3-Acyl-Benzamide and its use as a herbicide

Abstract

The present invention relates to 3-acyl-benzamide of the following chemical formula (I) as a herbicide. In chemical formula (I), X, Y, Z and Rx are groups such as alkyl, cycloalkyl, haloalkyl and halogen.

Description

Technology Field

[0001] The present invention relates to a herbicide for the selective control of broadleaf weeds and weeds in plant crops, particularly in the field of herbicide technology. Background Technology

[0002] WO 2012 / 028579 A1 discloses herbicidally active benzamides that may have various substituents at the 3rd position of the phenyl ring. WO 2017 / 005567 A1, EP 3 118 199 A1, and WO 2017 / 055146 A1 also describe herbicidally active phenylamides that may have various substituents at the 3rd position of the phenyl ring. Additionally, these disclosures disclose individual phenylamides having an acetyl or cyclopropylcarbonyl radical at the 3rd position of the phenyl ring, respectively, in Examples 1-364 to 1-367 and 1-426 to 1-429. Finally, WO2019 / 25540 discloses specific 3-acylbenzamides. However, the benzoylamides known in the aforementioned disclosures do not always possess adequate herbicidal efficacy and / or compatibility with crops.

[0003] The object of the present invention is to provide an alternative herbicidal active ingredient. This object is achieved by the benzamide of the present invention described below, which has an acyl radical at the 3rd position of the phenyl ring and additionally a haloalkoxy radical at the 4th position. Specific details for implementing the invention

[0004] Accordingly, the present invention provides a 3-acylbenzamide of the following formula (I) or a salt thereof:

[0005]

[0006] In the expression, the symbol and the exponent are defined as follows:

[0007] R x is a (C1-C6)-alkyl, and

[0008] X is a halogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl, and

[0009] Y is a halo-(C1-C6)-alkoxy, and

[0010] Z is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, or (C3-C6)-cycloalkyl-(C1-C6)-alkyl, and (C3-C6)-cycloalkyl is R 1 It is replaced by a radical,

[0011] R 1 is a halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C1-C6)-alkyl-O, and

[0012] m is 0, 1, 2, or 3.

[0013] In formula (I) and all formulas below, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n-propyl or isopropyl, n-, iso-, t- or 2-butyl, pentyl, hexyl, such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. In a similar manner, alkenyl means, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl means, for example, propargyl, but-2-in-1-yl, but-3-in-1-yl, and 1-methylbut-3-in-1-yl. Multiple bonds may be located at any position on each unsaturated radical. Cycloalkyl is a carbon-cyclic saturated ring system having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0014] Halogens refer to fluorine, chlorine, bromine, or iodine.

[0015] Depending on the properties of the substituents and the manner in which they are connected, compounds of formula (I) or (II) may exist as stereoisomers. In the presence of one or more asymmetrically substituted carbon atoms, enantiomers and diastereomers may exist, for example. Stereoisomers may be obtained from mixtures obtained during preparation through conventional separation methods, for example, chromatographic separation processes. Similarly, it is possible to selectively prepare stereoisomers using stereoselective reactions with optically active starting materials and / or auxiliaries. The present invention also relates to all stereoisomers and mixtures thereof that are covered by but not specifically defined in formula (I) or (II).

[0016] A compound of chemical formula (I) with the symbol and exponent defined as follows is preferred:

[0017] R x is a (C1-C6)-alkyl, and

[0018] X is a halogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl, and

[0019] Y is OCF3, OCHF2, OCH2CHF2 or OCF2Me, and

[0020] Z is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, or (C3-C6)-cycloalkyl-(C1-C6)-alkyl, and (C3-C6)-cycloalkyl is R 1 It is replaced by a radical,

[0021] R 1 is a halogen, (C1-C6)-alkyl or halo-(C1-C6)-alkyl, and

[0022] m is 0, 1, or 2.

[0023] Compounds of chemical formula (I) with symbols and indices defined as follows are particularly preferred:

[0024] R x is Me, Et and,

[0025] X is chlorine, bromine, methyl, ethyl, or cyclopropyl, and

[0026] Y is OCF3, OCHF2, or OCH2CHF2, and

[0027] Z is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, vinyl, allyl, ethinyl, prop-1-in-1-yl, methoxymethyl, chloromethyl, cyclopropylmethyl, 1-methylcyclopropyl or difluoromethyl.

[0028] In all chemical formulas specified below, substituents and symbols have the same definitions as those described in chemical formula (I) unless otherwise defined.

[0029] The compound of formula (II) is novel and highly suitable as an intermediate for the preparation of the compound of formula (I) of the present invention. Accordingly, the present invention further provides the compound of formula (II) below:

[0030]

[0031] In the expression, the symbol and the exponent are defined as follows:

[0032] L is a halogen or R 2 It is O, and,

[0033] X is a halogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl, and

[0034] Y is a halo-(C1-C6)-alkoxy, and

[0035] Z is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, or (C3-C6)-cycloalkyl-(C1-C6)-alkyl, and (C3-C6)-cycloalkyl is R 1 It is replaced by a radical,

[0036] R1 is a halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C1-C6)-alkyl-O, and

[0037] R 2 is hydrogen or (C1-C6)-alkyl.

[0038] L is chlorine, methoxy, or hydroxy, and

[0039] X is chlorine, bromine, methyl or ethyl or cyclopropyl, and

[0040] Y is OCF3, OCHF2, or OCH2CHF2, and

[0041] Compound (II) is preferred, wherein Z is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, vinyl, allyl, ethinyl, prop-1-in-1-yl, methoxymethyl, chloromethyl, cyclopropylmethyl, 1-methylcyclopropyl, or difluoromethyl.

[0042] In all chemical formulas specified below, substituents and symbols have the same definitions as those described in chemical formula (I) unless otherwise defined.

[0043] The compound of the present invention of general formula (I) is prepared, for example, by the reaction of a substituted aminotetrazole, also described in WO2012 / 028579, with the compound of the present invention of general formula (II-b: compound II, where L=hydroxyl):

[0044]

[0045] Compounds of general chemical formula (IIb) can be synthesized, for example, according to the following reaction scheme and methods known to those skilled in the art:

[0046]

[0047] A collection of compounds of formula (I) and / or salts thereof that can be synthesized by the reaction mentioned above may also be prepared in parallel, and this can be done manually, partially automated, or fully automated. For example, it is possible to automate the execution of the reaction, post-processing, or purification of the products and / or intermediates. Overall, this is understood to mean the procedure described, for example, in [D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999, on pages 1 to 34].

[0048] In the case of performing reaction and post-treatment in parallel, it is possible to use various commercially available equipment, for example, a Calypso reaction block from Barnstead International (Dubuque, Iowa 52004-0797, USA), a reaction station from Radleys (Shirehill, Saffron Walden, Essex, CB11 3AZ, England), or a MultiPROBE Workstation from Perkin Elmer (Waltham, Massachusetts 02451, USA). For the parallel purification of the compound of formula (I) and its salt or intermediates generated during the manufacturing process, available equipment includes, for example, chromatography equipment from ISCO, Inc. (4700 Superior Street, Lincoln, NE 68504, USA).

[0049] The equipment described above generates an automated modular procedure for each individual work step, but manual work must be performed between work steps. This can be avoided by using parts where each automation module is operated, for example, by a robot, or by using a fully integrated automation system. Such automation systems are available, for example, from Caliper (Hopkinton, MA 01748, USA).

[0050] The performance of individual or multiple synthesis steps can be supported by the use of polymer-supported reagent / scavenger resins. A series of experimental protocols are described in the literature, for example, [ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich)].

[0051] In addition to the methods described herein, the compound of formula (I) and its salts may be prepared wholly or partially by solid-phase support methods. For this purpose, individual intermediates or all intermediates are bonded to a synthetic resin in the synthesis or in a synthesis adapted to the relevant procedure. Solid-phase support synthesis methods are appropriately described in the technical literature, for example, [Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999]. The use of solid-phase support synthesis methods is known in the literature and allows for numerous protocols that may eventually be performed manually or automatically. The reaction may be carried out, for example, via IRORI technology in a microreactor at Nexus Biosystems (12140 Community Road, Poway, CA92064, USA).

[0052] In both the solid and liquid phases, the execution of individual or several synthesis steps may be supported by the use of microwave technology. Numerous experimental protocols are described in the literature, for example, [Microwaves in Organic and Medicinal Chemistry (editors: CO Kappe and A. Stadler), Wiley, 2005].

[0053] The manufacture by the process described herein provides compounds of formula (I) and salts thereof in the form of a collection of materials called a library. The present invention also provides a library comprising at least two compounds of formula (I) and salts thereof.

[0054] The compound of the present invention has excellent herbicidal efficacy against economically important monocotyledonous and dicotyledonous annual pest plants of a broad spectrum. The active ingredient also acts efficiently on perennial weeds that are difficult to control and produce shoots from rhizomes, root stems, or other perennial organs.

[0055] Accordingly, the present invention also provides a method for controlling the growth of plants, preferably plant crops, or controlling unwanted plants, and applies one or more of the compound(s) of the present invention to plants (e.g., harmful plants, such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds (e.g., grains, seeds, or vegetative propagules, such as tubers or budded shoots), or areas where plants are growing (e.g., areas being cultivated). The compounds of the present invention may be utilized before sowing (also by incorporation into the soil where appropriate), before or after germination. Some representative specific examples of monocotyledonous and dicotyledonous weed plants that can be controlled by the compounds of the present invention are as follows, but there is no intention to limit the listing to specific species.

[0056] Monocotyledonous harmful plant genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Iscaemum (Ischaemum), Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.

[0057] Dicotyledonous weed 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, Gallium, 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 (Sphenoclea), Stellaria, Taraxacum, Thlaspi, Tripolium,Urtica, Veronica, Viola, and Xanthium.

[0058] When the compound of the present invention is applied to the soil surface before germination, the emergence of weed seedlings is completely prevented, or the weed is allowed to grow until it reaches the cotyledon stage, after which growth is stopped and ultimately completely killed after 3 to 4 weeks.

[0059] When the active ingredient is applied to the green parts of a plant by a post-budding method, growth is halted after treatment, and harmful plants either maintain their growth stage at the time of application or die completely after a certain period; as a result, competition by weeds harmful to crop plants is eradicated in a continuous manner at a very early stage.

[0060] Although the compound of the present invention has excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, it is used against crop plants of economically important crops, e.g., dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or Allium, Ananas, Asparagus, and Avena Monocotyledonous crops of the genera Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea, particularly Zea and Triticum, will be damaged only to a negligible degree depending on the structure of the specific compound of the present invention and its application rate. For this reason, the compound of the present invention is highly suitable for the selective control of unwanted plant growth in plant crops, such as agriculturally useful plants or ornamental plants.

[0061] Furthermore, the compounds of the present invention possess excellent growth-regulating properties in crop plants, depending on their specific chemical structures and application rates. They act on the regulatory systems of the plant's own metabolism and can therefore be used to promote harvest by exerting controlled effects on plant components, for example, by inducing dehydration and growth retardation. Additionally, they are suitable for the overall control and inhibition of unwanted vegetative growth without killing the plant. Inhibition of vegetative growth plays a major role for many monocot and dicot crops, as it can, for example, reduce or completely prevent lodging.

[0062] Due to their herbicidal and plant growth-regulating properties, the active ingredients can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. Genetically modified plants are generally characterized by certain advantageous properties, for example, resistance to certain insecticides, particularly certain herbicides, and resistance to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria, or viruses. Other specific characteristics relate to yields, for example, quantity, quality, storability, composition, and specific components. For example, there exist known genetically modified plants with increased starch content or altered starch quality, or those with different fatty acid compositions in their yields.

[0063] It is desirable to use the compounds of the present invention in useful plants and ornamental plants from the perspective of genetically modified crops, for example, economically important genetically modified crops of grains such as wheat, barley, rye, oats, millet / sorghum, rice and corn, or other crops of sugar beets, cotton, soybeans, oilseed rapeseeds, potatoes, manioc, tomatoes, peas and other vegetables.

[0064] Preferably, the compound of the present invention can be used as a herbicide in crops of useful plants that are resistant to the phytotoxic effects of herbicides or have become resistant through genetic engineering.

