen“ bezeichnet, weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler annueller Schadpflanzen auf. BCS231028 Ausland - 10 - Auch schwer bekämpfbare perennierende Schadpflanzen, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfaßt. Gegenstand der vorliegenden Erfindung ist daher auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen oder zur Wachstumsregulierung von Pflanzen, vorzugsweise in Pflanzenkulturen, worin eine oder mehrere erfindungsgemäße Verbindung(en) auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden. Dabei können die erfindungsgemäßen Verbindungen z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Monokotyle Schadpflanzen der Gattungen: 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, Sorghum. Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, BCS231028 Ausland - 11 - Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, insbesondere Zea und Triticum, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Darüberhinaus weisen die erfindungsgemäßen Verbindungen (abhängig von ihrer jeweiligen Struktur und der ausgebrachten Aufwandmenge) hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten.Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe BCS231028 Ausland - 12 - gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A-0131624). Beschrieben wurden beispielsweise in mehreren Fällen - gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/11376, WO 92/14827, WO 91/19806), - transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosate (WO 92/00377) oder der Sulfonylharnstoffe (EP-A-0257993, US-A-5013659) resistent sind, - transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924, EP-A-0193259). - transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972). - gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte Krankheitsresistenz verursachen (EPA 309862, EPA0464461) - gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EPA 0305398). - Transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming“) - transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualitat auszeichnen - transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking“) Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt, siehe z. B. I. Potrykus und G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. oder Christou, "Trends in Plant Science" 1 (1996) 423-431). Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA- Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, BCS231028 Ausland - 13 - einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA- Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA- Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise 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). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden. Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen. So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Vorzugsweise können die erfindungsgemäßen Verbindungen in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Dicamba oder gegen Herbizide, die essentielle Pflanzenenzyme, z.B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydroxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. BCS231028 Ausland - 14 - Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen der Formel (I) und/oder deren Salze als Herbizide zur Bekämpfung von Schadpflanzen in Kulturen von Nutz- oder Zierpflanzen, gegebenenfalls in transgenen Kulturpflanzen. Die erfindungsgemäße Verwendung zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen schließt auch den Fall ein, bei dem der Wirkstoff der Formel (I) oder dessen Salz erst nach der Ausbringung auf der Pflanze, in der Pflanze oder im Boden aus einer Vorläufersubstanz ("Prodrug") gebildet wird. Gegenstand der Erfindung ist auch die Verwendung einer oder mehrerer Verbindungen der Formel (I) oder deren Salzen bzw. eines erfindungsgemäßen Mittels (wie nachstehend definiert) (in einem Verfahren) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass man eine wirksame Menge einer oder mehreren Verbindungen der Formel (I) oder deren Salzen auf die Pflanzen (Schadpflanzen, ggf. zusammen mit den Nutzpflanzen) Pflanzensamen, den Boden, in dem oder auf dem die Pflanzen wachsen, oder die Anbaufläche appliziert. Gegenstand der Erfindung ist auch ein herbizides und/oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass das Mittel (a) eine oder mehrere Verbindungen der Formel (I) und/oder deren Salze enthält wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere eine oder mehrere Verbindungen der Formeln 1-1 bis 1-33 und/oder deren Salze, jeweils wie oben definiert, und (b) ein oder mehrere weitere Stoffe ausgewählt aus den Gruppen (i) und/oder (ii): (i) ein oder mehrere weitere agrochemisch wirksame Stoffe, vorzugsweise ausgewählt aus der Gruppe bestehend aus Insektiziden, Akariziden, Nematiziden, weiteren Herbiziden (d.h. solche, die nicht der oben definierten Formel (I) entsprechen), Fungiziden, Safenern, Düngemitteln und/oder weiteren Wachstumsregulatoren, (ii) ein oder mehrere im Pflanzenschutz übliche Formulierungshilfsmittel. Die weiteren agrochemischen wirksamen Stoffe des Bestandteils (i) eines erfindungsgemäßen Mittels sind dabei vorzugsweise ausgewählt aus der Gruppe der Stoffe, die in "The Pesticide Manual", 19th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2021 genannt sind. Ein erfindungsgemäßes herbizides oder pflanzenwachstumsregulierendes Mittel, umfasst vorzugsweise ein, zwei, drei oder mehr im Pflanzenschutz übliche Formulierungshilfsmittel (ii) ausgewählt aus der Gruppe bestehend aus Tensiden, Emulgatoren, Dispergiermitteln, Filmbildnern, Verdickungsmitteln, BCS231028 Ausland - 15 - anorganischen Salzen, Stäubemitteln, bei 25 °C und 1013 mbar festen Trägerstoffen, vorzugsweise adsorptionsfähigen, granulierten Inertmaterialien, Netzmitteln, Antioxidationsmitteln, Stabilisatoren, Puffersubstanzen, Antischaummitteln, Wasser, organischen Lösungsmitteln, vorzugsweise bei 25 °C und 1013 mbar mit Wasser in jedem beliebigen Verhältnis mischbare organische Lösungsmittel. Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvern, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, welche die erfindungsgemäßen Verbindungen enthalten. Die erfindungsgemäßen Verbindungen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und Wasser-in-Öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Mikrokapseln und Wachse. Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl.1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd Ed.1979, G. Goodwin Ltd. London. Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y.1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J., Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl.1986. Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Geeignete Safener sind beispielsweise Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, Cloquintocet- mexyl und Dichlormid. BCS231028 Ausland - 16 - Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden. Emulsionen, z.B. Öl-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und BCS231028 Ausland - 17 - Extrusion ohne festes Inertmaterial hergestellt. Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. Verfahren in "Spray-Drying Handbook" 3rd ed.1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff, "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S.8-57. Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. Die agrochemischen Zubereitungen enthalten in der Regel 0.1 bis 99 Gew.-%, insbesondere 0.1 bis 95 Gew.-%, erfindungsgemäße Verbindungen. In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0.05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Beispiele für Formulierungshilfsmittel sind unter anderem in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998) beschrieben. Die Verbindungen der Formel (I) oder deren Salze können als solche oder in Form ihrer Zubereitungen (Formulierungen) mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Nematiziden, Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder Wachstumsregulatoren kombiniert eingesetzt werden, z.B. als Fertigformulierung oder als Tankmischungen. Die Kombinationsformulierungen können dabei auf Basis der obengenannten Formulierungen hergestellt werden, wobei die physikalischen Eigenschaften und Stabilitäten der zu kombinierenden Wirkstoffe zu berücksichtigen sind. BCS231028 Ausland - 18 - Von besonderem Interesse ist die selektive Bekämpfung von Schadpflanzen in Kulturen von Nutz- und Zierpflanzen. Obgleich die erfindungsgemäßen Verbindungen (I) bereits in vielen Kulturen sehr gute bis ausreichende Selektivität aufweisen, können prinzipiell in einigen Kulturen und vor allem auch im Falle von Mischungen mit anderen Herbiziden, die weniger selektiv sind, Phytotoxizitäten an den Kulturpflanzen auftreten. Diesbezüglich sind Kombinationen erfindungsgemäßer Verbindungen (I) von besonderem Interesse, welche die Verbindungen (I) bzw. deren Kombinationen mit anderen Herbiziden oder Pestiziden und Safenern enthalten. Die Safener, welche in einem antidotisch wirksamen Gehalt eingesetzt werden, reduzieren die phytotoxischen Nebenwirkungen der eingesetzten Herbizide/Pestizide, z.B. in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Roggen, Mais, Reis, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, vorzugsweise Getreide. Die Gewichtsverhältnisse von Herbizid(mischung) zu Safener hängt im Allgemeinen von der Aufwandmenge an Herbizid und der Wirksamkeit des jeweiligen Safeners ab und kann innerhalb weiter Grenzen variieren, beispielsweise im Bereich von 200:1 bis 1:200, vorzugsweise 100:1 bis 1:100, insbesondere 20:1 bis 1:20. Die Safener können analog den Verbindungen (I) oder deren Mischungen mit weiteren Herbiziden/Pestiziden formuliert werden und als Fertigformulierung oder Tankmischung mit den Herbiziden bereitgestellt und angewendet werden. Zur Anwendung werden die in handelsüblicher Form vorliegenden Herbizid- oder Herbizid-Safener- Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Äußere Bedingungen wie Temperatur, Feuchtigkeit etc. beeinflussen zu einem gewissen Teil die Aufwandmenge der Verbindungen der Formel (I) und/oder deren Salze. Die Aufwandmenge kann dabei innerhalb weiter Grenzen variieren. Für die Anwendung als Herbizid zur Bekämpfung von Schadpflanzen liegt die Gesamtmenge an Verbindungen der Formel (I) und deren Salze vorzugsweise im Bereich von 0,001 bis 10,0 kg/ha, bevorzugt im Bereich von 0,005 bis 5 kg/ha, weiter bevorzugt im Bereich von 0,01 bis 1,5 kg/ha, insbesondere bevorzugt im Bereich von 0,05 bis 1 kg/ha. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. Bei der Anwendung von Verbindungen der Formel (I) und/oder deren Salzen als Pflanzenwachstumsregulator, beispielsweise als Halmverkürzer bei Kulturpflanzen, wie sie oben genannt worden sind, vorzugsweise bei Getreidepflanzen wie Weizen, Gerste, Roggen, Triticale, Hirse, Reis oder Mais, liegt die Gesamt-Aufwandmenge vorzugsweise im Bereich von 0,001 bis 2 kg/ha, vorzugsweise im Bereich von 0,005 bis 1 kg/ha, insbesondere im Bereich von 10 bis 500 g/ha, ganz besonders bevorzugt im Bereich von 20 bis 250 g/ha. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. BCS231028 Ausland - 19 - Die Applikation als Halmverkürzer kann in verschiedenen Stadien des Wachstums der Pflanzen erfolgen. Bevorzugt ist beispielsweise die Anwendung nach der Bestockung am Beginn des Längenwachstums. Alternativ kommt bei der Anwendung als Pflanzenwachstumsregulator auch die Behandlung des Saatguts in Frage, welche die unterschiedlichen Saatgutbeiz- und Beschichtungstechniken einschließt. Die Aufwandmenge hängt dabei von den einzelnen Techniken ab und kann in Vorversuchen ermittelt werden. Als Kombinationspartner für die Verbindungen der allgemeinen Formel (I) in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA-Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat- Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen oder als Pflanzenwuchsregulatoren wirken, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021 und dort zitierter Literatur beschrieben sind. Als bekannte Herbizide oder Pflanzenwachstumsregulatoren, die mit Verbindungen der allgemeinen Formel (I) kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (die Verbindungen sind entweder mit dem "common name" nach der International Organization for Standardization (ISO) oder mit dem chemischen Namen oder mit der Codenummer bezeichnet) und umfassen stets sämtliche Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere. Dabei sind beispielhaft eine und zum Teil auch mehrere Anwendungsformen genannt: Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen-Natrium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-Natrium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3- chlor-6-(4-chlor-2-fluor-3-methylphenyl)-5-fluorpyridin-2-carbonsäure, Aminocyclopyrachlor, Aminocyclopyrachlor-Kalium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid- dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammoniumsulfamate, Anilofos, Asulam, Asulam-Kalium, Asulam-Natrium, Atrazin, Azafenidin, Azimsulfuron, Beflubutamid, (S)-(-)- Beflubutamid, Beflubutamid-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin- Klaium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulid, Bentazon, Bentazon- Natrium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-Natium, Bipyrazone, Bispyribac, Bispyribac-Natium, Bixlozon, Bromacil, Bromacil-lithium, Bromacil-Natrium, Bromobutid, Bromofenoxim, Bromoxynil, Bromoxynilbutyrat, Bromoxynil-Kalium, Bromoxynil- heptanoat und Bromoxynil-octanoat, Busoxinon, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylat, Cafenstrol, Cambendichlor, Carbetamide, Carfentrazon, Carfentrazon- Ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamin, Chlroamben-methyl, Chloramben- methylammonium, Chloramben-Natium, Chlorbromuron, Chlorfenac, Chlorfenac-ammonium, Chlorfenac-Natium, Chlorfenprop, Chlorfenprop-methyl, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlorophthalim, Chlorotoluron, Chlorsulfuron, Chlorthal, BCS231028 Ausland - 20 - Chlorthal-dimethyl, Chlorthal-monomethyl, Cinidon, Cinidon-ethyl, Cinmethylin, exo-(+)-Cinmethylin, d.h. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, exo-(-)- Cinmethylin, d.h. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, Cinosulfuron, Clacyfos, Clethodim, Clodinafop, Clodinafop-ethyl, Clodinafop-propargyl, Clomazon, Clomeprop, Clopyralid, Clopyralid-methyl, Clopyralid-olamin, Clopyralid-Kalium, Clopyralid-tripomin, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cycloat, Cyclopyranil, Cyclopyrimorat, Cyclosulfamuron, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Cyprazin, 2,4-D (sowie die Ammonium, Butotyl, Butyl, Cholin, Diethylammonium, Dimethylammonium, Diolamin, Doboxyl, Dodecylammonium, Etexyl, Ethyl, 2-Ethylhexyl, Heptylammonium, Isobutyl, Isooctyl, Isopropyl, Isopropylammonium, Lithium, Meptyl, Methyl, Kalium, Tetradecylammonium, Triethylammonium, Triisopropanolammonium, Tripromin and Trolamin Salze davon), 2,4-DB, 2,4-DB-butyl, 2,4-DB- Dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-Kalium und 2,4-DB-Natrium, Daimuron (Dymron), Dalapon, Dalapon-Calcium, Dalapon-Magnesium, Dalapon-Natium, Dazomet, Dazomet-Natrium, n- Decanol, 7-Deoxy-D-sedoheptulose, Desmedipham, Detosyl-pyrazolat (DTP), Dicamba und seine Salze (z.B. Dicamba-biproamin, Dicamba-N,N-Bis(3-aminopropyl)methylamin, Dicamba-butotyl, Dicamba- cholin, Dicamba-Diglycolamin, Dicamba-Dimethylammonium, Dicamba-Diethanolaminemmonium, Dicamba-Diethylammonium, Dicamba-isopropylammonium, Dicamba-methyl, Dicamba- monoethanolamin, Dicamba-olamin, Dicamba-Kalium, Dicamba-Natium, Dicamba-Triethanolamin), Dichlobenil, 2-(2,4-Dichlorbenzyl)-4,4-dimethyl-1,2-oxazolidin-3-on, 2-(2,5-Dichlorbenzyl)-4,4- dimethyl-1,2-oxazolidin-3-one, Dichlorprop, Dichlorprop-butotyl, Dichlorprop-Dimethylammonium, Dichhlorprop-etexyl, Dichlorprop-ethylammonium, Dichlorprop-isoctyl, Dichlorprop-methyl, Dichlorprop-Kalium, Dichlorprop-Natrium, Dichlorprop-P, Dichlorprop-P-Dimethylammonium, Dichlorprop-P-etexyl, Dichlorprop-P-Kalium, Dichlorprop-Natrium, Diclofop, Diclofop-methyl, Diclofop-P, Diclofop-P-methyl, Diclosulam, Difenzoquat, Difenzoquat-metilsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-Natrium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb- Acetate, Diphenamid, Diquat, Diquat-Dibromid, Diquat-Dichloride, Dithiopyr, Diuron, DNOC, DNOC- Ammonium, DNOC-Kalium, DNOC-Natrium, Endothal, Endothal-Diammonium, Endothal-Dikalium, Endothal-Dinatrium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, 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-1H-tetrazol-1-yl]-phenyl]- ethansulfonamid, F-7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-1H-benzimidazol-4-yl]-1-methyl-6- (trifluormethyl)pyrimidin-2,4(1H,3H)-dion, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-Ethyl, Fenoxaprop- P-Ethyl, Fenoxasulfone, Fenpyrazone, Fenquinotrione, Fentrazamid, Flamprop, Flamprop-Isoproyl, Flamprop-Methyl, Flamprop-M-Isopropyl, Flamprop-M-Methyl, Flazasulfuron, Florasulam, Florpyrauxifen, Florpyrauxifen-benzyl, Fluazifop, Fluazifop-Butyl, Fluazifop-Methyl, Fluazifop-P, Fluazifop-P-Butyl, Flucarbazone, Flucarbazone-Natrium, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpyr, Flufenpyr-Ethyl, Flumetsulam, Flumiclorac, Flumiclorac-Pentyl, Flumioxazin, Fluometuron, BCS231028 Ausland - 21 - Flurenol, Flurenol-Butyl, -Dimethylammonium und -Methyl, Fluoroglycofen, Fluoroglycofen-Ethyl, Flupropanat, Flupropanat-Natrium, Flupyrsulfuron, Flupyrsulfuron-Methyl, Flupyrsulfuron-Methyl- Natrium, Fluridon, Flurochloridon, Fluroxypyr, Fluroxypyr-Butometyl, Fluroxypyr-Meptyl, Flurtamon, Fluthiacet, Fluthiacet-Methyl, Fomesafen, Fomesafen-Natrium, Foramsulfuron, Foramsulfuron-Natrium, Fosamine, Fosamine-Ammonium, Glufosinat, Glufosinat-Ammonium, Glufosinat-Natrium, L- Glufosinat-Ammonium, L-Glufosinat-Natrium, Glufosinat-P-Natrium, Glufosinat-P-Ammonium, Glyphosat, Glyphosat-Ammonium, Glyphosat-Isopropylammonium, Glyphosat-Diammonium, Glyphosat-Dimethylammonium, Glyphosat-Kalium, Glyphosat-Natrium, Glyphosat-Sesquinatrium und Glyphosat-Trimesium, H-9201, d.h. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl- isopropylphosphoramidothioat, Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron- Methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-Ethoxyethyl, Haloxyfop-P-Ethoxyethyl, Haloxyfop- Methyl, Haloxyfop-P-Methyl, Haloxifop-Natrium, Hexazinon, HNPC-A8169, i.e. Prop-2-yn-1-yl (2S)-2- {3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoat, HW-02, d.h. 1-(Dimethoxyphosphoryl)-ethyl- (2,4-dichlorphenoxy)acetat, Hydantocidin, Icafolin, Icafolin-Methyl, Imazamethabenz, Imazamethabenz- Methyl, Imazamox, Imazamox-Ammonium, Imazapic, Imazapic-Ammonium, Imazapyr, Imazapyr- Isopropylammonium, Imazaquin, Imazaquin-Ammonium, Imazaquin-Methyl, Imazethapyr, Imazethapyr- Ammonium, Imazosulfuron, Indanofan, Indaziflam, Indolauxipyr, Iodosulfuron, Iodosulfuron-Methyl, Iodosulfuron-Methyl-Natrium, Ioxynil, Ioxynil-Lithium, -Octanoat, -Kalium und Natrium, Ipfencarbazon, Iptriazopyrid, i.e. 3-[(Isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5- (trifluormethyl)[1,2,4]triazolo-[4,3-a]pyridin-8-carboxamid, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Karbutilat, KUH-043, d.h. 3-({[5-(Difluormethyl)-1-methyl-3-(trifluormethyl)-1H-pyrazol-4- yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazol, Ketospiradox, Ketospiradox-Kalium, Lactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, -Dimethylammonium, -Diolamin, -2- Ethylhexyl, -Ethyl, -Isobutyl, Isoctyl, -Isopropyl, -Isopropylammonium, -Methyl, Olamin, -Kalium, – Natrium und -Trolamin, MCPB, MCPB-Methyl, -Ethyl und -Natrium, Mecoprop, Mecoprop-Butotyl, Mecoprop- dimethylammonium, Mecoprop-Diolamin, Mecoprop-Etexyl, Mecoprop-Ethadyl, Mecoprop- Isoctyl, Mecoprop-Methyl, Mecoprop-Kalium, Mecoprop-Natrium, und Mecoprop-Trolamin, Mecoprop- P, Mecoprop-P-Butotyl, -Dimethylammonium, -2-Ethylhexyl und -Kalium, Mefenacet, Mefluidid, Mefluidid-Diolamin, Mefluidid-Kalium, Mesosulfuron, Mesosulfuron-Methyl, Mesosulfuron-Natrium, Mesotrion, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methabenzthiazuron, Methiopyrsulfuron, Methiozolin, Methyl isothiocyanat, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metproxybicyclon, Metribuzin, Metsulfuron, Metsulfuron-Methyl, Molinat, Monolinuron, Monosulfuron, Monosulfuron-Methyl, MT-5950, d.h. N-[3- Chlor-4-(1-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, Napropamid, NC-310, i.e. 4-(2,4- Dichlorbenzoyl)-1-methyl-5-benzyloxypyrazol, 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, BCS231028 Ausland - 22 - Phenmedipham, Phenmedipham-Ethyl, Picloram, Picloram-dimethylammonium, Picloram-Etexyl, Picloram-Isoctyl, Picloram-Methyl, Picloram-Olamin, Picloram-Kalium, Picloram-Triethylammonium, Picloram-Tripromin, Picloram-Trolamin, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron-Methyl, Prodiamine, Profoxydim, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone- Natrium, Propyrisulfuron, Propyzamid, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen- Ethyl, Pyraquinat, Pyrasulfotol, Pyrazolynat (Pyrazolat), Pyrazosulfuron, Pyrazosulfuron-Ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-Isopropyl, Pyribambenz-Propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridat, Pyriftalid, Pyriminobac, Pyriminobac-Methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac- Natrium, Pyroxasulfon, Pyroxsulam, Quinclorac, Quinclorac-Dimethylammonium, Quinclorac-Methyl, Quinmerac, Quinoclamin, Quizalofop, Quizalofop-Ethyl, Quizalofop-P, Quizalofop-P-Ethyl, Quizalofop- P-Tefuryl, QYM201, i.e.1-{2-Chlor-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]- 6-(trifluormethyl)phe-nyl}piperidin-2-on, Rimisoxafen, Rimsulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron-Methyl, Sulfosulfuron, , SYP-249, d.h. 1-Ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chlor-4- (trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e.1-[7-Fluor-3-oxo-4-(prop-2-in-1-yl)-3,4-dihydro- 2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trichloressigsäure) und seine Salze, z.B. TCA-ammonium, TCA-Calcium, TCA-Ethyl, TCA-Magnesium, TCA-Natrium, Tebuthiuron, Tefuryltrione, Tembotrion, Tepraloxydim, Terbacil, Terbucarb, Terbumeton, Terbuthylazine, Terbutryn, Tetflupyrolimet, Thaxtomin, Thenylchlor, Thiazopyr, Thiencarbazone, Thiencarbazon-Methyl, Thifensulfuron, Thifensulfuron-Methyl, Thiobencarb, Tiafenacil, Tolpyralat, Topramezon, Tralkoxydim, Triafamon, Tri-allat, Triasulfuron, Triaziflam, Tribenuron, Tribenuron- Methyl, Triclopyr, Triclopyr-Butotyl, Triclopyr-Cholin, Triclopyr-Ethyl, Triclopyr-Triethylammonium, Trietazine, Trifloxysulfuron, Trifloxysulfuron-Natrium, Trifludimoxazin, Trifluralin, Triflusulfuron, Triflusulfuron-Methyl, Tritosulfuron, Harnstoffsulfat, Vernolat, XDE-848, ZJ-0862, d.h.3,4-Dichlor-N- {2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, 3-(2-Chlor-4-fluor-5-(3-methyl-2,6-dioxo-4- trifluormethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5- carbonsäuremethylester, 3-(2-Chlor-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6- dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5-carbonsäureethylester, 3-(2-Chlor- 4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5- dihydroisoxazol-5-carbonsäure, 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-methylpyridazin-3(2H)-on, 2-({2-[(2- Methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dion, (5-Hydroxy-1-methyl- 1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)methanon, 1-Methyl-4- [(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl propan-1- sulfonat, 4-{2-Chlor-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl- BCS231028 Ausland - 23 - 1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazol-4-carboxylat; Cyanomethyl-4-amino-3-chlor-5-fluor-6-(7- fluor-1H-indol-6-yl)pyridin-2-carboxylat, Prop-2-yn-1-yl 4-amino-3-chlor-5-fluor-6-(7-fluor-1H-indol- 