4-fluoroalkylbenzamides and their use as herbicides

Abstract

4-Fluoroalkylbenzamides of formula (I) are described as herbicides. In this formula (I), X, Y, Z and R represent, inter alia, groups such as alkyl, cycloalkyl, haloalkyl and halogen.

Description

[0001] BYC250025 Foreign Mak / lep 2025-12-05

[0002] -1- 4-Fluoroalkylbenzamides and their use as herbicides

[0003] The invention relates to the technical field of herbicides, in particular herbicides for the selective control of weeds and grasses in crop crops.

[0004] WO 2012 / 028579 discloses herbicidally active benzamides that can bear a variety of substituents at the 3-position of the phenyl ring. Additionally, 3-acylbenzamides and substituted isophthalamides are described in WO2019 / 25540, WO2021204665, and WO2021204666. However, the benzoylamides known from the aforementioned publications do not always exhibit sufficient herbicidal activity and / or compatibility with cultivated plants.

[0005] The object of the present invention is to provide alternative herbicidally active ingredients. This object is achieved by the 3-acylbenzamides and isophthalamides described below according to the invention, each of which carries a specific fluoroalkyl group at the 4-position.

[0006] One object of the present invention is therefore 4-fluoroalkylbenzamides of formula (I) or their salts:

[0007]

[0008] where the symbols and indices have the following meanings:

[0009] R stands for (Ci-Ce)-alkyl,

[0010] X means halogen or (Ci-Ce)-alkyl,

[0011] Y means CH2CHF2 or CH2CF3

[0012] Z means Z 1 or Z 2 ,

[0013] Z 1 means (Ci-Ce)-alkyl or (Cs-Cej-cycloalkyl,

[0014] Z 2 NR means 1 R 2 ,

[0015] R 1 , R2 Each of these means, independently of one another, hydrogen, (Ci-Ce)-alkyl, (Cs-Cej-cycloalkyl or halogen-(Ci-Ce)-alkyl 1.

[0016] In formula (I) and all subsequent formulas, alkyl groups with more than two carbon atoms can be straight-chain or branched. Alkyl groups include, for example, methyl (Me), ethyl (Et), n- or i-propyl (Pr), n-, i-, t- or 2-butyl, pentyl, and hexyls such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl. BYC250025 Abroad

[0017] -2- Analogously, alkenyl means, for example, allyl, l-methylprop-2-en-l-yl, 2-methylprop-2-en-l-yl, but-2-en-l-yl, but-3-en-l-yl, l-methylbut-3-en-l-yl, and l-methylbut-2-en-l-yl. Alkynyl means, for example, propargyl, but-2-yne-l-yl, but-3-yne-l-yl, and l-methylbut-3-yne-l-yl. The multiple bond can be located in any position on the unsaturated residue. Cycloalkyl means a carbocyclic, saturated ring system with three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Unless otherwise specified, in this document the abbreviations Me for methyl, Et for ethyl, and Pr for propyl are used, where propyl, without further specification, includes both n- and i-propyl. Generally, "n-" stands for "normal" (unbranched), "i-" for "iso", "t-" for "tertiary", and "c-" for "cyclo". Halogen stands for fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0018] If the compounds can form tautomers through hydrogen shifts, which would not be formally covered by formula (I) in a structural sense, these tautomers are nevertheless included in 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 and enol forms, both of which are covered by the definition of the compound of formula (I).

[0019] Compounds of formula (I) can form salts. Salt formation can occur through the action of a base on such compounds of formula (I) that bear an acidic hydrogen atom, e.g., in the case of R''. Suitable bases include, for example, organic amines such as trialkylamines, morpholine, piperidine, or pyridine, as well as ammonium, alkali, or alkaline earth metal hydroxides, carbonates, and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate, and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agricultural use, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines, or quaternary ammonium salts, for example, with cations of the formula [NRR*R**R***]. +, wherein R, R*, R** and R*** each independently represent an organic residue, in particular alkyl, aryl, arylalkyl or alkylaryl. Alkylsulfonium and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (Ci-Czij)-trialkylsulfoxonium salts, are also suitable.

[0020] The compounds of formula (I) can form salts by the addition of a suitable inorganic or organic acid, such as mineral acids like HCl, HBr, H₂SO₄, H₃PO₄, or HNO₃, or organic acids, e.g., carboxylic acids like formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or sulfonic acids like p-toluenesulfonic acid, to a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino, or pyridino. These salts then contain the conjugate base of the acid as the anion. BYC250025 Abroad

[0021] -3- The compounds of formula (I) can exist as stereoisomers depending on the type and combination of the substituents. For example, if one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be obtained from the mixtures obtained during production by conventional separation methods, for example, by chromatographic separation techniques. Likewise, stereoisomers can be selectively produced by using stereoselective reactions with optically active starting materials and / or auxiliary substances. The invention also relates to all stereoisomers and their mixtures that are included in formula (I) but are not specifically defined.

[0022] Compounds of formula (I) are preferred, wherein the symbols and indices have the following meanings:

[0023] R means Me, Et or Pr,

[0024] X means Cl, Br, Me or Et,

[0025] Y means CH2CF3 or CH2CHF2,

[0026] Z means Z 1 or Z 2 ,

[0027] Z 1 means Me, Et, n-Pr, i-Pr or c-Pr,

[0028] Z 2 NR means 1 R 2 ,

[0029] R 1 , R 2 Each of these terms independently represents hydrogen, Me, Et, Pr, i-Pr, c-Pr, CH2CHF2 or CH2CF3.

[0030] Compounds of formula (I) are particularly preferred, in which the symbols and indices have the following meanings:

[0031] R means Me or Et,

[0032] X means CI or Me,

[0033] Y means CH2CHF2,

[0034] Z means Z 1 or Z 2 ,

[0035] Z 1 means Me, Et or c-Pr,

[0036] Z 2 means NHMe, NHEt or NHc-Pr.

[0037] Further separate embodiments of the inventions are compounds of formula (I) as defined above, wherein Z represents Z 1 stands.BYC250025 Abroad

[0038] -4- Further separate embodiments of the inventions are compounds of formula (I) as defined above, wherein Z represents Z 2 stands.

[0039] In all the following formulas, the substituents and symbols have the same meaning as described under formula (I), unless otherwise defined.

[0040] Compounds of formula (II) are novel and are very suitable as intermediates for the preparation of the compounds of formula (I) according to the invention.

[0041] Another object of the present invention is therefore compounds of formula (II),

[0042]

[0043] where the symbols and indices have the following meanings:

[0044] L means halogen or R 3 0,

[0045] X means halogen or (Ci-Ce)-alkyl,

[0046] Y means CH2CHF2 or CH2CF3

[0047] Z means Z 1 or Z 2 ,

[0048] Z 1 means (Ci-Ce)-alkyl or (Cs-Cej-cycloalkyl,

[0049] Z 2 NR means 1 R 2 ,

[0050] R 1 , R 2 Each of these terms independently represents hydrogen, (Ci-Ce)-alkyl, (Cs-Cej-cycloalkyl or halogen-(Ci-Cj-alkyl I).

[0051] R 3 means hydrogen or (Ci-Ce)-alkyl.

[0052] Compounds of formula (II) are preferred, wherein the symbols and indices have the following meanings:

[0053] L means Cl, Methoxy or Hydroxy,

[0054] X means CI or Me,

[0055] Y means CH2CHF2,

[0056] Z means Z 1 or Z 2 ,BYC250025 Abroad

[0057] -5- Z1 means Me, Et or c-Pr,

[0058] Z 2 means NHMe, NHEt or NHc-Pr.

[0059] Further separate embodiments of the inventions are compounds of formula (II) as defined above, wherein Z represents Z 1 stands.

[0060] Further separate embodiments of the inventions are compounds of formula (II) as defined above, wherein Z represents Z 2 stands.

[0061] Compounds according to the invention of general formula (I) can, for example, as also described in WO2012 / 028579, be prepared by reacting the compounds according to the invention of general formula (Il-a) (compounds II, where L = hydroxy) with substituted 5-aminotetrazoles:

[0062]

[0063] The transformations to the compounds (Il-a) starting from (III) are described, among other places, in WO2019025540 and WO2021204665.

[0064]

[0065] Compounds of general formula (VI) can be prepared, inter alia, by reacting compounds of general formula (IV) with alkoxymethyltriphenylphosphonium compounds under Wittig conditions. Alternatively, compounds of general formula (V) can also be reacted with alkoxyvinylboronic acids or esters under Suzuki conditions to give compounds of general formula (VI). After hydrolysis with acids, such as toluenesulfonic acid, compounds of general formula (VII) can be obtained, which can be reacted with a fluorinating reagent, such as DAST, to give the compounds of general formula (VIII, Y = CH₂CHF₂). Alternatively, the analogous phenylacetic acids can be obtained by oxidation of the compounds of general formula (VII), which can then be reacted with, for example, sodium trifluoromethanesulfmate to give the compounds of general formula (VIII, Y = CH₂CF₃) (J. Org. Chem.2024, 89, 16114). After reaction, e.g., with bromine or NBS, of the compounds of general formula (VIII) to compounds of general formula (IX) and subsequent oxidation, compounds of general formula (III) can be prepared. BYC250025 Foreign.

[0066] -6-

[0067]

[0068] By reacting the compounds of general formula (III) under Grignard conditions, compounds of general formula (X) can be prepared, which can be converted by oxidation, e.g., with Jones' reagent, into the compounds of general formula (II-bl) according to the invention. By saponification with, e.g., sodium hydroxide or liquor in pyridine, the compounds of general formula (Il-al) according to the invention can be obtained. By oxidation, e.g., with Jones' reagent, the compounds of general formula (III) can be converted into the carboxylic acids of general formula (XI), which can be reacted with amines to give the compounds of general formula (II-b2) according to the invention. Saponification as described above yields the compounds of the invention.

[0069]

[0070] Different methods can be used to prepare compounds of general formula (I) with X = Me, including the preparation of compounds with general formula (III) by means of a chloro-methyl exchange, e.g. by means of a palladium-catalyzed reaction with trimethylboron or methylboronic acid.

[0071] Collections of compounds of formula (I) and / or their salts, which can be synthesized according to the reactions mentioned above, can also be produced in parallel, either manually, partially automated, or fully automated. For example, it is possible to automate the reaction procedure, the work-up, or the purification of the products or intermediates. Overall, this is referred to as a procedure BYC250025 Abroad

[0072] -7- understood as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (editor Günther Jung), Wiley Publishing 1999, on pages 1 to 34. A number of commercially available devices can be used for parallelized reaction execution and work-up, such as Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA, or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, England, or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA. For the parallelized purification of compounds of formula (I) and their salts or intermediate products obtained during production, chromatography equipment is available, for example from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

[0073] The listed equipment results in a modular approach where individual work steps are automated, but manual operations must be performed between steps. This can be avoided by using partially or fully integrated automation systems, where the respective automation modules are operated, for example, by robots. Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.

[0074] The execution of individual or multiple synthesis steps can be supported by the use of polymer-supported reagents / scavenger resins. A number of experimental protocols are described in the literature, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

[0075] In addition to the methods described here, the preparation of compounds of formula (I) and their salts can be carried out completely or partially using solid-phase-assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis, or of a synthesis adapted for the specific procedure, are bound to a synthetic resin. Solid-phase-assisted synthesis methods are well described in the literature, e.g., Barry A. Bunin in "The Combinatorial Index," Academic Press, 1998, and Combinatorial Chemistry - Synthesis, Analysis, Screening (edited by Günther Jung), Wiley, 1999. The use of solid-phase-assisted synthesis methods allows for a number of well-known protocols, which can be carried out manually or automatically.The reactions can be carried out, for example, using IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.

[0076] In both solid and liquid phases, the execution of individual or multiple synthesis steps can be supported by the use of microwave technology. (See literature BYC250025, international publication.)

[0077] -8- a number of experimental protocols are described, for example in Microwaves in Organic and Medicinal Chemistry (editors CO Kappe and a. Stadler), Wiley Publishing, 2005.

[0078] The preparation according to the methods described herein yields compounds of formula (I) and their salts in the form of substance collections called libraries. The present invention also relates to libraries containing at least two compounds of formula (I) and their salts.

[0079] The inventive compounds exhibit excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual weeds. Even difficult-to-control perennial weeds that sprout from rhizomes, rootstocks, or other dormant organs are effectively controlled by the active ingredients.

[0080] The present invention therefore relates to a method for controlling unwanted plants or for regulating plant growth, preferably in crops, wherein one or more compounds according to the invention are applied to the plants (e.g., weeds such as monocotyledonous or dicotyledonous weeds or unwanted cultivated plants), the seed (e.g., grains, seeds, or vegetative propagation organs such as tubers or shoots 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 (possibly also by incorporation into the soil), pre-emergence, or post-emergence application. By way of example, some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds according to the invention are mentioned, without this mention implying a limitation to specific species.

[0081] Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum.

[0082] Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola and Xanthium.

[0083] If the compounds according to the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is completely prevented or the weeds grow until the BYC250025 abroad

[0084] -9- They reach the germinal stage, but then cease their growth and finally die completely after three to four weeks.

[0085] When the active ingredients are applied to the green parts of the plants post-emergence, growth stops after treatment, and the weeds either remain at the growth stage they were at at the time of application or die completely after a certain period. This method thus eliminates weed competition that is harmful to cultivated plants very early and effectively. Although the invented compounds exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they are not suitable for commercially important crops, e.g.,Dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, are only minimally damaged or not damaged at all, depending on the structure of the respective invented compound and its application rate. For these reasons, the compounds are very well suited for the selective control of unwanted plant growth in crops such as agricultural crops or ornamental plantings.

[0086] Furthermore, depending on their respective chemical structure and the application rate, the invented compounds exhibit excellent growth-regulating properties in cultivated plants. They exert a regulatory influence on the plant's own metabolism and can therefore be used to selectively influence plant constituents and to facilitate harvesting, for example, by inducing 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 significant role in many monocot and dicot crops, as it can, for example, reduce or completely prevent lodging.