[0065] Conventional methods for producing new plants with modified properties compared to existing plants include, for example, traditional cultivation methods and the generation of mutants. Alternatively, new plants with modified properties can be generated with the help of recombination methods (see, e.g., EP-A-0221044, EP-A-0131624). For example, the following various examples are described:

[0066] - Genetic modification of crop plants for the purpose of modifying starch synthesized in plants (e.g., WO 92 / 11376, WO 92 / 14827, WO 91 / 19806),

[0067] - Genetically modified crop plants resistant to specific herbicides of the glufosinate type (see: e.g., EP-A-0242236, EP-A-242246) or glyphosate type (WO 92 / 00377) or sulfonylurea type (EP-A-0257993, US-A-5013659),

[0068] - Genetically modified crop plants capable of producing Bacillus thuringiensis toxin (Bt toxin) that makes plants resistant to certain pests, e.g., cotton (EP-A-0142924, EP-A-0193259),

[0069] - Genetically modified crop plant with modified fatty acid composition (WO 91 / 13972),

[0070] - Genetically modified crop plants having novel components or secondary metabolites that cause increased disease resistance, e.g., novel phytoalexins (EPA 309862, EPA0464461),

[0071] - Genetically modified plants with reduced photorespiration, higher yield, and higher stress tolerance (EPA 0305398),

[0072] - Genetically modified crop plants that produce pharmaceutically or diagnostically important proteins ("molecular farming"),

[0073] - Genetically modified crop plants characterized by higher yield or better quality,

[0074] - For example, a genetically modified crop plant ("gene stacking") characterized by a combination of the novel properties mentioned above.

[0075] Numerous molecular biology techniques that can be used to produce novel genetically modified plants with modified properties are generally known, for example, see the following literature: I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431.

[0076] For such genetic manipulation, nucleic acid molecules that allow for mutagenicity or sequence alteration via DNA sequence recombination may be introduced into a plasmid. With the aid of standard methods, it is possible, for example, to perform base exchanges, remove portions of the sequence, or add natural or synthetic sequences. To link a DNA fragment to another, it is possible to add an adapter or linker to the fragment: for example, refer to the following literature: Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd edition, 1996.

[0077] For example, the generation of plant cells with reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA or sense RNA to obtain a co-inhibitory effect, or by expressing at least one suitably constructed ribozyme that specifically cleaves the transcript of the aforementioned gene product. To this end, it is possible to use a DNA molecule containing the entire coding sequence of the gene product, including any possible adjacent sequence, and it is also possible to use a DNA molecule containing only a portion of the coding sequence, in which case these portions need to be long enough to have an antisense effect in the cell. It is also possible to use a DNA sequence that is not completely identical but has a high degree of homology to the coding sequence of the gene product.

[0078] When nucleic acid molecules are expressed in plants, the synthesized proteins may be localized to any desired compartment of the plant cell. However, to achieve localization to a specific compartment, it is possible, for example, to link the coding region to a DNA sequence that guarantees localization in a specific compartment. Such sequences are known to those skilled in the art (see, e.g., 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). Nucleic acid molecules may also be expressed in organelles of the plant cell.

[0079] Genetically modified plant cells can be regenerated by known technology to produce a whole plant. Generally, the genetically modified plant can be any desired plant species, namely monocots as well as dicotyledons.

[0080] In this way, genetically modified plants with altered properties can be obtained by overexpression, inhibition, or suppression of homologous (=natural) genes or gene sequences, or by the expression of heterologous (=foreign) genes or gene sequences.

[0081] The compounds of the present invention may preferably be used in genetically modified crops resistant to growth regulators, e.g., dicamba, or herbicides that inhibit essential plant enzymes, e.g., acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS), or hydroxyphenylpyruvate deoxygenase (HPPD), or herbicides of the group of sulfonylureas, glyphosate, glufosinates, or benzoylisoxazole and similar active ingredients.

[0082] When the active ingredient of the present invention is applied to a genetically modified crop, not only does the effect on harmful plants observed in other crops occur, but also frequently, effects specific to the application in a specific genetically modified crop occur, for example, a change or specifically an expansion of the spectrum of weeds that can be controlled, a modified application rate that can be used for application, preferably good compatibility with herbicides to which the genetically modified crop is resistant, and an effect on the growth and yield of the genetically modified crop plant.

[0083] Therefore, the present invention also provides a use of the compound of the present invention as a herbicide for controlling harmful plants in genetically modified crop plants.

[0084] The compounds of the present invention may be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, spray products, or granules in conventional formulations. Accordingly, the present invention also provides herbicides and plant growth regulating compositions comprising the compounds of the present invention.

[0085] The compounds of the present invention may be formulated in various ways depending on the required biological and / or physicochemical parameters. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifying 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), spray products (DP), granules for dressing, spreading and soil application, granules in the form of microgranules (GR), spray granules, absorbent and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.

[0086] These individual formulation types are generally known and are described, for example, in the following literature: Winnacker-Kuchler, "Chemische Technologie" [Chemical Engineering], 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.

[0087] Necessary formulation adjuvants, such as inert substances, surfactants, solvents, and additional additives, are likewise known; for example, refer to the following literature: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ, Hv; Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964, Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

[0088] The wetting powder is a formulation that is uniformly dispersed in water and, in addition to a diluent or inert substance, comprises, together with the active ingredient, an ionic and / or nonionic surfactant (wetting agent, dispersant), e.g., polyethoxylated alkylphenol, polyethoxylated fatty alcohol, polyethoxylated fatty amine, fatty alcohol polyglycol ether sulfate, alkane sulfonate, alkylbenzene sulfonate, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate, or sodium oleoylmethyltaurate. To produce the wetting powder, the active herbicidal ingredient is finely ground, for example, using conventional equipment such as a hammer mill, blow mill, and air-jet mill, and mixed with the formulation aid at the same time or subsequently.

[0089] An emulsifying concentrate is produced by dissolving an active ingredient in an organic solvent, e.g., butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of other relatively high-boiling point aromatics or hydrocarbons or organic solvents, while adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that may be used include calcium alkylarylsulfonate salts, e.g., calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, e.g., sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, e.g., polyoxyethylene sorbitan fatty acid esters.

[0090] The spray product is obtained by grinding the active ingredient into a finely distributed solid, for example, talc, natural clay, such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth.

[0091] Suspension concentrates may be water- or oil-based. They may also be produced, for example, by wet grinding using a commercially available bead mill, and, for example, by the optional addition of surfactants already listed above in other formulation types.

[0092] Emulsions, for example, oil-in-water emulsions (EW), can be produced using a solvent and optionally a surfactant as listed above, for example, in other formulation types, for example, through a stirrer, a colloid mill, and / or a static mixer.

[0093] Granules can be produced by spraying the active ingredient onto a granular inert material capable of adsorbing it, or by applying the active ingredient to the surface of a carrier material, such as sand, kaolinite, or a granular inert material, through an adhesive, such as polyvinyl alcohol, sodium polyacrylate, or other mineral oils. A suitable active ingredient can also be granulated in the usual manner for producing fertilizer granules, preferably as a mixture with fertilizer.

[0094] Water-dispersible granules are generally produced through conventional processes such as spray-drying, fluidized bed granulation, pan granulation, mixing using a high-speed mixer, and extrusion without solid inert material.

[0095] For the production of pan, fluidized bed granules, extruder granules, and spray granules, refer, for example, to the processes in the following literature: "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.

[0096] For further detailed descriptions regarding the formulation of crop protection agents, refer, for example, to the following literature: 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.

[0097] The pesticide formulation generally contains 0.1% to 99% by weight, particularly 0.1% to 95% by weight of the compound of the present invention.

[0098] In the wettable powder, the concentration of the active ingredient is, for example, about 10% by weight to 90% by weight, and the remainder consists of up to 100% by weight of conventional formulation ingredients. In the emulsifiable concentrate, the concentration of the active ingredient may be about 1% by weight to 90% by weight, preferably 5% by weight to 80% by weight. The sprayable formulation contains 1% by weight to 30% by weight of the active ingredient, preferably generally 5% by weight to 20% by weight of the active ingredient, and the sprayable solution contains about 0.05% by weight to 80% by weight, preferably 2% by weight to 50% by weight of the active ingredient. In the case of water-dispersible granules, the content of the active ingredient depends at least partially on whether the active ingredient is in liquid or solid form and whether granulation aids, fillers, etc. are used. In water-dispersible granules, the content of the active ingredient is, for example, between 1 weight% and 95 weight%, preferably between 10 weight% and 80 weight%.

[0099] In addition, the mentioned active ingredient formulations optionally include, each, conventional adhesives, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoaming agents, evaporation inhibitors and agents affecting pH and viscosity.

[0100] Based on these formulations, it is also possible to produce combinations with other insecticidal active substances, e.g., insecticides, miteicides, herbicides, fungicides, and also emphysicators, fertilizers, and / or growth regulators, e.g., as finished formulations or tank mixes.

[0101] For application, commercially available formulations are diluted with water in the usual manner where appropriate, for example, in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Preparations in spray form, granules for soil application or granules for spreading, and spray solutions are generally not further diluted with other inert substances before application.

[0102] The required application rate of the compound of formula (I) varies depending on external conditions, particularly temperature, humidity, and the type of herbicide used. Within a wide range of limits, it may vary between 0.001 kg / ha and 1.0 kg / ha or more based on the active substance, but preferably between 0.005 g / ha and 750 g / ha.

[0103] The compound of the present invention of formula (I) may also be applied as needed in a mixture with other herbicides. Combination partners available for use with the compound of formula (I) as a mixed formulation or tank mix are, for example, based on the inhibition of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyrubylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate deoxygenase, phytoene desaturase, photosystem I, photosystem II, or protoporpyrinogen oxidase, or are known active ingredients acting as plant growth regulators, for example, as known in the following literature: Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006, and the literature cited herein.

[0104] Examples of known herbicides or plant growth regulators that may be combined with the compound of formula (I) include the active ingredients listed below (compounds are referred to by their generic names, chemical names, or code numbers according to the International Organization for Standardization (ISO)) and always cover all forms of use, e.g., acids, salts, esters, and isomers, e.g., stereoisomers and optical isomers. The list includes, by example, one form of application and, in some cases, more than one form of application:

[0105] Acetochlor, asifluorphen, asifluorphen-methyl, asifluorphen-sodium, acloniphen, alachlor, alidochlor, alloxidim, alloxidim-sodium, ametrine, amicabazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralide, aminopyralide-dimethylammonium, aminopyralide-tripromin, amitrol, ammonium sulfamate, anilofos, asulam, asulam-potassium, asulam-sodium, atrazine, azaphenidine, azimsulfuron, beflubutamide, (S)-(-)-Beflubutamide, Beflubutamide-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-potassium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulide, Bentazone, Bentazone-sodium, Benzobicyclon, Benzophenap, Bicyclopyrone, Bifenox, Villanaphos, Villanaphos-sodium, Bipirazone, Bispiribac, Bispiribac-sodium, Bixloxone, Bromasil, Bromasil-lithium, Bromasil-sodium, Bromobutide, Bromofenoxim, Bromoxinyl, Bromoxinyl butyrate, Bromoxinyl-potassium, Bromoxinyl-heptanoate and Bromoxinyl-octanoate, Abscinone, Butachlor, Butafenacil, Butamiphos, butenachlor, butralin, butroxidim, butylate, capenstroll, cambendichlor, carbetamide, carpentrazone, carpentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamin, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromurone, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorimurone, chlorimurone-ethyl, chlorophthalim, chlortolurone, chlorsulfurone, chlortal, chlortal-dimethyl, chlortal-monomethyl, sinidone, sinidone-ethyl, synmethylline, exo-(+)-synmethylline, i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)-synmethylline, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, sinosulfuron, clasifos, cletodim, clodinapop, clodinapop-ethyl, clodinapop-propargyl, clomazone, clomeprop, clopyralide, clopyralide-methyl, clopyralide-olamin, clopyralide-potassium, clopyralide-triformin, chloransullam, chloransullam-methyl, cumilurone, cyanamide, cyanazine, cycloate, cyclopyranil, Cyclopyrimorate, cyclosulfamurone, cycloxidim, sihalofov, sihalofov-butyl, ciprazine, 2,4-D (and ammonium, butotyl, butyl, choline, diethylammonium, dimethylammonium, diolamin, dovoxyl, dodecylammonium, etexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, methyl, potassium, tetradecylammonium, triethylammonium, triisopropanolammonium, tripromine and trolamine salts thereof), 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isoooctyl, 2,4-DB-potassium and 2,4-DB-sodium, Daimuron (Dimron), Dalafon, Dalafon-Calcium, Dalafon-Magnesium, Dalafon-Sodium, Dazomet, Dazomet-Sodium, n-Decanol, 7-Deoxy-D-Sedoheptulose, Desmedipharma, Destosyl Pyrazolate (DTP), Dicamba and its salts (e.g., Dicamba-Biproamine, Dicamba-N,N-Bis(3-Aminopropyl)Methylamine, Dicamba-Butotyl, Dicamba-Choline, Dicamba-Diglycolamine, Dicamba-Dimethylammonium, Dicamba-DiethanolamineAmmonium, Dicamba-Diethylammonium, Dicamba-Isopropylammonium, Dicamba-Methyl, Dicamba-Monoethanolamine, Dicamba-Olamin, Dicamba-Potassium, Dicamba-Sodium, Dicamba-Triethanolamine), Dichlorobenyl, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one,Dichlorprop, dichlorprop-butothyl, dichlorprop-dimethylammonium, dichlorprop-ethexil, dichlorprop-ethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-ethexil, dichlorprop-P-potassium, dichlorprop-sodium, diclopov, diclopov-methyl, diclopov-P, diclopov-P-methyl, diclosulam, difenzoquat, difenzoquat-methylsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethsulfazet, dimetachlor, dimethamethrine, Dimethenamide, Dimethenamide-P, Dimetrasulfuron, Dinitramin, Dinoterb, Dinoterb-acetate, Diphenamide, Diquat, Diquat-Dibromide, Diquat-Dichloride, Dithiopyr, Diuron, DNOC, DNOC-Ammonium, DNOC-Potassium, DNOC-Sodium, Endothal, Endothal-Diammonium, Endothal-Dipotassium, Endothal-Disodium, Epirifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Etametsulfuron, Etametsulfuron-Methyl, Ethiozin, Ethofumesate, Ethoxyphen, Ethoxyphen-Ethyl, Ethoxysulfuron, Ethobenzanide, F-5231, i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazole-1-yl]phenyl]ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazole-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, phenoxaprop, phenoxaprop-P, phenoxaprop-ethyl, phenoxaprop-P-ethyl, phenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flampprop, flampprop-isoproyl, flampprop-methyl, flampprop-M-isopropyl, flampprop-M-methyl, plazasulfurone, florasulam, Florpyroxifen, Florpyroxifen-Benzyl, Fluazifop, Fluazifop-Butyl, Fluazifop-Methyl, Fluazifop-P, Fluazifop-P-Butyl, Flucarbazone,Flucarbazone-sodium, flucetosulfuron, fluchlorallin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometurone, fluorenol, fluorenol-butyl, -dimethylammonium and -methyl, fluoroglycopene, fluoroglycopene-ethyl, flupropanat, flupropanat-sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridone, fluorochloridone, fluroxipyr, fluroxipyr-butomethyl, fluroxipyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, pomesafen, pomesafen-sodium, poramsulfuron, Foramsulfurone-sodium, fosamin, fosamin-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium and glyphosate-trimethium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl isopropylphosphoramidothioate, halauxifene, Haloxifen-methyl, Halosaphen, Halosulfuron, Halosulfuron-methyl, Haloxifov, Haloxifov-P, Haloxifov-ethoxyethyl, Haloxifov-P-ethoxyethyl, Haloxifov-methyl, Haloxifov-P-methyl, Haloxifov-sodium, Hexazinone, HNPC-A8169, i.e., Prop-2-In-1-yl (2S)-2-{3-[(5-tert-butylpyridine-2-yl)oxy]phenoxy}propanoate, HW-02, i.e., 1-(Dimethoxyphosphoryl)ethyl (2,4-Dichlorophenoxy)acetate, Hydantocidin, Imazametabenz, Imazametabenz-methyl, Imazamox, Imazamox-ammonium, Imazapique, Imazapik-ammonium, Imazapyr, Imazapyr-isopropylammonium, Imazaquin, Imazaquin-ammonium, Imazaquin-methyl, Imazetapyr, Imazetapyr-ammonium, Imazosulfuron, Indanophan, Indaziflam, Iodosulfuron, Iodosulfuron-methyl,Iodosulfuron-methyl-sodium, ionyl, ionyl-lithium, -octanoate, -potassium and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutol, carbutylate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, ketospiradox-potassium, lactofen, renasil, linuron, MCPA, MCPA-butotyl, -butyl, -dimethylammonium, -diolamin, -2-ethylhexyl, -ethyl, -isobutyl, -isoctyl, -isopropyl, -isopropylammonium, -methyl, -olamin, -potassium, -sodium and -trolamin, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-butothyl, mecoprop-dimethylammonium, mecoprop-diolamin, mecoprop-ethexil, mecoprop-ethadyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium, and mecoprop-trolamin, mecoprop-P, mecoprop-P-butothyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluid, mefluid-diolamin, mefluid-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron-sodium, mesotrione, metabenzthiazuron, metam, metamifop, Metamitron, Metazachlor, Metazosulfuron, Metabenzthiazuron, Methiopyrsulfuron, Methiozoline, Methyl Isothiocyanate, Metabromurone, Metolachlor, S-Metolachlor, Methosullam, Methoxuron, Metribuzine, Metsulfuron, Metsulfuron-methyl, Molinate, Monolinuron, Monosulfuron, Monosulfuron-methyl, MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, Napropamide, NC-310, i.e., 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, NC-656, i.e., 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazole-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo-[4,3-a]pyridine-8-carboxamide, Neburon,Nicosulfurone, Nonanoic acid (Pelargonic acid), Norflurazone, Oleic acid (fatty acid), Orbencarb, Orthosulfamurone, Oryzalin, Oxadiargyl, Oxadiazone, Oxasulfurone, Oxaziclomefon, Oxyfluorphen, Paraquat, Paraquat-Dichloride, Paraquat-Dimethylsulfate, Febulate, Pendimethalin, Phenoxulam, Pentachlorophenol, Pentoxazone, Fetoxamide, Petrolum oil, Penmedipham, Penmedipham-Ethyl, Picloram, Picloram-Dimethylammonium, Picloram-Etexil, Picloram-Isocthyl, Picloram-Methyl, Picloram-Olamin, Picloram-Potassium, Picloram-Triethylammonium, Picloram-Tripromin, Picloram-Trolamine, Picolinaphen, Pinoxaden, Piperophos, Pretilachlor, Primyulfuron, Primyulfuron-Methyl, Prodiamine, Propoxydim, Prometone, Promethrin, Propachlor, Propanyl, Propakizapov, Propazine, Propam, Propisochlor, Propoxycarbazone, Propoxycarbazone-Sodium, Propirisulfuron, Propizamide, Prosulfocarb, Prosulfuron, Pyraclonil, Piraflufen, Piraflufen-Ethyl, Pyrasulphotol, Pyrazolinat (Pyrazolat), Pyrazosulfuron, Pyrazosulfuron-Ethyl, Pyrazoxifen, Piribambenz, Piribambenz-Isopropyl, Piribambenz-Propyl, Pyribenzoxime, Pyributicab, Pyridapol, Pyridat, Pyrifthalide, Pyriminobac, Pyriminobac-Methyl, Pirimilupan, Piritiobac, Pyritiobak-sodium, piroxasulfone, piroxulam, quinclolac, quinclolac-dimethylammonium, quinclolac-methyl, quinmerac, quinoclamin, quizalopov, quizalopov-ethyl, quizalopov-P, quizalopov-P-ethyl, quizalopov-P-tefuryl, QYM201, i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazole-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, limsulfuron, safluphenacil, cetoxydim, siduron, simazine, cymetrin, SL-261, sulfotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249, in other words,1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(prop-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazine-6-yl]-3-propyl-2-thioxomidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g., TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebutiurone, tefuryltrione, tembotrone, tefraroxidim, terbasyl, terbucarb, terbumetone, terbutylazine, Terbutrin, Tetflupyrrolimet, Taxtomin, Tenylchlor, Thiazopyr, Tiencarbazone, Tiencarbazone-methyl, Tifensulfuron, Tifensulfuron-methyl, Thiobencarb, Tiafenacil, Torpiralat, Topramesone, Tralcoccidim, Triapamon, Trialate, Triasulfuron, Triaziflam, Trivenuron, Trivenuron-methyl, Triclopyr, Triclopyr-butothyl, Triclopyr-choline, Triclopyr-ethyl, Triclopyr-triethylammonium, Triethazine, Trifloxysulfuron, Trifloxysulfuron-sodium, Trifludimoxazine, Triluralin, Trifloxysulfuron, Trifloxysulfuron-methyl, Tritosulfuron, Ureasulfate, Vernolate, XDE-848, ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidine-2-yl)oxy]benzyl}aniline, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidine-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, ethyl [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}pyridine-2-yl)oxy]acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl 5-chloropyrimidine-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazine-3(, 2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridine-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazole-4-yl)(3,3,4-trimethyl-1,1-deoxydo-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-deoxydo-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazole-5-yl propane-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazole-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazole-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate; Cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, prop-2-in-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indole-6-yl)pyridine-2-carboxylate, methyl 6-(1-acetyl-7-fluoro-1H-indole-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indole-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indole-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate,Sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridine-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazole-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridine-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridine-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazolin-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazolin-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidine-2-yl)pyridazine-1-ium salt (containing a suitable anion, e.g., chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazine-3-yl)pyridazine-1-ium salt (containing a suitable anion, e.g., chloride, acetate, or trifluoroacetate), 4-(pyrimidine-2-yl)-1-(2-sulfoethyl)pyridazine-1-ium salt (containing a suitable anion, e.g., chloride, acetate, or trifluoroacetate), 4-(pyridazine-3-yl)-1-(2-sulfoethyl)pyridazine-1-ium salt (containing a suitable anion, e.g., chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazole-2-yl)pyridazine-1-ium salt (containing suitable anions, e.g., chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3,4-thiadiazole-2-yl)pyridazine-1-ium salt (containing suitable anions, e.g., chloride, acetate, or trifluoroacetate), methyl (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2R / S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)-2-(trifluoromethyl)benzaldehyde O-{2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy]benzoyl} oxime, 2-fluoro-N-(5-methyl-1,3,4-oxadiazole-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid, 2-ethoxy-2-oxoethyl 1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}cyclopropanecarboxylate, 2-methoxy-2-oxoethyl 1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}cyclopropanecarboxylate, {[(1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, methyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylate, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylate.,

[0106] Absic acids and related analogs [e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, methyl (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoate, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, methyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid], acibenzola, acibenzola-S-methyl, S-adenosylhomocysteine, allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g., (isopropylidene)aminooxyacetic acid 2-(methoxy)-2-oxoethyl ester, (isopropylidene)aminooxyacetic acid 2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)aminooxyacetic acid-2-(isopropyloxy)-2-oxoethyl ester], 1-aminocycloprop-1-ylcarboxylic acid, N-methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, DE3335514, EP30287, Substituted 1-aminocyclopropyl-1-carboxylic acid derivatives described in DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxyamic acid, 5-aminolevulinic acid, anthimidol, 6-benzylaminopurine, viquinine, brassinolide, brassinolide-ethyl, L-canaline, catechol, and catechols (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-cromen-3,5,7-triol), chitooligosaccharides (CO; CO differs from LCO in that it lacks the characteristic fatty acid side chains of LCO. In some cases, CO is also constructed from GlcNAc units, but is referred to as N-acetylchitooligosaccharide, but the chitin molecule [(C8H. 13 NO5) n , CAS No. 1398-61-4] and chitosan molecule [(C5H 11 NO4) n, CAS No. 9012-76-4]) having a side chain distinct from), chitin-like compounds, chlormequat chloride, chloroprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropphenylmethanol, daminozide, dazomet, dazomet-sodium, n-decanol, dikegulac, dikegulac-sodium, endotal, endotal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, 1-ethylcyclopropene, flumetralin, fluorenol, Flurenol-butyl, fluorenol-methyl, flurprimidol, forchlorofenurone, giberelic acid, inabenpied, indole-3-acetic acid (IAA), 4-indole-3-ilbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid esters or other derivatives (e.g., methyl jasmonic acid ester, ethyl jasmonic acid ester), lipochitooligosaccharides (in some cases referred to as symbiotic nodule-forming signals (Nod or Nod factor) or Myc factor, β-1,4-linked having N-linked fatty acid side chains fused to the non-reducing end) NIt consists of an oligosaccharide backbone composed of acetyl-D-glucosamine residues ("GlcNAc"). As can be inferred from the literature, LCOs differ in the number of GlcNAc units in the backbone structure, the length and saturation of the fatty acid chains, and the substitution of reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleate hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabsic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinoline-6-yl)methanesulfonamide and related substituted (tetrahydroquinoline-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one and related lactones (described in EP2248421), 2-(1-naphthyl)acetamid, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenoxide mixtures, 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, prohydrozasmon, ryzovitoxin, salicylic acid, and methyl salicylate, sarcosine, sodium cycloprop-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-1-yl)propanoate, sodium 3-(cycloprop-1-en-1-yl)propanoate, sidefungin, spermidine, spermine, strigolactone, technagen, tidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tcitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)- 9H -purine-6-amine.