6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2- carboxylat, Benzyl-4-amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2-carboxylat, Ethyl-4- amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor- 6-(7-fluor-1-isobutyryl-1H-indol-6-yl)pyridin-2-carboxylat, Methyl 6-(1-acetyl-7-fluor-1H-indol-6-yl)- 4-amino-3-chlor-5-fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-6-[1-(2,2-dimethylpropanoyl)-7- fluor-1H-indol-6-yl]-5-fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-[7-fluor-1- (methoxyacetyl)-1H-indol-6-yl]pyridin-2-carboxylat, Kalium 4-amino-3-chlor-5-fluor-6-(7-fluor-1H- indol-6-yl)pyridin-2-carboxylat, Natrium-4-amino-3-chlor-5-fluor-6-(7-fluor-1H-indol-6-yl)pyridin-2- carboxylat, Butyl-4-amino-3-chlor-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylat, 4-Hydroxy- 1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-on, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4- hydroxy-1-methylimidazolidin-2-on, 3-[5-Chlor-4-(trifluormethyl)pyridin-2-yl]-4-hydroxy-1- methylimidazolidin-2-on, 4-Hydroxy-1-methoxy-5-methyl-3-[4-(trifluormethyl)pyridin-2- yl]imidazolidin-2-on, 6-[(2-Hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2- methylphenyl)chinazolin-2,4(1H,3H)-dion, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en- 1-yl)carbonyl]-1-methylchinazolin-2,4(1H,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), 1-(2-Carboxyethyl)-4- (pyridazin-3-yl)pyridazin-1-iumsalz (mit passenden Anionen wie z.B. Chlorid, Acetat oder Trifluoracetat), 4-(Pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat), 4-(Pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-iumsalz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat), 1-(2-Carboxyethyl)-4-(1,3-thiazol-2- yl)pyridazin-1-iumsalz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat), 1-(2- Carboxyethyl)-4-(1,3,4-thiadiazol-2-yl)pyridazin-1-iumsalz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat), Methyl (2R)-2-{[(E)-({2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methyliden)amino]oxy}propanoat, Methyl (2S)- 2-{[(E)-({2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)- yl]phenyl}methyliden)amino]oxy}propanoat, Methyl (2R/S)-2-{[(E)-({2-chlor-4-fluor-5-[3-methyl-2,6- dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methyliden)amino]oxy}propanoat, (E)- 2-(Trifluormethyl)benzaldehyd-O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxim, 2-Fluor- N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluormethyl)benzamid, (2R)-2-[(4- Amino-3,5-dichlor-6-fluor-2-pyridyl)oxy]propancarbonsäure, 2-Ethoxy-2-oxoethyl-1-{2-chlor-4-fluor- 5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)- yl]phenoxy}cyclopropancarboxylat, 2-Methoxy-2-oxoethyl-1-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropancarboxylat, {[(1-{2-Chlor-4-fluor- 5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)- yl]phenoxy}cyclopropyl)carbonyl]oxy}essigsäure, 2-(2-Brom-4-chlorbenzyl)-4,4-dimethyl-1,2- BCS231028 Ausland - 24 - oxazolidin-3-on, Methyl 3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6- dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazol-6a-carboxylat, Ethyl 3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)- yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazol-6a-carboxylat, Methyl-3-{2-chlor-4-fluor- 5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-6-methyl-3a,4,5,6- tetrahydro-6aH-cyclopenta[d][1,2]oxazol-6a-carboxylat, 3-{2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH- cyclopenta[d][1,2]oxazol-6a-carbonsäure, 3-{2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)- 3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazol-6a- carbonsäure Abscisinsäure und verwandte Analoga [z.B. (2Z,4E)-5-[6-Ethynyl-1-hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-diensäure, methyl-(2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6- dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoat, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-diensäure, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-diensäure, methyl (2E,4E)-5-(1-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoat, (2Z,4E)-5-(2-hydroxy-1,3- dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-diensäure], Acibenzolar, Acibenzolar-S- methyl, S-Adenosylhomocystein, Allantoin, 2-Aminoethoxyvinylglycin (AVG), Aminooxyessigsäure and verwandte Ester [z.B. (Isopropyliden)-aminooxyessigsäure-2-(methoxy)-2-oxoethylester, (Isopropyliden)-aminooxyessigsäure-2-(hexyloxy)-2-oxoethylester, (Cyclohexyliden)- aminooxyessigsäure-2-(isopropyloxy)-2-oxoethylester], 1-Aminocycloprop-1-ylcarbonsäure N-Methyl- 1-aminocyclopropyl-1-carbonsäure, 1-Aminocyclopropyl-1-carbonsäureamid, substituierte 1- Aminocyclopropyl-1-carbonsäurederivate wie sie in DE3335514, EP30287, DE2906507 oder US5123951 beschrieben werden, 1-Aminocyclopropyl-1-hydroxamsäure, 5-Aminolevulinsäure, Ancymidol, 6- Benzylaminopurin, Bikinin, Brassinolid, Brassinolide-ethyl, L-Canalin, Catechin und catechine (z.B. (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-chromen-3,5,7-triol), Chitooligosaccharides (CO; COs unterscheiden sich von LCOs dadurch, daß ihnen die für LCOs charakteristische Fettsäureseitenkette fehlt. COs, in manchen Fällen als N-Acetylchitooligosaccharide bezeichnet, sind auch aus GlcNAc- Einheiten aufgebaut, aber haben Seitenketten, durch die sies ich von Chitinmolekülen unterscheiden [(C8H13NO5)n, CAS No.1398-61-4] und chitosan Moleküle [(C5H11NO4)n, CAS No.9012-76-4]), Chitin- artige Verbindungen, Chlormequat chloride, Cloprop, Cyclanilide, 3-(Cycloprop-1-enyl)propionsäure, 1- [2-(4-Cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexancarbonsäure, 1-[2-(4-Cyano-3- cyclopropylphenyl)acetamido]cyclohexancarbonsäure, 1-Cyclopropenylmethanol, Daminozid, Dazomet, Dazomet-Natrium, n-Decanol, Dikegulac, Dikegulac-Natrium, Endothal, Endothal-di-Kalium, -di- Natrium, und mono(N,N-dimethylalkylammonium), Ethephon, 1-Ethylcyclopropen,Flumetralin, Flurenol, Flurenol-butyl, Flurenol-methyl, Flurprimidol, Forchlorfenuron, Gibberellinsäure, Inabenfid, Indol-3-essigsäure (IAA), 4-Indol-3-ylbuttersäure, Isoprothiolan, Probenazole, Jasmonsäure, Jasmonsäureester oder andere Derivate (z.B. Jasmonsäuremethylester, Jasmonsäureethylester), BCS231028 Ausland - 25 - Lipochitooligosaccharide (LCO, in manchen Fällen auch als Symbiotische Nodulationssignale (Nod oder Nod Faktoren) oder als Myc Faktoren bezeichnet, bestehen aus einem Oligosacchariderückgrat aus β-l,4verknüpften -N-Acetyl-D-Glucosaminresten (“GlcNAc”) mit einer N-verknüpften Fettsäureseitenkette, die am nicht reduzierenden Ende ankondensiert ist. Wie aus der Literatur zu entnehmen ist, unterscheiden sich LCOs in der Zahl an GlcNAc-EInheiten in der Rückgratstruktur, in der Länge und dem Sättigungsgrad der Fettsäurekette sowie in der Substitution der reduzierenden und nicht- reduzierenden Zuckereinheiten), Linoleinsäure oder ihre Derivate, Linolensäure oder ihre Derivate, Maleinsäurehydrazid, Mepiquatchlorid, Mepiquatpentaborat, 1-Methylcyclopropen, 3- Methylcyclopropen, Methoxyvinylglycin (MVG), 3’-Methylabscisinsäure, 1-(4-Methylphenyl)-N-(2- oxo-1-propyl-1,2,3,4-tetrahydrochinolin-6-yl)methansulfonamid und verwandte substituierte (Tetrahydrochinolin-6-yl)methansulfonamide, (3E,3aR,8bS)-3-({[(2R)-4-Methyl-5-oxo-2,5- dihydrofuran-2-yl]oxy}methylen)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-on und verwandte Laktone wie sie in EP2248421 beschrieben sind, 2-(1-Naphthyl)acetamid, 1-Naphthylessigsäure, 2- Naphthyloxyessigsäure, Nitrophenolatmischung, 4-Oxo-4[(2-phenylethyl)amino]buttersäure, Paclobutrazol, 4-Phenylbuttersäure and ihre Salze (z.B. Natrium-4-phenylbutanoat, Kalium-4- phenylbutanoat), Phenylalanine, N-Phenylphthalamsäure, Prohexadione, Prohexadion-Calcium, , 1-n- Propylcyclopropen, Putrescin, Prohydrojasmon, Rhizobitoxin, Salicylsäure und Salicyclsäuremethylester, Sarcosin, Natriumcycloprop-1-en-1-ylacetat, Natriumcycloprop-2-en-1-ylacetat, Natrium-3-(cycloprop- 2-en-1-yl)propanoat, Natrium-3-(cycloprop-1-en-1-yl)propanoat, Sidefungin, Spermidin, Spermine, Strigolactone, Tecnazene, Thidiazuron, Triacontanol, Trinexapac, Trinexapac-ethyl, Tryptophan, Tsitodef, Uniconazol, Uniconazol-P, 2-Fluor-N-(3-methoxyphenyl)-9H-purin-6-amin, 2-Chlor-N-(3- methoxyphenyl)-9H-purin-6-amin. Ebenfalls als Kombinationspartner für die erfindungsgemäßen Verbindungen der Formel (I) kommen beispielsweise die folgenden Safener in Frage: S1) Verbindungen der Formel (S1), O (RA 1)nA
Figure imgf000026_0001
wobei die Symbole und Indizes folgende Bedeutungen haben: nA ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; RA1 ist Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, Nitro oder (C1-C4)Haloalkyl; WA ist ein unsubstituierter oder substituierter divalenter heterocyclischer Rest aus der Gruppe der teilungesättigten oder aromatischen Fünfring-Heterocyclen mit 1 bis 3 Heteroringatomen aus der Gruppe
Figure imgf000027_0003
Figure imgf000027_0009
Figure imgf000027_0001
Figure imgf000027_0002
Figure imgf000027_0005
Figure imgf000027_0007
Figure imgf000027_0008
BCS231028 Ausland - 26 - N und O, wobei mindestens ein N-Atom und höchstens ein O-Atom im Ring enthalten ist, vorzugsweise ein Rest aus der Gruppe (WA1) bis (WA5),
Figure imgf000027_0006
Figure imgf000027_0004
R 2 ist ORA3, SRA der NRA3R der ein ge gter oder un ttigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S1) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (C1-C4)Alkyl, (C1-C4)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel ORA3, NHRA4 oder N(CH3)2, insbesondere der Formel ORA3; RA3 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen; RA4 ist Wasserstoff, (C1-C6)Alkyl, (C1-C6)Alkoxy oder substituiertes oder unsubstituiertes Phenyl; RA 5 ist H, (C1-C8)Alkyl, (C1-C8)Haloalkyl, (C1-C4)Alkoxy(C1-C8)Alkyl, Cyano oder COORA 9, worin RA9 Wasserstoff, (C1-C8)Alkyl, (C1-C8)Haloalkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C1-C6)Hydroxyalkyl, (C3-C12)Cycloalkyl oder Tri-(C1-C4)-alkyl-silyl ist; RA6, RA7, RA8 sind gleich oder verschieden Wasserstoff, (C1-C8)Alkyl, (C1-C8)Haloalkyl, (C3- C12)Cycloalkyl oder substituiertes oder unsubstituiertes Phenyl; RA 10 ist H, (C3-C12)Cycloalkyl, substituiertes oder unsubstituiertes Phenyl oder substituiertes oder unsubstituiertes Heteroaryl; vorzugsweise: a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (S1a), vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl- 2-pyrazolin-3-carbonsäure, 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäureethylester (S1-1) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind; b) Derivate der Dichlorphenylpyrazolcarbonsäure (S1b), vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S1-2), 1-(2,4-Di- chlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester (S1-3), 1-(2,4-Dichlor- BCS231028 Ausland - 27 - phenyl)-5-(1,1-dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S1-4) und verwandte Verbindungen, wie sie in EP-A-333131 und EP-A-269806 beschrieben sind; c) Derivate der 1,5-Diphenylpyrazol-3-carbonsäure (S1c), vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (S1-5), 1-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (S1-6) und verwandte Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind; d) Verbindungen vom Typ der Triazolcarbonsäuren (S1d), vorzugsweise Verbindungen wie Fenchlorazol(-ethylester), d.h.1-(2,4-Dichlorphenyl)-5-trichlormethyl-(1H)-1,2,4-triazol-3-carbonsäure- ethylester (S1-7), und verwandte Verbindungen wie sie in EP-A-174562 und EP-A-346620 beschrieben sind; e) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure oder der 5,5- Diphenyl-2-isoxazolin-3-carbonsäure (S1e), vorzugsweise Verbindungen wie 5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (S1-8) oder 5-Phenyl-2-isoxazolin-3- carbonsäureethylester (S1-9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-3-carbonsäure (S1-10) oder 5,5-Diphenyl-2-isoxazolin-3- carbonsäureethylester (S1-11) ("Isoxadifen-ethyl") oder -n-propylester (S1-12) oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3-carbonsäureethylester (S1-13), wie sie in der Patentanmeldung WO-A-95/07897 beschrieben sind. f) Verbindungen vom Typ der Triazolyloxyessigsäurederivate (S1f), vorzugsweise Verbindungen wie Methyl-{[1,5-bis(4-chlor-2-fluorphenyl)-1H-1,2,4-triazol-3-yl]oxy}acetat (S1-14) oder {[1,5-Bis(4- chlor-2-fluorphenyl)-1H-1,2,4-triazol-3-yl]oxy}essigsäure (S1-15) oder Methyl-{[5-(4-chlor-2- fluorphenyl)-1-(2,4-difluorphenyl)-1H-1,2,4-triazol-3-yl]oxy}acetat (S1-16) oder {[5-(4-Chlor-2- fluorphenyl)-1-(2,4-difluorphenyl)-1H-1,2,4-triazol-3-yl]oxy}essigsäure (S1-17) oder Methyl-{[1-(4- chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1H-1,2,4-triazol-3-yl]oxy}acetat (S1-18) oder {[1-(4-chlor-2- fluorphenyl)-5-(2,4-difluorphenyl)-1H-1,2,4-triazol-3-yl]oxy}essigsäure (S1-19), wie sie in der Patentanmeldung WO2021/105101 beschrieben sind. S2) Chinolinderivate der Formel (S2), nB
Figure imgf000028_0001
wobei die Symbole und Indizes folgende Bedeutungen haben: BCS231028 Ausland - 28 - RB1 ist Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, Nitro oder (C1-C4)Haloalkyl; nB ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; RB2 ist ORB3, SRB3 oder NRB3RB4 oder ein gesättigter oder ungesättigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S2) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (C1-C4)Alkyl, (C1-C4)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel ORB3, NHRB4 oder N(CH3)2, insbesondere der Formel ORB3; RB3 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen; RB4 ist Wasserstoff, (C1-C6)Alkyl, (C1-C6)Alkoxy oder substituiertes oder unsubstituiertes Phenyl; TB ist eine (C1 oder C2)-Alkandiylkette, die unsubstituiert oder mit einem oder zwei (C1- C4)Alkylresten oder mit [(C1-C3)-Alkoxy]-carbonyl substituiert ist; vorzugsweise: a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise (5-Chlor-8- chinolinoxy)essigsäure-(1-methylhexyl)ester ("Cloquintocet-mexyl") (S2-1), (5-Chlor-8- chinolinoxy)essigsäure-(1,3-dimethyl-but-1-yl)ester (S2-2), (5-Chlor-8-chinolinoxy)essigsäure-4- allyloxy-butylester (S2-3), (5-Chlor-8-chinolin-oxy)essigsäure-1-allyloxy-prop-2-ylester (S2-4), (5- Chlor-8-chinolinoxy)essigsäure-ethylester (S2-5), (5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6), (5-Chlor-8-chinolinoxy)essigsäureallylester (S2-7), (5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden- iminoxy)-1-ethylester (S2-8), (5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-1-ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86750, EP-A-94349 und EP-A-191736 oder EP-A-0492366 beschrieben sind, sowie (5-Chlor-8-chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A- 2002/34048 beschrieben sind; b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, (5-Chlor- 8-chinolinoxy)malonsäurediallylester, (5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0582198 beschrieben sind.
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RD3 O
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(R O
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D 4 )mD
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BCS231028 Ausland - 30 - RD1 ist CO-NRD5RD6 oder NHCO-RD7; RD2 ist Halogen, (C1-C4)-Haloalkyl, (C1-C4)-Haloalkoxy, Nitro, (C1-C4)-Alkyl, (C1-C4)-Alkoxy, (C1- C4)-Alkylsulfonyl, (C1-C4)-Alkoxycarbonyl oder (C1-C4)-Alkylcarbonyl; RD3 ist Wasserstoff, (C1-C4)Alkyl, (C2-C4)Alkenyl oder (C2-C4)-Alkinyl; RD4 ist 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 oder (C1-C4)Alkylcarbonyl; RD5 ist Wasserstoff, (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C5-C6)- Cycloalkenyl, Phenyl oder 3- bis 6-gliedriges Heterocyclyl enthaltend vD Heteroatome aus der Gruppe Stickstoff, Sauerstoff und Schwefel, wobei die sieben letztgenannten Reste durch vD Substituenten aus der Gruppe Halogen, (C1-C6)Alkoxy, (C1-C6)Haloalkoxy, (C1-C2)Alkylsulfinyl, (C1-C2)Alkylsulfonyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Alkylcarbonyl und Phenyl und im Falle cyclischer Reste auch (C1-C4) Alkyl und (C1-C4)Haloalkyl substituiert sind; RD6 ist Wasserstoff, (C1-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei die drei letztgenannten Reste durch vD Reste aus der Gruppe Halogen, Hydroxy, (C1-C4)Alkyl, (C1-C4)Alkoxy und (C1- C4)Alkylthio substituiert sind, oder RD5 und RD6 gemeinsam mit dem dem sie tragenden Stickstoffatom einen Pyrrolidinyl- oder Piperidinyl-Rest bilden; RD7 ist Wasserstoff, (C1-C4)Alkylamino, Di-(C1-C4)alkylamino, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch vD Substituenten aus der Gruppe Halogen, (C1-C4)Alkoxy, (C1-C6)Haloalkoxy und (C1-C4)Alkylthio und im Falle cyclischer Reste auch (C1-C4)Alkyl und (C1-C4)Haloalkyl substituiert sind; nD ist 0, 1 oder 2; mD ist 1 oder 2; vD ist 0, 1, 2 oder 3; davon bevorzugt sind Verbindungen vom Typ der N-Acylsulfonamide, z.B. der nachfolgenden Formel (S4a), die z. B. bekannt sind aus WO-A-97/45016 O O O (R 4 D )mD N N
Figure imgf000031_0001
BCS231028 Ausland - 31 - worin RD7 (C1-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch vD Substituenten aus der Gruppe Halogen, (C1-C4)Alkoxy, (C1-C6)Haloalkoxy und (C1-C4)Alkylthio und im Falle cyclischer Reste auch (C1-C4)Alkyl und (C1-C4)Haloalkyl substituiert sind; RD4 Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3; mD 1 oder 2; vD ist 0, 1, 2 oder 3 bedeutet; sowie Acylsulfamoylbenzoesäureamide, z.B. der nachfolgenden Formel (S4b), die z.B. bekannt sind aus WO-A-99/16744, R 5 D O O 4 z.B. solche worin
Figure imgf000032_0002
RD5 = Cyclopropyl und (RD4) = 2-OMe ist ("Cyprosulfamide", S4-1), RD5 = Cyclopropyl und (RD4) = 5-Cl-2-OMe ist (S4-2), RD5 = Ethyl und (RD4) = 2-OMe ist (S4-3), RD 5 = Isopropyl und (RD 4) = 5-Cl-2-OMe ist (S4-4) und RD 5 = Isopropyl und (RD 4) = 2-OMe ist (S4-5). sowie Verbindungen vom Typ der N-Acylsulfamoylphenylharnstoffe der Formel (S4c), die z.B. bekannt sind aus der EP-A-365484, R 8 D O O O (R 4 D )mD worin
Figure imgf000032_0001
RD8 und RD9 unabhängig voneinander Wasserstoff, (C1-C8)Alkyl, (C3-C8)Cycloalkyl, (C3-C6)Alkenyl, (C3-C6)Alkinyl, RD4 Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3 BCS231028 Ausland - 32 - mD 1 oder 2 bedeutet; beispielsweise 1-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylharnstoff, 1-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylharnstoff, 1-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylharnstoff. S5) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch-aliphatischen Carbonsäurederivate (S5), z.B. 3,4,5-Triacetoxybenzoesäureethylester, 3,5-Di-methoxy-4- hydroxybenzoesäure, 3,5-Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2- Hydroxyzimtsäure, 2,4-Dichlorzimtsäure, wie sie in der WO-A-2004/084631, WO-A-2005/015994, WO- A-2005/016001 beschrieben sind. S6) Wirkstoffe aus der Klasse der 1,2-Dihydrochinoxalin-2-one (S6), z.B. 1-Methyl-3-(2-thienyl)- 1,2-dihydrochinoxalin-2-on, 1-Methyl-3-(2-thienyl)-1,2-dihydrochinoxalin-2-thion, 1-(2-Aminoethyl)-3- (2-thienyl)-1,2-dihydro-chinoxalin-2-on-hydrochlorid, 1-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)- 1,2-dihydrochinoxa-lin-2-on, wie sie in der WO-A-2005/112630 beschrieben sind. S7) Verbindungen der Formel (S7),wie sie in der WO-A-1998/38856 beschrieben sind H2 C AE
Figure imgf000033_0001
worin die Symbole und Indizes folgende Bedeutungen haben: RE1, RE2 sind unabhängig voneinander Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkyl, (C1- C4)Alkylamino, Di-(C1-C4)Alkylamino, Nitro; AE ist COORE3 oder COSRE4 RE3, RE4 sind unabhängig voneinander Wasserstoff, (C1-C4)Alkyl, (C2-C6)Alkenyl, (C2-C4)Alkinyl, Cyanoalkyl, (C1-C4)Haloalkyl, Phenyl, Nitrophenyl, Benzyl, Halobenzyl, Pyridinylalkyl und Alkylammonium, nE1 ist 0 oder 1 nE2, nE3 sind unabhängig voneinander 0, 1 oder 2, BCS231028 Ausland - 33 - vorzugsweise Diphenylmethoxyessigsäure, Diphenylmethoxyessigsäureethylester, Diphenyl- methoxyessigsäuremethylester (CAS-Reg.Nr.41858-19-9) (S7-1). S8) Verbindungen der Formel (S8),wie sie in der WO-A-98/27049 beschrieben sind RF2 O Worin
Figure imgf000034_0001
XF CH oder N, nF für den Fall, dass XF=N ist, eine ganze Zahl von 0 bis 4 und für den Fall, dass XF=CH ist, eine ganze Zahl von 0 bis 5 , RF1 Halogen, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, Nitro, (C1- C4)Alkylthio, (C1-C4)-Alkylsulfonyl, (C1-C4)Alkoxycarbonyl, ggf. substituiertes. Phenyl, ggf. substituiertes Phenoxy, RF2 Wasserstoff oder (C1-C4)Alkyl RF3 Wasserstoff, (C1-C8)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; bedeuten, oder deren Salze, vorzugsweise Verbindungen worin XF CH, nF eine ganze Zahl von 0 bis 2 , RF1 Halogen, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, RF2 Wasserstoff oder (C1-C4)Alkyl, RF3 Wasserstoff, (C1-C8)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist, bedeuten, oder deren Salze. BCS231028 Ausland - 34 - S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B. 1,2-Dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon (CAS-Reg.Nr. 219479-18-2), 1,2- Dihydro-4-hydroxy-1-methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr. 95855-00-8), wie sie in der WO-A-1999/000020 beschrieben sind. S10) Verbindungen der Formeln (S10a) oder (S10b) wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind O O Z 3 G RG 2 G worin
Figure imgf000035_0001
RG1 Halogen, (C1-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 YG, ZG unabhängig voneinander O oder S, nG eine ganze Zahl von 0 bis 4, RG 2 (C1-C16)Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, RG 3 Wasserstoff oder (C1-C6)Alkyl bedeutet. S11) Wirkstoffe vom Typ der Oxyimino-Verbindungen (S11), die als Saatbeizmittel bekannt sind, wie z. B. "Oxabetrinil" ((Z)-1,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitril) (S11-1), das als Saatbeiz- Safener für Hirse gegen Schäden von Metolachlor bekannt ist, "Fluxofenim" (1-(4-Chlorphenyl)-2,2,2- trifluor-1-ethanon-O-(1,3-dioxolan-2-ylmethyl)-oxim) (S11-2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und "Cyometrinil" oder "CGA-43089" ((Z)-Cyanomethoxy- imino(phenyl)acetonitril) (S11-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist. S12) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl-[(3-oxo-1H-2- benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121-04-6) (S12-1) und verwandte Verbindungen aus WO-A-1998/13361. S13) Eine oder mehrere Verbindungen aus Gruppe (S13): "Naphthalic anhydrid" (1,8-Naphthalindicarbonsäureanhydrid) (S13-1), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, "Fenclorim" (4,6-Dichlor-2-phenylpyrimidin) (S13-2), das als BCS231028 Ausland - 35 - Safener für Pretilachlor in gesätem Reis bekannt ist, "Flurazole" (Benzyl-2-chlor-4-trifluormethyl-1,3- thiazol-5-carboxylat) (S13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist, "CL 304415" (CAS-Reg.Nr. 31541-57-8) (4-Carboxy-3,4-dihydro-2H-1- benzopyran-4-essigsäure) (S13-4) der Firma American Cyanamid, das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist, "MG 191" (CAS-Reg.Nr.96420-72-3) (2-Dichlormethyl-2-methyl-1,3- dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist, "MG-838" (CAS-Reg.Nr. 133993-74-5) (2-propenyl 1-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). S14) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B. "Dimepiperate" oder "MY-93" (S-1-Methyl-1-phenylethyl- piperidin-1-carbothioat), das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist, "Daimuron" oder "SK 23" (1-(1-Methyl-1-phenylethyl)-3-p-tolyl-harnstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist, "Cumyluron" = "JC-940" (3-(2- Chlorphenylmethyl)-1-(1-methyl-1-phenyl-ethyl)harnstoff, siehe JP-A-60087254), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4- methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "CSB" (1- Brom-4-(chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091-06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist. S15) Verbindungen der Formel (S15) oder deren Tautomere wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind O R 2 R 4 worin
Figure imgf000036_0001