[0087] Due to their herbicidal and plant growth-regulating properties, these active ingredients can also be used to control weeds in crops of genetically modified or conventionally mutagenic plants. Transgenic plants are generally characterized by particularly advantageous properties, such as resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens such as certain insects or microorganisms like fungi, bacteria, or viruses. Other special properties relate, for example, to the output material in terms of quantity, quality, storability, composition, and specific constituents. For instance, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the output material, are known. BYC250025 Abroad

[0088] -10- The application of the inventive compounds in economically important transgenic crops of useful and ornamental plants is preferred with regard to transgenic crops, e.g. cereals such as wheat, barley, rye, oats, millet, rice and maize or crops of sugar beet, cotton, soybean, rapeseed, potato, cassava, tomato, pea and other vegetables.

[0089] Preferably, the compounds according to the invention can be used as herbicides in crops that are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.

[0090] Conventional methods for producing new plants with modified characteristics compared to existing plants include classical breeding techniques and the creation of mutants. Alternatively, new plants with altered characteristics can be produced using genetic engineering techniques (see, for example, EP-A-0221044, EP-A-0131624). This has been described in several cases.

[0091] genetic modification of cultivated plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92 / 11376, WO 92 / 14827, WO 91 / 19806),

[0092] transgenic crops that are resistant to certain herbicides of the glufosinate type (see e.g. EP-A-0242236, EP-A-242246) or glyphosate type (WO 92 / 00377) or the sulfonylureas (EP-A-0257993, US-A-5013659),

[0093] transgenic crops, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259).

[0094] Transgenic crops with modified fatty acid composition (WO 91 / 13972). Genetically modified crops with new constituents or secondary metabolites, e.g., new phytoalexins that cause increased disease resistance (EPA 309862, EPA0464461). Genetically modified plants with reduced photorespiration that exhibit higher yields and higher stress tolerance (EPA 0305398).

[0095] Transgenic crops that produce pharmaceutically or diagnostically important proteins ("molecular pharming")

[0096] Transgenic crops characterized by higher yields or better quality; transgenic crops characterized by a combination of, for example, the aforementioned new traits ("gene stacking"). BYC250025 Abroad

[0097] -11- Numerous molecular biological techniques for producing new transgenic plants with altered properties are known in principle; see, for example, B.I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christen, "Trends in Plant Science" 1 (1996) 423-431).

[0098] For such genetic engineering manipulations, nucleic acid molecules can be introduced into plasmids, allowing mutagenesis or sequence modification through recombination of DNA sequences. Using standard procedures, base exchanges, partial sequences can be removed, or natural or synthetic sequences added. Adaptors or linkers can be attached to the DNA fragments to join them together; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker, "Genes and Clones," VCH Weinheim, 2nd ed.Edition 1996. The production of plant cells with reduced activity of a gene product can be achieved, for example, by expressing at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect, or the expression of at least one appropriately engineered 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, as well as DNA molecules that comprise only parts of the coding sequence, provided these parts are 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.

[0099] When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can be linked to DNA sequences that ensure localization in that 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). The expression of 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.

[0100] Thus, transgenic plants are available that exhibit altered characteristics through overexpression, suppression, or inhibition of homologous (= natural) genes or gene sequences, or expression of heterologous (= foreign) genes or gene sequences. BYC250025 Abroad

[0101] -12- Preferably, the compounds according to the invention can be used in transgenic cultures which are resistant to growth regulators 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), respectively, or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active substances.

[0102] When the application of the inventive active ingredients in transgenic crops, in addition to the effects observed in other crops against weeds, effects often occur that are specific to the application in the respective transgenic crop, for example, an altered or specifically extended weed spectrum that can be controlled, altered application rates that can be used for application, preferably good compatibility with the herbicides to which the transgenic crop is resistant, as well as influencing the growth and yield of the transgenic crop plants.

[0103] The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling pests in transgenic crops.

[0104] The compounds according to the invention can be used in the form of sprayable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in conventional preparations. The invention therefore also relates to herbicidal and plant growth regulator agents containing the compounds according to the invention.

[0105] The compounds according to the invention can be formulated in various ways, depending on the biological and / or physicochemical parameters. Possible formulations include, for example: sprayable 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), dusting agents (DP), pickling agents, granules for broadcast and ground application, granules (GR) in the form of micro-, sprayable, lift-off and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

[0106] These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology",

[0107] Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

[0108] 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 BYC250025 Abroad".

[0109] -13- Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ, Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY

[0110] 1964, Schönfeldt, "Interfacially Active Ethylene Oxide Adducts", Scientific Publishing Company, Stuttgart 1976, Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Publishing House Munich, 4th edition 1986. Spray powders are preparations that are uniformly dispersible in water and, in addition to the active ingredient, contain surfactants of ionic and / or non-ionic nature (wetting agents, dispersing agents), e.g., polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonate sodium, dibutylnaphthalenesulfonate sodium, or oleoylmethyltaurine sodium. To produce the spray powders, the herbicidal active ingredients are finely ground in common equipment such as hammer mills, blower mills and air jet mills and mixed with the formulation aids at the same time or afterwards.

[0111] Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g., butanol, cyclohexanone, dimethylformamide, xylene, or even higher-boiling aromatics or hydrocarbons, or mixtures of organic solvents, with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). Examples of emulsifiers include: alkylarylsulfonic acid calcium salts 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. Dusting agents 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.

[0112] Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet milling using commercially available bead mills and, if necessary, the addition of surfactants, such as those already listed above for the other formulation types.

[0113] Emulsions, e.g. oil-in-water emulsions (EW), can be produced, for example, using stirrers, colloid mills and / or static mixers, with aqueous organic solvents and, if necessary, surfactants, such as those already listed above for the other formulation types.

[0114] Granules can be produced either by atomizing the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, BYC250025 Abroad

[0115] -14-e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oils, onto the surface of carrier materials such as sand, kaolinite, or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules – optionally in mixture with fertilizers.

[0116] Water-dispersible granules are usually produced using standard methods such as spray drying, fluidized bed granulation, disc granulation, high-speed mixing, and extrusion without solid inert material.

[0117] For the production of disc-shaped, fluidized bed, extruded and spray-dried granules, see, for example, the processes 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.

[0118] For further details on the formulation of plant protection products, see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0119] The agrochemical preparations generally contain 0.1 to 99 wt.%, in particular 0.1 to 95 wt.%, compounds according to the invention.

[0120] In sprayable powders, the active ingredient concentration is, for example, approximately 10 to 90 wt%, with the remainder to 100 wt% consisting of usual formulation components. In emulsifiable concentrates, the active ingredient concentration can be approximately 1 to 90 wt%, preferably 5 to 80 wt%. Powder formulations contain

[0121] Sprayable solutions containing 1 to 30 wt% active ingredient, preferably usually 5 to 20 wt%, contain approximately 0.05 to 80 wt%, preferably 2 to 50 wt% active ingredient. For water-dispersible granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc., are used. For example, the active ingredient content of water-dispersible granules is between 1 and 95 wt%, preferably between 10 and 80 wt%.

[0122] In addition, the aforementioned active ingredient formulations may contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreeze and solvents, fillers, carriers and colorants, defoamers, evaporation inhibitors and agents that affect pH and viscosity. BYC250025 Abroad

[0123] -15- Based on these formulations, combinations with other pesticides, 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. For application, the commercially available formulations are diluted, if necessary, in the usual manner, e.g., in the case of spray powders, emulsifiable concentrates, dispersions and water-dispersible granules, with water. Powdery preparations, soil or granular coatings, and sprayable solutions are not usually diluted with further inert substances before application.

[0124] The required application rate of the compounds of formula (I) varies depending on external conditions such as temperature, humidity, and the type of herbicide used. It can fluctuate within wide limits, e.g., between 0.001 and 1.0 kg / ha or more of active substance, but preferably lies between 0.005 and 750 g / ha.

[0125] The compounds of formula (I) according to the invention can also be used in mixtures with other herbicides as required.

[0126] For example, 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, phytoendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, or that act as plant growth regulators, can be used as combination partners for the compounds of general formula (I) in mixture formulations or in tank mixes. These include, for example, known active ingredients that are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, or that act as plant growth regulators, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 1914th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 202106 and the literature cited therein.

[0127] Examples of well-known herbicides or plant growth regulators that can be combined with compounds of the general formula (I) include the following active ingredients (the compounds are designated either by their International Organization for Standardization (ISO) common name, their chemical name, or their code number) and always encompass all application forms such as acids, salts, esters, and isomers like stereoisomers and optical isomers. One, and in some cases several, application forms are listed as examples:

[0128] Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxy dim -sodium, Ametryn, Amicarbazone, Amidochlor, Amido sulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2 -carboxylic acid, Aminocyclopyrachlor, Aminocyclo _,pyrachlor-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-BYC250025 Ausland

[0129] -16- Kallaium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulid, Bentazon, Bentazon-Natrium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-Natrium, Bipyrazone, Bispyribac, Bispyribac-Natium, Bixlozon, Bromacil, Bromacil-lithium, Bromacil-Natrium, Bromobutid, Bromofenoxim, Bromoxynil, Bromoxynilbutyrat, Bromoxynil Kalium, Bromoxynil-heptanoat und Bromoxynil-octanoat, Busoxinon, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylat, Cafenstrol, Cambendichlor, Carbetamide, Carfentrazon, Carfentrazon-Ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamin, Chlroamben-methyl, Chlorambenmethylammonium, Chloramben-Natrium, Chlorbromuron, Chlorfenac, Chlorfenac -ammonium, Chlorfenac-Natrium, Chlorfenprop, Chlorfenprop-methyl, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlorophthalim, Chlorotoluron, Chlorsulfuron, Chlorthal, Chlorthal-dimethyl, Chlorthal-monomethyl, Cinidon,Cinidon-ethyl, Cinmethylin, exo-(+)-Cinmethylin, d.h. (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, exo-(-)-Cinmethylin, d.h. (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, Cinflubrolin, (1S,2R,4R)- 2-[(2-Brom-6-fluorphenyl)methoxy]-l-methyl-4-(l-methylethyl)-7-oxabicyclo[2.2.1]heptan, (1R,2S,4S)- 2-[(2-Brom-6-fhiorphenyl)methoxy]-l-methyl-4-(l-methylethyl)-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, TriisopropanoKammonium, 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-Natrium, Dicamba-Triethanolamin), Dichlobenil, 2-(2,4-Dichlorbenzyl)-4,4-dimethy 1-1,2-oxazolidin-3-on, 2-(2,5-Dichlorbenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, Dichlor^prop. 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, DifluMenican, Diflufenzopyr, Diflufenzopyr-Natrium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimctha^mctryn. Dimethenamid, Dimethenamid-P,BYC250025 Ausland,

[0130] -17- Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb-Acetate, Diphenamid, Diquat, Diquat-Dibromid, Diquat-Dichloride, Dithiopyr, Dimon, DNOC, DNOC-Ammonium, DNOC -Kalium, DNOC -Natrium, Endothal, Endothal-Diammonium, Endothal-Dikalium, Endothal-Dinatrium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethamct^sulfuron-Mcthyl. Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen-Ethyl, Ethoxy sulfuron, Etobenzanid, F-5231, d.h. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-yl]-phenyl]-ethansulfonamid, F-7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l-methyl-6-(trifluormethyl)pyrimidin-2,4(lH,3H)-dion, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-Ethyl, Fenoxaprop-P-Ethyl, Fenoxasulfone, Fenpyrazone, Fenquinotrione, Fentrazamid, Feproxydim, 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, Fluchloraminopyr, Fluchloraminopyr-tefuryl, Flufenacet, Flufenpyr, Flufenpyr-ethyl, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazine, Fluometuron, Flurenol, Flurenol-butyl, -dimethylammonium and -methyl, Fluoroglycofen, Fluoroglycofen-ethyl, Flupropanate, Flupropanate sodium, Flupyrsulfuron, Flupyrsulfmone-methyl, Flupyrsulfuron-methyl sodium, Fluridon, Flurochloridone, Fluroxypyr, Fluroxypyr-butometyl, Fluroxypyr-meptyl Fhirtamon, 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 isopropyl ammonium, glyphosate diammonium, glyphosate dimethyl ammonium, glyphosate potassium, glyphosate sodium,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-Ethoxy ethyl, Haloxyfop-Methyl, Haloxyfop-P -Methyl, Haloxifop-Natrium, Hexazinon, HNPC-A8169, di.he. Prop-2-iyn-l-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, Imazo sulfuron, Indanofan, Indaziflam, Indolauxipyr, lodosulfuron, lodosulfuron-Methyl, lodosulfuron-Methyl-Natrium, Ioxynil, loxynil-Lithium, -Octanoat, -Kalium und Natrium, Ipfencarbazon, Iptriazopyrid,d.h.i.e. 3-[(Isopropylsulfonyl)methyl]-N-(5-methyl-l,3,4-oxadiazol-2-yl)-5-(trifluormethyl)[l,2,4]triazolo-[4,3-a]pyridin-8-carboxamid, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Karbutilat, KUH-043, d.h. 3-({[5-(Difluormethyl)-l-methyl-3-(trifluormethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazol, Ketospiradox, Ketospiradox-Kalium, Lactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, Dimethyl-'ammonium, -Diolamin, -2-Ethylhexyl, -Ethyl, -Isobutyl, Isoctyl, -Isopropyl, Isopropylammonium, -Methyl, Olamin, -Kalium, -Natrium und -Trolamin, MCPB, MCPB-Methyl, EthylBYC250025 Ausland,

[0131] -18-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, Mctazo^sulfuron. Methabenzthiazuron, Methiopyrsulfuron, Methiozolin, Methyl isothiocyanat, Mcto^bromuron. Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metproxybicyclon, Metribuzin, Metsulfuron, Metsulfuron-Methyl, Molinat, Monolinuron, Monosulfuron, Monosulfuron-Methyl, MT-5950, d.h. N-[3-Chlor-4-(l-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, Napropamid, NC-310, d.h.i.e. 4-(2,4-Dichlorbenzoyl)-l-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, 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, PropSsochlor, Propoxycarbazone, Propoxycarbazone-Natrium, Propyrisulfuron, Propyzamid, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-Ethyl, Pyraquinat, Pyrasulfotol, Pyrazolynat (Pyrazolat), Pyrazo^sulfuron. Pyrazosulfuron-Ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-Isopropyl, Pyribambenz-Propyl,Pyribenzoxim, Pyributicarb, Pyridafol, Pyridat, Pyriftalid, Pyriminobac, Pyriminobac-Methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-Natrium, Pyroxasulfon, Pyroxsulam, Quinclorac, Quinclorac-Dimethylammonium, Quinclorac-Methyl, Quinmerac, Quinoclamin, Quizalofop, Quizalofop-Ethyl, Quizalofop-P, Quizalofop-P -Ethyl, Quizalofop-P-Tefuryl, QYM201, d.h.i.e. l-{2-Chlor-3-[(3-cyclopropyl-5-hydroxy-l-methyl-lH-pyrazol-4-yl)carbonyl]-6-(trifluormethyl)phe-nyl}piperidin-2-on, Rimisoxafen, Rimsulfuron, Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfo^mcturon. Sulfometuron-Methyl, Sulfosulfuron, , SYP-249, d.h. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, d.h.i.e. l-[7-Fluor-3-oxo-4-(prop-2-in-l-yl)-3,4-dihydro-2H- 1 ,4-benzoxazin-6-yl] -3 -propyl-2-thioxoimidazolidin-4,5 -dion, 2,3 ,6-TB A, TC A (Trichloressigsäure) und seine Salze, z.B. TCA-ammonium, TCA-Calcium, TCA-Ethyl, TCA-Magnesium,TCA-Natrium, Tebuthiuron, Tefuryltrione, Tembotrion, TepraKoxydim, Terbacil, Terbucarb, Terbumeton, Terbuthylazine, Terbutryn, Tetflupyrolimet, Thaxtomin, Thenylchlor, Thiazopyr, Thicn^carbazonc. 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,BYC250025 Ausland,