[0107] Although the compound of the present invention of formula (I) generally has good selectivity for crop plants, it may also be useful to combine it with known emollients.

[0108] A softening agent that can be used in combination with the compound of the present invention of formula (I) and optionally in combination with additional active ingredients such as insecticides, miteicides, herbicides, and fungicides listed above is preferably selected from the group consisting of:

[0109] S1) Compound of chemical formula (S1):

[0110]

[0111] In the expression, the symbol and the exponent are defined as follows:

[0112] n A is a natural number from 0 to 5, preferably from 0 to 3;

[0113] R A 1 is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro, or (C1-C4)-haloalkyl;

[0114]

[0115] W A is an unsubstituted or substituted divalent heterocyclic radical from the group of partially unsaturated or aromatic 5-membered heterocyclic radicals having 1 to 3 ring heteroatoms from the group of N and O, wherein at least one nitrogen atom and at most one oxygen atom are present in the ring, and preferably (W A 1 ) to (W A 5 It is a radical from the group of ), and

[0116] m A is 0 or 1 and;

[0117] R A 2 is OR A 3 , SR A 3or NR A 3 R A 4 or as a saturated or unsaturated 3-membered to 7-membered heterocyclic ring having at least one nitrogen atom and up to three heteroatoms from the group consisting of O and S, connected to the carbonyl group of (S1) through the nitrogen atom, and substituted or unsubstituted by a radical from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy, or optionally substituted phenyl, preferably formula OR A 3 , NHR A 4 or N(CH3)2, particularly the chemical formula OR A 3 It is a radical of;

[0118] R A 3 is hydrogen, or preferably an unsubstituted or substituted aliphatic hydrocarbon radical having a total of 1 to 18 carbon atoms;

[0119] R A 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, or substituted or unsubstituted phenyl;

[0120] R A 5 is H, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, cyano or COOR A 9 and, here R A 9 is hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-hydroxyalkyl, (C3-C 12 )-cycloalkyl or tri-(C1-C4)-alkylsilyl;

[0121] R A 6 , R A 7 , R A8 are the same or different, respectively hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C 12 )-cycloalkyl or substituted or unsubstituted phenyl;

[0122] R A 10 H, (C3-C 12 )-cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl;

[0123] Ideally:

[0124] a) Compound of the type dichlorophenylpyrazolin-3-carboxylic acid (S1 a ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylate (S1-1) ("mefenpyr-diethyl"), and related compounds described in WO-A-91 / 07874;

[0125] b) Derivative of dichlorophenylpyrazole carboxylic acid (S1 b ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4), and related compounds described in EP-A-333 131 and EP-A-269 806;

[0126] c) Derivative of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6), and, for example, related compounds described in EP-A-268554;

[0127] d) Compound of the triazolecarboxylic acid type (S1 d ), preferably compounds such as phenchlorazole (-ethyl ester), i.e., ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7), and related compounds described in EP-A-174 562 and EP-A-346 620;

[0128] e) Compounds of the type 5-benzyl- or 5-phenyl-2-isoxazolin-3-carboxylic acid or 5,5-diphenyl-2-isoxazolin-3-carboxylic acid (S1 e ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazolin-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazolin-3-carboxylate (S1-9) and related compounds described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazolin-3-carboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazolin-3-carboxylate (S1-11) ("isoxadipen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazolin-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazolin-3-carboxylate (S1-13) (patent application Described in WO-A-95 / 07897);

[0129] f) Compound of the type of triazolioxyacetic acid derivative (S1 f), preferably a compound such as methyl {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetate (S1-14) or {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetic acid (S1-15) or methyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetate (S1-16) or {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetic acid (S1-17) or methyl {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetate (S1-18) or {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetic acid (S1-19) (described in patent application WO2021105101).

[0130] S2) Quinoline derivative of chemical formula (S2):

[0131]

[0132] In the expression, the symbol and the exponent are defined as follows:

[0133] R B 1 is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro, or (C1-C4)-haloalkyl;

[0134] n B is a natural number from 0 to 5, preferably from 0 to 3;

[0135] R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4or as a saturated or unsaturated 3-membered to 7-membered heterocyclic ring having at least one nitrogen atom and preferably up to three heteroatoms from the group O and S, attached to the carbonyl group of (S) through the nitrogen atom, substituted or unsubstituted by a radical from the group of (C1-C4)-alkyl, (C1-C4)-alkoxy, or optionally substituted phenyl, preferably formula OR B 3 , NHR B 4 or N(CH3)2, particularly the chemical formula OR B 3 It is a radical of;

[0136] R B 3 It is hydrogen or, preferably, an unsubstituted or substituted aliphatic hydrocarbon radical having a total of 1 to 18 carbon atoms;

[0137] R B 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, or substituted or unsubstituted phenyl;

[0138] T B is a (C1 or C2)-alkanedyl chain, unsubstituted or substituted by one or two (C1-C4)-alkyl radicals or [(C1-C3)-alkoxy]carbonyl groups;

[0139] Ideally:

[0140] a) Compound of the 8-quinolineoxyacetic acid type (S2 a), preferably 1-methylhexyl(5-chloro-8-quinolineoxy)acetate ("chloroquintocet-mesil") (S2-1), 1,3-dimethylbut-1-yl(5-chloro-8-quinolineoxy)acetate (S2-2), 4-allyloxybutyl(5-chloro-8-quinolineoxy)acetate (S2-3), 1-allyloxyprop-2-yl(5-chloro-8-quinolineoxy)acetate (S2-4), ethyl(5-chloro-8-quinolineoxy)acetate (S2-5), methyl(5-chloro-8-quinolineoxy)acetate (S2-6), allyl(5-chloro-8-quinolineoxy)acetate (S2-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolineoxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolineoxy)acetate (S2-9) and related compounds described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, and also (5-chloro-8-quinolineoxy)acetic acid (S2-10), hydrates and salts thereof, e.g., lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof (described in WO-A-2002 / 34048);

[0141] b) Compound of the (5-chloro-8-quinolineoxy)malonic acid type (S2 b ), preferably compounds, such as diethyl (5-chloro-8-quinoline oxy)malonate, diallyl (5-chloro-8-quinoline oxy)malonate, methyl ethyl (5-chloro-8-quinoline oxy)malonate and related compounds described in EP-A-0 582 198.

[0142] S3) Compound of chemical formula (S3):

[0143]

[0144] In the expression, the symbol and the exponent are defined as follows:

[0145] R C 1It is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl;

[0146] R C 2 , R C 3 is the same or different, and each is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-haloalkyl, (C2-C4)-haloalkenyl, (C1-C4)-alkylcarbamoyl-(C1-C4)-alkyl, (C2-C4)-alkenylcarbamoyl-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, dioxolanyl-(C1-C4)-alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R C 2 and R C 3It forms a heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine, or benzoxazine ring, which is substituted or unsubstituted together; Preferably: active ingredients of the dichloroacetamide type are often used as pre-emergence emollients (soil-acting emollients), e.g., "Dichlormide" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidin) (Stauffer) (S3-2), "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidin) (Stauffer) (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(1,3-dioxolane-2-yl)methyl]dichloroacetamide) (PPG Industries) (S3-5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (Sagro-Chem) (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane) (Nitrokemia or Monsanto) (S3-7), "TI-35" (1-dichloroacetylasepan) (TRI-Chemical RT) (S3-8), "Diclonon" (Dicyclonone) or "BAS145138" or "LAB145138" (S3-9) There are ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) (BASF), “furilazole” or “MON 13900” ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-11).

[0147] S4) N-acylsulfonamide of chemical formula (S4) and its salt:

[0148]

[0149] In the expression, the symbol and the exponent are defined as follows:

[0150] X D is CH or N;

[0151] R D 1 CO-NR D 5 R D 6 or NHCO-R D 7 And;

[0152] R D 2 is a halogen, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl;

[0153] R D 3 It is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, or (C2-C4)-alkynyl;

[0154] R D 4 is a halogen, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C3-C6)-cycloalkyl, phenyl, (C1-C4)-alkoxy, cyano, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl, or (C1-C4)-alkylcarbonyl;

[0155] R D 5 3- to 6-membered heterocyclyl v containing hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl, or a heteroatom from the group consisting of nitrogen, oxygen, and sulfur DAnd, the latter seven radicals are halogens, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl and phenyl, and in the case of cyclic radicals, also v from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl. D Substituted by a substituent;

[0156] R D 6 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, or (C2-C6)-alkynyl, and the latter three radicals are v from the group consisting of halogen, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy, and (C1-C4)-alkylthio. D Substituted by radicals, or

[0157] R D 5 and R D 6 It forms pyrrolidinyl or piperidinyl radicals together with nitrogen atoms holding them;

[0158] R D 7 It is hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, and the latter two radicals are halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy, and (C1-C4)-alkylthio, and in the case of cyclic radicals, also v from the group of (C1-C4)-alkyl and (C1-C4)-haloalkyl. D Substituted by a substituent;

[0159] n D is 0, 1, or 2;

[0160] m D is 1 or 2 and;

[0161] v D is 0, 1, 2, or 3;

[0162] Among these, a preferred compound is of the N-acylsulfonamide type, for example, the following chemical formula (S4 a It is a compound of ), and is known, for example, in WO-A-97 / 45016:

[0163]

[0164] In the equation,

[0165] R D 7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, and the latter two radicals are halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy, and (C1-C4)-alkylthio, and in the case of cyclic radicals, also v from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl. D Substituted by a substituent;

[0166] R D 4 is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;

[0167] m D is 1 or 2 and;

[0168] v D is 0, 1, 2, or 3;

[0169] Also, for example, acylsulfamoylbenzamide, for example, known in WO-A-99 / 16744, the following chemical formula (S4 b A compound of ) is preferred:

[0170]

[0171] for example,

[0172] R D 5 = cyclopropyl and (R D 4 ) = 2-OMe ("ciprosulfamide", S4-1) and,

[0173] R D 5 = cyclopropyl and (R D 4) = 5-Cl-2-OMe (S4-2) and,

[0174] R D 5 = ethyl and, (R D 4 ) = 2-OMe (S4-3) and,

[0175] R D 5 = isopropyl, and (R D 4 ) = 5-Cl-2-OMe (S4-4) and,

[0176] R D 5 = isopropyl, and (R D 4 ) = 2-OMe (S4-5) ,

[0177] Also, for example, the chemical formula (S4 as disclosed in EP-A-365484). c A compound of the N-acylsulfamoylphenylurea type of ) is preferred:

[0178]

[0179] In the equation,

[0180] R D 8 and R D 9 is independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, and

[0181] R D 4 is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3, and

[0182] m D is 1 or 2;

[0183] for example,

[0184] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

[0185] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0186] It is 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea.

[0187] S5) Active ingredients of the class of hydroxyaromatic and aromatic-aliphatic carboxylic acid derivatives (S5), e.g., ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid (described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001).