RH1 einen (C1-C6)Haloalkylrest bedeutet und RH2 Wasserstoff oder Halogen bedeutet und RH3, RH4 unabhängig voneinander Wasserstoff, (C1-C16)Alkyl, (C2-C16)Alkenyl oder (C2-C16)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe 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, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, oder (C3-C6)Cycloalkyl, (C4-C6)Cycloalkenyl, (C3- BCS231028 Ausland - 36 - C6)Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe 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, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, bedeutet oder RH3 (C1-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet und RH4 Wasserstoff oder (C1-C4)-Alkyl bedeutet oder RH3 und RH4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen heterocyclischen Ring, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1- C4)Alkoxy, (C1-C4)Haloalkoxy und (C1-C4)Alkylthio substituiert ist, bedeutet. S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z.B. (2,4-Dichlorphenoxy)essigsäure (2,4-D), (4-Chlorphenoxy)essigsäure, (R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop), 4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB), (4- Chlor-o-tolyloxy)-essigsäure (MCPA), 4-(4-Chlor-o-tolyloxy)buttersäure, 4-(4-Chlorphenoxy)- buttersäure, 3,6-Dichlor-2-methoxybenzoesäure (Dicamba), 1-(Ethoxycarbonyl)ethyl-3,6-dichlor-2- methoxybenzoat (Lactidichlor-ethyl). Die nachstehenden Beispiele erläutern die Erfindung. A. Chemische Beispiele Synthese von 2-Chlor-4-cyclopropyl-3-(S-methylsulfonimidoyl)-N-(1,3,4-oxadiazol-2-yl)benzamid (Tabellenbeispiel Nr.1-4): Zu einer Lösung von 266,9 mg (0.79 mmol) 2-Chlor-4-cyclopropyl-3-(methylsulfanyl)-N-(1,3,4- oxadiazol-2-yl)benzamid in 4 ml Methanol wurden nacheinander 123,8 mg (1.58 mmol) Ammoniumcarbamat und portionsweise 638,3 mg (1.98 mmol) Iodosobenzoldiacetat zugegeben. Das Reaktionsgemisch wurde 20 Stunden bei Raumtemperatur gerührt und anschließend am BCS231028 Ausland - 37 - Rotationsverdampfer weitgehend vom Lösungsmittel befreit. Nach chromatographischer Reinigung des Rückstands erhielt man 106,7 mg (37,1%) des gewünschten Produkts. Synthese von 2-Chlor-4-cyclopropyl-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamid: Zu 0,50 g (1,82 mmol) 2-Chlor-4-cyclopropyl-3-(methylsulfanyl)benzoesäure, 0,17 g (2,00 mmol) 1,3,4- Oxadiazol-2-amin und 3,0 ml 3-Methylpyridin gab man 0,30 g (3,64 mmol) 1-Methyl-1H-imidazol und kühlte das Gemisch auf 0°C. Bei dieser Temperatur tropfte man 0,35 g (2,91 mmol) Thionylchlorid zu, ließ das Reaktionsgemisch langsam auf Raumtemperatur kommen und rührte 24h bei dieser Temperatur. Zur Aufarbeitung gab man gesättigte wässrige Natriumchloridlösung und Dichlormethan zu, trennte die organische Phase ab und entfernte das Lösungsmittel im Vakuum. Nach chromatographischer Reinigung des Rückstands erhielt man 267 mg (43,6%) des gewünschten Produkts als farblosen Feststoff. Synthese von 2-Methyl-3-(S-methylsulfonimidoyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluormethyl)benzamid (Tabellenbeispiel Nr.1-2): Zu einer Lösung von 130,0 mg (0.41 mmol) 2-Methyl-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)-4- (trifluormethyl)benzamid in 2 ml Methanol wurden nacheinander 64,0 mg (0.82 mmol) Ammoniumcarbamat und portionsweise 330,0 mg (1.02 mmol) Iodosobenzoldiacetat zugegeben. Das Reaktionsgemisch wurde 20 Stunden bei Raumtemperatur gerührt und anschließend am Rotationsverdampfer weitgehend vom Lösungsmittel befreit. Nach chromatographischer Reinigung des Rückstands erhielt man 50,0 mg (33,3%) des gewünschten Produkts. Synthese von 4-(Difluormethyl)-2-ethyl-3-(S-ethylsulfonimidoyl)-N-(1,3,4-oxadiazol-2-yl)benzamid (Tabellenbeispiel Nr.1-6): Zu einer Lösung von 185 mg (0.57 mmol) 4-(Difluormethyl)-2-ethyl-3-(ethylsulfanyl)-N-(1,3,4- oxadiazol-2-yl)benzamid in 15 ml Methanol wurden nacheinander 88.2 mg (1.13 mmol) Ammoniumcarbamat und portionsweise 455 mg (1.41 mmol) Iodosobenzoldiacetat zugegeben. Das Reaktionsgemisch wurde anschließend 20 Stunden bei Raumtemperatur gerührt. Zur Aufarbeitung wurde wenig Wasser und anschließend Natriumbisulfit zugegeben. Das Gemisch wurde am Rotationsverdampfer weitgehend vom Lösungsmittel befreit. Der Rückstand wurde mit Dichlormethan und wenig Wasser aufgenommen. Nach der Phasentrennung wurde die organische Phase am Rotationsverdampfer vom Lösungsmittel befreit. Der Rückstand wurde chromatographisch gereinigt, wobei 25.2 mg sauberes Produkt gewonnen wurden. Synthese von 4-(Difluormethyl)-2-ethyl-3-(ethylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamid: 634 mg (2.44 mmol) 4-(Difluormethyl)-2-ethyl-3-(ethylsulfanyl)benzoesäure wurden in 40 ml trockenem Tetrahydrofuran auf eine Temperatur von 55 °C bis 60 °C erhitzt, anschließend wurden 592 mg (3.65 mmol) 1,1´-Carbonyldiimidazol portionsweise zugegeben. Das Reaktionsgemisch wurde drei Stunden BCS231028 Ausland - 38 - unter Rückfluss gerührt. Danach wurde der Inhalt auf Raumtemperatur abgekühlt und es wurden 296 mg (1.83 mmol) 1,1´-Carbonyldiimidazol portionsweise zugegeben. Die Mischung wurde danach weitere vier Stunden unter Rückfluss gerührt. Im nächsten Schritt wurden bei Raumtemperatur nacheinander 327 mg (95 Gew.-% Reinheit; 3.65 mmol) 1,3,4-Oxadiazol-2-amin, 10 ml Acetonitril und 556 mg (3.65 mmol) 1,8-Diazabicyclo(5.4.0)undec-7-en zugegeben. Der Kolbeninhalt wurde anschließend drei Tage bei Raumtemperatur gerührt. Zur Vervollständigung der Reaktion wurde das Gemisch weitere fünf Stunden bei 50 °C gerührt, anschließend wurden 164 mg (95 Gew.-% Reinheit; 1.83 mmol) 1,3,4-Oxadiazol-2- amin und 278 mg (1.83 mmol) 1,8-Diazabicyclo(5.4.0)undec-7-en zugegeben. Der Inhalt wurde weitere zwei Tage bei Raumtemperatur gerührt. Zur Aufarbeitung wurde der Inhalt am Rotationsverdampfer vom Lösungsmittel weitgehend befreit. Der Rückstand wurde mit Wasser und Dichlormethan versetzt. Nach der Phasentrennung wurde die wässrige Phase mit verdünnter Salzsäure auf einen pH = 3 eingestellt. Danach wurde die wässrige Phase mit Dichlormethan extrahiert. Anschließend wurden die vereinigten organischen Phasen am Rotationsverdampfer vom Lösungsmittel befreit. Der Rückstand wurde chromatographisch gereinigt, wobei 505 mg sauberes Produkt erhalten wurden. Die in den nachfolgenden Tabellen aufgeführten Beispiele wurden analog oben genannten Methoden hergestellt beziehungsweise sind analog oben genannten Methoden erhältlic
Figure imgf000039_0003
h. Die in der nachfolgenden Tabelle aufgeführten Verbindungen sind ganz besonders bevorzugt. Die verwendeten Abkürzungen bedeuten: Me = Methyl Et = Ethyl c-Pr = Cyclopropyl Tabelle 1: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin R’, R’’ und W jeweils Wasserstoff bedeuten
Figure imgf000039_0002
Figure imgf000039_0001
Nr. X 1-1 Cl CHF2 Me Racemat 1-2 Me CF3 Me Racemat 1-3 Me CHF2 Me Racemat 1-4 Cl c-Pr Me Racemat BCS231028 Ausland - 39 - Nr. X Z R Bemerkung 1-5 Et CF3 Me Racemat 1-6 Et CHF2 Et Racemat 1-7 Cl CF3 Me Racemat 1-8 Cl CHF2 Me Enantiomer A 1-9 Cl CHF2 Me Enantiomer B 1-10 c-Pr CHF2 Me Racemat 1-11 Cl Me Me Racemat 1-12 c-Pr Cl Me Racemat 1-13 OMe CHF2 Me Racemat 1-14 Cl CF3 Me Enantiomer A 1-15 Cl CF3 Me Enantiomer B 1-16 Me CHF2 Me Enantiomer A 1-17 Me CHF2 Me Enantiomer B 1-18 Me CF3 Me Enantiomer A 1-19 Me CF3 Me Enantiomer B 1-20 Me CHF2 Et Racemat 1-21 Me CHF2 Et Enantiomer A 1-22 Me CHF2 Et Enantiomer B 1-23 Cl CHF2 Et Racemat 1-24 Cl CHF2 Et Enantiomer A 1-25 Cl CHF2 Et Enantiomer B 1-26 Me CF3 Et Racemat 1-27 Me CF3 Et Enantiomer A 1-28 Me CF3 Et Enantiomer B 1-29 Cl CF3 Et Racemat 1-30 Cl CF3 Et Enantiomer A 1-31 Cl CF3 Et Enantiomer B 1-32 Cl c-Pr Me Enantiomer A 1-33 Cl c-Pr Me Enantiomer B 1-34 Cl OCF3 Me Racemat 1-35 Cl OCF3 Me Enantiomer A 1-36 Cl OCF3 Me Enantiomer B NMR-Daten ausgewählter Beispiele: Die 1H-NMR-Daten ausgewählter Beispiele von Verbindungen der allgemeinen Formel (I) werden auf zwei verschiedene Weisen angegeben, und zwar (a) klassische NMR- Auswertung und Interpretation oder (b) in Form von 1H-NMR-Peaklisten nach der weiter unten beschriebenen Methode. a) klassische NMR-Interpretation BCS231028 Ausland - 40 - Bspl.1-10: 1H-NMR (DMSO-D6, ^, ppm): 12.26 (bs, 1H), 9.08 (s, 1H), 7.93 (t, 1H), 7.83-7.79 (m, 2H), 4.89 (s, 1H), 3.42 (s, 3H), 2.63-2.61 (m, 1H), 1.03-0.95 (m, 2H), 0.76-0.74 (m, 1H), 0.61-0.58 (m, 1H). Bspl.1-11: 1H-NMR (DMSO-D6, ^, ppm): 12.44 (bs, 1H), 9.05 (s, 1H), 7.66 (d, 1H), 7.45 (d, 1H), 4.83 (s, 1H), 3.30 (s, 3H), 2.76 (s, 3H). Bspl.1-12: 1H-NMR (DMSO-D6, ^, ppm): 12.23 (bs, 1H), 9.06 (s, 1H), 7.62-7.59 (m, 2H), 4.74 (s, 1H), 3.39 (s, 3H), 2.53-2.50 (m, 1H), 0.97-0.93 (m, 2H), 0.66-0.63 (m, 1H), 0.57-0.54 (m, 1H). Bspl.1-13: 1H-NMR (DMSO-D6, ^, ppm): 12.42 (bs, 1H), 9.09 (s, 1H), 7.98 (d, 1H), 7.89 (t, 1H), 7.72 (d, 1H), 3.88 (s, 3H), 3.44 (s, 3H). Bspl.1-34: 1HNMR (CDCl3, ^, ppm): 8.17 (bs, 1H), 7.79 (d, 1H), 7.46-7.39 (m, 1H), 3.44 (s, 3H). b) NMR-Peak-Listenverfahren Die 1H-NMR-Daten ausgewählter Beispiele werden in Form von 1H-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der ^-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die ^-Wert – Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die Peakliste eines Beispiels hat daher die Form: ^1 (Intensität1 ); ^2 (Intensität2);……..; ^i (Intensitäti );……; ^n (Intensitätn) Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. Die Listen der 1H-NMR-Peaks sind ähnlich den klassischen 1H-NMR-Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. Darüber hinaus können sie wie klassische 1H-NMR-Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. BCS231028 Ausland - 41 - Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 1H-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%). Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von “Nebenprodukt-Fingerabdrücken” zu erkennen. Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- Interpretation. Weitere Details zu 1H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. 1-1: 1H-NMR(600.3 MHz, d6-DMSO): δ= 12.6091 (1.8); 9.0661 (5.8); 8.0900 (3.9); 7.9987 (10.5); 7.9878 (10.9); 7.9713 (15.3); 7.9577 (6.2); 7.9068 (4.6); 5.2141 (7.2); 3.7974 (0.8); 3.4166 (0.3); 3.3915 (50.0); 3.3718 (1.6); 3.3518 (0.8); 3.3097 (8.6); 3.2735 (0.4); 2.5033 (10.8); 2.5003 (14.7); 2.4975 (10.6); -0.0001 (4.6) 1-2: 1H-NMR(600.3 MHz, CDCl3): δ= 8.2639 (3.9); 7.8999 (0.5); 7.8493 (4.3); 7.8358 (6.0); 7.7704 (3.9); 7.7569 (2.8); 7.2651 (17.7); 5.3011 (28.2); 4.1930 (0.4); 4.1803 (0.6); 4.1673 (0.4); 4.0412 (0.3); 4.0282 (0.5); 4.0151 (0.3); 3.8851 (0.5); 3.3368 (0.4); 3.3192 (50.0); 3.3090 (1.6); 3.2878 (0.8); 2.9552 (1.1); 2.9309 (0.4); 2.9135 (35.1); 2.8892 (0.3); 2.8771 (0.3); 2.8680 (0.4); 2.8610 (1.0); 2.8368 (0.6); 2.3934 (0.4); 2.3805 (0.6); 2.3675 (0.4); 2.0080 (1.1); 1.6364 (2.4); 1.4268 (2.3); 1.4097 (0.3); 1.2918 (0.6); 1.2847 (0.6); 1.2555 (3.7); 0.8915 (0.4) 1; 0.8802 (0.8); 0.8682 (0.5); -0.0001 (8.7) 1-3: H-NMR(400.6 MHz, CDCl3): δ= 7.5185 (2.9); 7.2880 (2.0); 7.2601 (551.0); 6.9965 (3.0); 3.4205 (3.4); 2.9523 (3.8); 2.8974 (2.0); 1.5503 (16.0); 1.3323 (1.8); 1.2838 (2.6); 1.2548 (3.7); 0.1582 (1.6); 0.1457 (3.1); 0.0688 (1.3); 0.0278 (3.0); 0.0080 (23.2); -0.0002 (759.1); -0.0085 (21.5); - 0.149 14 (2.7) 1-4: H-NMR(400.6 MHz, CDCl3): δ= 8.2209 (3.1); 7.5995 (1.8); 7.5791 (2.0); 7.2632 (11.3); 7.1892 (2.0); 7.1687 (1.9); 5.3009 (12.4); 3.4512 (16.0); 3.1237 (0.9); 3.1097 (0.5); 3.1025 (0.5); 1.1696 (1.5); 1.1647 (1.1); 1.1553 (1.0); 1.1484 (1.6); 1.1341 (0.6); 0.8914 (0.7); 0.8806 (0.6); 0.8772 (0.6); 0.7734 (0.5); 0.7682 (0.5); 0.7591 (0.7); 0.7544 (0.6); 0.7446 (0.6); 0.7357 (0.5); -0.0002 (12.4); -0.0085 (0.6) 1-5: 1H-NMR(400.6 MHz, d6-DMSO): δ= 9.0510 (1.3); 7.9145 (0.9); 7.8809 (0.6); 3.2525 (2.2); 3.2492 (2.2); 2.5407 (2.3); 2.5105 (3.8); 2.5059 (8.2); 2.5013 (11.4); 2.4966 (7.9); 2.4920 (3.4); 2.0882 (0.5); 2.0857 (16.0); 1.2103 (0.7); 1.1921 (1.6); 1.1738 (0.6); -0.0002 (11.5) 1-6: 1H-NMR(400.6 MHz, CDCl3): δ= 8.1960 (2.3); 8.1348 (1.7); 7.9996 (2.0); 7.9948 (1.9); 7.9154 (2.3); 7.8951 (3.3); 7.8596 (1.9); 7.8045 (3.3); 7.7843 (2.3); 7.2623 (24.9); 3.5364 (1.0); 3.5183 (3.3); 3.5000 (3.4); 3.4816 (1.1); 3.4098 (0.6); 3.3934 (1.0); 3.3797 (1.2); 3.3750 (3.0); 3.3616 (3.0); 3.3564 (3.2); 3.3432 (3.0); 3.3380 (1.2); 3.3255 (1.2); 3.3084 (0.6); 1.4291 (7.4); 1.4107 (16.0); 1.3921 (7.3); 1.2605 (3.7); 1.2424 (7.8); 1.2241 (3.6); 0.0080 (0.8); -0.0002 (35.4); -0.0085 (1.1) 1-7: 1H-NMR(400.6 MHz, d6-DMSO): δ= 9.0729 (0.5); 8.0749 (1.0); 8.0337 (0.6); 3.3681 (3.0); 3.3198 (0.6); 2.5105 (3.6); 2.5059 (7.9); 2.5013 (10.9); 2.4967 (7.6); 2.492 11 (3.3); 2.0856 (16.0); -0.0002 (5.9) 1-8: H-NMR(400.6 MHz, d6-DMSO): δ= 12.6242 (0.6); 9.0671 (3.0); 8.1317 (1.6); 8.1244 (0.6); 8.1036 (0.8); 8.0046 (1.4); 7.9946 (3.8); 7.9845 (5.0); 7.9707 (6.1); 7.9502 (1.7); 7.8572 (1.9); 7.4646 (0.9); 5.2259 (3.0); 4.0952 (0.6); 3.4270 (2.1); 3.4247 (2.0); 3.3909 (16.0); 3.3191 (5.8); 3.1711 (3.7); 3.1651 (3.7); 2.6744 (0.7); 2.6698 (0.9); 2.6652 (0.6); 2.5235 (2.4); 2.5189 (3.6); 2.5101 (51.8); 2.5056 (112.5); 2.5010 BCS231028 Ausland - 42 - (156.5); 2.4964 (107.2); 2.4918 (46.5); 2.4771 (0.5); 2.4721 (0.8); 2.4679 (0.9); 2.3327 (0.6); 2.3281 (0.9); 2.3234 (0.6); 1.0550 (0.6); 0.1459 (0.5); 0.0080 (5.2); -0.0002 (181.7); -0.0053 (1.3); -0.0062 (1.1); -0.0085 (4.9); -0.0285 (0.5); -0.0340 (0.5); -0.1492 (0.5) 1-9: 1H-NMR(400.6 MHz, d6-DMSO): δ= 9.0672 (1.9); 8.1316 (1.1); 8.0047 (1.0); 7.9944 (2.6); 7.9845 (3.7); 7.9708 (4.6); 7.9503 (1.3); 7.8571 (1.3); 5.2245 (2.0); 4.1088 (0.9); 4.0957 (2.7); 4.0827 (2.8); 4.0697 (1.0); 3.3914 (10.4); 3.3894 (10.2); 3.3198 (8.2); 3.1741 (16.0); 3.1615 (15.5); 2.6697 (0.5); 2.5235 (1.2); 2.5188 (1.7); 2.5101 (27.2); 2.5055 (60.0); 2.5009 (83.9); 2.4963 (57.6); 2.4917 (25.3); 1.0724 (0.6); 1.0550 (1.2); 1.0375 (0.6); 0.0080 (3.0); 0.0064 (0.9); 0.0055 (1.0); 0.0047 (1.3); 0.0038 (1.8); -0.0002 (97.4); -0.0026 (3.8); -0.0042 (1.3); -0.0051 (0.9); -0.0059 (0.7); -0.0067 (0.6); -0.0085 (2.6) B. Formulierungsbeispiele a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert. b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I) und/oder deren Salze, 64 Gew.-Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt. c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze mit 6 Gew.-Teilen Alkylphenolpolyglykolether (®Triton X 207), 3 Gew.-Teilen Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem Mineralöl (Siedebereich z.B. ca.255 bis über 277 C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer Verbindung der Formel (I) und/oder deren Salze, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertes Nonylphenol als Emulgator. e) Ein in Wasser dispergierbares Granulat wird erhalten indem man 75 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze, 10 Gew.-Teile ligninsulfonsaures Calcium, 5 Gew.-Teile Natriumlaurylsulfat, 3 Gew.-Teile Polyvinylalkohol und 7 Gew.-Teile Kaolin mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert. f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man BCS231028 Ausland - 43 - 25 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze, 5 Gew.-Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium 2 Gew.-Teile oleoylmethyltaurinsaures Natrium, 1 Gew.-Teil Polyvinylalkohol, 17 Gew.-Teile Calciumcarbonat und 50 Gew.-Teile Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. C. Biologische Beispiele 1. Herbizide Wirkung und Kulturverträglichkeit im Nachauflauf Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen wurden in Kunststoff- oder Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat wurden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 l/ha auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus, unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. In den nachstehenden Tabellen A1 bis A14 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 80 g/ha und niedriger, die gemäß zuvor genannter Versuchsvorschrift erhalten wurden, dargestellt. Die Appendices „a“, „b“ und „c“ differenzieren nach verwendeten Dosierungen bei ansonsten gleich geprüften Schadpflanzen. Tabelle A1a: Nachauflaufwirkung bei 20 g/ha gegen ALOMY in % Beispiel- Dosierung nummer [g/ha] ALOMY 1-5 20 80 BCS231028 Ausland - 44 - Tabelle A1b: Nachauflaufwirkung bei 80 g/ha gegen ALOMY in % Beispiel- Dosierung nummer [g/ha] ALOMY 1-4 80 80 1-6 80 80 1-3 80 90 1-8 80 80 1-34 80 80 Tabelle A2a: Nachauflaufwirkung bei 5 g/ha gegen AMARE in % Beispiel- Dosierung nummer [g/ha] AMARE 1-5 5 90 1-2 5 90 1-11 5 80 1-1 5 100 1-10 5 90 Tabelle A2b: Nachauflaufwirkung bei 20 g/ha gegen AMARE in % Beispiel- Dosierung nummer [g/ha] AMARE 1-5 20 100 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-12 20 90 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 BCS231028 Ausland Mak/lep 2024-08-30 - 1 - Herbicidally active sulfonimidoylbenzamides The invention relates to the technical field of herbicides, in particular to herbicides for the selective control of weeds and grass weeds in crops. WO 2011/035874 A1 discloses herbicidally active N-(1,2,5-oxadiazol-3-yl)benzamides. The prior-priority, non-prepublished European patent application EP10174893 discloses certain N-(tetrazol-5-yl)- and N-(triazol-5-yl)benzamides and -nicotinamides as herbicides. WO 2013/124228 discloses herbicidal 3-(sulfin- and sulfonimidoyl)-benzamides. However, the herbicidal efficacy and/or crop tolerance of the compounds mentioned in these documents is not always sufficient.
Figure imgf000002_0003
The object of the present invention was to provide herbicidally active compounds with improved properties compared to those known from the prior art. It has now been found that certain sulfonimidoylbenzamides bearing an unsubstituted 1,3,4-oxadiazole on the amide nitrogen are particularly suitable as herbicides. The present invention therefore provides sulfonimidoylbenzamides of the formula (I) or salts thereof.
Figure imgf000002_0002
Figure imgf000002_0001
where the (C3-C6)-cycloalkyl, Z means halogen, cyano, (C1-C6)-alkyl, halogen-(C1-C6)-alkyl, (C2-C6)-alkenyl, halogen-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halogen-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, Halogen-(C3-C6)-cycloalkyl, halogen-(C1-C6)-alkoxy, (C1-C6)-alkylsulfonyl, W means hydrogen, halogen, R means (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, R' means hydrogen, cyano, (C1-C6)alkyl, BCS231028 Foreign Countries - 2 - R'' denotes hydrogen or (C1-C6)-alkylcarbonyl. 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, and hexyls, such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl. Analogously, alkenyl denotes, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl means, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. The multiple bond can be located in any position of the unsaturated radical. "Cycloalkyl" means a carbocyclic, saturated ring system with three to six C atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. "Haloalkyl," "haloalkenyl," and "haloalkynyl" mean alkyl, alkenyl, or alkynyl that are partially or fully substituted by identical or different halogen atoms, e.g., monohaloalkyl (= monohaloalkyl) such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F; dihaloalkyl (= dihaloalkyl) such as CH2CHF2, CH2CHCl2, CH2CHBr2, CF2CH3, CHCl2, CHF2; Perhaloalkyl such as CCl3, CFCl2, CClF2, CF3, CF2CClF2, CF2CClFCF3; Polyhaloalkyl such as CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3; The term perhaloalkyl also includes the term perfluoroalkyl. “Alkoxy” means an alkyl radical bonded via an oxygen atom, e.g. B. (but not limited to) (C1-C6) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. "Alkoxyalkyl" means an alkoxy radical bonded via an alkyl group. "Haloalkoxy" means a haloalkyl radical bonded via an oxygen atom, e.g. (but not limited to) OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, and OCH2CH2Cl. According to the invention, "alkylthio" stands for straight-chain or branched S-alkyl, for example (C1-C6)-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 1,1-Dimethylpropylthio, 1,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1-Ethylpropylthio, Hexylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Tri- BCS231028 Foreign countries - 3 - methylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio. "Alkylcarbonyl" (alkyl-C(=O)-), unless defined otherwise elsewhere, refers to alkyl radicals bonded to the skeleton via -C(=O)-, such as (C1-C6)-alkylcarbonyl. The number of C atoms refers to the alkyl radical in the alkylcarbonyl group. The term "halogen" means, for example, fluorine, chlorine, bromine, or iodine. When used for a radical, "halogen" means, for example, a fluorine, chlorine, bromine, or iodine atom. If the compounds can form tautomers by hydrogen shift which would not be structurally covered by formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of formula (I) according to the invention, unless a specific tautomer is the subject of consideration. For example, many carbonyl compounds can exist in both the keto form and the enol form, both forms being encompassed by the definition of the compound of formula (I). The compounds of general formula (I) can exist as stereoisomers depending on the nature and linkage of the substituents. If, for example, one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers can occur. In addition, the sulfur atom in the sulfoximino group acts as a chiral center. Stereoisomers can be obtained from the mixtures obtained during production 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 which are encompassed by the general formula (I) but are not specifically defined. The invention also relates to all E-/Z-isomers and mixtures thereof which are encompassed by the general formula (I) but are not specifically defined. The compounds of the formula (I) can form salts. Salt formation can take place by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom, e.g. in the case of R''. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and also ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRR*R**R***]+where R, R*, R** and R*** are independently BCS231028 Foreign Countries - 4 - each represent an organic radical, in particular alkyl, aryl, aralkyl, or alkylaryl. Alkylsulfonium and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts, are also suitable. The compounds of formula (I) can be prepared by addition of a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H2SO4, H3PO4, or HNO3, or organic acids, e.g. carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid, with a basic group such as e.g. amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, to form salts. These salts then contain the conjugate base of the acid as an anion. Preferred compounds of the general formula (I) are those in which X is halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, (C3-C6)-cycloalkyl, Z is halogen, (C1-C3)-alkyl, halo-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, halo-(C1-C3)-alkoxy, W is hydrogen, fluorine, R is (C1-C3)-alkyl, R' is hydrogen, R'' is hydrogen. Particularly preferred are compounds of the general formula (I) in which X is chlorine, methyl, ethyl, methoxy, cyclopropyl, Z is chlorine, methyl, difluoromethyl, trifluoromethyl, cyclopropyl, trifluoromethoxy, W is hydrogen, R is methyl, ethyl, R' is hydrogen, R'' is hydrogen. The compounds according to the invention can be prepared by following the processes described in WO 2013/124228. For example, the compounds according to the invention can be prepared stepwise, first at the thioether stage of the formula (I-thioether) according to the method shown in Scheme 1 by base-catalyzed
Figure imgf000006_0001
Figure imgf000006_0011
Figure imgf000006_0002
Figure imgf000006_0005
Figure imgf000006_0006
Figure imgf000006_0007
BCS231028 Foreign Countries - 5 - reaction of a benzoic acid chloride (II) with a 2-amino-1,3,4-oxadiazole (VII). The thioether intermediates can then be prepared according to Scheme
Figure imgf000006_0008
a
Figure imgf000006_0010
Figure imgf000006_0012
4 are converted into the sulfonimidoylbenzamides of formula (I) according to the invention.