[0132] -19- Trifludimoxazin, Trifluralin, Triflusulfuron, Triflusulfuron-Methyl, Tritosulfuron, Hamstoffsulfat, Vemolat, XDE-848, ZJ-0862, d.h. 3,4-Dichlor-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, 3-(2-Chlor-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydropyrimidin-l(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5-carbonsäuremethylester, 3-(2-Chlor-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydropyrimidin-l(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-l(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-l(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetat, 3-Chlor-2-[3-(difluormethyl)isoxazolyl-5-yl]phenyl-5-chlorpyrimidin-2-ylether, 2-(3,4-Dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-l-en-l-yl)carbonyl]-6-methylpyridazin-3(2H)-on,2-({2-[(2- Methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-l,3-dion, (5-Hydroxy-l-methyl-lH-pyrazol-4-yl)(3,3,4-trimethyl-l,l-dioxido-2,3-dihydro-l-benzothiophen-5-yl)methanon, l-Methyl-4-[(3,3,4-trimethyl-l,l-dioxido-2,3-dihydro-l-benzothiophen-5-yl)carbonyl]-lH-pyrazol-5-yl propan-1-sulfonat, 4-{2-Chlor-3-[(3,5-dimethyl-lH-pyrazol-l-yl)methyl]-4-(methylsulfonyl)benzoyl}-l-methyl-lH-pyrazol-5-yl-l,3-dimethyl-lH-pyrazol-4-carboxylat; Cyanomethyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2 -carboxy lat, Prop-2-yn-l-yl 4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Benzyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Ethyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7-fluor-l-isobutyryl-lH-indol-6-yl)pyridin-2 -carboxy lat,Methyl 6-(l-acetyl-7-fluor-lH-indol-6-yl)- 4-amino-3-chlor-5-fluorpyridin-2 -carboxy lat, Methyl-4-amino-3-chlor-6-[l-(2,2-dimethylpropanoyl)-7-fluor-lH-indol-6-yl]-5-fluorpyridin-2 -carboxy lat, Methyl-4-amino-3-chlor-5-fluor-6-[7-fluor-l- (methoxyacetyl)-lH-indol-6-yl]pyridin-2-carboxylat, Kalium 4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Natrium-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Butyl-4-amino-3-chlor-5-fluoro-6-(7-fluoro-lH-indol-6-yl)pyridin-2 -carboxy lat, 4-Hy droxy -1 -methyl-3- [4-(trifluoromethy l)pyridin-2-yl] imidazolidin-2-on, 3 -(5 -tert-buty 1- 1 ,2-oxazol-3-yl)-4-hy droxy- 1 -methy limidazolidin-2-on, 3 -[5 -Chlor-4-(trifluormethyl)pyridin-2-y 1] -4-hy droxy- 1 -methylimidazolidin-2-on, 4-Hydroxy-l-methoxy-5-methyl-3-[4-(trifluormethyl)pyridin-2-yl]imidazolidin-2-on, 6-[(2-Hydroxy-6-oxocyclohex- 1 -en- 1 -y l)carbony 1] - 1 ,5 -dimethy 1-3 -(2-methylphenyl)chinazolin-2,4(lH,3H)-dion, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-l-en-l-yl)carbonyl]-l-methylquinazoline-2,4(lH,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholine-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-l-one, l-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazine-l-ium salt (with suitable anions such as chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazine-3-yl)pyridazine-l-ium salt (with suitable anions such as chloride, acetate, or trifluoroacetate), 4-(pyrimidin-2-yl)-l-(2-sulfoethyl)pyridazine-l-ium salt (with suitable anions such as chloride, acetate, or trifluoroacetate) Chloride, acetate or trifluoroacetate), 4-(pyridazine-3-yl)-l-(2-sulfoethyl)pyridazine-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-Carboxyethyl)-4-(l,3-thiazol-2-yl)pyridazine-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-BYC250025 Foreign country,

[0133] -20- Carboxyethyl)-4-(l,3,4-thiadiazol-2-yl)pyridazin-l-ium salz (mit passenden Anionen wie z.B Chlorid, Acetat oder Trifluoracetat), Methyl (2R)-2-{[(E)-({2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(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-l(2H)-yl]phenyl}methyliden)amino]oxy}propanoat, Methyl (2R / S)-2-{[(E)-({2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}methyliden)amino]oxy}propanoat, (E)-2-(Trifluormethyl)benzaldehyd-O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxim, 2 -Fluor -N-(5-methyl-l,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluormethyl)benzamid, (2R)-2-[(4-Amino-3,5-dichlor-6-fluor-2-pyridyl)oxy]propancarbonsäure, 2-Ethoxy-2-oxoethyl-l-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropancarboxylat,2 -Methoxy -2-oxoethy 1-1 -{2-chlor-4-fluor-5-[3-methy 1-2, 6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropancarboxylat, {[(l-{2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}essigsäure, 2-(2-Brom-4-chlorbenzyl)-4,4-dimethy 1-1,2-oxazolidin-3-on, Methyl 3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][l,2]oxazol-6a-carboxylat, Ethyl 3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][l,2]oxazol-6a-carboxylat, Methyl-3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][l,2]oxazol-6a-carboxylat, 3-{2-Chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][l,2]oxazole-6a-carboxylic acid, 3-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][l,2]oxazole-6a-carboxylic acid.,

[0134] Other growth regulators and plant stimulants that can be combined with compounds of the general formula (I) include, for example, the following active ingredients (the compounds are designated either by their International Organization for Standardization (ISO) common name, their chemical name, or their code number) and always encompass all application forms such as acids, salts, esters, and isomers like stereoisomers and optical isomers. One, and in some cases several, application forms are listed as examples:

[0135] Abscisinsäure und verwandte Analoga [z.B. (2Z,4E)-5-[6-Ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-diensäure, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoat, (2Z,4E)-3-ethyl-5-(l-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-l-yl)penta-2,4-diensäure, (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-diensäure, methyl (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoat, (2Z,4E)-5-(2-hydroxy-l,3-dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-diensäure], Acibenzolar, Acibenzolar-S-BYC250025 Ausland

[0136] -21-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-aminocyclopropyl-1-ylcarboxylic acid, N-methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxylic acid amide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl- 1-Hydroxamic acid, 5-Aminolevulinic acid, Ancymidol, 6-Benzylaminopurine, Bikinin, Brassinolide, Brassinolide-ethyl, L-Canalin, Catechin and catechins (e.g., (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), Chitooligosaccharides (CO; COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs. COs,In some cases referred to as N-acetylchitooligosaccharides, they are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(C8Hi3NO5)n, CAS No. 1398-61-4] and chitosan molecules [(C5HnNO4)n, CAS No. 9012-76-4]), chitinous compounds, chlormequat chloride, cloprop, cyclanilides, 3-(cycloprop-l-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, l-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet sodium, n-decanol, dikegulac, dikegulac sodium, endothal, endothal dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, l-ethylcyclopropene, flumetraline, flurenol, flurenol butyl, flurenol methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfid, Indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid,Jasmonic acid esters or other derivatives (e.g., jasmonic acid methyl ester, jasmonic acid ethyl ester), lipochytooligosaccharides (LCOs, in some cases also referred to as symbiotic nodulation signals (Nod or Nod factors) or as Myc factors, consist of an oligosaccharide backbone of β-1,4-linked α-actyl-D-glucosamine fragments (“GlcNAc”) with an N-linked fatty acid side chain condensed at the non-reducing end. As can be seen from the literature, LCOs differ in the number of GlcNAc units in the backbone structure, in the length and saturation of the fatty acid chain, and in the substitution of reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, l-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2, 3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl] oxy}methylen)-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, prohydrojasmon, rhizobitoxin, salicylic acid and methyl salicylate, BYC250025 Foreign,

[0137] -22- Sarcosine, sodium cycloprop-l-en-l-yl acetate, sodium cycloprop-2-en-l-yl acetate, sodium 3-(cycloprop-2-en-l-yl) propanoate, sodium 3-(cycloprop-l-en-l-yl) propanoate, sidefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, Trinexapac, Trinexapac-ethyl, Tryptophan, Tsitodef, Uniconazole, Uniconazole-P, 2-Fluoro-N-(3-methoxyphenyl)-9Ff-purine-6-amine, 2-chloro-N-(3-methoxyphenyl)-9Ff-purine-6-amine.

[0138] Although the compounds of formula (I) according to the invention generally exhibit good selectivity towards crops, it may be advantageous to combine them with known safeners. Safeners that can be used in combination with the compounds of formula (I) according to the invention and, if necessary, in combination with other active ingredients such as insecticides, acaricides, herbicides, and fungicides as listed above, are preferably selected from the group consisting of: (1) compounds of formula (1).

[0139]

[0140] where the symbols and indices have the following meanings:

[0141] n A is a natural number from 0 to 5, preferably 0 to 3;

[0142] RA 1 is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, nitro or (Ci-C4)-haloalkyl;

[0143] W A is an unsubstituted or substituted divalent heterocyclic residue from the group of division-saturated or aromatic five-membered heterocycles with 1 to 3 heteroring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained in the ring, preferably a residue from the group (WA 1 ) to (WA 5 ),

[0144]

[0145] (W A 1) (W A 2) (W A 3) (W A 4) (W A 5)

[0146] m A is 0 or 1;

[0147] RA 2 is ORA 3 , SRA 3or NR A 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle with 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 (Sl) and is unsubstituted or substituted by residues from the group (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenylBYC250025 Abroad

[0148] -23-substituted, preferably a residue of formula ORA 3 , NHR A 4 or N(CH3)2, in particular the formula ORA 3 ;

[0149] RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon residue, preferably with a total of 1 to 18 C atoms;

[0150] RA 4 is hydrogen, (Ci-Ce)-alkyl, (Ci-Ce)-alkoxy, or substituted or unsubstituted phenyl; RA 5is H, (Ci -Cs)-alkyl, (Ci-Cs)-haloalkyl, (Ci-C4)-alkoxy-(Ci-Cs)-alkyl, cyano or COORA 9 , in which R A 9 is hydrogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, (CiCe)-hydroxyalkyl, (C3-Ci2)-cycloalkyl or tri-(Ci-C4)-alkylsilyl;

[0151] RA 6 , RA 7 , RA 8 are the same or different hydrogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (C3-Ci2)-cycloalkyl or substituted or unsubstituted phenyl;

[0152] RA 10 is H, (C3-Ci2)-cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heteroaryl;

[0153] preferably:

[0154] a) Compounds of the type of dichlorophenylpyrazolin3carboxylic acid (Sl) a), preferably compounds such as l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid (SH) ("mefenpyr-diethyl"), and related compounds as described in WO- A-91 / 07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid (Sl b ), preferably compounds such as l-(2,4-Dichlorophenyl l)-5-methylpyrazole-3-carboxylic ethyl ester (S 12), 1-(2,4-Dichlorophenyl)-5-isopropylpyrazole-3-carboxylic ethyl ester (S13), l-(2,4-Dichlorophenyl)-5-(l,l-dimethylethyl)pyrazole-3-carboxylic ethyl ester (S14) and related compounds as described in EPA333 131 and EPA269806;

[0155] c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S l c), preferably compounds such as l-(2,4-Dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S15), l-(2-Chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (S16) and related compounds as described, for example, in EP-A-268554;

[0156] d) Compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as fenchlorazole(-ethyl ester), i.e., l-(2,4-dichlorophenyl)-5-trichloromethyl-(lH)-l,2,4-triazole-3-carboxylic acid ethyl ester (S17), and related compounds as described in EPA174562 and EPA346620;BYC250025 Foreign

[0157] -24-e) Compounds of the type of 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e), preferably compounds such as 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylic acid ethyl ester (S18) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S19) and related compounds as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl-10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sill) ("Isoxadifen-ethyl") or -n-propyl ester (S112) or the 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S113) as described in patent application WOA95 / 07897.

[0158] f) Compounds of the triazolyloxyacetic acid derivative type (Sl f), preferably compounds such as methyl-{[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (Sl-14) or {[1,5-Bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (Sl-15) or methyl-{[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (Sl-16) or {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (Sl-17) or methyl-{[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl) 1). Methyl {[5-(4-bromo-2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (Sl-20) or{[5-(4-bromo-2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Sl-21) or Methyl {[l-(4-bromo-2-fluorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (Sl-22) or {[l-(4-bromo-2-fluorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Sl-23), as described in patent applications W02021 / 105101, W02024 / 083670 and WO2024 / 083671.