[0188] S6) Active ingredient of the 1,2-dihydroquinoxalin-2-one class (S6), e.g.,

[0189] 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thion, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one (described in WO-A-2005 / 112630).

[0190] S7) A compound of the chemical formula (S7) as described in WO-A-1998 / 38856,

[0191]

[0192] In the expression, the symbol and the exponent are defined as follows:

[0193] R E 1 , R E 2 is independently a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, nitro;

[0194] A E is COOR E 3 or COSR E4 Igo

[0195] R E 3 , R E 4 Each is independently hydrogen, (C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl, (C1-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl, and alkylammonium, and

[0196] n E 1 is 0 or 1, and

[0197] n E 2 , n E 3 is independently 0, 1, or 2, and

[0198] Preferably, it is diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS reg. no. 41858-19-9) (S7-1).

[0199] S8) A compound of formula (S8) as described in WO-A-98 / 27049 or a salt thereof:

[0200]

[0201] In the equation,

[0202] X F is CH or N,

[0203] n F is X F In the case of = N, it is an integer from 0 to 4, and

[0204] X F In the case of = CH, it is an integer from 0 to 5, and

[0205] R F 1is a halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, and

[0206] R F 2 is hydrogen or (C1-C4)-alkyl, and

[0207] R F 3 The radical is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, and each of the above-mentioned carbon-containing radicals is substituted or unsubstituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogens and alkoxy;

[0208] Desirably

[0209] X F is CH and,

[0210] n F is 0 to 2, and

[0211] R F 1 is a halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, and

[0212] R F 2 is hydrogen or (C1-C4)-alkyl, and

[0213] R F 3 It is a compound or a salt thereof in which the radical is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, and each of the above-mentioned carbon-containing radicals is substituted or unsubstituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogens and alkoxy.

[0214] S9) Active ingredient of the 3-(5-tetrazolylcarbonyl)-2-quinolone class (S9), e.g.,

[0215] 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS reg. no. 95855-00-8) (described in WO-A-1999 / 000020).

[0216] S10) Chemical formula as described in WO-A-2007 / 023719 and WO-A-2007 / 023764 (S10 a ) or (S10 b Compound of )

[0217]

[0218] In the equation,

[0219] R G 1 It is a halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3, and

[0220] Y G , Z G is independently O or S, and

[0221] n G is an integer from 0 to 4, and

[0222] R G 2 is (C1-C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl; benzyl, halobenzyl, and

[0223] R G 3 It is hydrogen or (C1-C6)-alkyl.

[0224] S11) Active ingredients (S11) of the class of oxyimino compounds known as seed-dressing compositions, e.g., "oxabetrinil" ((Z)-1,3-dioxolalan-2-yl-methoxyimino(phenyl)acetonitrile) known as a seed-dressing emollient for millet / sorghum damage caused by metolachlor (S11-1), "bloxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolalan-2-ylmethyl)oxime) known as a seed-dressing emollient for millet damage caused by metolachlor (S11-2), and "ciometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) known as a seed-dressing emollient for millet / sorghum damage caused by metolachlor (S11-3).

[0225] 12) Active ingredients of the isothiochromatone class (S12), e.g., methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS reg. no. 205121-04-6) (S12-1) and related compounds of WO-A-1998 / 13361.

[0226] S13) One or more compounds from the following group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) known as a seed-dressing alleviator for corn damage caused by thiocarbamate preparations (S13-1), "Penchlorim" (4,6-dichloro-2-phenylpyrimidine) known as an alleviator for pretilachlor in sowing rice (S13-2), "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) known as a seed-dressing alleviator for millet damage caused by alachlor and metolachlor (S13-3), "CL 304415" (CAS reg. no. 31541-57-8) known as an alleviator for corn damage caused by imidazolinone (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) (American Cyanamid), "MG 191" (CAS reg. no. 96420-72-3), known as a corn laxative, (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) (Nitrokemia), "MG-838" (CAS reg. no. 133993-74-5) (2-propenyl 1-oxa-4-azspiro[4.5]decane-4-carbodithioate) (S13-6) (Nitrokemia), "Disulfon" (O,O-diethyl S-2-ethylthioethyl phosphodithioate) (S13-7), "Dietolate" (O,O-diethyl O-phenylphosphorothioate) (S13-8), "mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

[0227] S14) An active ingredient having, in addition to herbicidal action against harmful plants, also emphysemaphoretic action against crop plants such as rice, e.g., “dimepiperate” or “MY-93”, known as an emphysemaphore for rice damage caused by the herbicide molynate ( S-1-methyl 1-phenylethylpiperidine-1-carbothioate), "Dimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), known as a mitigator for rice damage caused by the herbicide imazosulfuron; "Cumiluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, known as a mitigator for rice damage caused by some herbicides, see JP-A-60087254); "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), known as a mitigator for rice damage caused by some herbicides; "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene), known as a mitigator for rice damage caused by some herbicides (Kumiai, (CAS reg. no. 54091-06-4).

[0228] S15) A compound of formula (S15) or a tautomer thereof as described in WO-A-2008 / 131861 and WO-A-2008 / 131860:

[0229]

[0230] In the equation,

[0231] R H 1 It is a (C1-C6)-haloalkyl radical, and

[0232] R H 2 is hydrogen or a halogen, and

[0233] R H 3 , R H 4 is independently hydrogen, (C1-C 16 )-alkyl, (C2-C 16 )-alkenyl or (C2-C 16As )-alkynyl, each of the latter three radicals is unsubstituted or halogen, hydroxy, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6))-cycloalkyl, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclyl, or (C3-C6)cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl fused to a 4- to 6-membered saturated or unsaturated carbon-cyclic ring on one side of the ring, or 4-membered to A 6-membered saturated or unsaturated carbon-cyclic ring fused to one or more radicals from the group (C4-C6)-cycloalkenyl, wherein each of the latter four radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclyl,

[0234] or

[0235] R H 3 is a (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkenyloxy, or (C2-C4)-haloalkoxy, and

[0236] R H 4 is hydrogen or (C1-C4)-alkyl, or

[0237] R together with directly attached nitrogen atoms H 3 and R H 4It is a tetanical to octanical heterocyclic ring, and in addition to the nitrogen atom, it may also contain additional ring heteroatoms from the group consisting of N, O and S, preferably two additional ring heteroatoms, and is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, and (C1-C4)-alkylthio.

[0238] S16) Active ingredients that are primarily used as herbicides but also have emphysulogenic action on crop plants, e.g., (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).

[0239] Particularly desirable laxatives are mefenpyr-diethyl, ciprosulfamide, isoxadifen-ethyl, cloquintocet-mesil, benoxacor, dichlormide, and metcamifene.

[0240] The following examples illustrate the present invention.

[0241] A. Chemical Examples

[0242] Synthesis of methyl 2-chloro-4-(difluoromethoxy)-3-formylbenzoate (2):

[0243] Step 1: Preparation of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10):

[0244] 10 g (47.35 mmol) of commercially available methyl 2-chloro-4-hydroxy-3-methylbenzoate (9) was added in part to a solution of 19.93 g of potassium hydroxide in 75 mL of acetonitrile and 75 mL of water at 0°C. Then, 17.52 mL (94.71 mmol) of diethyl [bromo(difluoro)methyl]phosphonate was added and the mixture was stirred at 0°C for 1 hour. After the addition of ethyl acetate, the organic layer was separated, dried, and concentrated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→85 / 15). 9.80 g (82%) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10) was obtained.

[0245] 1 H-NMR (400 MHz, DMSO-d6): δ = 7.71 (d, 1H); 7.33 (t, 1H); 7.27 (d, 1H); 3.86 (s, 3H); 2.31 (s, 3H).

[0246] Step 2: Preparation of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (11):

[0247] 20.65 (82.39 mmol) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (10) was dissolved in 200 ml of chlorobenzene, and 29.33 g (164.79 mmol) of N-bromosuccinimide and 1.35 g (8.24 mmol) of AIBN were added. The reaction mixture was stirred at 120°C for 8 hours. It was then concentrated, the residue was dissolved in water, and extracted with dichloromethane. The organic layer was separated, dried, and concentrated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). 26.47 g (97%) of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (11) was obtained.

[0248] 1H-NMR (400 MHz, DMSO-d6): δ = 7.89 (d, 1H); 7.48 (t, 1H); 7.36 (d, 1H); 4.73 (s, 2H); 3.88 (s, 3H).

[0249] Step 3: Preparation of methyl 2-chloro-4-(difluoromethoxy)-3-formylbenzoate (2):

[0250] 6.36 g (54 mmol) of N-methylmorpholine N-oxide was partially added to an initial charge of 5.96 g (18 mmol) of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (11) in 200 mL of acetonitrile at 10°C. After the exothermic reaction subsided, the reaction mixture was stirred at room temperature for 12 hours. The mixture was then concentrated, the residue dissolved in water, and repeatedly extracted with ethyl acetate. The organic layer was blended, dried, and concentrated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). 4.33 g (90%) of methyl 2-chloro-4-(difluoromethoxy)-3-formylbenzoate (1) was obtained. 1 H-NMR (400 MHz, DMSO-d6): δ = 10.34 (s, 1H); 8.06 (d, 1H); 7.44 (d, 1H); 7.39 (t, 1H); 3.89 (s, 3H).

[0251] Examples of preparation of compounds (II) and (I) of the present invention:

[0252] Preparation of 2-chloro-3-(cyclopropylcarbonyl)-N-(1-methyl-1H-tetrazole-5-yl)-4-(trifluoromethoxy)benzamide (1-25):

[0253] Step 1: ( R , S Preparation of )-methyl 2-chloro-3-[cyclopropyl(hydroxy)methyl]-4-(trifluoromethoxy)benzoate:

[0254] 1.00 g (3.53 mmol) of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1) formed an initial packing in 30 mL of anhydrous tetrahydrofuran under argon shielding gas. A 0.5 M solution of cyclopropyl magnesium bromide in 8.49 mL (4.24 mmol) of tetrahydrofuran was subsequently added dropwise at -60°C, and the reaction mixture was stirred at -60°C for 1 hour and then at room temperature for 1 hour. The mixture was then poured into 2 M hydrochloric acid and extracted with dichloromethane. The organic layer was separated, dried, and concentrated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). 1.01 g (84%) of ( R , S )-methyl 2-chloro-3-[cyclopropyl(hydroxy)methyl]-4-(trifluoromethoxy)benzoate was obtained.

[0255] 1 H-NMR (400 MHz, DMSO-d6): δ = 7.74 (d, 1H); 7.46 (br d, 1H); 5.58 (d, 1H); 4.47 (m, 1H); 3.87 (s, 3H); 1.48 (m, 1H); 0.60 (m, 1H); 0.48 (m, 1H); 0.37 (m, 1H); 0.18 (m, 1H).

[0256] Step 2: Preparation of methyl 2-chloro-3-(cyclopropylcarbonyl)-4-(trifluoromethoxy)benzoate (3-25): 1.01 g (3.11 mmol) of ( R , STo the initial charge of )-methyl 2-chloro-3-[cyclopropyl(hydroxy)methyl]-4-(trifluoromethoxy)benzoate, a 2.5 M solution of chromium(VI) oxide (1.5 mL, 3.73 mmol) in a 3:1 mixture of water and sulfuric acid was slowly added dropwise. The reaction mixture was then stirred at room temperature for 12 hours. After adding isopropanol to remove excess oxidizing agent, the reaction mixture was concentrated. The residue was dissolved in water and extracted with ethyl acetate, and the organic layer was separated, dried, and concentrated. The residue was purified by chromatography (HPLC, normal phase, heptane / ethyl acetate 100 / 0→60 / 40). 0.95 g (90%) of methyl 2-chloro-3-(cyclopropylcarbonyl)-4-(trifluoromethoxy)benzoate (3-25) was obtained.

[0257] Step 3: Preparation of 2-chloro-3-(cyclopropylcarbonyl)-4-(trifluoromethoxy)benzoic acid (4-25):

[0258] 2.2 mL (4.39 mmol) of 2 M sodium hydroxide solution was added to an initial charge of 946 mg (2.93 mmol) of methyl 2-chloro-3-(cyclopropylcarbonyl)-4-(trifluoromethoxy)benzoate (3-25) in 50 mL of methanol at room temperature. The reaction mixture was stirred at room temperature for 12 hours and then concentrated. The residue was dissolved in water, and the aqueous layer was adjusted to pH 1 using 2 M hydrochloric acid. The organic layer was separated, dried, and concentrated. 805 mg (85%) of 2-chloro-3-(cyclopropylcarbonyl)-4-(trifluoromethoxy)benzoic acid (4-25) was obtained.