Figure imgf000006_0003
Figure imgf000006_0004
Figure imgf000006_0009
E
Figure imgf000006_0015
Step of formula (I-thioether) can be prepared according to the method shown in Scheme 2 by reacting a benzoic acid of formula (IV) with a 2-amino-1,3,4-oxadiazole (VII). The thioether intermediates can then be converted into the inventive
Figure imgf000006_0014
sulfonimidoylbenzamides of formula (I) can be converted.
Figure imgf000006_0017
Figure imgf000006_0013
F for
Figure imgf000006_0016
Amidation reactions, such as 1,1'-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide 3P) can be used.
Figure imgf000007_0004
Figure imgf000007_0026
Figure imgf000007_0007
Figure imgf000007_0015
Figure imgf000007_0017
Figure imgf000007_0006
BCS231028 Abroad
Figure imgf000007_0005
Figure imgf000007_0019
- 6
Figure imgf000007_0029
Figure imgf000007_0003
-
Figure imgf000007_0024
Invention
Figure imgf000007_0002
corresponding compounds in which the substituent R’’ is ni
Figure imgf000007_0022
Which represents hydrogen, can be prepared, for example, according to the method shown in Scheme 3 by reacting an N-(1,3,4-oxadiazol-2-yl)-arylcarboxamide (I-NH) with a compound of the general formula (VIII), where L represents a leaving group such as chlorine, bromine, iodine, mesyloxy, tosyloxy, trifluorosulfonyloxy, etc.:
Figure imgf000007_0001
Figure imgf000007_0020
Figure imgf000007_0025
Figure imgf000007_0012
Figure imgf000007_0031
Figure imgf000007_0032
Figure imgf000007_0013
Figure imgf000007_0014
Figure imgf000007_0016
Figure imgf000007_0011
Figure imgf000007_0027
Figure imgf000007_0010
Figure imgf000007_0030
Figure imgf000007_0018
Figure imgf000007_0028
Figure imgf000007_0008
known in the literature
Figure imgf000007_0023
described methods.
Figure imgf000007_0009
Figure imgf000007_0021
The compounds of formula (I) according to the invention can be prepared, for example, from the corresponding thioethers of formula (I-thioether) (Scheme 4). For this purpose, the thioether is converted, for example, with cyanamide and an oxidizing agent (iodosobenzene diacetate, sodium hypochlorite, or N-bromosuccinimide) into the corresponding sulfilimine, which can then be further oxidized to the sulfoximine. Oxidizing agents such as meta-chloroperbenzoic acid, sodium permanganate, or a mixture of sodium periodate and ruthenium trichloride are suitable for the oxidation to the sulfoximine. NH-sulfoximines are accessible, for example, from sulfoxides with sodium azide and sulfuric acid and can be functionalized at the nitrogen atom with reagents such as cyanogen bromide, acid chlorides or acid anhydrides, chloroformate, nitric acid, or other compounds. The oxidation of N-sulfonated sulfilimines to the corresponding sulfoximines is achieved, for example, with hydrogen peroxide. Alternatively, sulfoxides can be converted to N-acylated or N-sulfonated sulfoximines. The carboxamide or sulfonamide can then be cleaved to the NH-sulfoximine. Such synthetic methods for the generation of sulfilimines and sulfoximines from thioethers or for the generation of sulfoximines from sulfoxides or for the derivatization of sulfilimines and sulfoximines, including NH-sulfoximines, can be found, for example, in Bolm, C. Org. Lett. 2004, 6, 1305; Bolm, C. Org. Lett. 2007, 9, 3809; Bolm, C. Synthesis 2010, 17, 2922; Bolm, C. Adv. Synth. Catal. 2010, 352, 309; WO 2007/095229, WO 2008/141843, US 2008/0207910, US 2008/0194634 and US 2010/0056534.
Figure imgf000008_0011
Figure imgf000008_0002
Figure imgf000008_0003
Figure imgf000008_0008
Figure imgf000008_0010
BCS231028 Abroad - 7 -
Figure imgf000008_0009
Figure imgf000008_0001
Figure imgf000008_0014
Figure imgf000008_0012
Figure imgf000008_0004
Figure imgf000008_0005
Figure imgf000008_0006
Figure imgf000008_0007
Figure imgf000008_0013
If necessary, additional protecting groups may be used for such syntheses to achieve sufficient selectivity. In particular, functionalization at the NH-sulfoximine is fundamentally in competition with the analogous functionalization at the amide nitrogen atom. It may be advantageous to change the order of reaction steps. Benzoic acids bearing a sulfoxide cannot be readily converted into their acid chlorides. In this case, it is advisable to first prepare the amide at the thioether stage and then oxidize the thioether to the sulfoxide. Sulfoximines, and especially sulfilimines, are not sufficiently stable under certain conditions (Bolm, C. Adv. Synth. Catal. 2010, 352, 309), so it can be advantageous, as shown in the schemes above, to first synthesize the benzamide at the thioether stage and only generate the sulfilimine or sulfoximine from the thioether at the end of the synthesis sequence. However, depending on the substitution pattern, if stability is sufficient, it may also be useful to first generate the sulfilimine or sulfoximine from the thioether at the benzoic acid stage (or in an even earlier step) and only then convert the benzoic acid into its amide. In some cases, it may be advantageous to use derivatives of benzoic acid rather than free benzoic acid for the reactions. Sometimes, for the stability of a functional group, it is sufficient to operate only in acidic or basic media, i.e., to work only with the free benzoic acid or its salt. In many cases, esters such as methyl or ethyl esters are suitable. Tert-butyl esters often provide steric protection against nucleophilic reagents and are easily cleavable in acidic media (T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd Edition, John Wiley & Sons, Inc. 1991, p. 227 ff.). Also suitable are residues that are significantly more stable than carboxyl groups, yet are readily accessible from carboxylic acids and can also be easily converted back into the free carboxylic acids. These include, for example, oxazolines.
Figure imgf000009_0008
Figure imgf000009_0033
Figure imgf000009_0017
Figure imgf000009_0022
BCS231028 Abroad
Figure imgf000009_0020
Figure imgf000009_0016
- 8 -
Figure imgf000009_0041
(T.W. Greene, P.G.M.
Figure imgf000009_0014
Figure imgf000009_0024
. Wuts, Protective Groups in Organic Synthesis, 2nd Edition
Figure imgf000009_0039
, John Wiley & Sons,
Figure imgf000009_0006
Inc.1991, p.
Figure imgf000009_0002
265 ff.; Z
Figure imgf000009_0011
. Hell et al, Tetrahedron Letters 43 (2002), 3985 - 3987).
Figure imgf000009_0003
Figure imgf000009_0004
Figure imgf000009_0009
Figure imgf000009_0027
Figure imgf000009_0029
Figure imgf000009_0035
In addition, it is also possible to obtain the inventive NH-sulfoximes of formula (I) in one step from the corresponding thioethers of formula (I-thioether) (Scheme 5). For this purpose, the thioether is, for example,
Figure imgf000009_0010
is converted directly into the corresponding NH-sulfoximines with ammonium carbamate and iodosobenzene diacetate (J. A. Bull et al. Synlett 2017, 28, 2525-2538).
Figure imgf000009_0001
Figure imgf000009_0025
Figure imgf000009_0032
Figure imgf000009_0018
Figure imgf000009_0019
Figure imgf000009_0021
Figure imgf000009_0036
Figure imgf000009_0042
Figure imgf000009_0012
Figure imgf000009_0015
Figure imgf000009_0040
Figure imgf000009_0038
Figure imgf000009_0007
Figure imgf000009_0013
Figure imgf000009_0023
Figure imgf000009_0037
Figure imgf000009_0005
Figure imgf000009_0031
In the above processes, the compounds of formula (I) are obtained as racemic mixtures. The pure enantiomers can be obtained therefrom by methods known to those skilled in the art.
Figure imgf000009_0026
Figure imgf000009_0028
Figure imgf000009_0030
Figure imgf000009_0034
Chiral separation methods, such as chromatographic enantiomer separation on chiral supports, can be used. The respective reaction mixtures are generally processed using known methods, for example, by crystallization, aqueous extractive processing, chromatographic methods, or a combination of these methods. Collections of compounds of formula (I) and/or their salts, which can be synthesized by the above-mentioned reactions, can also be prepared in parallel, which can be done manually, partially automated, or fully automated. For example, it is possible to automate the reaction procedure, the workup, or the purification of the products or intermediates. 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. A range of commercially available devices can be used for parallelized reaction execution and workup, for example, Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA; reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 113AZ, England; or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA. For the parallelized purification of compounds of general formula (I) and their salts, or intermediates obtained during their preparation, the following are available, among others: BCS231028 Foreign Countries - 9 - Chromatography equipment is available, for example, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. 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 circumvented by using partially or fully integrated automation systems, in which the respective automation modules are operated, for example, by robots. Such automation systems can be 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). In addition to the methods described here, the preparation of compounds of general formula (I) and their salts can be carried out completely 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 respective procedure, are bound to a synthesis 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, CA 92064, USA. The implementation of individual or multiple synthesis steps in both the solid and liquid phases can be supported by the use of microwave technology. A number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (editors C. O. Kappe and A. Stadler), Wiley Publishers, 2005. Preparation according to the processes described here yields compounds of formula (I) and their salts in the form of collections of substances called libraries. The present invention also relates to libraries containing at least two compounds of formula (I) and their salts. The compounds of formula (I) according to the invention (and/or their salts), hereinafter collectively referred to as “compounds according to the invention”, have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual weeds. BCS231028 Foreign Countries - 10 - Even difficult-to-control perennial weeds that sprout from rhizomes, rootstocks, or other permanent organs are effectively controlled by the active ingredients. 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., weeds such as monocotyledonous 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. Specifically, some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds according to the invention are mentioned by way of example, without implying a restriction to specific species. Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum. Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. If the compounds according to the invention are applied to the soil surface before germination, either the emergence of weed seedlings is completely prevented, or the weeds grow to the cotyledon stage, but then cease growth and finally die completely after three to four weeks. When the active ingredients are applied post-emergence to the green parts of the plant, growth stops after treatment, and the weeds remain in the growth stage present at the time of application or die completely after a certain period of time, thus eliminating weed competition harmful to the crop plants very early and sustainably. Although the compounds according to the invention exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, e.g., dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus,Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, are only slightly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate. For these reasons, the present compounds are very suitable for the selective control of undesirable plant growth in plant crops, such as agricultural crops or ornamental plants. Furthermore, the compounds according to the invention (depending on their respective structure and the application rate) exhibit excellent growth-regulating properties in crops. They regulate the plant's own metabolism and can therefore be used to specifically influence plant substances and to facilitate harvesting, for example by triggering desiccation and stunting. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as it can, for example, reduce or completely prevent lodging. Due to their herbicidal and plant growth regulatory properties, the active ingredients can also be used to control weeds in crops of plants modified genetically or by conventional mutagenesis. The transgenic plants are generally characterized by particularly advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens that cause plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to, for example, B. the harvest in terms of quantity, quality, storability, composition, and specific ingredients. Transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvest, are known. 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 corn, or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetables. The compounds according to the invention can preferably be used as herbicides in crops that are resistant to the phytotoxic effects of the herbicides or have been genetically engineered to be resistant. Conventional methods for producing new plants that have modified properties compared to previously existing plants include, for example, classical breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using BCS231028 Foreign countries - 12 - produced by genetic engineering techniques (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases: - genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806), - transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf. e.g. EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or sulfonylureas (EP-A-0257993, US-A-5013659), - transgenic crop plants, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259). - Transgenic crops with modified fatty acid composition (WO 91/13972). - Genetically modified crops with new ingredients or secondary substances, e.g., new phytoalexins, which cause increased disease resistance (EPA 309862, EPA0464461). - Genetically modified plants with reduced photorespiration that exhibit higher yields and greater stress tolerance (EPA 0305398). - Transgenic crops that produce pharmaceutically or diagnostically important proteins (“molecular pharming”) - Transgenic crops that are characterized by higher yields or better quality - Transgenic crops that are characterized by a combination of, e.g., the above-mentioned new properties (“gene stacking”). Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known in principle, see e.g. B. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, "Trends in Plant Science" 1 (1996) 423-431). For such genetic manipulations, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence modification by recombination of DNA sequences. Using standard procedures, base exchanges can be performed, partial sequences can be removed, or natural or synthetic sequences can be added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments, see e.g. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Genes and Clones", VCH Weinheim, 2nd ed. 1996. 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, ``` BCS231028 Foreign Countries - 13 - of a sense RNA to achieve a cosuppression effect or the expression of at least one correspondingly constructed ribozyme that specifically cleaves transcripts of the aforementioned gene product. For this purpose, DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences present, as well as DNA molecules that comprise only parts of the coding sequence, whereby these parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that exhibit a high degree of homology to the coding sequences of a gene product, but are not completely identical. When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, for example, a specific compartment can be used. For example, the coding region can be linked to DNA sequences that ensure localization in a specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of the nucleic acid molecules can also take place in the organelles of plant cells. The transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be plants of any plant species, i.e., both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are obtainable that exhibit altered properties through the overexpression, suppression, or inhibition of homologous (= natural) genes or gene sequences, or the expression of heterologous (= foreign) genes or gene sequences. The compounds according to the invention can preferably be used in transgenic crops that are resistant to growth promoters, such as dicamba, or to herbicides that inhibit essential plant enzymes, e.g., acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS), or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates, or benzoyl isoxazoles and analogous active ingredients. When the active ingredients according to the invention are used in transgenic crops, in addition to the effects on weeds observed in other crops, effects often occur which are specific to the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum that can be controlled, modified application rates that can be used for application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influence on the growth and yield of the transgenic crops. BCS231028 Foreign Countries - 14 - The invention therefore also relates to the use of the compounds of formula (I) according to the invention and/or their salts as herbicides for controlling weeds in crops of useful or ornamental plants, optionally in transgenic crops. The use according to the invention for controlling weeds or for regulating plant growth also includes the case in which the active ingredient of formula (I) or its salt is formed from a precursor substance ("prodrug") only after application to the plant, in the plant, or in the soil. The invention also relates to the use of one or more compounds of the formula (I) or salts thereof or of an agent according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the formula (I) or salts thereof is applied to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in or on which the plants grow, or the area under cultivation. The invention also relates to a herbicidal and/or plant growth regulating agent, characterized in that the agent contains (a) one or more compounds of the formula (I) and/or salts thereof as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas I-1 to I-33 and/or salts thereof, in each case as defined above, and (b) one or more further substances selected from groups (i) and/or (ii): (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those which do not correspond to the formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators, (ii) one or more formulation auxiliaries customary in plant protection. The further agrochemically active substances of component (i) of a composition according to the invention are preferably selected from the group of substances listed in "The Pesticide Manual", 19thedition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021. A herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, BCS231028 Foreign Countries - 15 - inorganic salts, dusts, carriers that are solid at 25°C and 1013 mbar, preferably adsorbent, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents that are miscible with water in any ratio at 25°C and 1013 mbar. The compounds according to the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in the usual preparations. The invention therefore also relates to herbicidal and plant growth-regulating compositions containing the compounds according to the invention. The compounds according to the invention can be formulated in various ways, depending on the biological and/or chemical-physical parameters specified. Possible formulation options include: 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. These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London. The necessary formulation aids such as inert materials, surfactants, solvents, and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J., Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986. Based on 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. Suitable safeners include mefenpyr diethyl, cyprosulfamide, isoxadifen ethyl, cloquintocetmexyl, and dichlormide. BCS231028 Foreign Countries - 16 - Wettable powders are preparations that are evenly dispersible in water. In addition to the active ingredient, they contain a diluent or inert substance as well as 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 herbicidal 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. 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 these organic solvents, with the addition of one or more ionic and/or non-ionic surfactants (emulsifiers). Examples of emulsifiers that can be used include calcium salts of alkylarylsulfonic acid, such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters. Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g., talc, natural clays such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth. Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, with the addition of surfactants, such as those listed above for the other formulation types. Emulsions, e.g., oil-in-water emulsions (EW), can be produced, for example, using stirrers, colloid mills, and/or static mixers using aqueous organic solvents and, if necessary, surfactants, such as those listed above for the other formulation types. 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, e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oils. Suitable active ingredients can also be granulated in the usual manner for the production of fertilizer granules—if desired, mixed with fertilizers. Water-dispersible granules are generally produced using conventional processes such as spray drying, fluidized-bed granulation, disc granulation, mixing with high-speed mixers, and ```BCS231028 Foreign Countries - 17 - Extrusion without solid inert material. For the production of disc, fluidized-bed, extruder, and spray granules, see, for example, the procedures in "Spray-Drying Handbook," 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration," Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection products, see, for example, G.C. Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pages 81-96; and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103. The agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, for example, the active ingredient concentration is about 10 to 90% by weight, with the remainder (to 100% by weight) consisting of conventional formulation components. In emulsifiable concentrates, the active ingredient concentration can be about 1 to 90% by weight, preferably 5 to 80% by weight. Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably 5 to 20% by weight of active ingredient, while sprayable solutions contain about 0.05 to 80% by weight, preferably 2 to 50% by weight of 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. For water-dispersible granules, the active ingredient content, for example, is between 1 and 95 wt.%, preferably between 10 and 80 wt.%. In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents, solvents, fillers, carriers, dyes, defoamers, evaporation inhibitors, and pH and viscosity modifiers. Examples of formulation aids are described, among others, in "Chemistry and Technology of Agrochemical Formulations," ed. D. A. Knowles, Kluwer Academic Publishers (1998). The compounds of formula (I) or their salts can be used as such or in the form of their preparations (formulations) in combination with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and/or growth regulators, e.g., as a ready-to-use formulation or as tank mixes. The combination formulations can be prepared based on the above-mentioned formulations, taking into account the physical properties and stability of the active ingredients to be combined. BCS231028 Foreign Countries - 18 - Of particular interest is the selective control of weeds in crops of useful and ornamental plants. Although the compounds (I) according to the invention already exhibit very good to sufficient selectivity in many crops, phytotoxicity can in principle occur in some crops, especially in the case of mixtures with other herbicides that are less selective. In this regard, combinations of compounds (I) according to the invention that contain the compounds (I) or their combinations with other herbicides or pesticides and safeners are of particular interest. The safeners, which are used in an antidote-effective concentration, reduce the phytotoxic side effects of the herbicides/pesticides used, e.g., in economically important crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton, and soybeans, preferably cereals. The weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the respective safener and can vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. The safeners can be formulated analogously to the compounds (I) or mixtures thereof with other herbicides/pesticides and supplied and applied as a ready-to-use formulation or tank mix with the herbicides. For use, the herbicide or herbicide-safener formulations available in commercial form are diluted, if appropriate, in the customary manner, e.g., with water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, soil-applied or broadcast granules, and sprayable solutions are not normally diluted with other inert substances before use. External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of formula (I) and/or their salts. The application rate can vary within wide limits. For use as a herbicide for controlling weeds, the total amount of compounds of formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, more preferably in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, particularly preferably in the range from 0.05 to 1 kg/ha. This applies to both pre-emergence and post-emergence application. When using compounds of formula (I) and/or their salts as plant growth regulators, for example as stalk shorteners in crops as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or maize, the total application rate is preferably in the range from 0.001 to 2 kg/ha, preferably in the range from 0.005 to 1 kg/ha, in particular in the range from 10 to 500 g/ha, very particularly preferably in the range from 20 to 250 g/ha. This applies to both pre-emergence and post-emergence applications. BCS231028 Foreign Countries - 19 - Application as a stem shortener can occur at various stages of plant growth. For example, application after tillering, at the beginning of longitudinal growth, is preferred. Alternatively, application as a plant growth regulator can also be applied to the seeds, which includes various seed dressing and coating techniques. The application rate depends on the individual techniques and can be determined in preliminary trials. As combination partners for the compounds of general formula (I) in mixture formulations or in tank mixes, known active ingredients that are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase or that act as plant growth regulators can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021 and literature cited therein. Known herbicides or plant growth regulators that can be combined with compounds of general formula (I) include, for example, the following active ingredients (the compounds are designated either by the "common name" according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. One and sometimes several application forms are mentioned as examples: Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammonium sulfamate, Anilofos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azafenidine, Azimsulfuron, Beflubutamid, (S)-(-)- Beflubutamid, Beflubutamid-M, Benazoline, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-Klaium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulide, Bentazon, Bentazon-Sodium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos sodium, bipyrazone, bispyribac, bispyribac sodium, bixlozone, bromacil, bromacil lithium, bromacil sodium, bromobutide, bromofenoxime, bromoxynil, bromoxynil butyrate, bromoxynil potassium, bromoxynil heptanoate and bromoxynil octanoate, busoxinone, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrol, Cambendichlor, Carbetamide, Carfentrazone, Carfentrazone-Ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamine, Chroamben-methyl, Chloramben-methylammonium, Chloramben-sodium, Chlorbromuron, Chlorfenac, Chlorfenac-ammonium, Chlorfenac-sodium, Chlorfenprop, Chlorfenprop-methyl, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlorophthalim, Chlorotoluron, Chlorsulfuron, Chlorthal, BCS231028 Foreign countries - 20 - Chlorthal-dimethyl, Chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)- Cinmethylin, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, Cinosulfuron, Clacyfos, Clethodim, Clodinafop, Clodinafop-ethyl, Clodinafop-propargyl, Clomazone, Clomeprop, Clopyralid, Clopyralid-methyl, Clopyralid-olamine, Clopyralid-potassium, Clopyralid-tripomin, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cycloate, Cyclopyranil, Cyclopyrimorate, Cyclosulfamuron, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Cyprazine, 2,4-D (as well as the ammonium, Butotyl, Butyl, Choline, Diethylammonium, dimethylammonium, diolamine, doboxyl, dodecylammonium, etexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, meptyl, methyl, potassium, tetradecyl ammonium, triethylammonium, triisopropanolammonium, tripromine and trolamine salts thereof). 