[0159] S2) quinoline derivatives of the formula (S2),

[0160]

[0161] where the symbols and indices have the following meanings:

[0162] RB 1 is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, nitro or (Ci-C4)-haloalkyl;

[0163] n B is a natural number from 0 to 5, preferably 0 to 3;

[0164] RB 2 is ORB 3 , SRB 3 or NR B 3 RB 4 or a saturated one

[0165] or unsaturated 3- to 7-membered heterocycle with 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 by residues from the group (Ci-C4)-alkyl, (Ci-C4)-alkoxyBYC250025 Abroad

[0166] -25- or optionally substituted phenyl, preferably a residue of formula ORB 3 , NHR B 4 or N(CH3)2, in particular the formula ORB 3 ;

[0167] RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon residue, preferably with a total of 1 to 18 C atoms;

[0168] RB 4 is hydrogen, (Ci-Ce)-alkyl, (Ci-Ce)-alkoxy, or substituted or unsubstituted phenyl; T Bis a (Ci or C2)-alkanediyl chain that is unsubstituted or substituted with one or two (C1-C4)-alky or with [(Ci-C3)-alkoxy]-carbonyl;

[0169] preferably:

[0170] a) Compounds of the type of 8-quinoline oxyacetic acid (S2 a), preferably (5-chloro-8-quinolineoxy)acetic acid (1-methylhexyl) ester ("cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolineoxy)acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro-8-quinolineoxy)acetic acid 4-allyloxy-butyl ester (S2-3), (5-chloro-8-quinolineoxy)acetic acid 1-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolineoxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinolineoxy)acetic acid methyl ester (S2-6), (5-chloro-8-quinolineoxy)acetic acid allyl ester (S2-7), (5-chloro-8-quinolineoxy)acetic acid 2-(2-propylidene- (5-chloro-8-quinolineoxy)-l-ethyl ester (S2-8), (5-chloro-8-quinolineoxy)acetic acid 2-oxo-prop-l-yl ester (S2-9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191 736 or EP-A-0492366, as well as (5-chloro-8-quinolineoxy)acetic acid (S2-10), its hydrates and salts, for example its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium,or phosphonium salts as described in WO-A- 2002 / 34048;

[0171] b) Compounds of the (5-chloro-8-quinolineoxy)malonic acid type (S2 b ), preferably compounds such as (5-chloro-8-quinolineoxy)malonic diethyl ester, (5-chloro-8-quinolineoxy)malonic diallyl ester, (5-chloro-8-quinolineoxy)malonic methyl ethyl ester and related compounds as described in EP-A-0582 198.

[0172]

[0173] where the symbols and indices have the following meanings:

[0174] RC 1 is (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl;BYC250025 abroad

[0175] -26- Rc 2 , RC 3 are the same or different: hydrogen, (Ci-C4)-alkyl, (C2-C4)-alkenyl,

[0176] (C2-C4)-Alkinyl, (Ci-C4)-Haloalkyl, (C2-C4)-Haloalkenyl, (Ci-C4)-Alkylcarbamoyl-(Ci-C4)-alkyl, (C2- C4)-Alkenylcarbamoyl-(Ci -C4)alkyl, (Ci -C4)-Alkoxy-(Ci -C4)-alkyl, Dioxolanyl-(Ci -C4)-alkyl, Thiazolyl, Furyl, Furylalkyl, Thienyl, Piperidyl, substituiertes oder unsubstituiertes Phenyl, oder R c 2 und Rc 3together they form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably: active ingredients of the dichloroacetamide type, which are frequently used as pre-emergence safeners (soil-active safeners), such as... B. "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG Industries (S3-5), "DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-Dichloroacetyl-l-oxa-3-aza-spiro[4,5]decane) from Nitrokemia orMonsanto (S3-7), "TI-35" (1-Dichloroacetyl-azepine) of TRI-Chemical RT (S3-8), "Diclonon" (Dicyclonon) or "BAS145138" or "LAB145138" (S3-9) ((RS)-1-Dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) of BASF, "Furilazol" or "MON 13900" ((RS)-3-Dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10); and its (R)-isomer (S3-11).

[0177] S4) N-acylsulfonamides of formula (S4) and their salts,

[0178]

[0179] where the symbols and indices have the following meanings:

[0180] X D is CH or N;

[0181] RD 1 is CONR D 5 RD 6 or NHCO-RD 7 ;

[0182] RD 2 is halogen, (Ci-C4)-haloalkyl, (Ci-C4)-haloalkoxy, nitro, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, (Ci-C4)-alkylsulfonyl, (Ci-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl;

[0183] RD 3is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl;

[0184] RD 4 is halogen, nitro, (C1-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-haloalkoxy, (C3-Ce)-cycloalkyl, phenyl, (C1-C4)-alkoxy, cyano, (Ci-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (Ci-C4)-alkylsulfonyl, (Ci-C4)-alkoxy carbonyl or (Ci-C4)-alkylcarbonyl; BYC250025 foreign countries

[0185] -27- RD 5 is hydrogen, (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (C2-Ce)-alkenyl, (C2-C6)-alkynyl, (Cs-Ce)-cycloalkenyl, phenyl, or 3- to 6-membered heterocyclyl containing heteroatoms from the group consisting of nitrogen, oxygen, and sulfur, wherein the last seven substituents are replaced by substituents from the group consisting of halogen, (Ci-Ce)-alkoxy, (Ci-Ce)-haloalkoxy, (Ci-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, (C3-Ce)-cycloalkyl, (Ci-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, and phenyl, and in the case of cyclic substituents also (C1-C4)-alkyl and (Ci-C4)-haloalkyl. are substituted;

[0186] RD 6 is hydrogen, (Ci-Ce)-alkyl, (C2-Ce)-alkenyl or (C2-C6)-alkynyl, wherein the last three mentioned residues are substituted by VD residues from the group halogen, hydroxy, (C1-C4)-alkyl, (Ci-C4)-alkoxy and (Ci-C4)-alkylthio, or

[0187] RD 5 and RD 6 together with the nitrogen atom it carries, they form a pyrrolidinyl or piperidinyl residue;

[0188] RD 7 is hydrogen, (Ci-C4)-alkylamino, di-(Ci-C4)-alkylamino, (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, wherein the last two residues are substituted by VD substituents from the group halogen, (Ci-C4)-alkoxy, (Ci-Ce)-haloalkoxy and (Ci-C4)-alkylthio and in the case of cyclic residues also (Ci-C4)-alkyl and (C1-C4)-haloalkyl;

[0189] n D is 0, 1 or 2;

[0190] m D is 1 or 2;

[0191] VD is 0, 1, 2 or 3;

[0192] Preferred are compounds of the type N-acylsulfonamides, e.g. of the following formula

[0193]

[0194] wherein

[0195] RD 7 (CI-Ce)-alkyl, (C3-Ce)-cycloalkyl, wherein the last two substituents are substituted by VD substituents from the group halogen, (Ci-C4)-alkoxy, (Ci-Ce)-haloalkoxy and (Ci-C4)-alkylthio and in the case of cyclic substituents also (Ci-C4)-alkyl and (Ci-C4)-haloalkyl;

[0196] RD 4 Halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF 3;

[0197] m D 1 or 2;

[0198] VD is 0, 1, 2 or 3 means; BYC250025 Abroad

[0199] -28-and acylsulfamoylbenzoic acid amides, e.g. of the following formula (S4 b ), which are known, for example, from WO-A-99 / 16744,

[0200]

[0201] e.g. such in which

[0202] RD 5 = Cyclopropyl and (RD 4) = 2-OMe ("Cyprosulfamide", S4-1),

[0203] RD 5 = Cyclopropyl and (RD 4 ) = 5-Cl-2-OMe is (S4-2),

[0204] RD 5 = Ethyl and (R D 4 ) = 2-OMe is (S4-3),

[0205] RD 5 = Isopropyl and (RD 4 ) = 5-Cl-2-OMe is (S4-4) and

[0206] RD 5 = Isopropyl and (RD 4 ) = 2-OMe is (S4-5).

[0207] as well as compounds of the type of N-acylsulfamoylphenyl amines of the formula (S4 C ), which are known, for example, from EP-A-365484,

[0208]

[0209] wherein

[0210] RD 8 and RD 9 independently of each other hydrogen, (Ci-Cs)-alkyl, (C3-Cs)-cycloalkyl, (Cs-Ce)-alkenyl, (C3-C6)-alkynyl,

[0211] RD 4 Halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3

[0212] m D 1 or 2 means;

[0213] for example

[0214] l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methyl urea,

[0215] l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0216] l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methyl urea.BYC250025 Foreign countries

[0217] -29- 55) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-di-methoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001.

[0218] 56) Active substances from the class of l,2-dihydroquinoxalin-2-ones (S6), e.g.

[0219] 1-Methy 1-3-(2-thienyl)- 1,2-dihy drochinoxalin-2-one, 1-Methyl-3-(2-thienyl 1)- 1,2-dihy drochinoxalin-2-thione, l-(2-Aminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-one hydrochloride, l-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydrochinoxa-lin-2-one, as described in WO-A-2005 / 112630.

[0220] S7) Compounds of formula (S7) as described in WO-A- 1998 / 38856

[0221]

[0222] where the symbols and indices have the following meanings:

[0223] RE 1 , RE 2 are independently halogen, (Ci-C / -alkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkyl, (Ci-C4)-alkylamino, di-(Ci-C4)-alkylamino, nitro;

[0224] A E is COORE 3 or COSRE 4

[0225] RE 3 , RE 4are independently hydrogen, (C1-C4)-alkyl, (C2-Ce)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl, (Ci-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium,

[0226] n E ! is 0 or 1

[0227] n E 2 , n E 3 are independent of each other: 0, 1 or 2,

[0228] preferably diphenyl methoxyacetic acid, diphenyl methoxyacetic acid ethyl ester, diphenyl methoxyacetic acid methyl ester (CAS Reg. No. 41858-19-9) (S7-1).BYC250025 Abroad

[0229] -30- 58) Compounds of formula (S8), as described in WO-A-98 / 27049

[0230]

[0231] <

[0232] wherein

[0233] X F CH or N

[0234] n F in the event that X F =N is an integer from 0 to 4 and

[0235] in the event that X F=CH is an integer from 0 to 5 ,

[0236] RF 1 Halogen, (C1-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C i)-alkoxy. (Ci-C4)-haloalkoxy, nitro, (C1-C4)-alkylthio, (Ci-C4)-alkylsulfonyl, (Ci-C4)-alkoxy carbonyl, optionally substituted. phenyl, optionally substituted phenoxy,

[0237] RF 2 Hydrogen or (Cl-C4)-alkyl

[0238] RF 3 Hydrogen, (Ci-Cs)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, wherein each of the aforementioned C-containing residues is unsubstituted or substituted by one or more, preferably up to three, identical or different residues from the group consisting of halogen and alkoxy; or their salts,

[0239] preferably compounds wherein

[0240] X F CH,

[0241] n F an integer from 0 to 2 ,

[0242] RF 1Halogen, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy,

[0243] RF 2 Hydrogen or (CI-C4) alkyl,

[0244] RF 3 Hydrogen, (Ci-Cs)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, wherein each of the aforementioned C-containing residues is unsubstituted or substituted by one or more, preferably up to three identical or different residues from the group consisting of halogen and alkoxy, mean

[0245] or their salts.

[0246] 59) Active substances 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-BYC250025 Abroad

[0247] -31- Dihydro-4-hydroxy-l-methyl-3-(5-tetrazolyl-carbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A- 1999 / 000020.

[0248] S10) Connections of the formulas (S10 a) or (S10 b )

[0249] as described in WO-A-2007 / 023719 and WO-A-2007 / 023764

[0250]

[0251] wherein

[0252] RG 1 Halogen, (Ci-C4)-Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3

[0253] YG, Z G independently of each other O or S,

[0254] n G an integer from 0 to 4,

[0255] RG 2 (Ci-Cie)-alkyl, (C2-Ce)-alkenyl, (C3-Ce)-cycloalkyl, aryl; benzyl, halobenzyl,

[0256] RG 3 Hydrogen or (Ci-Ce) alkyl means.

[0257] SI 1) Active substances of the oxyimino compound (SH) type, known as seed dressings, such as e.g. B. "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (Sll-1), known as a seed treatment safener for millet against damage caused by metolachlor, "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (Sll-2), known as a seed treatment safener for millet against damage caused by metolachlor, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxy-imino(phenyl)acetonitrile) (Sll-3), known as a seed treatment safener for millet against damage caused by metolachlor.

[0258] 512) Active substances 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.

[0259] 513) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed treatment safener for maize against damage from thiocarbama herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in sown rice, "Flurazole" (benzyl 1,2-chloro-4-trifluoromethyl 1,1,3-thiazol-5-carboxylate) (S13-3), known as a seed treatment safener for millet against damage from alachlor and BYC250025 foreign

[0260] -32- Metolachlor is known as "CL 304415" (CAS Reg. No. 31541-57-8) (4-Carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid) (S13-4) of the company American Cyanamid, which is known as a safener for corn against damage from imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-Dichloromethyl 1-2-methyl-1,3-dioxolane) (S13-5) of the company Nitrokemia, which is known as a safener for corn, "MG-838" (CAS Reg. No.

[0261] 133993-74-5) (2-propenyl l-oxa-4-azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia, "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), "Dietholate" (O,O-Diethyl-O-phenylphosphorothioat) (S13-8), "Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9).

[0262] 514) Active substances which, in addition to a herbicidal effect against weeds, also have a safener effect on cultivated plants such as rice, such as e.g. B. "Dimepiperate" or "MY-93" (Sl-methyl-1-phenylethyl-piperidine-l-carbothioate), known as a safener for rice against damage from the herbicide Molinate; "Daimuron" or "SK 23" (l-(l-methyl-l-phenylethyl)-3-p-tolyl-ham), known as a safener for rice against damage from the herbicide Imazosulfuron; "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-l-(l-methyl-l-phenylethyl)ham, see JP-A-60087254), known as a safener for rice against damage from some herbicides; "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), known as a safener for rice against damage from some herbicides; "CSB" (1-Bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage caused by some herbicides in rice.