[0259] Step 4: Preparation of 2-chloro-3-(cyclopropylcarbonyl)-N-(1-methyl-1H-tetrazole-5-yl)-4-(trifluoromethoxy)benzamide (1-25): 0.09 mL (0.97 mmol) of oxalyl chloride was added dropwise to an initial charge of 200 mg (0.64 mmol) of 2-chloro-3-(cyclopropylcarbonyl)-4-(trifluoromethoxy)benzoic acid (4-25) and 98.3 mg (0.97 mmol) of 5-amino-1-methyl-1H-tetrazole in 3 mL of pyridine at room temperature. The reaction mixture was stirred at room temperature for 12 hours. After adding 10 mL of water, the mixture was stirred for an additional 10 minutes and then extracted with dichloromethane. The organic layer was separated, dried, and concentrated. The residue was purified by chromatography (HPLC, C18, concentration gradient: acetonitrile / water (+0.05% trifluoroacetic acid) 10 / 90→100 / 0). 156 mg (59%) of 2-chloro-3-(cyclopropylcarbonyl)-N-(1-methyl-1H-tetrazole-5-yl)-4-(trifluoromethoxy)benzamide (1-25) was obtained.

[0260] The examples listed in the table below may be prepared or obtained in a manner similar to the method mentioned above. These compounds are particularly preferred.

[0261] The abbreviations used have the following meanings:

[0262] Me = methyl Et = Ethyl Pr = Profile Bu = Butyl i-Pr = isopropyl

[0263] c-Pr = cyclopropyl i-Bu = Isobutyl s-Bu = sec-butyl

[0264] Table 1: R x A compound of the present invention of formula (I), wherein α is a methyl group and the remaining substituents have the definitions provided below.

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271] Table 2: R x A compound of the present invention of formula (I), wherein α is an ethyl group and the remaining substituents have the definitions provided below.

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278] Table 3: Compound of the present invention of formula (II), wherein L is methoxy and the remaining substituents have the definitions provided below.

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285] Table 4: Compound of the present invention of formula (II) in which L is a hydroxyl group and the remaining substituents have the definitions provided below.

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292] Table 5: Compound of the present invention of formula (II), in which L is chlorine and the remaining substituents have the definitions provided below.

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] NMR data for the compounds of the present invention of formulas (I) and (II) mentioned in the table above are disclosed below for further characterization:

[0300] Example No. 1-1: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.68 (br s, 1H); 7.84 (d, 1H); 7.50 (d, 1H); 3.99 (s, 3H); 2.54 (s, 3H); 2.32 (s, 3H);

[0301] Example No. 1-2: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.68 (br s, 1H); 7.84 (d, 1H); 7.49 (br d, 1H); 3.99 (s, 3H); 2.82 (q, 2H); 2.28 (s, 3H); 1.11 (t, 3H);

[0302] Example Nos. 1-5: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.69 (br s, 1H); 7.85 (d, 1H); 7.51 (br d, 1H); 3.99 (s, 3H); 2.34 (s, 3H); 2.33 (m, 1H); 1.18 (m, 4H);

[0303] Example No. 1-11: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 7.86 (d, 1H); 7.51 (br d, 1H); 3.99 (s, 3H); 2.67 (q, 2H); 2.56 (s, 3H); 1.13 (t, 3H);

[0304] Example No. 1-12: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 7.86 (d, 1H); 7.51 (br d, 1H); 3.99 (s, 3H); 2.83 (q, 2H); 2.63 (q, 2H); 1.12 (t, 6H);

[0305] Example No. 1-21: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H), 7.99 (d, 1H); 7.71 (d, 1H); 4.00 (s, 3H); 2.59 (s, 3H);

[0306] Example No. 1-22: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 7.99 (d, 1H); 7.71 (d, 1H); 4.00 (s, 3H); 2.87 (q, 2H); 1.13 (t, 3H);

[0307] Example No. 1-23: 1H-NMR (400 MHz, DMSO-d6): δ = 11.92 (br s, 1H); 7.98 (d, 1H); 7.70 (d, 1H); 4.00 (s, 3H); 2.84 (t, 2H); 1.67 (m, 2H); 0.95 (t, 3H);

[0308] Example No. 1-24: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.91 (br s, 1H); 7.99 (d, 1H); 7.70 (d, 1H); 4.00 (s, 3H); 3.06 (m, 1H); 1.16 (d, 6H);

[0309] Example No. 1-25: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.93 (br s, 1H); 7.99 (d, 1H); 7.71 (d, 1H); 4.01 (s, 3H); 2.37 (m, 1H); 1.24 (m, 2H); 1.19 (m, 2H);

[0310] Example No. 1-41: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.60 (br s, 1H); 7.78 (d, 1H); 7.40 (t, 1H); 7.30 (d, 1H); 3.98 (s, 3H); 2.29 (s, 3H);

[0311] Example No. 1-42: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.60 (br s, 1H); 7.78 (d, 1H); 7.39 (t, 1H); 7.29 (d, 1H); 3.98 (s, 3H); 2.79 (q, 2H); 2.25 (s, 3H); 1.09 (t, 3H);

[0312] Example No. 1-45: 1H-NMR (400 MHz, DMSO-d6): δ = 11.60 (br s, 1H); 7.79 (d, 1H); 7.38 (t, 1H); 7.30 (d, 1H); 3.98 (s, 3H); 2.30 (s, 3H); 2.29 (m, 1H); 1.13 (m, 4H);

[0313] Example No. 1-51: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.63 (br s, 1H); 7.80 (d, 1H); 7.41 (t, 1H); 7.31 (d, 1H); 3.98 (s, 3H); 2.65 (q, 2H); 2.52 (s, 3H); 1.12 (t, 3H);

[0314] Example No. 1-52: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.63 (br s, 1H); 7.80 (d, 1H); 7.40 (t, 1H); 7.30 (d, 1H); 3.98 (s, 3H); 2.80 (q, 2H); 2.61 (q, 2H); 1.10 (t, 6H);

[0315] Example No. 1-55: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.64 (br s, 1H); 7.80 (d, 1H); 7.38 (t, 1H); 7.31 (d, 1H); 3.99 (s, 3H); 2.68 (q, 2H); 2.31 (m, 1H); 1.13 (m, 7H);

[0316] Example No. 1-61: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.91 (d, 1H); 7.48 (d, 1H); 7.44 (t, 1H); 3.99 (s, 3H); 2.54 (s, 3H);

[0317] Example No. 1-62: 1H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.91 (d, 1H); 7.48 (d, 1H); 7.43 (t, 1H); 3.99 (s, 3H); 2.83 (q, 2H); 1.11 (t, 3H);

[0318] Example No. 1-63: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.90 (d, 1H); 7.47 (d, 1H); 7.43 (t, 1H); 3.98 (s, 3H); 2.80 (t, 2H); 1.66 (m, 2H); 0.95 (t, 3H);

[0319] Example No. 1-64: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.91 (d, 1H); 7.47 (d, 1H); 7.46 (t, 1H); 3.99 (s, 3H); 3.04 (m, 1H); 1.15 (d, 6H);

[0320] Example No. 1-65: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.86 (br s, 1H); 7.91 (d, 1H); 7.48 (d, 1H); 7.43 (t, 1H); 4.00 (s, 3H); 2.32 (m, 1H); 1.17 (m, 4H);

[0321] Example No. 1-103: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.85 (br s, 1H); 7.90 (d, 1H); 7.47 (d, 1H); 7.44 (t, 1H); 3.99 (s, 3H); 2.73 (d, 2H); 2.20 (m, 1H); 0.97 (d, 6H);

[0322] Example No. 1-109: 1H-NMR (400 MHz, DMSO-d6): δ = 11.65 (br s, 1H); 7.75 (d, 1H); 7.51 (d, 1H); 4.03 (s, 3H); 2.60 (s, 3H); 2.23 (m, 1H); 0.91 (m, 2H); 0.52 (m, 2H);

[0323] Example No. 1-110: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.64 (br s, 1H); 7.74 (d, 1H); 7.51 (d, 1H); 4.02 (s, 3H); 2.90 (q, 2H); 2.20 (m, 1H); 1.14 (t, 3H); 0.88 (m, 2H); 0.50 (m, 2H);

[0324] Example No. 1-111: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.65 (br s, 1H); 7.75 (d, 1H); 7.52 (d, 1H); 4.03 (s, 3H); 2.41 (m, 1H); 2.22 (m, 1H); 1.18 (m, 4H); 0.91 (m, 2H); 0.55 (m, 2H);

[0325] Example No. 1-112: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.56 (br s, 1H); 7.67 (d, 1H); 7.34 (t, 1H); 7.31 (d, 1H); 4.02 (s, 3H); 2.55 (s, 3H); 2.19 (m, 1H); 0.88 (m, 2H); 0.49 (m, 2H);

[0326] Example No. 1-113: 1H-NMR (400 MHz, DMSO-d6): δ = 11.57 (br s, 1H); 7.67 (d, 1H); 7.33 (t, 1H); 7.31 (d, 1H); 4.02 (s, 3H); 2.87 (q, 2H); 2.16 (m, 1H); 1.13 (t, 3H); 0.85 (m, 2H); 0.48 (m, 2H);

[0327] Example No. 1-114: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.57 (br s, 1H); 7.68 (d, 1H); 7.32 (t, 1H); 7.32 (d, 1H); 4.02 (s, 3H); 2.37 (m, 1H); 2.18 (m, 1H); 1.15 (m, 4H); 0.88 (m, 2H); 0.52 (m, 2H);

[0328] Example No. 1-115: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 7.82 (d, 1H); 7.36 (d, 1H); 6.41 (tt, 1H); 4.54 (td, 2H); 3.98 (s, 3H); 2.49 (s, 3H);

[0329] Example No. 1-116: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.72 (br s, 1H); 7.82 (d, 1H); 7.35 (d, 1H); 6.39 (tt, 1H); 4.52 (td, 2H); 3.98 (s, 3H); 2.77 (q, 2H); 1.09 (t, 3H);

[0330] Example No. 1-117: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.73 (br s, 1H); 7.82 (d, 1H); 7.35 (d, 1H); 6.37 (tt, 1H); 4.52 (td, 2H); 3.98 (s, 3H); 2.25 (, 1H); 1.09 (m, 4H);

[0331] Example No. 2-1: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.57 (br s, 1H); 7.83 (d, 1H); 7.50 (br d, 1H); 4.34 (q, 2H); 2.55 (s, 3H); 2.32 (s, 3H); 1.46 (t, 3H);

[0332] Example No. 2-2: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.57 (br s, 1H); 7.83 (d, 1H); 7.49 (br d, 1H); 4.34 (q, 2H); 2.82 (q, 2H); 2.28 (s, 3H); 1.46 (t, 3H); 1.11 (t, 3H);

[0333] Example No. 2-5: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.58 (br s, 1H); 7.84 (d, 1H); 7.51 (br d, 1H); 4.34 (q, 2H); 2.34 (s, 3H); 2.33 (m, 1H); 1.47 (t, 3H); 1.17 (m, 4H);

[0334] Example No. 2-11: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.61 (br s, 1H); 7.85 (d, 1H); 7.51 (br d, 1H); 4.34 (q, 2H); 2.67 (q, 2H); 2.56 (s, 3H); 1.47 (t, 3H); 1.13 (t, 3H);

[0335] Example No. 2-21: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.98 (d, 1H); 7.71 (d, 1H); 4.36 (q, 2H); 2.59 (s, 3H); 1.47 (t, 3H);

[0336] Example No. 2-22: 1H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.98 (d, 1H); 7.70 (d, 1H); 4.36 (q, 2H); 2.87 (q, 2H); 1.46 (t, 3H); 1.13 (t, 3H);

[0337] Example No. 2-23: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.82 (br s, 1H); 7.98 (d, 1H); 7.70 (d, 1H); 4.36 (q, 2H); 2.85 (t, 2H); 1.68 (m, 2H); 1.47 (t, 3H); 0.96 (t, 3H);