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB potassium and 2,4-DB sodium, Daimuron (Dymron), Dalapon, Dalapon calcium, Dalapon magnesium, Dalapon sodium, Dazomet, Dazomet sodium, n-Decanol, 7-Deoxy-D-sedoheptulose, Desmedipham, Detosyl pyrazolate (DTP), Dicamba and its salts (e.g., Dicamba biproamine, Dicamba N,N-bis(3-aminopropyl)methylamine, Dicamba butotyl, Dicamba choline, Dicamba diglycolamine, Dicamba dimethylammonium, Dicamba diethanolamine ammonium, Dicamba diethylammonium, Dicamba isopropylammonium, Dicamba methyl, Dicamba monoethanolamine, Dicamba olamine, Dicamba potassium, Dicamba sodium, dicamba triethanolamine), dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, Dichlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-etexyl, dichlorprop-P-potassium, dichlorprop-sodium, diclofop, diclofop-methyl, diclofop-P, Diclofop-P-methyl, Diclosulam, Difenzoquat, Difenzoquat metilsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr sodium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb-Acetate, Diphenamide, Diquat, Diquat-Dibromide, Diquat dichloride, dithiopyr, diuron, DNOC, DNOC ammonium, DNOC potassium, DNOC sodium, endothal, endothal diammonium, endothal dipotassium, endothal disodium, epyrifenacil (S-3100), EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiocin, ethofumesate, Ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethanesulfonamide, F-7967, i.e. 3-[7-Chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-Ethyl, Fenoxaprop-P-Ethyl, Fenoxasulfone, Fenpyrazone, Fenquinotrione, Fentrazamide, Flamprop, Flamprop-Isoproyl, Flamprop-Methyl, Flamprop-M-Isopropyl, Flamprop-M-Methyl, Flazasulfuron, Florasulam, Florpyrauxifen, Florpyrauxifen-benzyl, Fluazifop, Fluazifop-Butyl, Fluazifop-Methyl, Fluazifop-P, fluazifop-P-butyl, flucarbazone, Flucarbazone sodium, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpyr, Flufenpyr-Ethyl, Flumetsulam, Flumiclorac, Flumiclorac-Pentyl, Flumioxazin, Fluometuron, BCS231028 Foreign countries - 21 - Flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupropanate sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, Fluroxypyr-Butometyl, Fluroxypyr-Meptyl, Flurtamon, Fluthiacet, Fluthiacet-Methyl, Fomesafen, Fomesafen Sodium, Foramsulfuron, Foramsulfuron Sodium, Fosamine, Fosamine Ammonium, Glufosinate, Glufosinate Ammonium, Glufosinate Sodium, L-Glufosinate Ammonium, L-glufosinate sodium, Glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquinosodium and glyphosate-trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioate, Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron-Methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-Ethoxyethyl, Haloxyfop-P-Ethoxyethyl, Haloxyfop-Methyl, Haloxyfop-P-Methyl, Haloxifop sodium, Hexazinone, HNPC-A8169, i.e. Prop-2-yn-1-yl (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoate, HW-02, i.e. 1-(dimethoxyphosphoryl)-ethyl-(2,4-dichlorophenoxy)acetate, hydantocidin, icafolin, icafolin-methyl, imazamethabenz, imazamethabenz-methyl, Imazamox, Imazamox ammonium, Imazapic, Imazapic ammonium, Imazapyr, Imazapyr isopropyl ammonium, Imazaquin, Imazaquin ammonium, Imazaquin methyl, Imazethapyr, Imazethapyr ammonium, Imazosulfuron, Indanofan, Indaziflam, Indolauxipyr, Iodosulfuron, Iodosulfuron-Methyl, Iodosulfuron-Methyl-Sodium, Ioxynil, ioxynil lithium, octanoate, potassium and sodium, ipfencarbazone, iptriazopyride, i.e. 3-[(Isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo-[4,3-a]pyridine-8-carboxamide, isoproturon, isourone, isoxaben, isoxaflutole, carbutilate, KUH-043, i.e. 3-({[5-(Difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, Ketospiradox, Ketospiradox-potassium, Lactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, -Dimethylammonium, -diolamine, -2-ethylhexyl, -ethyl, -isobutyl, Isoctyl, -isopropyl, -isopropylammonium, -methyl, olamine, -potassium, -sodium and -trolamine, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-etexyl, mecoprop-ethadyl, mecoprop-isoctyl, Mecoprop-methyl, mecoprop potassium, mecoprop sodium, and mecoprop trolamine, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mefluidide-diolamine, mefluidide-potassium, mesosulfuron, mesosulfuron-methyl, Mesosulfuron sodium, mesotrione, methabenzthiazuron, metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methabenzthiazuron, Methiopyrsulfuron, Methiozoline, Methyl isothiocyanate, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metproxybicyclon, Metribuzin, Metsulfuron, Metsulfuron-Methyl, Molinat, Monolinuron, Monosulfuron, monosulfuron-methyl, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, Neburon, Nicosulfuron, Nonanoic acid (Pelargonic acid), Norflurazon, Oleic acid (Fatty acids), Orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Paraquat dichloride, Paraquat dimethyl sulfate, Pebulate, Pendimethalin, Penoxsulam, Pentachlorophenol, Pentoxazone, Pethoxamide, Petroleum oil, BCS231028 Foreign countries - 22 - Phenmedipham, Phenmedipham-Ethyl, Picloram, Picloram-dimethylammonium, Picloram-Etexyl, Picloram-Isoctyl, Picloram-Methyl, Picloram-Olamin, Picloram-Potassium, Picloram-Triethylammonium, Picloram-Tripromin, Picloram-Trolamin, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron-Methyl, Prodiamine, Profoxydim, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-Sodium, Propyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-Ethyl, Pyraquinate, Pyrasulfotol, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Pyrazosulfuron-Ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-Isopropyl, Pyribambenz-Propyl, Pyribenzoxime, Pyributicarb, Pyridafol, Pyridate, Pyriftalide, Pyriminobac, Pyriminobac-Methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac- Sodium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinclorac-Dimethylammonium, Quinclorac-Methyl, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-Ethyl, Quizalofop-P, Quizalofop-P-Ethyl, Quizalofop-P-Tefuryl, QYM201, i.e.1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phe-nyl}piperidin-2-one, Rimisoxafen, Rimsulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron-Methyl, Sulfosulfuron, , SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e.1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g. TCA-ammonium, TCA-Calcium, TCA-Ethyl, TCA-Magnesium, TCA-Sodium, Tebuthiuron, Tefuryltrione, Tembotrion, Tepraloxydim, Terbacil, Terbucarb, Terbumetone, Terbuthylazine, Terbutryn, Tetflupyrolimet, Thaxtomin, Thenylchlor, Thiazopyr, Thiencarbazone, Thiencarbazone-Methyl, Thifensulfuron, Thifensulfuron-Methyl, Thiobencarb, Tiafenacil, Tolpyralate, Topramezone, Tralkoxydim, Triafamon, Tri-allate, Triasulfuron, Triaziflam, Tribenuron, Tribenuron-Methyl, Triclopyr, Triclopyr-Butotyl, Triclopyr-Choline, Triclopyr-Ethyl, Triclopyr-Triethylammonium, Trietazine, Trifloxysulfuron, Trifloxysulfuron sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, 3-(2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid methyl ester, 3-(2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6- dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid, Ethyl [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidin-2-yl ether, 2-(3,4-Dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazin-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl- 1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-Methyl-4-[(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl propan-1- sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl- BCS231028 Foreign countries - 23 - 1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate; Cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, Prop-2-yn-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, Methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, Benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, Ethyl-4- amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro- 6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-carboxylate, methyl 6-(1-acetyl-7-fluoro-1H-indol-6-yl)- 4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7- fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H- indol-6-yl)pyridine-2-carboxylate, Sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, 4-hydroxy- 1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1- methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-Hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en- 1-yl)carbonyl]-1-methylquinazolin-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-1-ium salt (with appropriate Anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4- (pyridazin-3-yl)pyridazin-1-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3,4-thiadiazol-2-yl)pyridazin-1-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), methyl (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}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-chloro-4-fluoro-5-[3-methyl-2,6- dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)- 2-(trifluoromethyl)benzaldehyde-O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxime, 2-fluoro- N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid, 2-ethoxy-2-oxoethyl-1-{2-chloro-4-fluoro- 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropanecarboxylate, 2-methoxy-2-oxoethyl-1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4- (trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropane carboxylate, {[(1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-Bromo-4-chlorobenzyl)-4,4-dimethyl-1,2- BCS231028 Foreign countries - 24 - oxazolidin-3-one, Methyl 3-{2-chloro-4-fluoro-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]oxazole-6a-carboxylate, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)- yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylate, methyl 3-{2-chloro-4-fluoro- 5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylate, 3-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylic acid, 3-{2-Chloro-4-fluoro-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]oxazole-6a-carboxylic acid Abscisic acid and related analogues [e.g. (2Z,4E)-5-[6-Ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6- dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid, methyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-1,3- dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid], acibenzolar, acibenzolar-S-methyl, S-adenosylhomocysteine, allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g. (Isopropylidene)-aminooxyacetic acid 2-(methoxy)-2-oxoethyl ester, (Isopropylidene)-aminooxyacetic acid 2-(hexyloxy)-2-oxoethyl ester, (Cyclohexylidene)-aminooxyacetic acid 2-(isopropyloxy)-2-oxoethyl ester], 1-Aminocycloprop-1-ylcarboxylic acid N-Methyl-1-aminocyclopropyl-1-carboxylic acid, 1-Aminocyclopropyl-1-carboxamide, substituted 1-Aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1-Aminocyclopropyl-1-hydroxamic acid, 5-Aminolevulinic acid, Ancymidol, 6-Benzylaminopurine, Bikinin, Brassinolide, Brassinolide-ethyl, L-canalin, catechin and catechins (e.g. (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chitooligosaccharides (CO; COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(C8H13NO5)n, CAS No.1398-61-4] and chitosan molecules [(C5H11NO4)n, CAS No.9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet sodium, n-decanol, dikegulac, dikegulac sodium, endothal, endothal-di-potassium, -di-sodium, and mono(N,N-dimethylalkylammonium), ethephon, 1-ethylcyclopropene, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, Gibberellic acid, inabenfid, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid esters or other derivatives (e.g., jasmonic acid methyl ester, jasmonic acid ethyl ester), BCS231028 Foreign Countries - 25 - Lipochitooligosaccharides (LCO, sometimes also referred to as symbiotic nodulation signals (Nod or Nod factors) or Myc factors, consist of an oligosaccharide backbone of β-1,4-linked N-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain fused to the non-reducing end. As can be seen from the literature, LCOs differ in the number of GlcNAc units in the backbone structure, the length and degree of saturation of the fatty acid chain, and the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, Methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one and related lactones as described in EP2248421, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and its salts (e.g. sodium 4-phenylbutanoate, potassium 4-phenylbutanoate), phenylalanine, N-phenylphthalamic acid, prohexadione, prohexadione calcium, 1-n-propylcyclopropene, putrescine, prohydrojasmone, rhizobitoxin, salicylic acid and salicyclic acid methyl ester, sarcosine, sodium cycloprop-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-1-yl)propanoate, sodium 3-(cycloprop-1-en-1-yl)propanoate, sidefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, Trinexapac, Trinexapac-ethyl, Tryptophan, Tsitodef, Uniconazole, Uniconazole-P, 2-Fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine, 2-Chloro-N-(3-methoxyphenyl)-9H-purin-6-amine. Also suitable as combination partners for the compounds of formula (I) according to the invention are, for example, the following safeners: S1) Compounds of formula (S1), O (RA 1)n/a
Figure imgf000026_0001
where the symbols and indices have the following meanings: nA is a natural number from 0 to 5, preferably 0 to 3; RA1is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl; WA is an unsubstituted or substituted divalent heterocyclic radical from the group of partially saturated or aromatic five-membered ring heterocycles with 1 to 3 hetero ring atoms from the group
Figure imgf000027_0003
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Figure imgf000027_0001
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Figure imgf000027_0008
BCS231028 Foreign Countries - 26 - 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 (WA1) to (WA5),
Figure imgf000027_0006
Figure imgf000027_0004
R2is ORA3, SRA of the NRA3R is 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 ORA3, NHRA4or N(CH3)2, in particular of the formula ORA3; RA3is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms; RA4is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl; RA 5is H, (C1-C8)Alkyl, (C1-C8)Haloalkyl, (C1-C4)Alkoxy(C1-C8)Alkyl, cyano or COORA 9, where RA9 is hydrogen, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C6)hydroxyalkyl, (C3-C12)cycloalkyl or tri-(C1-C4)alkylsilyl; R.A6, Attorney7, Attorney8are identical or different and are hydrogen, (C1-C8)alkyl, (C1-C8)haloalkyl, (C3-C12)cycloalkyl or substituted or unsubstituted phenyl; RA 10is H, (C3-C12)Cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heteroaryl; preferably: a) compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (S1a), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazole-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazole-3-carboxylic acid ethyl ester (S1-1) ("Mefenpyr-diethyl"), and related compounds as described in WO-A-91/07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid (S1b), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methyl-pyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-pyrazole-3-carboxylate (S1-3), 1-(2,4-dichloro- BCS231028 Foreign countries - 27 - phenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806; c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1c), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554; d) compounds of the triazolecarboxylic acid type (S1d), preferably compounds such as fenchlorazole (ethyl ester), i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP-A-346620; e) compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1e), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds as described in WO-A-91/08202, or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("Isoxadifen-ethyl") or -n-propyl ester (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13) as described in patent application WO-A-95/07897. f) Compounds of the triazolyloxyacetic acid derivative type (S1f), preferably compounds such as methyl {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-14) or {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-15) or methyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-16) or {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-17) or methyl {[1-(4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-18) or {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (S1-19), as described in patent application WO2021/105101. S2) Quinoline derivatives of the formula (S2), nB
Figure imgf000028_0001
where the symbols and indices have the following meanings: BCS231028 Foreign - 28 - RB1is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl; nB is a natural number from 0 to 5, preferably 0 to 3; RB2is ORB3, SRB3or NRB3RB4or 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 linked 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 ORB3, NHRB4or N(CH3)2, in particular of the formula ORB3; RB3is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms; RB4is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl; TB 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 (S2a), preferably (5-chloro-8-quinolinoxy)acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy)acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro-8-quinolinoxy)acetic acid 4-allyloxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy)acetic acid 1-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy)acetate methyl ester (S2-6), (5-chloro-8-quinolinoxy)acetate allyl ester (S2-7), (5-chloro-8-quinolinoxy)acetic acid 2-(2-propylideneiminoxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy)acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366, and (5-chloro-8-quinolinoxy)acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002/34048; b) Compounds of the type (5-chloro-8-quinolinoxy)malonic acid (S2b), preferably compounds such as (5-chloro-8-quinolinoxy)malonic acid diethyl ester, (5-chloro-8-quinolinoxy)malonic acid diallyl ester, (5-chloro-8-quinolinoxy)malonic acid methyl ethyl ester and related compounds as described in EP-A-0582198.
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RD3O
Figure imgf000030_0355
(RO
Figure imgf000030_0357
D 4 )mD
Figure imgf000030_0359
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BCS231028 Foreign - 30 - RD1is CO-NRD5RD6or NHCO-RD7; RD2 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; RD3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl; RD4 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; RD5is 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 are substituted; RD6is 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 RD5and RD6together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl residue; RD7is 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 residues also (C1-C4)alkyl and (C1-C4)haloalkyl substituted; nD is 0, 1 or 2; mD is 1 or 2; vD is 0, 1, 2 or 3; of these, preferred compounds are of the N-acylsulfonamide type, e.g. of the following formula (S4a), which are known, for example, from WO-A-97/45016 O O O (R 4 D )mDN N
Figure imgf000031_0001
BCS231028 Foreign Countries - 31 - where RD7(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; RD4Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3; mD is 1 or 2; vD is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, e.g. of the following formula (S4b), which are known e.g. from WO-A-99/16744, R 5 DOO4 e.g. those in which
Figure imgf000032_0002
RD5= Cyclopropyl and (RD4) = 2-OMe is ("Cyprosulfamide", S4-1), RD5= Cyclopropyl and (RD4) = 5-Cl-2-OMe is (S4-2), RD5= Ethyl and (RD4) = 2-OMe is (S4-3), RD 5= Isopropyl and (RD 4) = 5-Cl-2-OMe is (S4-4) and RD 5= Isopropyl and (RD 4) = 2-OMe (S4-5). as well as compounds of the N-acylsulfamoylphenylurea type of the formula (S4c), which are known e.g. from EP-A-365484, R 8 D O OO(R 4 D )mDin which
Figure imgf000032_0001
RD8and RD9independently of one another hydrogen, (C1-C8)alkyl, (C3-C8)cycloalkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, RD4 Halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3 BCS231028 Foreign Countries - 32 - mD 1 or 2 means; for example, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea. S5) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 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. S6) Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g. 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630. S7) Compounds of formula (S7), as described in WO-A-1998/38856 H2CAE
Figure imgf000033_0001
where the symbols and indices have the following meanings: RE1, RE2 are independently halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl, (C1-C4)alkylamino, di-(C1-C4)alkylamino, nitro; AE is COORE3or COSRE4RE3, RE4 are independently hydrogen, (C1-C4)alkyl, (C2-C6)alkenyl, (C2-C4)alkynyl, cyanoalkyl, (C1-C4)haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, nE1is 0 or 1 nE2, nE3are independently 0, 1 or 2, BCS231028 Foreign Countries - 33 - preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1). S8) Compounds of formula (S8), as described in WO-A-98/27049 RF2 O Wherein
Figure imgf000034_0001
XF CH or N, nF in the case that XF=N, an integer from 0 to 4 and in the case that XF=CH, an integer from 0 to 5 , RF1 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, RF2Hydrogen or (C1-C4)alkyl RF3hydrogen, (C1-C8)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, preferably compounds wherein XF is CH, nF is an integer from 0 to 2, RF1 Halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, RF2Hydrogen or (C1-C4)alkyl, RF3Hydrogen, (C1-C8)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or their salts. BCS231028 Foreign Countries - 34 - S9) Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g., 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020. S10) Compounds of the formulas (S10)a) or (S10b) as described in WO-A-2007/023719 and WO-A-2007/023764 O O Z 3 G RG2 G where
Figure imgf000035_0001
RG1Halogen, (C1-C4)alkyl, methoxy, nitro, cyano, CF3, OCF3 YG, ZG independently of one another are O or S, nG is an integer from 0 to 4, RG 2(C1-C16)Alkyl, (C2-C6)Alkenyl, (C3-C6)cycloalkyl, aryl; Benzyl, halobenzyl, RG 3Hydrogen or (C1-C6)Alkyl. S11) Active ingredients of the oxyimino compound type (S11), which are known as seed dressings, such as B. "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet against metolachlor damage, "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), which is known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet against metolachlor damage. S12) Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361. S13) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as BCS231028 Foreign Countries - 35 - Safener for pretilachlor in sown rice, "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage from imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for maize, "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia, "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphodithioate) (S13-7), "Dietholate" (O,O-Diethyl-O-phenylphosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methylcarbamate) (S13-9). S14) Active ingredients that, in addition to herbicidal activity against harmful plants, also have safener effects on crops such as rice, such as: B. "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), which is known as a safener for rice against damage from the herbicide Molinate, "Daimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage from the herbicide Imazosulfuron, "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), 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. S15) Compounds of formula (S15) or their tautomers as described in WO-A-2008/131861 and WO-A-2008/131860 O R 2 R 4 wherein
Figure imgf000036_0001
RH1a (C1-C6)haloalkyl radical and RH2hydrogen or halogen and RH3, RH4independently of one another are hydrogen, (C1-C16)alkyl, (C2-C16)alkenyl or (C2-C16)alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of 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- BCS231028 Foreign Countries - 36 - (C6)cycloalkyl fused on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)cycloalkenyl fused on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, wherein each of the latter four radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxy, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylamino, di[(C1-C4)alkyl]amino, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, (C3-C6)cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, is substituted, or RH3 (C1-C4)-alkoxy, (C2-C4)alkenyloxy, (C2-C6)alkynyloxy or (C2-C4)haloalkoxy and RH4hydrogen or (C1-C4)-alkyl or RH3and RH4together with the directly bonded N atom, forms a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio. S16) Active ingredients that are primarily used as herbicides but also have safener effects on crops, e.g. (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl). The following examples illustrate the invention. A. Chemical Examples Synthesis of 2-chloro-4-cyclopropyl-3-(S-methylsulfonimidoyl)-N-(1,3,4-oxadiazol-2-yl)benzamide (Table Example No. 1-4): To a solution of 266.9 mg (0.79 mmol) of 2-chloro-4-cyclopropyl-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamide in 4 ml of methanol, 123.8 mg (1.58 mmol) of ammonium carbamate and 638.3 mg (1.98 mmol) of iodosobenzene diacetate were added successively. The reaction mixture was stirred at room temperature for 20 hours and then evaporated onBCS231028 Foreign Countries - 37 - The solvent was largely removed by rotary evaporation. After chromatographic purification of the residue, 106.7 mg (37.1%) of the desired product was obtained. Synthesis of 2-chloro-4-cyclopropyl-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamide: 0.30 g (3.64 mmol) of 1-methyl-1H-imidazole was added to 0.50 g (1.82 mmol) of 2-chloro-4-cyclopropyl-3-(methylsulfanyl)benzoic acid, 0.17 g (2.00 mmol) of 1,3,4-oxadiazol-2-amine, and 3.0 ml of 3-methylpyridine, and the mixture was cooled to 0°C. At this temperature, 0.35 g (2.91 mmol) of thionyl chloride was added dropwise, the reaction mixture was allowed to warm slowly to room temperature, and stirred at this temperature for 24 h. For workup, saturated aqueous sodium chloride solution and dichloromethane were added, the organic phase was separated, and the solvent was removed in vacuo. After chromatographic purification of the residue, 267 mg (43.6%) of the desired product was obtained as a colorless solid. Synthesis of 2-methyl-3-(S-methylsulfonimidoyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethyl)benzamide (Table Example No. 1-2): 64.0 mg (0.82 mmol) of ammonium carbamate and 330.0 mg (1.02 mmol) of iodosobenzene diacetate were added successively to a solution of 130.0 mg (0.41 mmol) of 2-methyl-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethyl)benzamide in 2 ml of methanol. The reaction mixture was stirred at room temperature for 20 hours and then largely freed from solvent using a rotary evaporator. After chromatographic purification of the residue, 50.0 mg (33.3%) of the desired product was obtained. Synthesis of 4-(Difluoromethyl)-2-ethyl-3-(S-ethylsulfonimidoyl)-N-(1,3,4-oxadiazol-2-yl)benzamide (Table Example No. 1-6): 88.2 mg (1.13 mmol) of ammonium carbamate and 455 mg (1.41 mmol) of iodosobenzene diacetate were added successively to a solution of 185 mg (0.57 mmol) of 4-(difluoromethyl)-2-ethyl-3-(ethylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamide in 15 ml of methanol. The reaction mixture was then stirred at room temperature for 20 hours. For workup, a little water and then sodium bisulfite were added. The mixture was largely freed of solvent using a rotary evaporator. The residue was taken up with dichloromethane and a little water. After phase separation, the organic phase was freed from solvent using a rotary evaporator. The residue was purified by chromatography, yielding 25.2 mg of pure product. Synthesis of 4-(difluoromethyl)-2-ethyl-3-(ethylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamide: 634 mg (2.44 mmol) of 4-(difluoromethyl)-2-ethyl-3-(ethylsulfanyl)benzoic acid in 40 ml of dry tetrahydrofuran was heated to a temperature of 55 °C to 60 °C, then 592 mg (3.65 mmol) of 1,1'-carbonyldiimidazole was added portionwise. The reaction mixture was stirred for three hours.BCS231028 Ausland - 38 - stirred under reflux. The contents were then cooled to room temperature, and 296 mg (1.83 mmol) of 1,1'-carbonyldiimidazole was added portionwise. The mixture was then stirred under reflux for a further four hours. In the next step, 327 mg (95 wt% purity; 3.65 mmol) of 1,3,4-oxadiazol-2-amine, 10 ml of acetonitrile, and 556 mg (3.65 mmol) of 1,8-diazabicyclo(5.4.0)undec-7-ene were added successively at room temperature. The contents of the flask were then stirred at room temperature for three days. To complete the reaction, the mixture was stirred for a further five hours at 50 °C, then 164 mg (95 wt% purity; 1.83 mmol) of 1,3,4-oxadiazol-2-amine and 278 mg (1.83 mmol) of 1,8-diazabicyclo(5.4.0)undec-7-ene were added. The contents were stirred for a further two days at room temperature. For workup, the contents were largely freed of solvent using a rotary evaporator. The residue was treated with water and dichloromethane. After phase separation, the aqueous phase was adjusted to pH 3 with dilute hydrochloric acid. The aqueous phase was then extracted with dichloromethane. The combined organic phases were then freed of solvent using a rotary evaporator. The residue was purified by chromatography, yielding 505 mg of pure product. The examples listed in the following tables were prepared analogously to the methods mentioned above or are available analogously to the methods mentioned above.
Figure imgf000039_0003
h. The compounds listed in the table below are particularly preferred. The abbreviations used mean: Me = Methyl Et = Ethyl c-Pr = Cyclopropyl Table 1: Compounds according to the invention of the general formula (I), wherein R', R'', and W each represent hydrogen.