[0263] 515) Compounds of formula (S15) or their tautomers

[0264] as described in WO-A-2008 / 131861 and WO-A-2008 / 131860

[0265]

[0266] wherein

[0267] RH 1 a (Ci-C6)haloalkyl group means and

[0268] RH 2 Hydrogen or halogen means and

[0269] RH 3 , RH 4independently of one another hydrogen, (Ci-Cie)-alkyl, (C2-Cie)-alkenyl or (C2-Ci6)-alkynyl, each of the latter 3 residues being unsubstituted or substituted by one or more residues from the group halogen, hydroxy, cyano, (Cj-C iJ-alkoxy, (Ci-C i)-haloalkoxy, (Ci-Ci)-alkvlthio, (Ci-C' i)-alkvlamino, di[(Ci-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(Ci-C4)-haloalkoxy]-carbonyl, (Cs-Ce)-cycloalkyl, unsubstituted or substituted, phenyl, unsubstituted or substituted, and heterocyclyl, unsubstituted or substituted. is, or (Cs-Cej-cycloalkyl, (C4-Ce)-cycloalkenyl, (Cs-Cej-cycloalkyl, which is fused to one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-Ce)-cycloalkenyl, which is fused to one side BYC250025 Abroad

[0270] -33- of the ring is condensed with a 4- to 6-membered saturated or unsaturated carbocyclic ring, each of the latter 4 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (C1-C4)-alkyl, (Ci-Ci)-haloalkvl. (Ci-Ci)-alkoxy, (C1-C4)-haloalkoxy, (Ci-C4)-alkylthio, (Ci-C'i)-alkvlamino. Di[(Ci-C4)-alkyl]amino, [(Ci-C4)-alkoxy]carbonyl, [(Ci-C4)-haloalkoxy]-carbonyl, (Cs-Ce)-cycloalkyl, unsubstituted or substituted, phenyl, unsubstituted or substituted, and heterocyclyl, unsubstituted or substituted,

[0271] means or

[0272] RH 3 (Ci-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy and RH 4 Hydrogen or (Ci-C4) alkyl means or

[0273] RH 3 and RH 4together with the directly bonded N atom, a four- to eight-membered heterocyclic ring, which in addition to the N atom may also contain further heteroring atoms, preferably up to two further heteroring atoms from the group N, O and S, and which is unsubstituted or substituted by one or more residues from the group halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy and (Ci-C4)-alkylthio.

[0274] S16) Active substances primarily used as herbicides, but which also have a safener effect on crops, e.g. (2,4-Dichlorophenoxy)acetic acid (2,4-D), (4-Chlorphenoxy)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-Chlorphenoxy)butyric acid, 3,6-Dichloro-2-methoxybenzoic acid (Dicamba), l-(Ethoxycarbonyl)ethyl-3,6-dichloro-2-methoxybenzoate (Lactidichloro-ethy 1) .

[0275] Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, dichlormide, metcamifen and methyl-{[5-(4-chloro-2-fluorophenyl)-l-(2,4-difluorophenyl)- 1H- 1 ,2,4-triazol-3-yl] oxy acetate (S 1 - 16) .

[0276] The general synthesis of compounds of general formula (Ilb) as well as that of compounds of general formula (I) are described below by way of example:

[0277] A. Chemical Examples

[0278] Synthesis of methyl 2-chloro-4-(2,2-difluoroethyl)-3-formyl benzoate (1):BYC250025 Abroad

[0279] -34-

[0280]

[0281] Step 1: Preparation of Methyl 2-chloro-4-[(E7Z)-2-methoxyvinyl]-3-methylbenzoate (3): Under argon, 500 mg (2.35 mmol) of Methyl 2-chloro-4-formyl-3-methylbenzoate (2) (known from, e.g., CN117510466), 1.17 g (3.41 mmol) of (methoxy)methyltriphenylphosphonium chloride, and 435 mg (3.75 mmol) of potassium tert-butoxide were mixed with 10 ml of dichloromethane pre-cooled to -20°C. The mixture was then stirred for 30 min under ice bath cooling. It was then slowly warmed to room temperature and stirred for 60 min. The mixture was treated with water and extracted with dichloromethane. The organic phase was extracted and evaporated. The residue was purified chromatographically (HPLC, normal phase, heptane / ethyl acetate 100 / 0—>80 / 20). 560 mg (93%) of methyl 2-chloro-4-[(E / Z)-2-methoxyvinyl]-3-methylbenzoate (3) were obtained. 1H-NMR (400 MHz, DMSO-de): 5 = 7.78 (d, 1H); 7.50 (d, 1H); 7.48 (d, 1H); 7.42 (d, 1H); 7.22 (d, 1H); 6.52 (d, 1H); 6.00 (d, 1H); 5.40 (d, 1H); 3.83 (s, 6H); 3.77 (s, 3H); 3.71 (s, 3H); 2.36 (s, 3H); 2.34 (s, 3H).

[0282] Step 2: Preparation of methyl 2-chloro-3-methyl-4-(2-oxoethyl)benzoate (4): Under argon, 1.6 g (5.98 mmol) of methyl 2-chloro-4-[(E7Z)-2-methoxyvinyl]-3-methylbenzoate (3) was placed in 20 ml of a mixture of acetonitrile / water (4 / 1) and 1.71 g (8.97 mmol) of p-toluenesulfonic acid monohydrate were added. The mixture was stirred for 1 h at 80°C. After evaporation of the mixture, the residue was extracted with water and dichloromethane, and the organic phase was separated and evaporated. 1.5 g (99%) of crude methyl 2-chloro-3-methyl-4-(2-oxoethyl)benzoate (4) was obtained, which was used in further syntheses without further work-up. 'H-NMR (400 MHz, DMSO-de): 5 = 9.70 (s, 1H); 7.52 (d, 1H); 7.26 (d, 1H); 4.03 (s, 2H); 3.85 (s, 3H); 2.24 (s, 3H).

[0283] Step 3: Preparation of methyl 2-chloro-4-(2,2-difluoroethyl)-3-methyl benzoate (5): 1.5 g (5.95 mmol) of methyl 2-chloro-3-methyl-4-(2-oxoethyl) benzoate (4) were reacted with 2.88 g (17.8 mmol) of diethylaminosulfur trifluoride (DAST) in 12 M dichloromethane at 0°C and stirred at room temperature for 3 h. After completion of the reaction, the mixture was cooled back to 0°C and quenched with a small amount of methanol. After evaporation of the mixture, the residue was taken up with dichloromethane and stirred with 2 N HCl, and the organic phase was separated and evaporated. The residue was purified chromatographically (HPLC, normal phase, heptane / ethyl acetate 100 / 0—>80 / 20). 1.35g (89%) of methyl 2-chloro-4-(2,2-difluoroethyl)-3-methylbenzoate (5) were obtained. 'H-NMR (400 MHz, DMSO-de): 5 = 7.53 (d, 1H); 7.35 (d, 1H); 6.30 (dd, 1H); 3.85 (s, 3H); 3.37 (td, 2H); 2.39 (s, 3H).BYC250025 Abroad

[0284] -35- Step 4: Preparation of Methyl 3-(bromomethyl)-2-chloro-4-(2,2-difluoroethyl)benzoate (6): 4.57 g (18.3 mmol) of Methyl 2-chloro-4-(2,2-difluoroethyl)-3-methylbenzoate (5) were placed in 10 ml of chlorobenzene and, at room temperature, treated with 6.54 g (36.7 mmol) of N-bromosuccinimide and 302 mg (1.83 mmol) of azobis(isobutyronitrile). The mixture was then stirred for 5 h at 130°C. After evaporation of the mixture, the residue was dissolved in water and extracted with dichloromethane. The organic phase was separated, dried, and evaporated. The residue was purified chromatographically (HPLC, normal phase, heptane / ethyl acetate 100 / 0— >80 / 20). 5.75g (86%) Methyl-3-(bromomethyl)-2-chloro-4-(2,2-difluoroethyl)benzoate was obtained (6). 1 H-NMR (400 MHz, DMSO-de): 5 = 7.72 (d, 1H); 7.46 (d, 1H); 6.40 (dd, 1H); 4.87 (s, 2H); 3.88 (s, 3H); 3.47 (td, 2H).

[0285] Step 5: Preparation of Methyl 2-chloro-4-(2,2-difluoroethyl)-3-formyl benzoate (1): 66.48 g (17.8 mmol) of Methyl 3-(bromomethyl)-2-chloro-4-(2,2-difluoroethyl) benzoate (6) were placed in 100 ml of acetonitrile and reacted with 6.26 g (53.4 mmol) of N-methylmorpholine N-oxide at room temperature. The reaction mixture was stirred for 3 h at room temperature and then evaporated. The residue was dissolved in dichloromethane and washed with water. The organic phase was separated, dried, and evaporated. The residue was purified chromatographically (HPLC, normal phase, heptane / ethyl acetate 100 / 0—>50 / 50). 4.64 g (89%) of Methyl 2-chloro-4-(2,2-difluoroethyl)-3-formyl benzoate (1) were obtained. 'H-NMR (400 MHz, DMSO-de): 5 = 10.48 (s, 1H); 7.96 (d, 1H); 7.55 (d, 1H); 6.24 (dd, 1H); 3.91 (s, 3H); 3.53 (td, 2H).

[0286] Syntheses of 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)benzoic acid (4-9) and 2-chloro-4-(2,2-difluoroethyl)-3-(methylcarbamoyl)benzoic acid (4-10):

[0287]

[0288] Preparation of (R / S)-methyl-2-chloro-3-[cyclopropyl(hydroxy)methyl]-4-(2,2-difluoroethyl)benzoate (7): Under argon, 7.20 g (27.4 mmol) of methyl-2-chloro-4-(2,2-difluoroethyl)-3-formylbenzoate (1) were placed in 150 ml of dry THF and cooled to -60°C. A solution of 65.8 ml (32.8 mmol) of 0.5 M cyclopropylmagnesium bromide in THF was then slowly added dropwise, and the mixture was stirred for 1 h at -60°C. The mixture was then warmed to room temperature and stirred for another 1 h at this temperature. After the addition of 2 N HCl, the mixture was stirred with dichloromethane. The organic phase was separated and evaporated. The residue was purified by chromatography (HPLC, BYC250025).

[0289] -36- Normalphase, Heptan / Essigsäureethylester 100 / 0— >70 / 30). Man erhielt 7.0g (80%) (R / S)-Methyl-2-chlor-3-[cyclopropyl(hydroxy)methyl]-4-(2,2-difluorethyl)benzoat (7). 'H-NMR (400 MHz, DMSO-de): 5 = 7.55 (d, 1H); 7.38 (d, 1H); 6.24 (m, 1H); 5.80 (d, 1H); 4.82 (m, 1H); 3.85 (s, 3H); 3.80 (m, 1H); 3.42 (m, 1H); 1.25 (m, 1H); 0.58 (m, 1H); 0.45 (m, 1H); 0.40 (m, 2H)

[0290] Preparation of Methyl 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)benzoate (3-9): 890 mg (2.92 mmol) of (R / S)-methyl 2-chloro-3-[cyclopropyl(hydroxy)methyl]-4-(2,2-difluoroethyl)benzoate (7) were placed in 30 ml of acetone and slowly treated with 1.4 ml of a 2.5 M solution of chromium(VI) oxide (3.5 mmol) in a 3:1 mixture of water and sulfuric acid. The mixture was stirred at room temperature for 4 h. After completion of the reaction, excess oxidizing agent was quenched with isopropanol and the mixture was evaporated. The residue was taken up with water and extracted with ethyl acetate. The organic phase was separated, dried, and evaporated. 800 mg (90%) Methyl-2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)benzoate (3-9) was obtained.

[0291] Preparation of 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)benzoic acid (4-9): A solution of 850 mg (2.80 mmol) of methyl 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)benzoate (3-9) in 10 ml of pyridine was reacted with 1.5 mg (11.2 mmol) of lithium iodide at 80°C, and the mixture was stirred under reflux for 4 h. The pyridine was then removed by distillation, the residue dissolved in water, and the resulting solution adjusted to pH 1-2 with intravenous hydrochloride. Extraction with ethyl acetate was then carried out, the organic phase was removed, and the mixture was dried and evaporated. 670 mg (74%) of crude 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)benzoic acid (4-9) was obtained.

[0292] Preparation of 2-chloro-6-(2,2-difluoroethyl)-3-(methoxycarbonyl)benzoic acid (8): 7.00 g (26.6 mmol) of methyl 2-chloro-4-(2,2-difluoroethyl)-3-formyl benzoate (1) were placed in 75 ml of acetone, cooled to 0°C, and slowly reacted with 12.8 ml of a cooled 2.5 M solution of chromium(VI) oxide (31.9 mmol) in a 3:1 mixture of water and sulfuric acid. After warming to room temperature, the mixture was stirred for 24 h. Under ice-cooled conditions, excess oxidizing agent was quenched with isopropanol, and the mixture was evaporated. The residue was taken up with water and extracted with dichloromethane; the organic phase was separated, dried, and evaporated. This gave 8.11g (87%) of 2-chloro-6-(2,2-difluoroethyl)-3-(methoxycarbonyl)benzoic acid (8). 'H-NMR (400 MHz, DMSO-de): 5 = 14.12 (br s, 1H); 7.82 (d, 1H); 7.52 (d, 1H); 6.26 (dd, 1H); 3.88 (s, 3H); 3.27 (td, 2H)

[0293] Preparation of Methyl 2-chloro-4-(2,2-difluoroethyl)-3-(methylcarbamoyl)benzoate (3-10): 2.00 g (5.74 mmol) of 2-chloro-6-(2,2-difluoroethyl)-3-(methoxycarbonyl)benzoic acid (8) were placed in 40 ml of dichloromethane and a catalytic amount of dimethylformamide and treated with 0.8 ml (8.61 mmol) of oxalyl chloride. The mixture was stirred for 1 h. It was then evaporated and co-evaporated with toluene. The residue was dissolved in a small amount of dry dichloromethane and added dropwise to an ice-cold solution of 4.31 ml (8.61 mmol) of a 2.5 M solution of methylamine in THF and 2.5 ml (14.3 mmol) of Hünig's base in 40 ml of dry dichloromethane. The mixture was stirred at room temperature for 2 h. PostBYC250025 Abroad

[0294] -37- Upon addition of further dichloromethane, the mixture was washed with 2N HCl. The organic phase was separated, dried, and evaporated. The residue was purified chromatographically (HPLC, normal phase, heptane / ethyl acetate 90 / 10—>50 / 50). 1.6 g (86%) of methyl 2-chloro-4-(2,2-difluoroethyl l)-3-(methyl icarbamoyl l)benzoate (3-10) was obtained.

[0295] Preparation of 2-chloro-4-(2,2-difluoroethyl)-3-(methylcarbamoyl)benzoic acid (4-10): A solution of 1.00 g (3.42 mmol) of methyl 2-chloro-4-(2,2-difluoroethyl)-3-(methylcarbamoyl)benzoate (3-10) in 10 ml of pyridine was reacted with 1.84 mg (13.7 mmol) of lithium iodide at 80°C, and the mixture was stirred under reflux for 4 h. The pyridine was then removed by distillation, the residue dissolved in water, and the resulting solution adjusted to pH 1-2 with intradermal hydrochloride. Extraction with ethyl acetate was then carried out, the organic phase was removed, and the mixture was dried and evaporated. 930 mg (83%) of crude 2-chloro-4-(2,2-difluoroethyl)-3-(methylcarbamoyl)benzoic acid (4-10) was obtained.