[0338] Example No. 2-25: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.83 (br s, 1H); 7.99 (d, 1H); 7.71 (d, 1H); 4.36 (q, 2H); 2.38 (m, 1H); 1.47 (t, 3H); 1.23 (m, 2H); 1.19 (m, 2H);

[0339] Example No. 2-41: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.49 (br s, 1H); 7.77 (d, 1H); 7.40 (t, 1H); 7.30 (d, 1H); 4.33 (q, 2H); 2.28 (s, 3H); 1.46 (t, 3H);

[0340] Example No. 2-42: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.49 (br s, 1H); 7.77 (d, 1H); 7.39 (t, 1H); 7.29 (d, 1H); 4.32 (q, 2H); 2.79 (q, 2H); 2.25 (s, 3H); 1.46 (t, 3H); 1.09 (t, 3H);

[0341] Example No. 2-45: 1H-NMR (400 MHz, DMSO-d6): δ = 11.50 (br s, 1H); 7.78 (d, 1H); 7.38 (t, 1H); 7.31 (d, 1H); 4.33 (q, 2H); 3.32 (s, 3H); 2.30 (s, 3H); 2.29 (m, 1H); 1.46 (t, 3H); 1.13 (m, 4H);

[0342] Example No. 2-51: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.52 (br s, 1H); 7.78 (d, 1H); 7.41 (t, 1H); 7.31 (d, 1H); 4.33 (q, 2H); 2.65 (q, 2H); 1.47 (t, 3H); 1.12 (t, 3H);

[0343] Example No. 2-52: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.52 (br s, 1H); 7.79 (d, 1H); 7.40 (t, 1H); 7.30 (d, 1H); 4.33 (q, 2H); 2.80 (q, 2H); 2.61 (q, 2H); 1.47 (t, 3H); 1.10 (t, 6H);

[0344] Example No. 2-55: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.54 (br s, 1H); 7.79 (d, 1H); 7.38 (t, 1H); 7.32 (d, 1H); 4.34 (q, 2H); 2.67 (q, 2H); 2.31 (m, 1H); 1.47 (t, 3H); 1.12 (m, 7H);

[0345] Example No. 2-61: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.75 (br s, 1H); 7.91 (d, 1H); 7.48 (d, 1H); 7.44 (t, 1H); 4.35 (q, 2H); 2.54 (s, 3H); 1.46 (t, 3H);

[0346] Example No. 2-62: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.75 (br s, 1H); 7.90 (d, 1H); 7.48 (d, 1H); 7.43 (t, 1H); 4.35 (q, 2H); 2.82 (q, 2H); 1.46 (t, 3H); 1.11 (t, 3H);

[0347] Example No. 2-65: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.76 (br s, 1H); 7.90 (d, 1H); 7.48 (d, 1H); 7.43 (t, 1H); 4.36 (q, 2H); 2.31 (m, 1H); 1.47 (t, 3H); 1.17 (m, 4H);

[0348] Example No. 2-103: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.75 (br d, 1H); 7.90 (d, 1H); 7.47 (d, 1H); 7.44 (t, 1H); 4.35 (q, 2H); 2.73 (d, 2H); 2.20 (m, 1H); 1.46 (t, 3H); 0.98 (d, 6H);

[0349] Example No. 2-109: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.53 (br s, 1H); 7.74 (d, 1H); 7.51 (d, 1H); 4.37 (q, 2H); 2.60 (s, 3H); 2.23 (m, 1H); 1.48 (t, 3H); 0.91 (m, 2H); 0.53 (m, 2H);

[0350] Example No. 2-110: 1H-NMR (400 MHz, DMSO-d6): δ = 11.52 (br s, 1H); 7.74 (d, 1H); 7.51 (d, 1H); 4.37 (q, 2H); 2.90 (q, 2H); 2.20 (m, 1H); 1.48 (t, 3H); 1.14 (t, 3H); 0.88 (m, 2H); 0.51 (m, 2H);

[0351] Example No. 2-111: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.53 (br s, 1H); 7.75 (d, 1H); 7.52 (d, 1H); 4.37 (q, 2H); 2.41 (m, 1H); 2.21 (m, 1H); 1.49 (t, 3H); 1.19 (m, 4H); 0.90 (m, 2H); 0.56 (m, 2H);

[0352] Example No. 2-112: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.44 (br s, 1H); 7.67 (d, 1H); 7.34 (t, 1H); 7.31 (d, 1H); 4.36 (q, 2H); 2.56 (s, 3H); 2.18 (m, 1H); 1.48 (t, 3H); 0.88 (m, 2H); 0.50 (m, 2H);

[0353] Example No. 2-113: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.45 (br s, 1H); 7.66 (d, 1H); 7.33 (t, 1H); 7.31 (d, 1H); 4.36 (q, 2H); 2.87 (q, 2H); 2.16 (m, 1H); 1.48 (t, 3H); 1.13 (t, 3H); 0.85 (m, 2H); 0.48 (m, 2H);

[0354] Example No. 2-114: 1H-NMR (400 MHz, DMSO-d6): δ = 11.45 (br s, 1H); 7.67 (d, 1H); 7.32 (t, 1H); 7.32 (d, 1H); 4.36 (q, 2H); 2.37 (m, 1H); 2.17 (m, 1H); 1.49 (t, 3H); 1.15 (m, 4H); 0.88 (m, 2H); 0.52 (m, 2H);

[0355] Example No. 2-115: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.62 (br s, 1H); 7.81 (d, 1H); 7.36 (d, 1H); 6.41 (tt, 1H); 4.54 (td, 2H); 4.33 (q, 2H); 2.50 (s, 3H); 1.46 (t, 3H);

[0356] Example No. 2-116: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.62 (br s, 1H); 7.81 (d, 1H); 7.35 (d, 1H); 6.39 (tt, 1H); 4.52 (td, 2H); 4.33 (q, 2H); 2.77 (q, q, 2H); 1.46 (t, 3H); 1.09 (t, 3H);

[0357] Example No. 2-117: 1 H-NMR (400 MHz, DMSO-d6): δ = 11.62 (br s, 1H); 7.81 (d, 1H); 7.35 (d, 1H); 6.37 (tt, 1H); 4.52 (td, 2H); 4.34 (q, 2H); 2.24 (m, 1H); 1.46 (t, 3H); 1.10 (m, 4H);

[0358] Example No. 3-1: 1 H-NMR (400 MHz, CDCl3): δ = 7.92 (d, 1H); 7.18 (d, 1H); 3.91 (s, 3H); 2.52 (s, 3H); 2.48 (s, 3H);

[0359] Example No. 3-2:1 H-NMR (400 MHz, DMSO-d6): δ = 7.94 (d, 1H); 7.43 (br d, 1H); 3.86 (s, 3H); 2.79 (q, 2H); 2.34 (s, 3H); 1.09 (t, 3H);

[0360] Example No. 3-5: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.96 (d, 1H); 7.45 (br d, 1H); 3.86 (s, 3H); 2.40 (s, 3H); 3.32 (m, 1H); 1.16 (m, 4H);

[0361] Example No. 3-11: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.94 (d, 1H); 7.45 (br d, 1H); 3.86 (s, 3H); 2.74 (q, 2H); 2.53 (s, 3H); 1.09 (t, 3H);

[0362] Example No. 3-12: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.94 (d, 1H); 7.44 (br d, 1H); 3.86 (s, 3H); 2.80 (q, 2H); 2.70 (q, 2H); 1.10 (t, 3H); 1.08 (t, 3H);

[0363] Example No. 3-15: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.94 (d, 1H); 7.46 (br d, 1H); 3.87 (s, 3H); 2.79 (q, 2H); 2.33 (m, 1H); 1.17 (m, 4H); 1.11 (t, 3H);

[0364] Example No. 3-21: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.02 (d, 1H); 7.64 (d, 1H); 3.90 (s, 3H); 2.56 (s, 3H);

[0365] Example No. 3-22:1 H-NMR (400 MHz, CDCl3): δ = 7.90 (d, 1H); 7.28 (d, 1H); 3.95 (s, 3H); 2.81 (q, 2H); 1.23 (t, 3H);

[0366] Example No. 3-23: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.02 (d, 1H); 7.64 (br d, 1H); 3.89 (s, 3H); 2.82 (t, 2H); 1.65 (m, 2H); 0.94 (t, 3H);

[0367] Example No. 3-24: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.04 (d, 1H); 7.64 (br d, 1H); 3.90 (s, 3H); 3.04 (m, 1H); 1.14 (d, 6H);

[0368] Example No. 3-25: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.03 (d, 1H); 7.65 (d, 1H); 3.90 (s, 3H); 2.38 (m, 1H); 1.21 (m, 2H); 1.17 (m, 2H);

[0369] Example No. 3-41: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.90 (d, 1H); 7.39 (t, 1H); 7.24 (d, 1H); 3.84 (s, 3H); 2.35 (s, 3H);

[0370] Example No. 3-42: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.91 (d, 1H); 7.38 (t, 1H); 7.24 (d, 1H); 3.83 (s, 3H); 2.76 (q, 2H); 2.31 (s, 3H); 1.08 (t, 3H);

[0371] Example No. 3-45: 1H-NMR (400 MHz, DMSO-d6): δ = 7.92 (d, 1H); 7.37 (t, 1H); 7.25 (d, 1H); 3.84 (s, 3H); 2.37 (s, 3H); 2.28 (m, 1H); 1.11 (m, 4H);

[0372] Example No. 3-51: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.90 (d, 1H); 7.40 (t, 1H); 7.25 / d, 1H); 3.84 (s, 3H); 2.73 (q, 2H); 1.09 (t, 3H);

[0373] Example No. 3-52: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.91 (d, 1H); 7.39 (t, 1H); 7.24 (d, 1H); 3.84 (s, 3H); 2.78 (q, 2H); 2.69 (q, 2H); 1.08 (t, 3H); 1.07 (t, 3H);

[0374] Example No. 3-55: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.91 (d, 1H); 7.38 (t, 1H); 7.26 (d, 1H); 3.85 (s, 3H); 2.77 (q, 2H); 2.30 (m, 1H); 1.12 (m, 4H); 1.09 (t, 3H);

[0375] Example No. 3-61: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.98 (d, 1H); 7.43 (t, 1H); 7.43 (d, 1H); 3.87 (s, 3H); 2.52 (s, 3H);

[0376] Example No. 3-62: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.98 (d, 1H); 7.42 (d, 1H); 7.42 (t, 1H); 3.87 (s, 3H); 2.80 (q, 2H); 1.10 (t, 3H);

[0377] Example No. 3-63: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.97 (d, 1H); 7.43 (d, 1H); 7.42 (t, 1H); 3.87 (s, 3H); 2.78 (t, 2H); 1.64 (m, 2H); 0.94 (t, 3H);

[0378] Example No. 3-64: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.98 (d, 1H); 7.45 (t, 1H); 7.42 (d, 1H); 3.87 (s, 3H); 3.01 (m, 1H); 1.14 (d, 6H);

[0379] Example No. 3-65: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.97 (d, 1H); 7.43 (d, 1H); 7.42 (t, 1H); 3.88 (s, 3H); 2.31 (m, 1H); 1.17 (m, 2H); 1.13 (m, 2H);

[0380] Example No. 3-103: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.97 (d, 1H); 7.43 (t, 1H); 7.41 (d, 1H); 3.87 (s, 3H); 2.70 (d, 2H); 2.19 (m, 1H); 0.96 (d, 6H);

[0381] Example No. 3-107: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.07 (d, 1H); 7.50 (d, 1H); 7.49 (t, 1H); 5.41 (1H); 3.88 (s, 3H);

[0382] Example No. 3-108: 1 H-NMR (400 MHz, DMSO-d6): δ = 8.02 (d, 1H); 7.45 (d, 1H); 7.45 (t, 1H); 3.88 (s, 3H); 2.16 (s, 3H);

[0383] Example No. 3-109: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.72 (d, 1H); 7.45 (br d, 1H); 3.88 (s, 3H); 2.58 (s, 3H); 2.16 (m, 1H); 0.89 (m, 2H); 0.39 (m, 2H);