Figure imgf000039_0002
Figure imgf000039_0001
No BCS231028 Foreign - 39 - No. X Z R Remark 1-5 Et CF3 Me Racemate 1-6 Et CHF2 Et Racemate 1-7 Cl CF3 Me Racemate 1-8 Cl CHF2 Me Enantiomer A 1-9 Cl CHF2 Me Enantiomer B 1-10 c-Pr CHF2 Me Racemate 1-11 Cl Me Me Racemate 1-12 c-Pr Cl Me Racemate 1-13 OMe CHF2 Me Racemate 1-14 Cl CF3 Me Enantiomer A 1-15 Cl CF3 Me Enantiomer B 1-16 Me CHF2 Me Enantiomer A 1-17 Me CHF2 Me Enantiomer B 1-18 Me CF3 Me Enantiomer A 1-19 Me CF3 Me Enantiomer B 1-20 Me CHF2 Et Racemate 1-21 Me CHF2 Et enantiomer A 1-22 Me CHF2 Et enantiomer B 1-23 Cl CHF2 Et racemate 1-24 Cl CHF2 Et enantiomer A 1-25 Cl CHF2 Et enantiomer B 1-26 Me CF3 Et racemate 1-27 Me CF3 Et enantiomer A 1-28 Me CF3 Et enantiomer B 1-29 Cl CF3 Et racemate 1-30 Cl CF3 Et Enantiomer A 1-31 Cl CF3 Et Enantiomer B 1-32 Cl c-Pr Me Enantiomer A 1-33 Cl c-Pr Me Enantiomer B 1-34 Cl OCF3Me Racemate 1-35 Cl OCF3 Me Enantiomer A 1-36 Cl OCF3 Me Enantiomer B NMR data of selected examples: The1H-NMR data of selected examples of compounds of general formula (I) are presented in two different ways, namely (a) classical NMR evaluation and interpretation or (b) in the form of1H NMR peak lists according to the method described below. a) Classical NMR interpretation BCS231028 Foreign Countries - 40 - Examples 1-10:1H-NMR (DMSO-D6, ^, ppm): 12.26 (bs, 1H), 9.08 (s, 1H), 7.93 (t, 1H), 7.83-7.79 (m, 2H), 4.89 (s, 1H), 3.42 (s, 3H), 2.63-2.61 (m, 1H), 1.03-0.95 (m, 2H), 0.76-0.74 (m, 1H), 0.61-0.58 (m, 1H). Ex.1-11: 1H NMR (DMSO-D6, ^, ppm): 12.44 (bs, 1H), 9.05 (s, 1H), 7.66 (d, 1H), 7.45 (d, 1H), 4.83 (s, 1H), 3.30 (s, 3H), 2.76 (s, 3H). Examples 1-12: 1H-NMR (DMSO-D6, ^, ppm): 12.23 (bs, 1H), 9.06 (s, 1H), 7.62-7.59 (m, 2H), 4.74 (s, 1H), 3.39 (s, 3H), 2.53-2.50 (m, 1H), 0.97-0.93 (m, 2H), 0.66-0.63 (m, 1H), 0.57-0.54 (m, 1H). Ex.1-13: 1H NMR (DMSO-D6, ^, ppm): 12.42 (bs, 1H), 9.09 (s, 1H), 7.98 (d, 1H), 7.89 (t, 1H), 7.72 (d, 1H), 3.88 (s, 3H), 3.44 (s, 3H). Ex.1-34: 1HNMR (CDCl3, ^, ppm): 8.17 (bs, 1H), 7.79 (d, 1H), 7.46-7.39 (m, 1H), 3.44 (s, 3H). b) NMR peak list method The 1H-NMR data of selected examples are presented in the form of1H-NMR peak lists are recorded. For each signal peak, the ^ value in ppm is listed first, followed by the signal intensity in parentheses. The ^ value – signal intensity number pairs of different signal peaks are listed separated by semicolons. The peak list of an example therefore has the form: ^1(Intensity1 ); ^2(Intensity2);……..; ^i(Intensityi );……; ^n(Intensityn) The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown. For calibration of the chemical shift of1For H-NMR spectra, we use tetramethylsilane and/or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not appear in NMR peak lists.1H-NMR peaks are similar to the classical1H-NMR printouts and thus usually contain all peaks that are recorded in a classical NMR interpretation. In addition, they can be interpreted like classical1H-NMR printouts show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and/or peaks from impurities. BCS231028 Foreign Countries - 41 - When specifying compound signals in the delta range of solvents and/or water, our lists of1H-NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D6 and the peak of water, which usually have a high average intensity. The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower average intensity than the peaks of the target compounds (for example, with a purity of >90%). Such stereoisomers and/or impurities can be typical for the respective manufacturing process. Their peaks can thus help to identify the reproduction of our manufacturing process based on “by-product fingerprints.” An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also empirically evaluated expected values) can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to the relevant peak picking in classical1H-NMR interpretation. Further details on1H-NMR peak lists can be found in Research Disclosure Database Number 564025. 1-1:1H-NMR(600.3 MHz, d6-DMSO): δ= 12.6091 (1.8); 9.0661 (5.8); 8.0900 (3.9); 7.9987 (10.5); 7.9878 (10.9); 7.9713 (15.3); 7.9577 (6.2); 7.9068 (4.6); 5.2141 (7.2); 3.7974 (0.8); 3.4166 (0.3); 3.3915 (50.0); 3.3718 (1.6); 3.3518 (0.8); 3.3097 (8.6); 3.2735 (0.4); 2.5033 (10.8); 2.5003 (14.7); 2.4975 (10.6); -0.0001 (4.6) 1-2:1H-NMR (600.3 MHz, CDCl3): δ= 8.2639 (3.9); 7.8999 (0.5); 7.8493 (4.3); 7.8358 (6.0); 7.7704 (3.9); 7.7569 (2.8); 7.2651 (17.7); 5.3011 (28.2); 4.1930 (0.4); 4.1803 (0.6); 4.1673 (0.4); 4.0412 (0.3); 4.0282 (0.5); 4.0151 (0.3); 3.8851 (0.5); 3.3368 (0.4); 3.3192 (50.0); 3.3090 (1.6); 3.2878 (0.8); 2.9552 (1.1); 2.9309 (0.4); 2.9135 (35.1); 2.8892 (0.3); 2.8771 (0.3); 2.8680 (0.4); 2.8610 (1.0); 2.8368 (0.6); 2.3934 (0.4); 2.3805 (0.6); 2.3675 (0.4); 2.0080 (1.1); 1.6364 (2.4); 1.4268 (2.3); 1.4097 (0.3); 1.2918 (0.6); 1.2847 (0.6); 1.2555 (3.7); 0.8915 (0.4) 1; 0.8802 (0.8); 0.8682 (0.5); -0.0001 (8.7) 1-3: H-NMR(400.6 MHz, CDCl3): δ= 7.5185 (2.9); 7.2880 (2.0); 7.2601 (551.0); 6.9965 (3.0); 3.4205 (3.4); 2.9523 (3.8); 2.8974 (2.0); 1.5503 (16.0); 1.3323 (1.8); 1.2838 (2.6); 1.2548 (3.7); 0.1582 (1.6); 0.1457 (3.1); 0.0688 (1.3); 0.0278 (3.0); 0.0080 (23.2); -0.0002 (759.1); -0.0085 (21.5); - 0.149 14 (2.7) 1-4: H-NMR (400.6 MHz, CDCl3): δ= 8.2209 (3.1); 7.5995 (1.8); 7.5791 (2.0); 7.2632 (11.3); 7.1892 (2.0); 7.1687 (1.9); 5.3009 (12.4); 3.4512 (16.0); 3.1237 (0.9); 3.1097 (0.5); 3.1025 (0.5); 1.1696 (1.5); 1.1647 (1.1); 1.1553 (1.0); 1.1484 (1.6); 1.1341 (0.6); 0.8914 (0.7); 0.8806 (0.6); 0.8772 (0.6); 0.7734 (0.5); 0.7682 (0.5); 0.7591 (0.7); 0.7544 (0.6); 0.7446 (0.6); 0.7357 (0.5); -0.0002 (12.4); -0.0085 (0.6) 1-5:1H-NMR(400.6 MHz, d6-DMSO): δ= 9.0510 (1.3); 7.9145 (0.9); 7.8809 (0.6); 3.2525 (2.2); 3.2492 (2.2); 2.5407 (2.3); 2.5105 (3.8); 2.5059 (8.2); 2.5013 (11.4); 2.4966 (7.9); 2.4920 (3.4); 2.0882 (0.5); 2.0857 (16.0); 1.2103 (0.7); 1.1921 (1.6); 1.1738 (0.6); -0.0002 (11.5) 1-6: 1H-NMR (400.6 MHz, CDCl3): δ= 8.1960 (2.3); 8.1348 (1.7); 7.9996 (2.0); 7.9948 (1.9); 7.9154 (2.3); 7.8951 (3.3); 7.8596 (1.9); 7.8045 (3.3); 7.7843 (2.3); 7.2623 (24.9); 3.5364 (1.0); 3.5183 (3.3); 3.5000 (3.4); 3.4816 (1.1); 3.4098 (0.6); 3.3934 (1.0); 3.3797 (1.2); 3.3750 (3.0); 3.3616 (3.0); 3.3564 (3.2); 3.3432 (3.0); 3.3380 (1.2); 3.3255 (1.2); 3.3084 (0.6); 1.4291 (7.4); 1.4107 (16.0); 1.3921 (7.3); 1.2605 (3.7); 1.2424 (7.8); 1.2241 (3.6); 0.0080 (0.8); -0.0002 (35.4); -0.0085 (1.1) 1-7:1H-NMR(400.6 MHz, d6-DMSO): δ= 9.0729 (0.5); 8.0749 (1.0); 8.0337 (0.6); 3.3681 (3.0); 3.3198 (0.6); 2.5105 (3.6); 2.5059 (7.9); 2.5013 (10.9); 2.4967 (7.6); 2,492 11 (3.3); 2.0856 (16.0); -0.0002 (5.9) 1-8: H-NMR(400.6 MHz, d6-DMSO): δ= 12.6242 (0.6); 9.0671 (3.0); 8.1317 (1.6); 8.1244 (0.6); 8.1036 (0.8); 8.0046 (1.4); 7.9946 (3.8); 7.9845 (5.0); 7.9707 (6.1); 7.9502 (1.7); 7.8572 (1.9); 7.4646 (0.9); 5.2259 (3.0); 4.0952 (0.6); 3.4270 (2.1); 3.4247 (2.0); 3.3909 (16.0); 3.3191 (5.8); 3.1711 (3.7); 3.1651 (3.7); 2.6744 (0.7); 2.6698 (0.9); 2.6652 (0.6); 2.5235 (2.4); 2.5189 (3.6); 2.5101 (51.8); 2.5056 (112.5); 2.5010 BCS231028 Foreign - 42 - (156.5); 2.4964 (107.2); 2.4918 (46.5); 2.4771 (0.5); 2.4721 (0.8); 2.4679 (0.9); 2.3327 (0.6); 2.3281 (0.9); 2.3234 (0.6); 1.0550 (0.6); 0.1459 (0.5); 0.0080 (5.2); -0.0002 (181.7); -0.0053 (1.3); -0.0062 (1.1); -0.0085 (4.9); -0.0285 (0.5); -0.0340 (0.5); -0.1492 (0.5) 1-9:1H-NMR(400.6 MHz, d6-DMSO): δ= 9.0672 (1.9); 8.1316 (1.1); 8.0047 (1.0); 7.9944 (2.6); 7.9845 (3.7); 7.9708 (4.6); 7.9503 (1.3); 7.8571 (1.3); 5.2245 (2.0); 4.1088 (0.9); 4.0957 (2.7); 4.0827 (2.8); 4.0697 (1.0); 3.3914 (10.4); 3.3894 (10.2); 3.3198 (8.2); 3.1741 (16.0); 3.1615 (15.5); 2.6697 (0.5); 2.5235 (1.2); 2.5188 (1.7); 2.5101 (27.2); 2.5055 (60.0); 2.5009 (83.9); 2.4963 (57.6); 2.4917 (25.3); 1.0724 (0.6); 1.0550 (1.2); 1.0375 (0.6); 0.0080 (3.0); 0.0064 (0.9); 0.0055 (1.0); 0.0047 (1.3); 0.0038 (1.8); -0.0002 (97.4); -0.0026 (3.8); -0.0042 (1.3); -0.0051 (0.9); -0.0059 (0.7); -0.0067 (0.6); -0.0085 (2.6) B. Formulation examples a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or salts thereof and 90 parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill. b) A wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurine as wetting and dispersing agent and milling the mixture in a pin mill. c) A dispersion concentrate readily dispersible in water is obtained by mixing 20 parts by weight of a compound of formula (I) and/or its salts with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO), and 71 parts by weight of paraffinic mineral oil (boiling range, e.g., approximately 255 to over 277°C) and grinding 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 mixing 75 parts by weight of a compound of formula (I) and/or its salts, 10 parts by weight of calcium ligninsulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol, and 7 parts by weight of kaolin, grinding the mixture in a pin mill, and granulating the powder in a fluidized bed by spraying water as the granulation liquid. f) Water-dispersible granules are also obtained by BCS231028 Foreign Countries - 43 - 25 parts by weight of a compound of formula (I) and/or its salts, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurine, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate, and 50 parts by weight of water were homogenized and pre-comminuted in a colloid mill, then ground in a bead mill, and the resulting suspension was atomized and dried in a spray tower using a single-component nozzle. C. Biological Examples 1. Herbicidal Activity and Post-Emergence Crop Tolerance Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants were sown in plastic or wood fiber pots in sandy loam soil, covered with soil, and grown in a greenhouse under controlled growth conditions. Two to three weeks after sowing, the test plants were treated at the single-leaf stage. The compounds of the invention, formulated as wettable powders (WP) or as emulsion concentrates (EC), were then sprayed onto the green plant parts as an aqueous suspension or emulsion with the addition of 0.5% additive at a water application rate equivalent to 600 l/ha. After approximately three weeks of the test plants standing in the greenhouse under optimal growth conditions, the effect of the preparations was visually assessed in comparison to untreated controls. For example, 100% effect means plants have died, 0% effect means the same as the control plants. Tables A1 to A14 below show the effects of selected compounds of general formula (I) according to Table 1 on various weeds and at an application rate corresponding to 80 g/ha and lower, obtained according to the aforementioned test procedure. The appendices "a," "b," and "c" differentiate according to the dosages used for otherwise identically tested weeds. Table A1a: Postemergence effect at 20 g/ha against ALOMY in % Example Dosage Number [g/ha] ALOMY 1-5 20 80 BCS231028 Foreign Countries - 44 - Table A1b: Post-emergence effect at 80 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY 1-4 80 80 1-6 80 80 1-3 80 90 1-8 80 80 1-34 80 80 Table A2a: Post-emergence effect at 5 g/ha against AMARE in % Example Dosage number [g/ha] AMARE 1-5 5 90 1-2 5 90 1-11 5 80 1-1 5 100 1-10 5 90 Table A2b: Post-emergence effect at 20 g/ha against AMARE in % Example Dosage number [g/ha] AMARE 1-5 20 100 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-12 20 90 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100

BCS231028 Ausland - 45 - Tabelle A2c: Nachauflaufwirkung bei 80 g/ha gegen AMARE in % Beispiel- Dosierung nummer [g/ha] AMARE 1-4 80 90 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Tabelle A3a: Nachauflaufwirkung bei 20 g/ha gegen AVEFA in % Beispiel- Dosierung nummer [g/ha] AVEFA 1-1 20 80 1-4 20 90 1-6 20 80 1-3 20 100 1-9 20 80 Tabelle A3b: Nachauflaufwirkung bei 80 g/ha gegen AVEFA in % Beispiel- Dosierung nummer [g/ha] AVEFA 1-4 80 100 1-6 80 80 1-3 80 100 1-9 80 100 1-8 80 90 1-34 80 90 Tabelle A4a: Nachauflaufwirkung bei 5 g/ha gegen DIGSA in % Beispiel- Dosierung nummer [g/ha] DIGSA 1-5 5 90 1-2 5 100 1-1 5 100 Tabelle A4b: Nachauflaufwirkung bei 20 g/ha gegen DIGSA in % Beispiel- Dosierung nummer [g/ha] DIGSA 1-5 20 90 BCS231028 Ausland - 46 - Beispiel- Dosierung nummer [g/ha] DIGSA 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 90 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 90 1-8 20 90 Tabelle A4c: Nachauflaufwirkung bei 80 g/ha gegen DIGSA in % Beispiel- Dosierung nummer [g/ha] DIGSA 1-4 80 90 1-6 80 90 1-3 80 100 1-9 80 90 1-8 80 90 Tabelle A5a: Nachauflaufwirkung bei 5 g/ha gegen ECHCG in % Beispiel- Dosierung nummer [g/ha] ECHCG 1-5 5 90 Tabelle A5b: Nachauflaufwirkung bei 20 g/ha gegen ECHCG in % Beispiel- Dosierung nummer [g/ha] ECHCG 1-5 20 90 1-2 20 100 1-7 20 100 1-11 20 80 1-1 20 100 1-10 20 100 1-4 20 100 1-6 20 90 1-3 20 100 1-9 20 100 1-8 20 100 BCS231028 Ausland - 47 - Tabelle A5c: Nachauflaufwirkung bei 80 g/ha gegen ECHCG in % Beispiel- Dosierung nummer [g/ha] ECHCG 1-4 80 100 Tabelle A6a: Nachauflaufwirkung bei 20 g/ha gegen LOLRI in % Beispiel- Dosierung nummer [g/ha] LOLRI 1-3 20 80 Tabelle A6b: Nachauflaufwirkung bei 80 g/ha gegen LOLRI in % Beispiel- Dosierung nummer [g/ha] LOLRI 1-4 80 90 1-6 80 80 1-3 80 100 1-9 80 90 1-8 80 90 Tabelle A7a: Nachauflaufwirkung bei 5 g/ha gegen MATIN in % Beispiel- Dosierung nummer [g/ha] MATIN 1-5 5 80 1-1 5 90 Tabelle A7b: Nachauflaufwirkung bei 20 g/ha gegen MATIN in % Beispiel- Dosierung nummer [g/ha] MATIN 1-5 20 80 1-2 20 100 1-7 20 90 1-1 20 100 1-10 20 80 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 90 1-8 20 100 1-34 20 100 BCS231028 Ausland - 48 - Tabelle A7c: Nachauflaufwirkung bei 80 g/ha gegen MATIN in % Beispiel- Dosierung nummer [g/ha] MATIN 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 90 1-8 80 100 1-34 80 100 Tabelle A8a: Nachauflaufwirkung bei 5 g/ha gegen PHBPU in % Beispiel- Dosierung nummer [g/ha] PHBPU 1-5 5 80 Tabelle A8b: Nachauflaufwirkung bei 20 g/ha gegen PHBPU in % Beispiel- Dosierung nummer [g/ha] PHBPU 1-5 20 90 1-2 20 100 1-7 20 90 1-1 20 90 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 80 1-8 20 100 Tabelle A8c: Nachauflaufwirkung bei 80 g/ha gegen PHBPU in % Beispiel- Dosierung nummer [g/ha] PHBPU 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Ausland - 49 - Tabelle A9a: Nachauflaufwirkung bei 80 g/ha gegen POLCO in % Beispiel- Dosierung nummer [g/ha] POLCO 1-4 80 100 1-6 80 80 1-3 80 80 1-9 80 90 1-8 80 90 Tabelle A10a: Nachauflaufwirkung bei 5 g/ha gegen SETVI in % Beispiel- Dosierung nummer [g/ha] SETVI 1-5 5 90 1-1 5 90 Tabelle A10b: Nachauflaufwirkung bei 20 g/ha gegen SETVI in % Beispiel- Dosierung nummer [g/ha] SETVI 1-5 20 90 1-2 20 100 1-7 20 90 1-11 20 100 1-1 20 100 1-10 20 90 1-4 20 90 1-6 20 90 1-3 20 90 1-9 20 100 1-8 20 100 Tabelle A10c: Nachauflaufwirkung bei 80 g/ha gegen SETVI in % Beispiel- Dosierung nummer [g/ha] SETVI 1-4 80 90 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Ausland - 50 - Tabelle A11a: Nachauflaufwirkung bei 5 g/ha gegen VERPE in % Beispiel- Dosierung nummer [g/ha] VERPE 1-5 5 80 1-2 5 90 1-7 5 90 1-11 5 80 1-1 5 90 Tabelle A11b: Nachauflaufwirkung bei 20 g/ha gegen VERPE in % Beispiel- Dosierung nummer [g/ha] VERPE 1-5 20 90 1-2 20 100 1-7 20 100 1-11 20 90 1-1 20 100 1-10 20 100 1-12 20 80 1-4 20 90 1-6 20 80 1-3 20 100 1-9 20 90 1-8 20 100 Tabelle A11c: Nachauflaufwirkung bei 80 g/ha gegen VERPE in % Beispiel- Dosierung nummer [g/ha] VERPE 1-4 80 100 1-6 80 90 1-3 80 100 1-9 80 100 1-8 80 100 Tabelle A12a: Nachauflaufwirkung bei 5 g/ha gegen VIOTR in % Beispiel- Dosierung nummer [g/ha] VIOTR 1-5 5 90 1-2 5 100 1-7 5 100 1-11 5 90 BCS231028 Ausland - 51 - Beispiel- Dosierung nummer [g/ha] VIOTR 1-1 5 100 1-10 5 100 Tabelle A12b: Nachauflaufwirkung bei 20 g/ha gegen VIOTR in % Beispiel- Dosierung nummer [g/ha] VIOTR 1-5 20 100 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-4 20 100 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 1-34 20 100 Tabelle A12c: Nachauflaufwirkung bei 80 g/ha gegen VIOTR in % Beispiel- Dosierung nummer [g/ha] VIOTR 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 1-34 80 100 Tabelle A13a: Nachauflaufwirkung bei 5 g/ha gegen ABUTH in % Beispiel- Dosierung nummer [g/ha] ABUTH 1-2 5 100 1-7 5 80 1-11 5 100 1-1 5 100 1-10 5 100 1-12 5 90 BCS231028 Ausland - 52 - Tabelle A13b: Nachauflaufwirkung bei 20 g/ha gegen ABUTH in % Beispiel- Dosierung nummer [g/ha] ABUTH 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-12 20 100 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 100 1-8 20 100 Tabelle A13c: Nachauflaufwirkung bei 80 g/ha gegen ABUTH in % Beispiel- Dosierung nummer [g/ha] ABUTH 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Tabelle A14a: Nachauflaufwirkung bei 20 g/ha gegen KCHSC in % Beispiel- Dosierung nummer [g/ha] KCHSC 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Tabelle A14b: Nachauflaufwirkung bei 80 g/ha gegen KCHSC in % Beispiel- Dosierung nummer [g/ha] KCHSC 1-4 80 90 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Ausland - 53 - In den nachstehenden Tabellen A15 bis A19 sind die Kulturpflanzenverträglichkeiten ausgewählter Verbindungen der allgemeinen Formel (I) gemäß gemäß Tabelle 1 bei einer Aufwandmenge entsprechend 20 g/ha oder niedriger, die bei Versuchen gemäß zuvor genannter Versuchvorschrift beobachtet wurden, dargestellt. Es werden dabei die beobachteten Effekte an ausgewählten Kulturpflanzen im Vergleich zu den unbehandelten Kontrollen angegeben (Werte in %). Die Appendices „a“, „b“ und „c“ differenzieren nach verwendeten Dosierungen bei ansonsten gleich geprüften Kulturpflanzen. Tabelle A15a: Nachauflaufwirkung bei 5g/ha gegen ZEAMX in % Beispiel- Dosierung nummer [g/ha] ZEAMX 1-5 5 10 1-2 5 0 1-7 5 0 1-11 5 0 1-1 5 0 1-10 5 0 1-12 5 0 1-13 5 0 Tabelle A15b: Nachauflaufwirkung bei 20g/ha gegen ZEAMX in % Beispiel- Dosierung nummer [g/ha] ZEAMX 1-5 20 20 1-2 20 0 1-7 20 0 1-11 20 0 1-10 20 0 1-12 20 0 1-13 20 0 1-4 20 10 1-8 20 0 Tabelle A16a: Nachauflaufwirkung bei 5g/ha gegen TRZAS in % Beispiel- Dosierung nummer [g/ha] TRZAS 1-5 5 10 1-2 5 0 1-7 5 0 BCS231028 Ausland - 54 - 1-11 5 0 1-1 5 0 1-10 5 0 1-12 5 0 1-13 5 0 Tabelle A16b: Nachauflaufwirkung bei 20g/ha gegen TRZAS in % Beispiel- Dosierung nummer [g/ha] TRZAS 1-7 20 0 1-11 20 0 1-1 20 0 1-10 20 0 1-12 20 0 1-13 20 0 1-9 20 20 1-8 20 20 Tabelle A17a: Nachauflaufwirkung bei 5g/ha gegen ORYSA in % Beispiel- Dosierung nummer [g/ha] ORYSA 1-5 5 20 1-2 5 0 1-7 5 0 1-11 5 0 1-10 5 0 1-12 5 0 1-13 5 0 Tabelle A17b: Nachauflaufwirkung bei 20g/ha gegen ORYSA in % Beispiel- Dosierung nummer [g/ha] ORYSA 1-11 20 0 1-10 20 20 1-12 20 0 1-13 20 0 BCS231028 Ausland - 55 - Tabelle A18a: Nachauflaufwirkung bei 5g/ha gegen GLXMA in % Beispiel- Dosierung nummer [g/ha] GLXMA 1-13 5 0 Tabelle A18b: Nachauflaufwirkung bei 20g/ha gegen GLXMA in % Beispiel- Dosierung nummer [g/ha] GLXMA 1-13 20 0 Tabelle A19a: Nachauflaufwirkung bei 5g/ha gegen BRSNW in % Beispiel- Dosierung nummer [g/ha] BRSNW 1-13 5 0 Tabelle A19b: Nachauflaufwirkung bei 20g/ha gegen BRSNW in % Beispiel- Dosierung nummer [g/ha] BRSNW 1-13 20 0 Wie die Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen der allgemeinen Formel (I) bei Behandlung im Nachauflauf eine gute herbizide Wirksamkeit gegen Schadpflanzen auf wie z. B. Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE) und Viola tricolor (VIOTR) bei einer Aufwandmenge von 0,08 kg Aktivsubstanz oder weniger pro Hektar, sowie eine gute Kulturpflanzenverträglichkeit bei Oganismen auf wie z.B. Oryza sativa (ORYSA), Zea mays (ZEAMX), Brassica napus (BRSNW), Glycine max (GLXMA) und Triticum aestivum (TRZAS) bei einer Aufwandmenge von 0.02 kg und weniger pro Hektar. BCS231028 Ausland - 56 - 2. Herbizide Wirkung und Kulturverträglichkeit im Vorauflauf Samen von mono- bzw. dikotylen Unkraut und Kulturpflanzen wurden in Kunststoff- oder organischen Pflanztöpfen ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 l/ha auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Nach ca.3 Wochen wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen in Prozentwerten bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. In den nachstehenden Tabellen B1 bis B14 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 80 g/ha und niedriger, die gemäß zuvor genannter Versuchsvorschrift erhalten wurden, dargestellt. Die Appendices „a“, „b“ und „c“ differenzieren nach verwendeten Dosierungen bei ansonsten gleich geprüften Schadpflanzen. Tabelle B1a: Vorauflaufwirkung bei 80 g/ha gegen ALOMY in % Beispiel- Dosierung nummer [g/ha] ALOMY 1-5 80 90 1-2 80 80 1-6 80 90 1-3 80 80 1-34 80 80 Tabelle B2a: Vorauflaufwirkung bei 20 g/ha gegen AMARE in % Beispiel- Dosierung nummer [g/ha] AMARE 1-5 20 100 1-2 20 100 1-11 20 90 1-1 20 100 1-10 20 80 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 BCS231028 Ausland - 57 - Tabelle B2b: Vorauflaufwirkung bei 80 g/ha gegen AMARE in % Beispiel- Dosierung nummer [g/ha] AMARE 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Tabelle B3a: Vorauflaufwirkung bei 20 g/ha gegen AVEFA in % Beispiel- Dosierung nummer [g/ha] AVEFA 1-3 20 80 Tabelle B3b: Vorauflaufwirkung bei 80 g/ha gegen AVEFA in % Beispiel- Dosierung nummer [g/ha] AVEFA 1-2 80 90 1-7 80 90 1-1 80 90 1-6 80 90 1-3 80 100 1-9 80 100 1-8 80 90 1-34 80 90 BCS231028 Foreign Countries - 45 - Table A2c: Post-emergence effect at 80 g/ha against AMARE in % Example Dosage number [g/ha] AMARE 1-4 80 90 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Table A3a: Post-emergence effect at 20 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA 1-1 20 80 1-4 20 90 1-6 20 80 1-3 20 100 1-9 20 80 Table A3b: Post-emergence effect at 80 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA 1-4 80 100 1-6 80 80 1-3 80 100 1-9 80 100 1-8 80 90 1-34 80 90 Table A4a: Post-emergence effect at 5 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA 1-5 5 90 1-2 5 100 1-1 5 100 Table A4b: Post-emergence effect at 20 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA 1-5 20 90 BCS231028 Foreign Countries - 46 - Example Dosage number [g/ha] DIGSA 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 90 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 90 1-8 20 90 Table A4c: Post-emergence effect at 80 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA 1-4 80 90 1-6 80 90 1-3 80 100 1-9 80 90 1-8 80 90 Table A5a: Post-emergence effect at 5 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG 1-5 5 90 Table A5b: Post-emergence effect at 20 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG 1-5 20 90 1-2 20 100 1-7 20 100 1-11 20 80 1-1 20 100 1-10 20 100 1-4 20 100 1-6 20 90 1-3 20 100 1-9 20 100 1-8 20 100 BCS231028 Foreign Countries - 47 - Table A5c: Post-emergence effect at 80 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG 1-4 80 100 Table A6a: Post-emergence effect at 20 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI 1-3 20 80 Table A6b: Post-emergence effect at 80 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI 1-4 80 90 1-6 80 80 1-3 80 100 1-9 80 90 1-8 80 90 Table A7a: Post-emergence effect at 5 g/ha against MATIN in % Example Dosage number [g/ha] MATIN 1-5 5 80 1-1 5 90 Table A7b: Post-emergence effect at 20 g/ha against MATIN in % Example Dosage number [g/ha] MATIN 1-5 20 80 1-2 20 100 1-7 20 90 1-1 20 100 1-10 20 80 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 90 1-8 20 100 1-34 20 100 BCS231028 Foreign Countries - 48 - Table A7c: Post-emergence effect at 80 g/ha against MATIN in % Example Dosage number [g/ha] MATIN 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 90 1-8 80 100 1-34 80 100 Table A8a: Post-emergence effect at 5 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU 1-5 5 80 Table A8b: Post-emergence effect at 20 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU 1-5 20 90 1-2 20 100 1-7 20 90 1-1 20 90 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 80 1-8 20 100 Table A8c: Post-emergence effect at 80 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Foreign Countries - 49 - Table A9a: Post-emergence effect at 80 g/ha against POLCO in % Example Dosage number [g/ha] POLCO 1-4 80 100 1-6 80 80 1-3 80 80 1-9 80 90 1-8 80 90 Table A10a: Post-emergence effect at 5 g/ha against SETVI in % Example Dosage number [g/ha] SETVI 1-5 5 90 1-1 5 90 Table A10b: Post-emergence effect at 20 g/ha against SETVI in % Example Dosage number [g/ha] SETVI 1-5 20 90 1-2 20 100 1-7 20 90 1-11 20 100 1-1 20 100 1-10 20 90 1-4 20 90 1-6 20 90 1-3 20 90 1-9 20 100 1-8 20 100 Table A10c: Post-emergence effect at 80 g/ha against SETVI in % Example Dosage number [g/ha] SETVI 1-4 80 90 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Foreign Countries - 50 - Table A11a: Post-emergence effect at 5 g/ha against VERPE in % Example Dosage number [g/ha] VERPE 1-5 5 80 1-2 5 90 1-7 5 90 1-11 5 80 1-1 5 90 Table A11b: Post-emergence effect at 20 g/ha against VERPE in % Example Dosage number [g/ha] VERPE 1-5 20 90 1-2 20 100 1-7 20 100 1-11 20 90 1-1 20 100 1-10 20 100 1-12 20 80 1-4 20 90 1-6 20 80 1-3 20 100 1-9 20 90 1-8 20 100 Table A11c: Post-emergence effect at 80 g/ha against VERPE in % Example Dosage number [g/ha] VERPE 1-4 80 100 1-6 80 90 1-3 80 100 1-9 80 100 1-8 80 100 Table A12a: Post-emergence effect at 5 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR 1-5 5 90 1-2 5 100 1-7 5 100 1-11 5 90 BCS231028 Foreign Countries - 51 - Example Dosage number [g/ha] VIOTR 1-1 5 100 1-10 5 100 Table A12b: Post-emergence effect at 20 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR 1-5 20 100 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-4 20 100 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 1-34 20 100 Table A12c: Post-emergence effect at 80 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 1-34 80 100 Table A13a: Post-emergence effect at 5 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH 1-2 5 100 1-7 5 80 1-11 5 100 1-1 5 100 1-10 5 100 1-12 5 90 BCS231028 Foreign Countries - 52 - Table A13b: Post-emergence effect at 20 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-12 20 100 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 100 1-8 20 100 Table A13c: Post-emergence effect at 80 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Table A14a: Post-emergence effect at 20 g/ha against KCHSC in % Example Dosage number [g/ha] KCHSC 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Table A14b: Post-emergence effect at 80 g/ha against KCHSC in % Example Dosage number [g/ha] KCHSC 1-4 80 90 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Foreign Countries - 53 - Tables A15 to A19 below show the crop tolerances of selected compounds of general formula (I) according to Table 1 at an application rate corresponding to 20 g/ha or lower, as observed in tests according to the aforementioned test procedure. The observed effects on selected crops are given in comparison to the untreated controls (values in %). The appendices "a", "b", and "c" differentiate according to the dosages used on otherwise identically tested crops. Table A15a: Post-emergence effect at 5g/ha against ZEAMX in % Example Dosage number [g/ha] ZEAMX 1-5 5 10 1-2 5 0 1-7 5 0 1-11 5 0 1-1 5 0 1-10 5 0 1-12 5 0 1-13 5 0 Table A15b: Post-emergence effect at 20g/ha against ZEAMX in % Example Dosage number [g/ha] ZEAMX 1-5 20 20 1-2 20 0 1-7 20 0 1-11 20 0 1-10 20 0 1-12 20 0 1-13 20 0 1-4 20 10 1-8 20 0 Table A16a: Post-emergence effect at 5g/ha against TRZAS in % Example Dosage number [g/ha] TRZAS 1-5 5 10 1-2 5 0 1-7 5 0 BCS231028 Foreign Countries - 54 - 1-11 5 0 1-1 5 0 1-10 5 0 1-12 5 0 1-13 5 0 Table A16b: Post-emergence effect at 20g/ha against TRZAS in % Example Dosage number [g/ha] TRZAS 1-7 20 0 1-11 20 0 1-1 20 0 1-10 20 0 1-12 20 0 1-13 20 0 1-9 20 20 1-8 20 20 Table A17a: Post-emergence effect at 5g/ha against ORYSA in % Example Dosage number [g/ha] ORYSA 1-5 5 20 1-2 5 0 1-7 5 0 1-11 5 0 1-10 5 0 1-12 5 0 1-13 5 0 Table A17b: Post-emergence effect at 20g/ha against ORYSA in % Example Dosage number [g/ha] ORYSA 1-11 20 0 1-10 20 20 1-12 20 0 1-13 20 0 BCS231028 Foreign countries - 55 - Table A18a: Post-emergence activity at 5g/ha against GLXMA in % Example dosage number [g/ha] GLXMA 1-13 5 0 Table A18b: Post-emergence activity at 20g/ha against GLXMA in % Example dosage number [g/ha] GLXMA 1-13 20 0 Table A19a: Post-emergence activity at 5g/ha against BRSNW in % Example dosage number [g/ha] BRSNW 1-13 5 0 Table A19b: Post-emergence activity at 20g/ha against BRSNW in % Example dosage number [g/ha] BRSNW 1-13 20 0 As the results show, compounds of the general formula (I) according to the invention have good herbicidal activity against harmful plants such as, for example, B. Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE) and Viola tricolor (VIOTR) at an application rate of 0.08 kg active ingredient or less per hectare, as well as good crop tolerance in organisms such as Oryza sativa (ORYSA), Zea mays (ZEAMX), Brassica napus (BRSNW), Glycine max (GLXMA) and Triticum aestivum (TRZAS) at an application rate of 0.02 kg and less per hectare. BCS231028 Foreign Countries - 56 - 2. Herbicidal Activity and Crop Compatibility in Pre-Emergence Seeds of monocotyledonous and dicotyledonous weeds and cultivated plants were sown in plastic or organic plant pots and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), were then applied to the surface of the covering soil as an aqueous suspension or emulsion with the addition of 0.5% additive at a water application rate of the equivalent of 600 l/ha. After treatment, the pots were placed in the greenhouse and maintained under good growth conditions for the test plants. After approximately 3 weeks, the activity of the preparations was visually assessed in percentages compared to untreated controls. For example, 100% activity = plants have died, 0% activity = same as control plants. Tables B1 to B14 below show the effects of selected compounds of general formula (I) according to Table 1 on various weeds and at an application rate corresponding to 80 g/ha and lower, obtained according to the aforementioned test procedure. Appendices "a,""b," and "c" differentiate according to the dosages used on otherwise identical weeds. Table B1a: Pre-emergence effect at 80 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY 1-5 80 90 1-2 80 80 1-6 80 90 1-3 80 80 1-34 80 80 Table B2a: Pre-emergence effect at 20 g/ha against AMARE in % Example Dosage number [g/ha] AMARE 1-5 20 100 1-2 20 100 1-11 20 90 1-1 20 100 1-10 20 80 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 BCS231028 Foreign Countries - 57 - Table B2b: Pre-emergence effect at 80 g/ha against AMARE in % Example Dosage number [g/ha] AMARE 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Table B3a: Pre-emergence effect at 20 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA 1-3 20 80 Table B3b: Pre-emergence effect at 80 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA 1-2 80 90 1-7 80 90 1-1 80 90 1-6 80 90 1-3 80 100 1-9 80 100 1-8 80 90 1-34 80 90

BCS231028 Ausland - 58 - Tabelle B4a: Vorauflaufwirkung bei 20 g/ha gegen DIGSA in % Beispiel- Dosierung nummer [g/ha] DIGSA 1-5 20 100 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-4 20 100 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Tabelle B4b: Vorauflaufwirkung bei 80 g/ha gegen DIGSA in % Beispiel- Dosierung nummer [g/ha] DIGSA 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Tabelle B5a: Vorauflaufwirkung bei 20 g/ha gegen ECHCG in % Beispiel- Dosierung nummer [g/ha] ECHCG 1-2 20 100 1-7 20 100 1-1 20 100 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 BCS231028 Ausland - 59 - Tabelle B5b: Vorauflaufwirkung bei 80 g/ha gegen ECHCG in % Beispiel- Dosierung nummer [g/ha] ECHCG 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Tabelle B6a: Vorauflaufwirkung bei 80 g/ha gegen LOLRI in % Beispiel- Dosierung nummer [g/ha] LOLRI 1-6 80 80 1-3 80 90 1-8 80 80 Tabelle B7a: Vorauflaufwirkung bei 20 g/ha gegen MATIN in % Beispiel- Dosierung nummer [g/ha] MATIN 1-5 20 90 1-2 20 100 1-7 20 100 1-1 20 100 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 1-34 20 100 BCS231028 Ausland - 60 - Tabelle B7b: Vorauflaufwirkung bei 80 g/ha gegen MATIN in % Beispiel- Dosierung nummer [g/ha] MATIN 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 1-34 80 100 Tabelle B8a: Vorauflaufwirkung bei 20 g/ha gegen PHBPU in % Beispiel- Dosierung nummer [g/ha] PHBPU 1-1 20 80 1-4 20 80 1-6 20 90 1-3 20 90 1-8 20 80 Tabelle B8b: Vorauflaufwirkung bei 80 g/ha gegen PHBPU in % Beispiel- Dosierung nummer [g/ha] PHBPU 1-5 80 100 1-2 80 100 1-1 80 100 1-10 80 80 1-4 80 90 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Ausland - 61 - Tabelle B9a: Vorauflaufwirkung bei 20 g/ha gegen POLCO in % Beispiel- Dosierung nummer [g/ha] POLCO 1-6 20 80 Tabelle B9b: Vorauflaufwirkung bei 80 g/ha gegen POLCO in % Beispiel- Dosierung nummer [g/ha] POLCO 1-7 80 80 1-11 80 100 1-1 80 90 1-10 80 90 1-6 80 90 1-3 80 90 Tabelle B10a: Vorauflaufwirkung bei 20 g/ha gegen SETVI in % Beispiel- Dosierung nummer [g/ha] SETVI 1-5 20 90 1-2 20 100 1-1 20 100 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Tabelle B10b: Vorauflaufwirkung bei 80 g/ha gegen SETVI in % Beispiel- Dosierung nummer [g/ha] SETVI 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 90 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Ausland - 62 - Tabelle B11a: Vorauflaufwirkung bei 20 g/ha gegen VERPE in % Beispiel- Dosierung nummer [g/ha] VERPE 1-5 20 100 1-6 20 90 1-3 20 100 1-9 20 80 Tabelle B11b: Vorauflaufwirkung bei 80 g/ha gegen VERPE in % Beispiel- Dosierung nummer [g/ha] VERPE 1-5 80 100 1-2 80 100 1-1 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Tabelle B12a: Vorauflaufwirkung bei 20 g/ha gegen VIOTR in % Beispiel- Dosierung nummer [g/ha] VIOTR 1-5 20 100 1-2 20 90 1-7 20 100 1-11 20 80 1-1 20 100 1-10 20 90 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 100 1-8 20 100 Tabelle B12b: Vorauflaufwirkung bei 80 g/ha gegen VIOTR in % Beispiel- Dosierung nummer [g/ha] VIOTR 1-5 80 100 1-2 80 100 1-7 80 100 BCS231028 Ausland - 63 - Beispiel- Dosierung nummer [g/ha] VIOTR 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 1-34 80 100 Tabelle B13a: Vorauflaufwirkung bei 20 g/ha gegen ABUTH in % Beispiel- Dosierung nummer [g/ha] ABUTH 1-5 20 100 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Tabelle B13b: Vorauflaufwirkung bei 80 g/ha gegen ABUTH in % Beispiel- Dosierung nummer [g/ha] ABUTH 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-12 80 90 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Ausland - 64 - Tabelle B14a: Vorauflaufwirkung bei 20 g/ha gegen KCHSC in % Beispiel- Dosierung nummer [g/ha] KCHSC 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Tabelle B14b: Vorauflaufwirkung bei 80 g/ha gegen KCHSC in % Beispiel- Dosierung nummer [g/ha] KCHSC 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 In den nachstehenden Tabellen B15 bis B19 sind die Kulturpflanzenverträglichkeiten ausgewählter Verbindungen der allgemeinen Formel (I) gemäß gemäß Tabelle 1 bei einer Aufwandmenge entsprechend 80 g/ha oder niedriger, die bei Versuchen gemäß zuvor genannter Versuchvorschrift beobachtet wurden, dargestellt. Es werden dabei die beobachteten Effekte an ausgewählten Kulturpflanzen im Vergleich zu den unbehandelten Kontrollen angegeben (Werte in %). Die Appendices „a“, „b“ und „c“ differenzieren nach verwendeten Dosierungen bei ansonsten gleich geprüften Kulturpflanzen. Tabelle B15a: Vorauflaufwirkung bei 20g/ha gegen ZEAMX in % Beispiel- Dosierung nummer [g/ha] ZEAMX 1-5 20 0 1-2 20 0 1-7 20 0 1-11 20 0 1-1 20 0 1-10 20 0 1-12 20 0 1-13 20 0 1-9 20 0 1-8 20 0 BCS231028 Ausland - 65 - Tabelle B15b: Vorauflaufwirkung bei 80/ha gegen ZEAMX in % Beispiel- Dosierung nummer [g/ha] ZEAMX 1-5 80 0 1-2 80 0 1-7 80 0 1-11 80 0 1-1 80 0 1-10 80 0 1-12 80 0 1-13 80 0 1-4 80 10 1-9 80 0 1-8 80 20 Tabelle B16a: Vorauflaufwirkung bei 20g/ha gegen TRZAS in % Beispiel- Dosierung nummer [g/ha] TRZAS 1-5 20 10 1-11 20 0 1-10 20 0 1-12 20 0 1-13 20 0 1-4 20 0 1-9 20 0 1-34 20 10 Tabelle B16b: Vorauflaufwirkung bei 80/ha gegen TRZAS in % Beispiel- Dosierung nummer [g/ha] TRZAS 1-10 80 0 1-12 80 0 1-13 80 0 BCS231028 Ausland - 66 - Tabelle B17a: Vorauflaufwirkung bei 20g/ha gegen ORYSA in % Beispiel- Dosierung nummer [g/ha] ORYSA 1-5 20 20 1-12 20 0 1-13 20 0 Tabelle B18a: Vorauflaufwirkung bei 20g/ha gegen GLXMA in % Beispiel- Dosierung nummer [g/ha] GLXMA 1-13 20 0 1-4 20 10 Tabelle B18b: Vorauflaufwirkung bei 80g/ha gegen GLXMA in % Beispiel- Dosierung nummer [g/ha] GLXMA 1-13 80 0 Tabelle B19a: Vorauflaufwirkung bei 20g/ha gegen BRSNW in % Beispiel- Dosierung nummer [g/ha] BRSNW 1-12 20 0 1-13 20 0 Tabelle B19b: Vorauflaufwirkung bei 80g/ha gegen BRSNW in % Beispiel- Dosierung nummer [g/ha] BRSNW 1-13 80 0 BCS231028 Ausland - 67 - Wie die Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen der allgemeinen Formel (I) bei Behandlung im Vorauflauf eine gute herbizide Wirksamkeit gegen Schadpflanzen auf wie z. B. Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE) und Viola tricolor (VIOTR) bei einer Aufwandmenge von 0,08 kg Aktivsubstanz oder weniger pro Hektar, sowie eine gute Kulturpflanzenverträglichkeit bei Oganismen auf wie z.B. Oryza sativa (ORYSA), Zea mays (ZEAMX), Brassica napus (BRSNW), Glycine max (GLXMA) und Triticum aestivum (TRZAS) bei einer Aufwandmenge von 0.08 kg und weniger pro Hektar. 3. Vergleichende herbizide Wirkung und Kulturpflanzenverträglichkeit von erfindungsgemäßen Verbindungen mit literaturbekannten, strukturnahen Verbindungen aus WO2013/124228 im Nach- und Vorauflauf. In der nachstehenden Tabelle C1 sind die erfindungsgemäßen Verbindungen und die literaturbekannten, strukturnahen Verbindungen aus WO2013/124228 gegenübergestellt. Hierbei unterscheiden sich die erfindungsgemäßen Verbindungen durch Varianz eines signifikanten Strukturmerkmals von den literaturbekannten Verbindungen. Die erfindungsgemäßen Verbindungen (1-1, 1-2, 1-7, 1-11, 1-13) tragen im Gegensatz zu den literaturbekannten Verbindungen keinen Methylsubstituenten am Oxadiazolring. Tabelle C1 Erfindungsgemäße Verbindung Strukturnahe Verbindung aus WO2013/124228 1-1 (erfindungsgemäß) * 7-18 (WO2013/124228) * 1-2 (erfindungsgemäß) * 7-6 (WO2013/124228) * 1-7 (erfindungsgemäß) * 7-17 (WO2013/124228) * 1-11 (erfindungsgemäß) * 7-12 (WO2013/124228) * 1-13 (erfindungsgemäß) * 7-29 (WO2013/124228) * In den nachstehenden Tabellen C2-C11 sind die Nachauflaufwirkungen auf verschiedene Schadpflanzen von erfindungsgemäßen Verbindungen und literaturbekannten strukturnahen Verbindung aus BCS231028 Ausland - 68 - WO2013/124228 bei einer Aufwandmenge entsprechend 20 g/ha und niedriger, die gemäß zuvor genannter Versuchsvorschrift erhalten wurden, dargestellt. Tabelle C2 Verbindung ABUTH Aufwandmenge (Wirkung in %) [g/ha] 1-11 (erfindungsgemäß) 100 5 7-12 (WO2013/124228) 0 5 Tabelle C3 Verbindung AMARE Aufwandmenge (Wirkung in %) [g/ha] 1-11 (erfindungsgemäß) 100 20 7-12 (WO2013/124228) 60 20 1-2 (erfindungsgemäß) 90 5 7-6 (WO2013/124228) 40 5 Tabelle C4 Verbindung AVEFA Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 80 20 7-18 (WO2013/124228) 30 20 Tabelle C5 Verbindung DIGSA Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 100 5 7-18 (WO2013/124228) 70 5 1-11 (erfindungsgemäß) 100 20 7-12 (WO2013/124228) 80 20 BCS231028 Ausland - 69 - Tabelle C6 Verbindung ECHCG Aufwandmenge (Wirkung in %) [g/ha] 1-11 (erfindungsgemäß) 80 20 7-12 (WO2013/124228) 0 20 Tabelle C7 Verbindung MATIN Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 90 5 7-18 (WO2013/124228) 70 5 1-2 (erfindungsgemäß) 100 20 7-6 (WO2013/124228) 70 20 Tabelle C8 Verbindung PHPBU Aufwandmenge (Wirkung in %) [g/ha] 1-11 (erfindungsgemäß) 90 20 7-12 (WO2013/124228) 70 20 Tabelle C9 Verbindung SETVI Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 90 5 7-18 (WO2013/124228) 70 5 1-11 (erfindungsgemäß) 100 20 7-12 (WO2013/124228) 0 20 BCS231028 Ausland - 70 - Tabelle C10 Verbindung VERPE Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 90 5 7-18 (WO2013/124228) 70 5 1-2 (erfindungsgemäß) 90 5 7-6 (WO2013/124228) 70 5 1-11 (erfindungsgemäß) 80 5 7-12 (WO2013/124228) 0 5 Tabelle C11 Verbindung VIOTR Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 100 5 7-18 (WO2013/124228) 70 5 1-2 (erfindungsgemäß) 100 5 7-6 (WO2013/124228) 80 5 1-7 (erfindungsgemäß) 100 5 7-17 (WO2013/124228) 70 5 1-11 (erfindungsgemäß) 90 5 7-12 (WO2013/124228) 50 5 Wie die in den Tabellen C2 bis C11 dargestellten Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen (1-1, 1-2, 1-7, 1-11) im Vergleich zu den strukturnahen literaturbekannten Verbindungen „7-18“, „7-6“, „7-17“, „7-12“, (WO2013/124228) eine deutlich verbesserte herbizide Wirksamkeit im Nachauflauf gegen Schadpflanzen, wie Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Setaria viridis (SETVI), Veronica persica (VERPE) und Viola tricolor (VIOTR) bei einer Aufwandmenge von 20 g Aktivsubstanz oder weniger pro Hektar auf. In den nachstehenden Tabellen C12-C16 sind die Kulturpflanzenverträglichkeiten im Nachauflauf von erfindungsgemäßen Verbindungen und literaturbekannten strukturnahen Verbindung aus WO2013/124228 bei einer Aufwandmenge entsprechend 20 g/ha und niedriger, die gemäß zuvor genannter Versuchsvorschrift erhalten wurden, dargestellt. BCS231028 Ausland - 71 - Tabelle C12 Verbindung BRSNW Aufwandmenge (Wirkung in %) [g/ha] 1-13 (erfindungsgemäß) 0 20 7-29 (WO2013/124228) 80 20 Tabelle C13 Verbindung GLXMA Aufwandmenge (Wirkung in %) [g/ha] 1-13 (erfindungsgemäß) 0 20 7-29 (WO2013/124228) 80 20 Tabelle C14 Verbindung ORYSA Aufwandmenge (Wirkung in %) [g/ha] 1-7 (erfindungsgemäß) 0 5 7-17 (WO2013/124228) 30 5 Tabelle C15 Verbindung TRZAS Aufwandmenge (Wirkung in %) [g/ha] 1-7 (erfindungsgemäß) 0 20 7-17 (WO2013/124228) 60 20 Tabelle C16 Verbindung ZEAMX Aufwandmenge (Wirkung in %) [g/ha] 1-7 (erfindungsgemäß) 0 20 7-17 (WO2013/124228) 20 20 1-13 (erfindungsgemäß) 0 20 7-29 (WO2013/124228) 20 20 BCS231028 Ausland - 72 - Wie die in den Tabellen C12 bis C16 dargestellten Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen (1-7, 1-13) im Vergleich zu den strukturnahen literaturbekannten Verbindungen „7-17“, „7-29“, (WO2013/124228) eine deutlich verbesserte Verträglichkeit im Nachauflauf hinsichtlich der Kulturpflanzen Brassica napus (BRSNW), Glycine max (GLXMA), Oryza sativa (ORYSA), Triticum aestivum (TRZAS) und Zea mays (ZEAMX), bei einer Aufwandmenge von 20 g und weniger pro Hektar. In den nachstehenden Tabellen C17-C28 sind die Vorauflaufwirkungen auf verschiedene Schadpflanzen von erfindungsgemäßen Verbindungen und literaturbekannten strukturnahen Verbindung aus WO2013/124228 bei einer Aufwandmenge entsprechend 80 g/ha und niedriger, die gemäß zuvor genannter Versuchsvorschrift erhalten wurden, dargestellt. Tabelle C17 Verbindung ALOMY Aufwandmenge (Wirkung in %) [g/ha] 1-2 (erfindungsgemäß) 80 80 7-6 (WO2013/124228) 50 80 Tabelle C18 Verbindung ABUTH Aufwandmenge (Wirkung in %) [g/ha] 1-2 (erfindungsgemäß) 100 20 7-6 (WO2013/124228) 40 20 1-7 (erfindungsgemäß) 100 20 7-17 (WO2013/124228) 30 20 1-11 (erfindungsgemäß) 100 20 7-12 (WO2013/124228) 0 20 Tabelle C19 Verbindung AMARE Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 100 20 7-18 (WO2013/124228) 70 20 1-2 (erfindungsgemäß) 100 20 7-6 (WO2013/124228) 70 20 1-11 (erfindungsgemäß) 90 20 7-12 (WO2013/124228) 10 20 BCS231028 Ausland - 73 - Tabelle C20 Verbindung AVEFA Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 90 80 7-18 (WO2013/124228) 60 80 1-2 (erfindungsgemäß) 90 80 7-6 (WO2013/124228) 40 80 1-7 (erfindungsgemäß) 90 80 7-17 (WO2013/124228) 60 80 Tabelle C21 Verbindung DIGSA Aufwandmenge (Wirkung in %) [g/ha] 1-11 (erfindungsgemäß) 100 20 7-12 (WO2013/124228) 20 20 Tabelle C22 Verbindung ECHCG Aufwandmenge (Wirkung in %) [g/ha] 1-2 (erfindungsgemäß) 100 20 7-6 (WO2013/124228) 20 20 1-7 (erfindungsgemäß) 100 20 7-17 (WO2013/124228) 80 20 1-11 (erfindungsgemäß) 100 80 7-12 (WO2013/124228) 0 80 Tabelle C23 Verbindung MATIN Aufwandmenge (Wirkung in %) [g/ha] 1-2 (erfindungsgemäß) 100 20 7-6 (WO2013/124228) 70 20 1-11 (erfindungsgemäß) 100 80 7-12 (WO2013/124228) 0 80 BCS231028 Ausland - 74 - Tabelle C24 Verbindung PHPBU Aufwandmenge (Wirkung in %) [g/ha] 1-11 (erfindungsgemäß) 80 20 7-12 (WO2013/124228) 0 20 1-2 (erfindungsgemäß) 100 80 7-6 (WO2013/124228) 70 80 Tabelle C25 Verbindung POLCO Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 90 80 7-18 (WO2013/124228) 70 80 1-7 (erfindungsgemäß) 80 80 7-17 (WO2013/124228) 10 80 1-11 (erfindungsgemäß) 100 80 7-12 (WO2013/124228) 30 80 Tabelle C26 Verbindung SETVI Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 100 20 7-18 (WO2013/124228) 60 20 1-2 (erfindungsgemäß) 100 20 7-6 (WO2013/124228) 80 20 1-11 (erfindungsgemäß) 90 80 7-12 (WO2013/124228) 20 80 Tabelle C27 Verbindung VERPE Aufwandmenge (Wirkung in %) [g/ha] 1-1 (erfindungsgemäß) 100 80 7-18 (WO2013/124228) 80 80 1-2 (erfindungsgemäß) 100 80 7-6 (WO2013/124228) 20 80 BCS231028 Ausland - 75 - Tabelle C28 Verbindung VIOTR Aufwandmenge (Wirkung in %) [g/ha] 1-2 (erfindungsgemäß) 100 80 7-6 (WO2013/124228) 80 80 1-11 (erfindungsgemäß) 100 80 7-12 (WO2013/124228) 20 80 Wie die in den Tabellen C17 bis C28 