[0296] Synthesis of 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)-N-(l-ethyl-lH-tetrazol-5-yl)benzamide (2-9) and 2-chloro-4-(2,2-difluoroethyl)-N 1 -(l-ethyl-lH-tetrazol-5-yl)-N 3 - methylisophthalamide (2-10):

[0297]

[0298] Preparation of 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)-N-(1-ethyl-1H-tetrazol-5-yl)benzamide (2-9): 210.0 mg (0.72 mmol) of 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)benzoic acid (4-9) were reacted with 112.6 mg (0.94 mmol) of 5-amino-1-ethyl-1H-tetrazol in 3 ml of THF and treated with 1.3 ml of a 50% solution of propanephosphonic anhydride (2.18 mmol) in THF and subsequently with 0.4 ml (2.91 mmol) of triethylamine. The mixture was then microwaved at 110°C for 30 min at 360 watts. After adding 2N HCl, the mixture was extracted with dichloromethane, the organic phase was separated, and evaporated. The residue was purified chromatographically (HPLC, C18, gradient: acetonitrile / water (+0.05% trifluoroacetic acid)).

[0299]

[0300] 100 / 0). 140 mg (48%) of 2-chloro-3-(cyclopropylcarbonyl)-4-(2,2-difluoroethyl)-N-(1-ethyl-1H-tetrazol-5-yl)benzamide (2-9) were obtained.

[0301] Production of 2-chloro-4-(2,2-difluoroethyl)-N 1 -(1-ethyl-lH-tetrazol-5-yl)-N 3 -methylisophthalamide (2- 10):

[0302] 240.0 mg (0.86 mmol) of 2-chloro-4-(2,2-difluoroethyl)-3-(methylcarbamoyl)benzoic acid (4-10) were placed together with 133.8 mg (1.12 mmol) of 5-amino-1-ethyl-IH-tetrazol in 3 ml of THF and diluted with 1.5 ml of BYC250025 from abroad

[0303] -38- a 50% solution of propanephosphonic anhydride (2.59 mmol) in THF and subsequently treated with 0.5 ml (3.45 mmol) of triethylamine. The mixture was then microwaved at 110°C for 30 min at 360 watts. After the addition of 2 N HCl, the mixture was extracted with dichloromethane, the organic phase was separated, and evaporated. The residue was purified chromatographically (HPLC, C18, gradient: acetonitrile / water (+0.05% trifluoroacetic acid) 10 / 100

[0304]

[0305] 100 / 0). 160 mg (46%) of 2-chloro-4-(2,2-difluoroethyl)-N was obtained. 1-(l-ethyl-lH-tetrazol-5-yl)-N 3 -methylisophthalamide (2-10).

[0306] The examples listed in the following tables were produced or are available using methods described above. These compounds are particularly preferred.

[0307] The abbreviations used mean:

[0308] Me = Methyl Et = Ethyl c-Pr = Cyclopropyl

[0309] Table 1: Inventory compounds of formula (I), where R represents a methyl group and the other substituents have the meanings given below.

[0310]

[0311]

[0312] BYC250025 Abroad

[0313] -39- Table 2: Compounds of the inventive formula (I), wherein R represents an ethyl group and the other substituents have the meanings given below.

[0314]

[0315]

[0316] Table 3: Inventory compounds of formula (II), where L stands for methoxy and the other substituents have the meanings given below,

[0317]

[0318]

[0319] BYC250025 Abroad

[0320] -40-

[0321]

[0322] Table 4: Inventory compounds of formula (II), where L stands for hydroxy and the other substituents have the meanings given below,

[0323]

[0324]

[0325] Table 5: Compounds according to the invention of formula (II), wherein L stands for chlorine and the other substituents have the meanings mentioned below.

[0326]

[0327]

[0328] BYC250025 Abroad

[0329] -41-

[0330]

[0331] For numerous compounds of the invention of formula (I) and (II) mentioned in the tables above, NMR data are disclosed below for further characterization:

[0332] Example no. 1-1: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.59 (br s, 1H); 7.67 (d, 1H); 7.41 (d, 1H); 6.22 (dd, 1H); 3.98 (s, 3H); 3.15 (td, 2H); 2.54 (s, 3H); 2.31 (s, 3H);

[0333] Example no. 1-2: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.59 (br s, 1H); 7.68 (d, 1H); 7.41 (d, 1H); 6.22 (dd, 1H); 3.98 (s, 1H); 3.09 (td, 2H); 2.83 (q, 2H); 2.26 (s, 3H); 1.11 (t, 3H);

[0334] Example no. 1-3: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.60 (br s, 1H); 7.69 (d, 1H); 7.43 (d, 1H); 6.22 (dd, 1H); 3.99 (s, 3H); 3.16 (td, 2H); 2.36 (s, 3H); 2.32 (m, 1H); 1.19 (m, 4H);

[0335] Beispiel-Nr. 1-4: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.55 (br s, 1H); 8.44 (br q, 1H); 7.64 (d, 1H); 7.35 (d, 1H); 6.21 (tt, 1H); 3.97 (s, 3H); 3.15 (td, 2H); 2.80 (d, 3H); 2.31 (s, 3H);

[0336] Beispiel-Nr. 1-5: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.55 (br s, 1H); 7.64 (d, 1H); 7.35 (d, 1H); 6.22 (tt, 1H); 3.97 (s, 3H); 3.30 (m, 2H); 3.17 (td, 2H); 2.33 (s, 3H); 1.12 (t, 3H);

[0337] Beispiel-Nr. 1-6: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.54 (br s, 1H); 8.61 (d, 1H); 7.64 (d, 1H); 7.34 (d, 1H); 6.20 (tt, 1H); 3.97 (s, 3H); 3.15 (td, 2H); 2.87 (m, 1H); 2.31 (s, 3H); 0.71 (m, 2H); 0.51 (m, 2H); Beispiel-Nr. 1-7: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.86 (br s, 1H); 7.81 (d, 1H); 7.58 (d, 1H); 6.26 (tt, 1H); 4.00 (s, 3H); 3.22 (td, 2H); 2.59 (s, 3H);

[0338] Beispiel-Nr. 1-8: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.85 (br s, 1H); 7.81 (d, 1H); 7.58 (d, 1H); 6.25 (tt, 1H); 3.99 (s, 3H); 3.17 (td, 2H); 2.99 (q, 2H); 1.13 (t, 3H);BYC250025 Ausland

[0339] -42- Beispiel-Nr. 1-9: 'H-NMR (400 MHz, DMSO-d6): 5 = 11.86 (br s, 1H); 7.81 (d, 1H); 7.59 (d, 1H); 6.26 (tt, 1H); 4.00 (s, 3H); 3.21 (td, 2H); 2.35 (m, 1H); 1.22 (m, 4H);

[0340] Beispiel-Nr. 1-10: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.81 (br s, 1H); 8.62 (br q, 1H); 7.74 (d, 1H); 7.51 (d, 1H); 6.23 (tt, 1H); 3.99 (s, 3H); 3.20 (td, 2H); 2.81 (d, 3H);

[0341] Beispiel-Nr. 1-11: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.82 (br s, 1H); 8.71 (br t, 1H); 7.74 (d, 1H); 7.50 (d, 1H); 6.23 (tt, 1H); 3.99 (s, 3H); 3.30 (m, 2H); 3.22 (td, 2H); 1.13 (t, 3H);

[0342] Beispiel-Nr. 1-12: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.81 (br s, 1H); 8.77 (br d, 1H); 7.73 (d, 1H); 7.49 (d, 1H); 6.22 (tt, 1H); 3.98 (s, 3H); 3.20 (td, 2H); 2.86 (m, 1H); 0.73 (m, 2H); 0.53 (m, 2H);

[0343] Beispiel-Nr. 2-1: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.48 (br s, 1H); 7.66 (d, 1H); 7.41 (d, 1H); 6.22 (tt, 1H); 4.33 (q, 2h); 3.15 (td, 2H); 2.54 (s, 3H); 2.31 (s, 3H); 1.46 (t, 3H);

[0344] Beispiel-Nr. 2-2: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.48 (br s, 1H); 7.66 (d, 1H); 7.42 (d, 1H); 6.22 (tt, 1H); 4.33 (q, 2H); 3.10 (td, 2H); 2.83 (q, 2H); 2.26 (s, 3H); 1.46 (t, 3H); 1.11 (t, 3H);

[0345] Beispiel-Nr. 2-3: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.50 (br s, 1H); 7.68 (d, 1H); 7.43 (d, 1H); 6.22 (tt, 1H); 4.34 (q, 2H); 3.16 (td, 2H); 2.36 (s, 3H); 2.32 (m, 1H); 1.47 (t, 3H); 1.19 (m, 4H);

[0346] Beispiel-Nr. 2-4: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.44 (br s, 1H); 8.44 (br q, 1H); 7.63 (d, 1H); 7.36 (d, 1H); 6.21 (tt, 1H); 4.33 (q, 2H); 3.15 (td, 2H); 2.80 (d, 3H); 2.31 (s, 3H); 1.46 (t, 3H);

[0347] Beispiel-Nr. 2-5: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.44 (br s, 1H); 8.55 (br t, 1H); 7.63 (d, 1H); 7.35 (d, 1H); 6.22 (tt, 1H); 4.33 (q, 2H); 3.31 (m, 2H); 3.17 (tf, 2H); 2.33 (s, 3H); 1.46 (t, 3H); 1.12 (t, 3H); Beispiel-Nr. 2-6: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.43 (br s, 1H); 8.61 (d, 1H); 7.63 (d, 1H); 7.35 (d, 1H); 6.20 (tt, 1H); 4.32 (q, 2H); 3.15 (td, 2H); 2.87 (m, 1H); 2.31 (s, 3H); 1.46 (t, 3H); 0.72 (m, 2H); 0.50 (m, 2H);

[0348] Beispiel-Nr. 2-7: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.76 (br s, 1H); 7.80 (d, 1H); 7.58 (d, 1H); 6.26 (tt, 1H); 4.36 (q, 2H); 3.22 (td, 2H); 2.60 (s, 3H); 1.47 (t, 3H);

[0349] Beispiel-Nr. 2-8: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.76 (br s, 1H); 7.80 (d, 1H); 7.59 (d, 1H); 6.25 (tt, 1H); 4.35 (q, 2H); 3.17 (td, 2H); 2.90 (q, 2H); 1.46 (t, 3H); 1.13 (t, 3H);

[0350] Beispiel-Nr. 2-9: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.77 (br s, 1H); 7.81 (d, 1H); 7.60 (d, 1H); 6.26 (tt, 1H); 4.36 (q, 2H); 3.21 (td, 2H); 2.35 (m, 1H); 1.47 (t, 3H); 1.22 (m, 4H);

[0351] Beispiel-Nr. 2-10: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.71 (br s, 1); 8.62 (br q, 1H); 7.74 (d, 1H); 7.51 (d, 1H); 6.23 (tt, 1H); 4.35 (q, 2H); 3.21 (td, 2H); 2.81 (d, 3H); 1.45 (t, 3H);BYC250025 Ausland

[0352] -43- Beispiel-Nr. 2-11: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.71 (br s, 1H); 8.71 (br t, 1H); 7.73 (d, 1H); 7.51 (d, 1H); 6.23 (tt, 1H); 4.35 (q, 2H); 3.30 (m, 2H); 3.22 (td, 2H); 1.46 (t, 3H); 1.13 (t, 3H);

[0353] Beispiel-Nr. 2-12: ’H-NMR (400 MHz, DMSO-d6): 5 = 11.71 (br s, 1H); 8.77 (br d, 1H); 7.73 (d, 1H); 7.50 (d, 1H); 6.22 (tt, 1H); 4.35 (q, 2H); 3.20 (td, 2H); 2.85 (m, 1H); 1.46 (t, 3H); 0.73 (m, 2H); 0.52 (m, 2H);

[0354] Beispiel-Nr. 3-1: ’H-NMR (400 MHz, DMSO-d6): 5 = 7.78 (d, 1H); 7.37 (d, 1H); 6.20 (tt, 1H); 3.84 (s, 3H); 3.12 (td, 2H); 2.36 (s, 3H);

[0355] Beispiel-Nr. 3-2: 'H-NMR (400 MHz, DMSO-d6): 5 = 7.78 (d, 1H); 7.37 (d, 1H); 6.20 (tt, 1H); 3.84 (s, 3H); 3.07 (td, 2H); 2.80 (q, 2H); 2.31 (s, 3H); 1.09 (t, 3H);

[0356] Beispiel-Nr. 3-3: ’H-NMR (400 MHz, DMSO-d6): 5 = 7.79 (d, 1H); 7.38 (d, 1H); 6.20 (tt, 1H); 3.84 (s, 3H); 3.13 (td, 2H); 2.42 (s, 3H); 2.31 (m, 1H); 1.17 (m, 4H);

[0357] Beispiel-Nr. 3-4: ’H-NMR (400 MHz, DMSO-d6): 5 = 8.43 (br q, 1H); 7.74 (d, 1H); 7.31 (d, 1H); 6.19 (tt, 1H); 3.83 (s, 3H); 3.12 (td, 2H); 2.78 (d, 3H); 2.37 (s, 3H);

[0358] Beispiel-Nr. 3-5: ’H-NMR (400 MHz, DMSO-d6): 5 = 8.53 (br t, 1H); 7.74 (d, 1H); 7.31 (d, 1H); 6.20 (tt, 1H); 3.83 (s, 3H); 3.28 (m, 2H); 3.14 (td, 2H); 2.39 (s, 3H); 1.11 (t, 3H);

[0359] Beispiel-Nr. 3-6: ’H-NMR (400 MHz, DMSO-d6): 5 = 8.58 (br d, 1H); 7.73 (d, 1H); 7.30 (d, 1H); 6.18 (tt, 1H); 3.84 (s, 3H); 3.12 (td, 2H); 2.85 (m, 1H); 2.37 (s, 3H); 0.71 (m, 2H); 0.49 (m, 2H);

[0360] Beispiel-Nr. 3-7: ’H-NMR (400 MHz, DMSO-d6): 5 = 7.85 (d, 1H); 7.54 (d, 1H); 6.24 (tt, 1H); 3.88 (s, 3H); 3.19 (td, 2H); 2.57 (s, 3H);

[0361] Beispiel-Nr. 3-8: ’H-NMR (400 MHz, DMSO-d6): 5 = 7.85 (d, 1H); 7.54 (d, 1H); 6.23 (tt, 1H); 3.87 (s, 3H); 3.14 (td, 2H); 2.87 (q, 2H); 1.12 (t, 3H);

[0362] Beispiel-Nr. 3-9: ’H-NMR (400 MHz, DMSO-d6): 5 = 7.85 (d, 1H); 7.55 (d, 1H); 6.24 (tt, 1H); 3.88 (s, 3H); 3.17 (td, 2H); 2.35 (m, 1H); 1.20 (m, 4H);

[0363] Beispiel-Nr. 3-10: ’H-NMR (400 MHz, DMSO-d6): 5 = 8.60 (br q, 1H); 7.76 (d, 1H); 7.47 (d, 1H); 6.21 (tt, 1H); 3.87 (s, 3H); 3.18 (td, 2H); 2.79 (d, 3H);

[0364] Beispiel-Nr. 3-11: ’H-NMR (400 MHz, DMSO-d6): 5 = 8.68 (br t, 1H); 7.76 (d, 1H); 7.46 (d, 1H); 6.22 (tt, 1H); 3.87 (s, 3H); 3.29 (m, 2H); 3.19 (td, 2H); 1.11 (t, 3H);

[0365] Beispiel-Nr. 3-12: ’H-NMR (400 MHz, DMSO-d6): 5 = 8.73 (br d, 1H); 7.76 (d, 1H); 7.46 (d, 1H); 6.20 (tt, 1H); 3.87 (s, 3H); 3.18 (td, 2H); 2.84 (m, 1H); 0.72 (m, 2H); 0.51 (m, 2H);BYC250025 Ausland

[0366] -44- Beispiel-Nr. 4-1: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.09 (br s, 1H); 7.77 (d, 1H); 7.33 (d, 1H); 6.19 (tt, 1H); 3.10 (td, 2H); 2.51 (s, 3H); 2.38 (s, 3H);

[0367] Beispiel-Nr. 4-2: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.08 (br s, 1H); 7.78 (d, 1H); 7.34 (d, 1H); 6.19 (tt, 1H); 3.05 (td, 2H); 2.80 (q, 2H); 2.33 (s, 3H); 1.09 (t, 3H);

[0368] Beispiel-Nr. 4-4: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.01 (br s, 1H); 8.41 (br q, 1H); 7.74 (d, 1H); 7.28 (d, 1H); 6.18 (tt, 1H); 3.11 (td, 2H); 2.78 (d, 3H); 2.38 (s, 3H);

[0369] Beispiel-Nr. 4-5: 'H-NMR (400 MHz, DMSO-d6): 5 = 12.90 (br s, 1H); 8.51 (brt, 1H); 7.74 (d, 1H); 7.27 (d, 1H); 6.19 (tt, 1H); 3.28 (m, 2H); 3.13 (td, 2H); 2.40 (s, 3H); 1.11 (t, 3H);

[0370] Beispiel-Nr. 4-6: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.01 (br s, 1H); 8.56 (br d, 1H); 7.74 (d, 1H); 7.27 (d, 1H); 6.17 (tt, 1H); 3.11 (td, 2H); 2.85 (m, 1H); 2.39 (s, 3H); 0.70 (m, 2H); 0.48 (m, 2H);

[0371] Beispiel-Nr. 4-7: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.63 (br s, 1H); 7.81 (d, 1H); 7.50 (d, 1H); 6.23 (tt, 1H); 3.17 (td, 2H); 2.56 (s, 3H);

[0372] Beispiel-Nr. 4-8: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.63 (br s, 1H); 7.81 (d, 1H); 7.50 (d, 1H); 6.23 (tt, 1H); 3.12 (td, 2H); 2.86 (q, 2H); 1.11 (t, 3H);

[0373] Beispiel-Nr. 4-9: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.50 (br s, 1H); 7.82 (d, 1H); 7.51 (d, 1H); 6.23 (tt, 1H); 3.16 (td, 2H); 2.35 (m, 1H); 1.20 (m, 4H);

[0374] Example no. 4-10: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.58 (br s, 1H); 8.57 (br q, 1H); 7.73 (d, 1H); 7.43 (d, 1H); 6.20 (dd, 1H); 3.16 (td, 2H); 2.78 (d, 3H);

[0375] Example no. 4-11: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.49 (br s,l H); 8.66 (br t, 1H); 7.73 (d, 1H); 7.42 (d, 1H); 6.21 (dd, 1H); 3.29 (m, 2H); 3.17 (td, 2H); 1.11 (t, 3H);

[0376] Example no. 4-12: 'H-NMR (400 MHz, DMSO-d6): 5 = 13.55 (br s, 1H); 8.72 (br d, 1H); 7.73 (d, 1H); 7.42 (d, 1H); 6.19 (dd, 1H); 3.16 (td, 2H); 2.83 (m, 1H); 0.72 (m, 2H); 0.50 (m, 2H).

[0377] B. Examples of wording

[0378] a) A dusting agent is obtained by mixing 10 parts by weight of a compound of formula (I) and / or its salts and 90 parts by weight of talc as an inert material and grinding in a percussion mill.

[0379] b) A readily dispersible, wettable powder is obtained by combining 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as an inert material, 10 parts by weight of potassium ligninsulfonate, and 1 part by weight of BYC250025 Abroad

[0380] -45- mixes sodium oleoylmethyltauric acid as a wetting and dispersing agent and grinds it in a pin mill.

[0381] 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. approx. 255 to over 277 C) and grinding in a ball mill to a fineness of less than 5 microns.

[0382] 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 oxyethylated nonylphenol as emulsifier.

[0383] e) A water-dispersible granulate is obtained by

[0384] 75 parts by weight of a compound of formula (I) and / or its salts,

[0385] 10 parts by weight of calcium ligninsulfonate,

[0386] 5 parts by weight sodium lauryl sulfate,

[0387] 3 parts by weight of polyvinyl alcohol and

[0388] 7 parts by weight kaolin

[0389] mixes, grinds on a pin mill and granulates the powder in a fluidized bed by spraying on water as a granulating liquid.

[0390] f) A water-dispersible granulate is also obtained by

[0391] 25 parts by weight of a compound of formula (I) and / or its salts,

[0392] 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-sodium disulfonate

[0393] 2 parts by weight of sodium oleoylmethyltaurinate,

[0394] 1 part by weight polyvinyl alcohol,

[0395] 17 parts by weight calcium carbonate and

[0396] 50 parts by weight water

[0397] homogenized and pre-crushed in a colloid mill, then ground in a bead mill, and the resulting suspension is atomized and dried in a spray tower using a single-component nozzle. BYC250025 Abroad

[0398] -46- C. Biological Examples

[0399] The abbreviations used for the harmful plants mean:

[0400] ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides

[0401] AVEFA Avena fatua AMAPA Amaranthus palmeri

[0402] DIGSA Digitaria sanguinalis ECHCG Echinochloa crus-galli

[0403] KCHSC Kochia scoparia LOLRI Lolium rigidum

[0404] MATIN Matricaria inodora PHBPU Pharbitis purpurea

[0405] POLCO Polygonum convolvulus SETVI Setaria viridis

[0406] VERPE Veronica persica VIOTR Viola tricolor

[0407] 1. Herbicidal effect against weeds in pre-emergence

[0408] Seeds of monocotyledonous and dicotyledonous weeds and cultivated plants are placed in wood fiber pots in sandy loam soil and covered with soil. The inventive compounds, formulated as wettable powders (WP) or emulsion concentrates (EC), are then applied as an aqueous suspension or emulsion to the surface of the covering soil at a water volume of approximately 600 to 800 liters per hectare, with the addition of 0.2% wetting agent. After treatment, the pots are placed in a greenhouse and kept under optimal growing conditions for the test plants. The damage to the test plants is visually assessed after a trial period of three weeks in comparison to untreated controls (herbicidal efficacy in percent (%): 100% efficacy = plants are dead, 0% efficacy = same as control plants). Numerous inventive compounds demonstrated very good efficacy against a wide range of significant weeds.The following tables show examples of the herbicidal activity of the invention compounds in pre-emergence applications, with the herbicidal activity given as a percentage. Table Cl: Pre-emergence activity at 20 g / ha against ALOMY in %.

[0409]

[0410] BYC250025 Abroad

[0411] -47-

[0412]

[0413] Table C-2: Pre-emergence efficacy at 80 g / ha against ALOMY in %

[0414]

[0415] Table C-3: Pre-emergence efficacy at 20 g / ha against AVEFA in %

[0416]

[0417] BYC250025 Abroad

[0418] -48-

[0419]

[0420] Table C-4: Pre-emergence efficacy at 80 g / ha against AVEFA in %

[0421]

[0422] BYC250025 Abroad

[0423] -49- Table C-5: Pre-emergence efficacy at 20 g / ha against LOLRI in %

[0424]

[0425] Table C-6: Pre-emergence efficacy at 80 g / ha against LOLRI in %

[0426]

[0427] BYC250025 Abroad

[0428] -50- Table C-7: Pre-emergence activity at 5 g / ha against MATIN in %

[0429]

[0430] Table C-8: Pre-emergence efficacy at 20 g / ha against MATIN in %

[0431]

[0432] Table C-9: Pre-emergence activity at 80 g / ha against MATIN in %

[0433]

[0434] BYC250025 Abroad

[0435] -51-

[0436]

[0437] Table C-10: Pre-emergence efficacy at 20 g / ha against Viotr in %

[0438]

[0439] BYC250025 Abroad

[0440] -52- Table Cl 1 : Pre-emergence efficacy at 80 g / ha against VIOTR in %

[0441]

[0442] Table C-12: Pre-emergence efficacy at 20 g / ha against PHBPU in %

[0443]

[0444] BYC250025 Abroad

[0445] -53-

[0446]

[0447] Table C-13: Pre-emergence efficacy at 80 g / ha against PHBPU in %

[0448]

[0449] Table C-14: Pre-emergence efficacy at 5 g / ha against VERPE in %

[0450]

[0451] BYC250025 Abroad

[0452] -54- Table C-15: Pre-emergence efficacy at 20 g / ha against VERPE in %

[0453]

[0454] Table C-16: Pre-emergence efficacy at 80 g / ha against VERPE in %

[0455]

[0456] Table C-17: Pre-emergence efficacy at 5 g / ha against ABUTH in %

[0457]

[0458] BYC250025 Abroad

[0459] -55-

[0460]

[0461] Table C-18: Pre-emergence efficacy at 20 g / ha against ABUTH in %

[0462]

[0463] Table C-19: Pre-emergence efficacy at 80 g / ha against ABUTH in %

[0464]

[0465] BYC250025 Abroad

[0466] -56-

[0467]

[0468] Table C-20: Pre-emergence efficacy at 5 g / ha against DIGSA in %

[0469]

[0470] Table C-21: Pre-emergence efficacy at 20 g / ha against DIGSA in %

[0471]

[0472] BYC250025 Abroad

[0473] -57- Table C-22: Pre-emergence efficacy at 80 g / ha against DIGSA in %

[0474]

[0475] Table C-23: Pre-emergence efficacy at 5 g / ha against ECHCG in %

[0476]

[0477] Table C-24: Pre-emergence efficacy at 20 g / ha against ECHCG in %

[0478]

[0479] BYC250025 Abroad

[0480] -58- Table C-25: Pre-emergence efficacy at 80 g / ha against ECHCG in %

[0481]

[0482] Table C-26: Pre-emergence efficacy at 5 g / ha against KCHSC in %

[0483]

[0484] BYC250025 Abroad

[0485] -59- Table C-27: Pre-emergence efficacy at 20 g / ha against KCHSC in %

[0486]

[0487] Table C-28: Pre-emergence efficacy at 80 g / ha against KCHSC in %

[0488]

[0489] BYC250025 Abroad

[0490] -60- Table C-29: Pre-emergence activity at 5 g / ha against AMAPA in %

[0491]

[0492] Table C-30: Pre-emergence activity at 20 g / ha against AMAPA in %

[0493]

[0494] Table C-31: Pre-emergence efficacy at 80 g / ha against AMAPA in %

[0495]

[0496] BYC250025 Abroad

[0497] -61-

[0498]

[0499] Table C-32: Pre-emergence efficacy at 20 g / ha against SETVI in %

[0500]

[0501] Table C-33: Pre-emergence efficacy at 80 g / ha against SETVI in %

[0502]

[0503] BYC250025 Abroad

[0504] -62-

[0505]

[0506] Table C-34: Pre-emergence efficacy at 80 g / ha against POLCO in %

[0507]

[0508] 2. Herbicidal effect against weeds after emergence

[0509] Seeds of monocotyledonous and dicotyledonous weeds and cultivated plants are sown in wood fiber pots in sandy loam soil, covered with soil, and cultivated in a greenhouse under optimal growing conditions. Two to three weeks after sowing, the experimental plants are treated at the one-leaf stage. The inventive compounds, formulated as wettable powders (WP) or emulsion concentrates (EC), are then sprayed onto the green parts of the plants as an aqueous suspension or emulsion at a water volume of approximately 600 to 8000 liters per hectare, with the addition of 0.2% wetting agent. After approximately three weeks of the experimental plants remaining in the greenhouse under optimal growing conditions, the efficacy of the preparations is visually assessed in comparison to untreated controls (herbicidal efficacy in percent (%): 100% efficacy = plants are dead, 0% efficacy = same as control plants).Numerous compounds according to the invention demonstrated good efficacy against a wide variety of important weeds. The following tables show, by way of example, the post-emergence herbicidal activity of the compounds according to the invention, with the herbicidal activity given as a percentage.