dargestellten Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen (1-1, 1-2, 1-7, 1-11) im Vergleich zu den strukturnahen literaturbekannten Verbindungen „7-18“, „7-6“, „7-17“, „7-12“, (WO2013/124228) eine deutlich verbesserte herbizide Wirksamkeit im Vorauflauf gegen Schadpflanzen, wie Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE) und Viola tricolor (VIOTR) bei einer Aufwandmenge von 80 g Aktivsubstanz oder weniger pro Hektar auf. In den nachstehenden Tabellen C29-C32 sind die Kulturpflanzenverträglichkeiten im Vorauflauf von erfindungsgemäßen Verbindungen und literaturbekannten strukturnahen Verbindung aus WO2013/124228 bei einer Aufwandmenge entsprechend 80 g/ha und niedriger, die gemäß zuvor genannter Versuchsvorschrift erhalten wurden, dargestellt. Tabelle C29 Verbindung BRSNW Aufwandmenge (Wirkung in %) [g/ha] 1-13 (erfindungsgemäß) 0 80 7-29 (WO2013/124228) 60 80 Tabelle C30 Verbindung GLXMA Aufwandmenge (Wirkung in %) [g/ha] 1-13 (erfindungsgemäß) 0 80 7-29 (WO2013/124228) 20 80 BCS231028 Ausland - 76 - Tabelle C31 Verbindung ORYSA Aufwandmenge (Wirkung in %) [g/ha] 1-13 (erfindungsgemäß) 0 20 7-29 (WO2013/124228) 20 20 Tabelle C32 Verbindung ZEAMX Aufwandmenge (Wirkung in %) [g/ha] 1-7 (erfindungsgemäß) 0 80 7-17 (WO2013/124228) 20 80 Wie die in den Tabellen C29 bis C32 dargestellten Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen (1-7, 1-13) im Vergleich zu den strukturnahen literaturbekannten Verbindungen „7-17“, „7-29“, (WO2013/124228) eine deutlich verbesserte Verträglichkeit im Vorauflauf hinsichtlich der Kulturpflanzen Brassica napus (BRSNW), Glycine max (GLXMA), Oryza sativa (ORYSA) und Zea mays (ZEAMX), bei einer Aufwandmenge von 80 g und weniger pro Hektar. BCS231028 Foreign Countries - 58 - Table B4a: Pre-emergence effect at 20 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA 1-5 20 100 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-4 20 100 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Table B4b: Pre-emergence effect at 80 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Table B5a: Pre-emergence effect at 20 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG 1-2 20 100 1-7 20 100 1-1 20 100 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 BCS231028 Foreign Countries - 59 - Table B5b: Pre-emergence effect at 80 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Table B6a: Pre-emergence effect at 80 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI 1-6 80 80 1-3 80 90 1-8 80 80 Table B7a: Pre-emergence effect at 20 g/ha against MATIN in % Example Dosage number [g/ha] MATIN 1-5 20 90 1-2 20 100 1-7 20 100 1-1 20 100 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 1-34 20 100 BCS231028 Foreign Countries - 60 - Table B7b: Pre-emergence effect at 80 g/ha against MATIN in % Example Dosage number [g/ha] MATIN 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 1-34 80 100 Table B8a: Pre-emergence effect at 20 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU 1-1 20 80 1-4 20 80 1-6 20 90 1-3 20 90 1-8 20 80 Table B8b: Pre-emergence effect at 80 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU 1-5 80 100 1-2 80 100 1-1 80 100 1-10 80 80 1-4 80 90 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Foreign Countries - 61 - Table B9a: Pre-emergence effect at 20 g/ha against POLCO in % Example Dosage number [g/ha] POLCO 1-6 20 80 Table B9b: Pre-emergence effect at 80 g/ha against POLCO in % Example Dosage number [g/ha] POLCO 1-7 80 80 1-11 80 100 1-1 80 90 1-10 80 90 1-6 80 90 1-3 80 90 Table B10a: Pre-emergence effect at 20 g/ha against SETVI in % Example Dosage number [g/ha] SETVI 1-5 20 90 1-2 20 100 1-1 20 100 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Table B10b: Pre-emergence effect at 80 g/ha against SETVI in % Example Dosage number [g/ha] SETVI 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 90 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Foreign Countries - 62 - Table B11a: Pre-emergence effect at 20 g/ha against VERPE in % Example Dosage number [g/ha] VERPE 1-5 20 100 1-6 20 90 1-3 20 100 1-9 20 80 Table B11b: Pre-emergence effect at 80 g/ha against VERPE in % Example Dosage number [g/ha] VERPE 1-5 80 100 1-2 80 100 1-1 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 Table B12a: Pre-emergence effect at 20 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR 1-5 20 100 1-2 20 90 1-7 20 100 1-11 20 80 1-1 20 100 1-10 20 90 1-4 20 90 1-6 20 90 1-3 20 100 1-9 20 100 1-8 20 100 Table B12b: Pre-emergence effect at 80 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR 1-5 80 100 1-2 80 100 1-7 80 100 BCS231028 Foreign Countries - 63 - Example Dosage number [g/ha] VIOTR 1-11 80 100 1-1 80 100 1-10 80 100 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 1-34 80 100 Table B13a: Pre-emergence effect at 20 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH 1-5 20 100 1-2 20 100 1-7 20 100 1-11 20 100 1-1 20 100 1-10 20 100 1-4 20 90 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Table B13b: Pre-emergence effect at 80 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH 1-5 80 100 1-2 80 100 1-7 80 100 1-11 80 100 1-1 80 100 1-10 80 100 1-12 80 90 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 BCS231028 Foreign Countries - 64 - Table B14a: Pre-emergence effect at 20 g/ha against KCHSC in % Example Dosage number [g/ha] KCHSC 1-6 20 100 1-3 20 100 1-9 20 100 1-8 20 100 Table B14b: Pre-emergence effect at 80 g/ha against KCHSC in % Example Dosage number [g/ha] KCHSC 1-4 80 100 1-6 80 100 1-3 80 100 1-9 80 100 1-8 80 100 The following Tables B15 to B19 show the crop tolerances of selected compounds of the general formula (I) according to Table 1 at an application rate corresponding to 80 g/ha or lower, which were observed in tests according to the above test procedure. The observed effects on selected crops are shown in comparison to the untreated controls (values in %). The appendices "a", "b" and "c" differentiate according to the dosages used on otherwise identically tested crops. Table B15a: Pre-emergence effect at 20g/ha against ZEAMX in % Example Dosage Number [g/ha] ZEAMX 1-5 20 0 1-2 20 0 1-7 20 0 1-11 20 0 1-1 20 0 1-10 20 0 1-12 20 0 1-13 20 0 1-9 20 0 1-8 20 0 BCS231028 Foreign Countries - 65 - Table B15b: Pre-emergence effect at 80/ha against ZEAMX in % Example Dosage number [g/ha] ZEAMX 1-5 80 0 1-2 80 0 1-7 80 0 1-11 80 0 1-1 80 0 1-10 80 0 1-12 80 0 1-13 80 0 1-4 80 10 1-9 80 0 1-8 80 20 Table B16a: Pre-emergence effect at 20g/ha against TRZAS in % Example Dosage number [g/ha] TRZAS 1-5 20 10 1-11 20 0 1-10 20 0 1-12 20 0 1-13 20 0 1-4 20 0 1-9 20 0 1-34 20 10 Table B16b: Pre-emergence effect at 80/ha against TRZAS in % Example Dosage number [g/ha] TRZAS 1-10 80 0 1-12 80 0 1-13 80 0 BCS231028 Foreign Countries - 66 - Table B17a: Pre-emergence effect at 20g/ha against ORYSA in % Example Dosage number [g/ha] ORYSA 1-5 20 20 1-12 20 0 1-13 20 0 Table B18a: Pre-emergence effect at 20g/ha against GLXMA in % Example Dosage number [g/ha] GLXMA 1-13 20 0 1-4 20 10 Table B18b: Pre-emergence effect at 80g/ha against GLXMA in % Example Dosage number [g/ha] GLXMA 1-13 80 0 Table B19a: Pre-emergence effect at 20g/ha against BRSNW in % Example Dosage number [g/ha] BRSNW 1-12 20 0 1-13 20 0 Table B19b: Pre-emergence effect at 80g/ha against BRSNW in % Example Dosage number [g/ha] BRSNW 1-13 80 0 BCS231028 Foreign countries - 67 - As the results show, compounds of the general formula (I) according to the invention have good herbicidal activity against harmful plants such as, for example, B. Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE) and Viola tricolor (VIOTR) at an application rate of 0.08 kg active ingredient or less per hectare, as well as good crop tolerance in organisms such as Oryza sativa (ORYSA), Zea mays (ZEAMX), Brassica napus (BRSNW), Glycine max (GLXMA) and Triticum aestivum (TRZAS) at an application rate of 0.08 kg or less per hectare. 3. Comparative herbicidal activity and crop plant tolerance of compounds according to the invention with structurally similar compounds from WO2013/124228 known from the literature during post- and pre-emergence. Table C1 below compares the compounds according to the invention and the structurally similar compounds from WO2013/124228 known from the literature. The compounds according to the invention differ from the compounds known from the literature by varying a significant structural feature. In contrast to the compounds known from the literature, the compounds according to the invention (1-1, 1-2, 1-7, 1-11, 1-13) do not bear a methyl substituent on the oxadiazole ring. Table C1 Compound according to the invention Structurally close compound from WO2013/124228 1-1 (according to the invention) * 7-18 (WO2013 /124228) * 1-2 (according to the invention) * 7-6 (WO2013/124228) * 1-7 (according to the invention) * 7-17 (WO2013/124228) * 1-11 (according to the invention) * 7-12 (WO2013/124228) * 1-13 (according to the invention) * 7-29 (WO2013/124228) * In the following tables C2-C11 the post-emergence effects on various weeds of compounds according to the invention and literature-known structurally close compound from BCS231028 Foreign countries - 68 - WO2013/124228 at an application rate corresponding to 20 g/ha and lower, which were obtained according to the aforementioned test procedure. Table C2 Compound ABUTH Application rate (effect in %) [g/ha] 1-11 (according to the invention) 100 5 7-12 (WO2013/124228) 0 5 Table C3 Compound AMARE Application rate (effect in %) [g/ha] 1-11 (according to the invention) 100 20 7-12 (WO2013/124228) 60 20 1-2 (according to the invention) 90 5 7-6 (WO2013/124228) 40 5 Table C4 Compound AVEFA Application rate (effect in %) [g/ha] 1-1 (according to the invention) 80 20 7-18 (WO2013/124228) 30 20 Table C5 Compound DIGSA Application rate (effect in %) [g/ha] 1-1 (according to the invention) 100 5 7-18 (WO2013/124228) 70 5 1-11 (according to the invention) 100 20 7-12 (WO2013/124228) 80 20 BCS231028 Foreign Countries - 69 - Table C6 Compound ECHCG Application rate (effect in %) [g/ha] 1-11 (according to the invention) 80 20 7-12 (WO2013/124228) 0 20 Table C7 Compound MATIN Application rate (effect in %) [g/ha] 1-1 (according to the invention) 90 5 7-18 (WO2013/124228) 70 5 1-2 (according to the invention) 100 20 7-6 (WO2013/124228) 70 20 Table C8 Compound PHPBU Application rate (effect in %) [g/ha] 1-11 (according to the invention) 90 20 7-12 (WO2013/124228) 70 20 Table C9 Compound SETVI Application rate (efficacy in %) [g/ha] 1-1 (according to the invention) 90 5 7-18 (WO2013/124228) 70 5 1-11 (according to the invention) 100 20 7-12 (WO2013/124228) 0 20 BCS231028 Foreign Countries - 70 - Table C10 Compound VERPE Application rate (effect in %) [g/ha] 1-1 (according to the invention) 90 5 7-18 (WO2013/124228) 70 5 1-2 (according to the invention) 90 5 7-6 (WO2013/124228) 70 5 1-11 (according to the invention) 80 5 7-12 (WO2013/124228) 0 5 Table C11 Compound VIOTR Application rate (effect in %) [g/ha] 1-1 (according to the invention) 100 5 7-18 (WO2013/124228) 70 5 1-2 (according to the invention) 100 5 7-6 (WO2013/124228) 80 5 1-7 (according to the invention) 100 5 7-17 (WO2013/124228) 70 5 1-11 (according to the invention) 90 5 7-12 (WO2013/124228) 50 5 As the results shown in Tables C2 to C11 show, compounds according to the invention (1-1, 1-2, 1-7, 1-11) have a significantly improved postemergence herbicidal activity against weeds such as Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Setaria viridis (SETVI), Veronica persica (VERPE), and Viola tricolor (VIOTR) at an application rate of 20 g of active ingredient or less per hectare. Tables C12-C16 below show the post-emergence crop tolerance of compounds according to the invention and the structurally similar compound from WO2013/124228, which are known from the literature, at an application rate corresponding to 20 g/ha and lower, obtained according to the aforementioned test procedure. BCS231028 Foreign Countries - 71 - Table C12 Compound BRSNW Application rate (effect in %) [g/ha] 1-13 (according to the invention) 0 20 7-29 (WO2013/124228) 80 20 Table C13 Compound GLXMA Application rate (effect in %) [g/ha] 1-13 (according to the invention) 0 20 7-29 (WO2013/124228) 80 20 Table C14 Compound ORYSA Application rate (effect in %) [g/ha] 1-7 (according to the invention) 0 5 7-17 (WO2013/124228) 30 5 Table C15 Compound TRZAS Application rate (effect in %) [g/ha] 1-7 (according to the invention) 0 20 7-17 (WO2013/124228) 60 20 Table C16 Compound ZEAMX Application rate (efficacy in %) [g/ha] 1-7 (according to the invention) 0 20 7-17 (WO2013/124228) 20 20 1-13 (according to the invention) 0 20 7-29 (WO2013/124228) 20 20 BCS231028 Foreign Countries - 72 - As the results presented in Tables C12 to C16 show, compounds according to the invention (1-7, 1-13) exhibit significantly improved postemergence tolerance compared to the structurally similar compounds known from the literature "7-17", "7-29", (WO2013/124228) with respect to the crop plants Brassica napus (BRSNW), Glycine max (GLXMA), Oryza sativa (ORYSA), Triticum aestivum (TRZAS) and Zea mays (ZEAMX) at an application rate of 20 g and less per hectare. Tables C17-C28 below show the preemergence effects on various weeds of compounds according to the invention and the structurally similar compound from WO2013/124228 obtained according to the aforementioned test procedure at an application rate corresponding to 80 g/ha and lower. Table C17 Compound ALOMY Application rate (effect in %) [g/ha] 1-2 (according to the invention) 80 80 7-6 (WO2013/124228) 50 80 Table C18 Compound ABUTH Application rate (effect in %) [g/ha] 1-2 (according to the invention) 100 20 7-6 (WO2013/124228) 40 20 1-7 (according to the invention) 100 20 7-17 (WO2013/124228) 30 20 1-11 (according to the invention) 100 20 7-12 (WO2013/124228) 0 20 Table C19 Compound AMARE Application rate (effect in %) [g/ha] 1-1 (according to the invention) 100 20 7-18 (WO2013/124228) 70 20 1-2 (according to the invention) 100 20 7-6 (WO2013/124228) 70 20 1-11 (according to the invention) 90 20 7-12 (WO2013/124228) 10 20 BCS231028 Foreign Countries - 73 - Table C20 Compound AVEFA Application rate (effect in %) [g/ha] 1-1 (according to the invention) 90 80 7-18 (WO2013/124228) 60 80 1-2 (according to the invention) 90 80 7-6 (WO2013/124228) 40 80 1-7 (according to the invention) 90 80 7-17 (WO2013/124228) 60 80 Table C21 Compound DIGSA Application rate (effect in %) [g/ha] 1-11 (according to the invention) 100 20 7-12 (WO2013/124228) 20 20 Table C22 Compound ECHCG Application rate (effect in %) [g/ha] 1-2 (according to the invention) 100 20 7-6 (WO2013/124228) 20 20 1-7 (according to the invention) 100 20 7-17 (WO2013/124228) 80 20 1-11 (according to the invention) 100 80 7-12 (WO2013/124228) 0 80 Table C23 Compound MATIN Application rate (effect in %) [g/ha] 1-2 (according to the invention) 100 20 7-6 (WO2013/124228) 70 20 1-11 (according to the invention) 100 80 7-12 (WO2013/124228) 0 80 BCS231028 Foreign Countries - 74 - Table C24 Compound PHPBU Application rate (effect in %) [g/ha] 1-11 (according to the invention) 80 20 7-12 (WO2013/124228) 0 20 1-2 (according to the invention) 100 80 7-6 (WO2013/124228) 70 80 Table C25 Compound POLCO Application rate (effect in %) [g/ha] 1-1 (according to the invention) 90 80 7-18 (WO2013/124228) 70 80 1-7 (according to the invention) 80 80 7-17 (WO2013/124228) 10 80 1-11 (according to the invention) 100 80 7-12 (WO2013/124228) 30 80 Table C26 Compound SETVI Application rate (effect in %) [g/ha] 1-1 (according to the invention) 100 20 7-18 (WO2013/124228) 60 20 1-2 (according to the invention) 100 20 7-6 (WO2013/124228) 80 20 1-11 (according to the invention) 90 80 7-12 (WO2013/124228) 20 80 Table C27 Compound VERPE Application rate (effect in %) [g/ha] 1-1 (according to the invention) 100 80 7-18 (WO2013/124228) 80 80 1-2 (according to the invention) 100 80 7-6 (WO2013/124228) 20 80 BCS231028 Foreign Countries - 75 - Table C28 Compound VIOTR Application rate (activity in %) [g/ha] 1-2 (according to the invention) 100 80 7-6 (WO2013/124228) 80 80 1-11 (according to the invention) 100 80 7-12 (WO2013/124228) 20 80 As the results shown in Tables C17 to C28 show, compounds according to the invention (1-1, 1-2, 1-7, 1-11) have a significantly improved pre-emergence herbicidal activity against weeds such as Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE), and Viola tricolor (VIOTR) at an application rate of 80 g of active ingredient or less per hectare. Tables C29-C32 below show the pre-emergence crop tolerances of compounds according to the invention and the structurally similar compound from WO2013/124228, which are known from the literature, at an application rate corresponding to 80 g/ha and lower, obtained according to the aforementioned test procedure. Table C29 Compound BRSNW Application rate (efficacy in %) [g/ha] 1-13 (according to the invention) 0 80 7-29 (WO2013/124228) 60 80 Table C30 Compound GLXMA Application rate (efficacy in %) [g/ha] 1-13 (according to the invention) 0 80 7-29 (WO2013/124228) 20 80 BCS231028 Foreign Countries - 76 - Table C31 Compound ORYSA Application rate (effect in %) [g/ha] 1-13 (according to the invention) 0 20 7-29 (WO2013/124228) 20 20 Table C32 Compound ZEAMX Application rate (effect in %) [g/ha] 1-7 (according to the invention) 0 80 7-17 (WO2013/124228) 20 80 As the results presented in Tables C29 to C32 show, compounds according to the invention (1-7, 1-13) have a significantly improved pre-emergence tolerance with regard to the crop plants Brassica napus (BRSNW), Glycine max (GLXMA), Oryza sativa (ORYSA) and Zea mays (ZEAMX), at an application rate of 80 g and less per hectare.

Claims

Figure imgf000078_0003
BCS231028 Ausland - 77 - Patentansprüche 1. Sulfonimidoylbenzamide der Formel (I) oder deren Salze
Figure imgf000078_0002
Figure imgf000078_0001
worin die Symbole folgende X bedeutet Halogen, Cyano, (C1-C6)-Alkyl, (C1-C6)-Alkoxy, (C1-C6)-Alkylthio, Halogen- (C1-C6)-alkyl, (C1-C6)-Alkoxy-(C1-C6)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, Z bedeutet Halogen, Cyano, (C1-C6)-Alkyl, Halogen-(C1-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, Halogen-(C1-C6)-alkoxy, (C1-C6)-Alkylsulfonyl, W bedeutet Wasserstoff, Halogen, R bedeutet (C1-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(C1-C6)-alkyl, (C1-C6)- Alkoxy-(C1-C6)-alkyl, R’ bedeutet Wasserstoff, Cyano, (C1-C6)-Alkyl, R’’ bedeutet Wasserstoff, (C1-C6)-Alkylcarbonyl. 2. Sulfonimidoylbenzamide nach Anspruch 1, worin X bedeutet Halogen, (C1-C3)-Alkyl, (C1-C3)-Alkoxy, (C3-C6)-Cycloalkyl, Z bedeutet Halogen, (C1-C3)-Alkyl, Halogen-(C1-C3)-alkyl, (C3-C6)-Cycloalkyl, Halogen- (C1-C3)-alkoxy, W bedeutet Wasserstoff, Fluor, R bedeutet (C1-C3)-Alkyl, R’ bedeutet Wasserstoff, R’’ bedeutet Wasserstoff. 3. Sulfonimidoylbenzamide nach Anspruch 1 oder 2, worin BCS231028 Ausland - 78 - X bedeutet Chlor, Methyl, Ethyl, Methoxy, Cyclopropyl, Z bedeutet Chlor, Methyl, Difluormethyl, Trifluormethyl, Cyclopropyl, Trifluormethoxy, W bedeutet Wasserstoff, R bedeutet Methyl, Ethyl, R’ bedeutet Wasserstoff, R’’ bedeutet Wasserstoff. 4. Herbizide Mittel enthaltend mindestens ein Sulfonimidoylbenzamid gemäß einem der Ansprüche 1 bis 3 in Mischung mit Formulierungshilfsmitteln. 5. Herbizide Mittel gemäß Anspruch 4 enthaltend mindestens einen weiteren pestizid wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und Wachstumsregulatoren. 6. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, dass man eine wirksame Menge mindestens eines Sulfonimidoylbenzamids gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach Anspruch 4 oder 5 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 7. Verwendung von Sulfonimidoylbenzamiden der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach Anspruch 4 oder 5 zur Bekämpfung unerwünschter Pflanzen. 8. Verwendung nach Anspruch 7, dadurch gekennzeichnet, dass die Sulfonimidoylbenzamide der Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden. 9. Verwendung nach Anspruch 8, dadurch gekennzeichnet, dass die Nutzpflanzen transgene Nutzpflanzen sind.
Figure imgf000078_0003
BCS231028 Foreign countries - 77 - Patent claims 1. Sulfonimidoylbenzamides of the formula (I) or their salts
Figure imgf000078_0002
Figure imgf000078_0001
where the following symbols (C3-C6)-cycloalkyl, Z means halogen, cyano, (C1-C6)-alkyl, halogen-(C1-C6)-alkyl, (C2-C6)-alkenyl, halogen-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halogen-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halogen-(C 3 -C 6 )-cycloalkyl, halogen-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylsulfonyl, W means hydrogen, halogen, R means (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, R' means hydrogen, cyano, (C 1 -C 6 )-alkyl, R'' means hydrogen, (C1-C6)-alkylcarbonyl. 2. Sulfonimidoylbenzamides according to claim 1, wherein X is halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, (C3-C6)-cycloalkyl, Z is halogen, (C1-C3)-alkyl, halo-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, halo-(C1-C3)-alkoxy, W is hydrogen, fluorine, R is (C1-C3)-alkyl, R' is hydrogen, R'' is hydrogen. 3. Sulfonimidoylbenzamides according to claim 1 or 2, wherein BCS231028 Foreign Countries - 78 - X is chlorine, methyl, ethyl, methoxy, cyclopropyl, Z is chlorine, methyl, difluoromethyl, trifluoromethyl, cyclopropyl, trifluoromethoxy, W is hydrogen, R is methyl, ethyl, R' is hydrogen, R'' is hydrogen. 4. Herbicidal compositions comprising at least one sulfonimidoylbenzamide according to any one of claims 1 to 3 in a mixture with formulation auxiliaries. 5. Herbicidal compositions according to claim 4 comprising at least one further pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators. 6. Method for controlling unwanted plants, characterized in that an effective amount of at least one sulfonimidoylbenzamide according to any 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 the unwanted plant growth. 7. Use of sulfonimidoylbenzamides of the formula (I) according to any one of claims 1 to 3 or of herbicidal compositions according to claim 4 or 5 for controlling unwanted plants. 8. Use according to claim 7, characterized in that the sulfonimidoylbenzamides of the formula (I) are employed for controlling unwanted plants in crops of useful plants. 9. Use according to claim 8, characterized in that the useful plants are transgenic useful plants.
PCT/EP2024/081863 2023-11-14 2024-11-11 Sulfonimidoyl benzamides with herbicidal action Pending WO2025103939A1 (en)

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