[0510] Table C-35: Post-emergence efficacy at 20 g / ha against ALOMY in %

[0511]

[0512] BYC250025 Abroad

[0513] -63-

[0514]

[0515] Table C-36: Post-emergence efficacy at 80 g / ha against ALOMY in %

[0516]

[0517] BYC250025 Abroad

[0518] -64-

[0519]

[0520] Table C-37: Post-emergence efficacy at 20 g / ha against AVEFA in %

[0521]

[0522] Table C-38: Post-emergence efficacy at 80 g / ha against AVEFA in %

[0523]

[0524] BYC250025 Abroad

[0525] -65-

[0526]

[0527] Table C-39: Post-emergence efficacy at 20 g / ha against LOLRI in %

[0528]

[0529] Table C-40: Post-emergence efficacy at 80 g / ha against LOLRI in %

[0530]

[0531] BYC250025 Abroad

[0532] -66-

[0533]

[0534] Table C-41: Post-emergence effect at 5 g / ha against MATIN in %

[0535]

[0536] Table C-42: Post-emergence effect at 20 g / ha against MATIN in %

[0537]

[0538] BYC250025 Abroad

[0539] -67-

[0540]

[0541] Table C-43: Post-emergence efficacy at 80 g / ha against MATIN in %

[0542]

[0543] Table C-44: Post-emergence efficacy at 5 g / ha against Viotr in %

[0544]

[0545] Table C-45: Post-emergence efficacy at 20 g / ha against VIOTR in %BYC250025 Abroad

[0546] -68-

[0547]

[0548] Table C-46: Post-emergence efficacy at 80 g / ha against Viotr in %

[0549]

[0550] BYC250025 Abroad

[0551] -69-

[0552]

[0553] Table C-47: Post-emergence efficacy at 5 g / ha against PHBPU in %

[0554]

[0555] BYC250025 Abroad

[0556] -70- Table C-48: Post-emergence efficacy at 20 g / ha against PHBPU in %

[0557]

[0558] Table C-49: Post-emergence efficacy at 80 g / ha against PHBPU in %

[0559]

[0560] BYC250025 Abroad

[0561] -71- Table C-50: Post-emergence efficacy at 5 g / ha against VERPE in %

[0562]

[0563] Table C-51: Post-emergence efficacy at 20 g / ha against VERPE in %

[0564]

[0565] Table C-52: Post-emergence efficacy at 80 g / ha against VERPE in %

[0566]

[0567] BYC250025 Abroad

[0568] -72-

[0569]

[0570] Table C-53: Post-emergence efficacy at 5 g / ha against DIGSA in %

[0571]

[0572] Table C-54: Post-emergence efficacy at 20 g / ha against DIGSA in %

[0573]

[0574] BYC250025 Abroad

[0575] -73-

[0576]

[0577] Table C-55: Post-emergence efficacy at 80 g / ha against DIGSA in %

[0578]

[0579] Table C-56: Post-emergence efficacy at 5 g / ha against ECHCG in %

[0580]

[0581] BYC250025 Abroad

[0582] -74-

[0583]

[0584] Table C-57: Post-emergence efficacy at 20 g / ha against ECHCG in %

[0585]

[0586] Table C-58: Post-emergence efficacy at 80 g / ha against ECHCG in %

[0587]

[0588] BYC250025 Abroad

[0589] -75-

[0590]

[0591] Table C-59: Post-emergence efficacy at 5 g / ha against KCHSC in %

[0592]

[0593] Table C-60: Post-emergence efficacy at 20 g / ha against KCHSC in %

[0594]

[0595] BYC250025 Abroad

[0596] -76-

[0597]

[0598] Table C-61: Post-emergence efficacy at 80 g / ha against KCHSC in %

[0599]

[0600] Table C-62: Post-emergence efficacy at 5 g / ha against SETVI in %

[0601]

[0602] BYC250025 Abroad

[0603] -77- Table C-63: Post-emergence efficacy at 20 g / ha against SETVI in %

[0604]

[0605] Table C-64: Post-emergence efficacy at 80 g / ha against SETVI in %

[0606]

[0607] BYC250025 Abroad

[0608] -78- Table C-65: Post-emergence effect at 5 g / ha against POLCO in %

[0609]

[0610] Table C-66: Post-emergence efficacy at 20 g / ha against POLCO in %

[0611]

[0612] Table C-67: Post-emergence efficacy at 80 g / ha against POLCO in %

[0613]

[0614] BYC250025 Abroad

[0615] -79-

[0616]

[0617] 3. Comparative herbicidal effect of compounds according to the invention with structurally similar compounds known from the literature made of WO2019 / 025540.

[0618] Table D1 below compares the compounds according to the invention with the structurally similar compounds known from W02019 / 025540 in the literature. The compounds according to the invention differ from the compounds known from the literature by a significant structural feature. The compounds according to the invention (examples 1-2, 1-3, 1-9, 2-2, 2-3, 2-8, 2-9) have a 2,2-difluoroethyl group at the 4-position of the benzamide, whereas in the compounds known from W02019 / 025540, the difluoromethyl group at this position is directly bonded to the benzamide – they consequently have a difluoromethyl group at this position. Table D1

[0619]

[0620] BYC250025 Abroad

[0621] -80-

[0622]

[0623] In the tables below D-2, D-3, D-4 and D-5, the pre-emergence effects on various weeds of compounds according to the invention and structurally similar compounds known from the literature from WO2019 / 025540 at an application rate corresponding to 20 g / ha and lower, which were obtained according to the aforementioned experimental procedure, are shown.

[0624] Table D-2: Pre-emergence efficacy at 20 g / ha against ALOMY in %

[0625]

[0626] Table D-3: Pre-emergence efficacy at 20 g / ha against AVEFA in %

[0627]

[0628] BYC250025 Abroad

[0629] -81- Table D-4: Pre-emergence efficacy at 20 g / ha against LOLRI in %

[0630]

[0631] Table D-5: Pre-emergence efficacy at 5 g / ha against VERPE in %

[0632]

[0633] As the results shown in Tables D-2, D-3, D-4 and D-5 demonstrate, compounds according to the invention (examples 1-2, 1-3, 1-9, 2-2, 2-3, 2-8, 2-9) exhibit significantly improved herbicidal efficacy in pre-emergence against weeds such as Alopecurus myosuroides (ALOMY), Avena fatua (AVEFA), Lolium rigidum (LOLRI) and Veronica persica (VERPE) compared to the structurally similar compounds known from the literature 1-42, 1-43, 1-168, 2-42, 2-43, 2-165, 2-168 (W02019 / 025540) at an application rate of 20 g of active substance or less per hectare.

[0634] Table D-6 below shows the post-emergence effects on the weed Polygonum convolvulus (POLCO) of a compound according to the invention and a structurally similar compound known from the literature from W02019 / 025540 at an application rate of 20 g / ha, obtained according to the aforementioned experimental procedure. BYC250025 Abroad

[0635] -82- Table D-6: Post-emergence effect at 20 g / ha against POLCO in %

[0636]

[0637] As the results shown in Table D-6 demonstrate, the inventive compound (Example 2-2) exhibits a significantly improved herbicidal efficacy in post-emergence against the weed Polygonum convolvulus (POLCO) compared to the structurally similar compound known from the literature at an application rate of 20 g of active substance per hectare.

[0638] 4. Comparative herbicidal effect of compounds according to the invention with structurally similar compounds known from the literature made of WO2021 / 204665.

[0639] Comparison of the substituents 2,2-difluoroethyl and difluoromethyl in the 4-position of the benzamide. Table D-7 below compares the compounds according to the invention with the structurally similar compounds known from the literature, derived from WO2021 / 204665. The compounds according to the invention differ from the compounds known from the literature by a significant structural feature. The compounds according to the invention (examples 1-4, 1-5, 1-6, 1-12, 2-5, 2-6, 2-10) have a 2,2-difluoroethyl group in the 4-position of the benzamide, whereas in the compounds known from the literature derived from WO2021 / 204665, the difluoromethyl group is directly bonded to the benzamide at this position – they consequently have a difluoromethyl group at this position. Table D-7

[0640]

[0641] BYC250025 Abroad

[0642] -83-

[0643]

[0644] Tables D-8 and D-9 below show the pre-emergence effects on various weeds of compounds according to the invention and of structurally similar compounds known from the literature from WO2021 / 204665 at an application rate of 20 g / ha and lower, which were obtained according to the aforementioned experimental procedure.

[0645] Table D-8: Pre-emergence efficacy at 20 g / ha against ALOMY in %

[0646]

[0647] Table D-9: Pre-emergence efficacy at 5 g / ha against VERPE in %

[0648]

[0649] As the results shown in Tables D-8 and D-9 demonstrate, the inventive compounds (examples 1-12, 2-6, 2-10) exhibit a significantly improved herbicidal efficacy in pre-emergence against weeds such as Alopecurus myosuroides (ALOMY) and Veronica persica (VERPE) compared to the structurally similar compounds known from the literature 1-149, 2-46, 2-147 (WO2021 / 204665) at an application rate of 20 g of active substance or less per hectare.

[0650] Tables D-10 and D-11 below show the post-emergence effects on various weeds of compounds according to the invention and of structurally similar compounds known from the literature from WO2021 / 204665 at an application rate corresponding to 20 g / ha, which were obtained according to the aforementioned experimental procedure.

[0651] Table D-10: Post-emergence efficacy at 20 g / ha against ALOMY in %BYC250025 Abroad

[0652] -84-

[0653]

[0654] Table Dl 1: Post-emergence efficacy at 20 g / ha against VIOTR in %

[0655]

[0656] As the results shown in Tables D-10 and D-11 demonstrate, the compounds according to the invention (examples 1-4, 1-5, 1-6, 2-5, 2-6) exhibit a significantly improved herbicidal efficacy in post-emergence against weeds such as Alopecurus myosuroides (ALOMY) and Viola tricolor (VIOTR) compared to the structurally similar compounds known from the literature 1-44, 1-45, 1-46, 2-45, 2-46 (WO2021 / 204665) at an application rate of 20 g of active substance per hectare.

[0657] Comparison of the substituents 2,2-difluoroethyl and pentafluoroethyl in the 4-position of the benzamide. Table D-12 below compares compounds according to the invention with structurally similar compounds from WO2021 / 204665 known in the literature. Even in these comparisons, the compounds according to the invention differ from the compounds known in the literature by a significant structural feature. The compounds according to the invention (Examples 1-10, 1-11) have a 2,2-difluoroethyl group in the 4-position of the benzamide, while in the compounds known in the literature from WO2021 / 204665, a pentafluoroethyl group is bonded to the benzamide at this position. BYC250025 Foreign

[0658] -85- Table D-12

[0659]

[0660] Table D-13 below shows the post-emergence effects on various weeds of compounds according to invention and structurally similar compounds known from WO2021 / 204665 at an application rate corresponding to 20 g / ha, which were obtained according to the aforementioned experimental procedure.

[0661] Table D-13: Post-emergence efficacy at 20 g / ha against MATIN and VIOTR in %

[0662]

[0663] As the results shown in Table D-13 demonstrate, the inventive compounds (examples 1-10, 1-11) exhibit a significantly improved herbicidal efficacy in post-emergence against weeds such as Matricaria inodora (MATIN) and Viola tricolor (VIOTR) compared to the structurally similar compounds known from the literature 1-165, 1-166 (WO2021 / 204665) at an application rate of 20 g of active substance per hectare.

Claims

BYC250025 Abroad -86- Claims:

1. 4-Fluoroalkylbenzamides of formula (I) or their salts where the symbols and indices have the following meanings: R stands for (Ci-Ce)-alkyl, X means halogen or (Ci-Ce) alkyl, Y means CH2CHF2 or CH2CF3 Z means Z 1 or Z 2 , Z 1 means (Ci-Ce)-alkyl or (C3-C6)-cycloalkyl, Z 2 NR means 1 R 2 , R 1 , R 2 Each of these terms independently represents hydrogen, (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl or halogen-(Ci-C6)-alkyl.

2. Compounds according to claim 1, wherein the symbols and indices have the following meanings: R means Me, Et or Pr, X means Cl, Br, Me or Et, Y means CH2CF3 or CH2CHF2, Z means Z 1 or Z 2 , Z 1 means Me, Et, n-Pr, i-Pr or c-Pr, Z 2 NR means 1 R 2 , R 1 , R 2 Each of these terms independently represents hydrogen, Me, Et, Pr, i-Pr, c-Pr, CH2CHF2 or CH2CF3.

3. Compounds according to claim 1 or 2, wherein the symbols and indices have the following meanings: BYC250025 Abroad -87- R means Me or Et, X means CI or Me, Y means CH2CHF2, Z means Z 1 or Z 2 , Z 1 means Me, Et or c-Pr, Z 2 means NHMe, NHEt or NHc-Pr.

4. Compounds according to any one of claims 1 to 3, wherein Z represents Z 1 stands.

5. Compounds according to any one of claims 1 to 3, wherein Z represents Z 2 stands.

6. Herbicidal compositions comprising at least one compound according to any one of claims 1 to 5 in a mixture with formulation aids.

7. Herbicidal composition according to claim 6 comprising at least one further pesticidal substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

8. Herbicidal composition according to claim 7, wherein the further pesticidal substance is a herbicide.

9. Herbicidal composition according to claim 7, wherein the further pesticidal active substance is a safener.

10. Method for controlling unwanted plants, characterized in that an effective amount of at least one compound of formula (I) according to one of claims 1 to 5 or of at least one herbicidal agent according to one of claims 6 to 9 is applied to the plants or to the site of unwanted plant growth.

11. Use of a compound of formula (I) according to any one of claims 1 to 5 or of a herbicidal agent according to any one of claims 6 to 9 for controlling unwanted plants.

12. Use according to claim 11, characterized in that the compound of formula (I) is used to control unwanted plants in crops of useful plants.

13. Use according to claim 12, characterized in that the crop plants are transgenic crop plants.

14. Connections of formula (II),BYC250025 Abroad -88- .. where the symbols and indices have the following meanings: L means halogen or R 3 0, X means halogen or (Ci-Ce) alkyl, Y means CH2CHF2 or CH2CF3 Z means Z 1 or Z 2 , Z 1 means (Ci-Ce)-alkyl or (C3-C6)-cycloalkyl, Z 2NR means 1 R 2 , R 1 , R 2 Each of these terms independently represents hydrogen, (Ci-Ce)-alkyl, (Cs-Ce)-cycloalkyl, or halogen-(Ci-Ce)-alkyl. R 3 means hydrogen or (Ci-Ce)-alkyl.

15. Compounds according to claim 14, wherein the symbols and indices have the following meanings: L means chlorine, methoxy or hydroxy, X means chlorine or me Y means CH2CHF2, Z means Z 1 or Z 2 , Z 1 means Me, Et or c-Pr, Z 2 means NHMe, NHEt or NHc-Pr.

16. Compounds according to one of claims 14 or 15, wherein Z represents Z 1 stands.

17. Compounds according to one of claims 14 or 15, wherein Z represents Z 2 stands.

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