[0384] Example No. 3-110: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.72 (d, 1H); 7.44 (br d, 1H); 3.88 (s, 3H); 2.89 (q, 2H); 2.14 (m, 1H); 1.12 (t, 3H); 0.86 (m, 2H); 0.36 (m, 2H);

[0385] Example No. 3-111: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.73 (d, 1H); 7.46 (br d, 1H); 3.88 (s, 3H); 2.42 (m, 1H); 2.12 (m, 1H); 1.16 (m, 4H); 0.88 (m, 2H); 0.40 (m, 2H);

[0386] Example No. 3-112: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.66 (d, 1H); 7.32 (t, 1H); 7.25 (d, 1H); 3.85 (s, 3H); 2.53 (s, 3H); 2.10 (m, 1H); 0.86 (m, 2H); 0.35 (m, 2H);

[0387] Example No. 3-113: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.66 (d, 1H); 7.31 (t, 1H); 7.24 (d, 1H); 3.85 (s, 3H); 2.85 (br q, 2H); 2.10 (m, 1H); 1.11 (br t, 3H); 0.83 (m, 2H); 0.33 (m, 2H);

[0388] Example No. 3-114: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.67 (d, 1H); 7.30 (t, 1H); 7.26 (d, 1H); 3.85 (s, 3H); 2.37 (m, 1H); 2.08 (m, 1H); 1.13 (m, 4H); 0.86 (m, 2H); 0.38 (m, 2H);

[0389] Example No. 3-115: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.92 (d, 1H); 7.31 (d, 1H); 6.39 (tt, 1H); 4.52 (td, 2H); 3.84 (s, 3H); 2.46 (s, 3H);

[0390] Example No. 3-116: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.92 (d, 1H); 7.30 (d, 1H); 6.37 (tt, 1H); 4.50 (td, 2H); 3.84 (s, 3H); 2.74 (q, 2H); 1.07 (t, 3H);

[0391] Example No. 3-117: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.92 (d, 1H); 7.30 (d, 1H); 6.36 (tt, 1H); 4.50 (td, 2H); 3.84 (s, 3H); 2.23 (m, 1H); 1.08 (m, 4H);

[0392] Example No. 4-1: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.34 (br s, 1H); 7.94 (d, 1H); 7.40 (d, 1H); 2.50 (s, 3H); 2.39 (s, 3H);

[0393] Example No. 4-2: 1H-NMR (400 MHz, DMSO-d6): δ = 13.33 (br s, 1H); 7.94 (d, 1H); 7.40 (br d, 1H); 2.79 (q, 2H); 2.35 (s, 3H); 1.09 (t, 3H);

[0394] Example Nos. 4-5: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.34 (br s, 1H); 7.95 (d, 1H); 7.41 (br d, 1H); 2.42 (s, 3H); 2.32 (m, 1H); 1.15 (m, 4H);

[0395] Example No. 4-11: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.39 (br s, 1H); 7.93 (d, 1H); 7.41 (br d, 1H); 2.78 (q, 2H); 2.53 (s, 3H); 1.10 (t, 3H);

[0396] Example No. 4-12: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.93 (d, 1H); 7.40 (br d, 1H); 2.80 (q, 2H); 2.74 (q, 2H); 1.10 (t, 3H); 1.09 (t, 3H);

[0397] Example No. 4-21: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.86 (br s, 1H); 7.99 (d, 1H); 7.60 (d, 1H); 2.56 (s, 3H);

[0398] Example No. 4-22: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.86 (br s, 1H); 7.99 (d, 1H); 7.59 (d, 1H); 2.83 (q, 2H); 1.11 (t, 3H);

[0399] Example No. 4-23: 1H-NMR (400 MHz, DMSO-d6): δ = 13.86 (br s, 1H); 7.99 (d, 1H); 7.59 (bd, 1H); 2.81 (t, 2H); 1.65 (m, 2H); 0.94 (t, 3H);

[0400] Example No. 4-24: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.90 (br s, 1H); 8.00 (d, 1H); 7.60 (br d, 1H); 3.03 (m, 1H); 1.14 (d, 6H);

[0401] Example No. 4-25: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.85 (br s, 1H); 7.99 (d, 1H); 7.61 (d, 1H); 2.37 (m, 1H); 1.23-1.14 (m, 4H);

[0402] Example No. 4-41: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.21 (br s, 1H); 7.90 (d, 1H); 7.37 (t, 1H); 7.21 (d, 1H); 2.48 (s, 3H); 2.36 (s, 3H);

[0403] Example No. 4-42: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.11 (br s, 1H); 7.90 (d, 1H); 7.36 (t, 1H); 7.20 (d, 1H); 2.76 (q, 2H); 2.33 (s, 3H); 1.08 (t, 3H);

[0404] Example No. 4-45: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.11 (br s, 1H); 7.92 (d, 1H); 7.35 (t, 1H); 7.21 (d, 1H); 2.38 (s, 3H); 2.27 (m, 1H); 1.10 (m, 4H);

[0405] Example No. 4-51: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.15 (br s, 1H); 7.90 (d, 1H); 7.38 (t, 1H); 7.21 (d, 1H); 2.77 (q, 2H); 2.49 (s, 3H); 1.09 (t, 3H);

[0406] Example No. 4-52: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.13 (br s, 1H); 7.91 (d, 1H); 7.37 (t, 1H); 7.21 (d, 1H); 2.77 (m, 4H); 1.08 (m, 6H);

[0407] Example No. 4-55: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.14 (br s, 1H); 7.91 (d, 1H); 7.36 (t, 1H); 7.22 (d, 1H); 2.81 (q, 2H); 2.29 (m, 1H); 1.11 (m, 4H); 1.09 (t, 3H);

[0408] Example No. 4-61: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.63 (br s, 1H); 7.95 (d, 1H); 7.41 (t, 1H); 7.39 (d, 1H); 2.53 (s, 3H);

[0409] Example No. 4-62: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.63 (br s, 1H); 7.95 (d, 1H); 7.40 (t, 1H); 7.38 (d, 1H); 2.79 (q, 2H); 1.09 (t, 3H); Example No. 4-63: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.62 (br d, 1H); 7.95 (d, 1H); 7.40 (t, 1H); 7.38 (d, 1H); 2.77 (t, 2H); 1.64 (m, 2H); 0.94 (t, 3H);

[0410] Example No. 4-64: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.65 (br s, 1H); 7.95 (d, 1H); 7.43 (t, 1H); 7.38 (d, 1H); 3.01 (m, 1H); 1.13 (d, 6H);

[0411] Example No. 4-65: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.62 (br s, 1H); 7.95 (d, 1H); 7.40 (t, 1H); 7.39 (d, 1H); 2.30 (m, 1H); 1.19-1.09 (m, 4H);

[0412] Example No. 4-103: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.94 (d, 1H); 7.41 (t, 1H); 7.37 (d, 1H); 2.70 (d, 2H); 2.19 (m, 1H); 0.96 (d, 6H);

[0413] Example No. 4-109: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.30 (br s, 1H); 7.70 (d, 1H); 7.41 (d, 1); 2.59 (s, 3H); 2.16 (m, 1H); 0.89 (m, 2H); 0.43 (m, 2H);

[0414] Example No. 4-110: 1 H-NMR (400 MHz, DMSO-d6): δ = 7.67 (d, 1H); 7.39 (br d, 1H); 2.88 (q, 2H); 2.14 (m, 1H); 1.12 (t, 3H); 0.85 (m, 2H); 0.41 (m, 2H);

[0415] Example No. 4-111: 1H-NMR (400 MHz, DMSO-d6): δ = 13.29 (br s, 1H); 7.71 (d, 1H); 7.42 (br d, 1H); 2.40 (m, 1H); 2.11 (m, 1H); 1.15 (m, 4H); 0.88 (m, 2H); 0.46 (m, 2H);

[0416] Example No. 4-112: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.12 (br s, 1H); 7.64 (d, 1H); 7.29 (t, 1H); 7.21 (d, 1H); 2.49 (s, 3H); 2.11 (m, 1H); 0.86 (m, 2H); 0.40 (m, 2H);

[0417] Example No. 4-113: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.11 (br s, 1H); 7.64 (d, 1H); 7.28 (t, 1H); 7.21 (d, 1H); 2.85 (q, 2H); 2.11 (m, 1H); 1.10 (t, 3H); 0.83 (m, 2H); 0.38 (m, 2H);

[0418] Example No. 4-114: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.10 (br s, 1H); 7.65 (d, 1H); 7.27 (t, 1H); 7.22 (d, 1H); 2.36 (m, 1H); 2.09 (m, 1H); 1.12 (m, 4H); 0.86 (m, 2H); 0.41 (m, 2H);

[0419] Example No. 4-115: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.30 (br s, 1H); 7.90 (d, 1H); 7.27 (d, 1H); 6.39 (tt, 1H); 4.50 (td, 2H); 2.46 (s, 3H);

[0420] Example No. 4-116: 1H-NMR (400 MHz, DMSO-d6): δ = 13.30 (br s, 1H); 7.90 (d, 1H); 7.27 (d, 1H); 6.37 (tt, 1H); 4.49 (td, 2H); 2.74 (q, 2H); 1.07 (t, 3H);

[0421] Example No. 4-117: 1 H-NMR (400 MHz, DMSO-d6): δ = 13.29 (br s, 1H); 7.90 (d, 1H); 7.27 (d, 1H); 6.35 (tt, 1H); 4.48 (td, 2H); 2.22 (m, 1H); 1.07 (m, 4H).

[0422] B. Formulation Examples

[0423] a) The spray product is obtained by mixing 10 parts by weight of the compound of formula (I) and / or its salt and 90 parts by weight of talc as an inert substance and crushing the mixture with a hammer mill.

[0424] b) An easily water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of formula (I) and / or a salt thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pin-disk mill.

[0425] c) An easily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of the compound of formula (I) and / or its salt 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 (e.g., boiling range of about 255 to 277°C or higher), and grinding the mixture to a fineness of less than 5 microns in a friction ball mill.

[0426] d) An emulsifying concentrate is obtained from 15 parts by weight of the compound of formula (I) and / or its salt, 75 parts by weight of cyclohexanone as a solvent, and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.

[0427] e) Water-dispersible granules are

[0428] 75 parts by weight of a compound of formula (I) and / or a salt thereof,

[0429] 10 parts by weight of calcium lignosulfonate,

[0430] 5 parts by weight of sodium lauryl sulfate,

[0431] 3 parts by weight of polyvinyl alcohol, and

[0432] Mix 7 parts by weight of kaolin, and

[0433] The mixture is ground in a pin-disk mill and the powder is obtained by granulating it in a fluidized bed by spraying water as a granulating liquid.

[0434] f) Water-dispersible granules are also in colloid mills,

[0435] 25 parts by weight of a compound of formula (I) and / or a salt thereof,

[0436] 5 parts by weight of sodium 2,2'-dinapthylmethane-6,6'-disulfonate

[0437] 2 parts by weight of sodium oleoylmethyltaurate,

[0438] 1 part by weight of polyvinyl alcohol,

[0439] 17 parts by weight of calcium carbonate, and

[0440] After homogenizing and pre-crushing 50 parts by weight of water,

[0441] The mixture is ground in a bead mill, and the final suspension is obtained by finely grinding and drying it in a spray tower through one-phase furnaces.

[0442] C. Biological Examples

[0443] The abbreviations used in this specification mean the following:

[0444] ABUTH Abutilon theophrasti

[0445] ALOMY Alopecurus myosuroides

[0446] AVEFA Avena fatua

[0447] AMARE Amaranthus retroflexus

[0448] CYPES Cyperus esculentus

[0449] DIGSA Digitalia sangunalis

[0450] ECHCG Echinochloa crus-galli

[0451] HORMU Hordeum murinum

[0452] KCHSC Kochia scoparia

[0453] LOLMU Lolium multiflorum

[0454] LOLRI Lolium rigidum

[0455] MATIN Matricaria inodora

[0456] PHBPU Pharbitis purpurea

[0457] POLCO Polygonum convolvulus

[0458] SETVI Setaria viridis

[0459] STEME Stellaria Media

[0460] VERPE Veronica Persica

[0461] VIOTR Viola tricolor

[0462] 1. Pre-emergence herbicidal action against harmful plants

[0463] Seeds of monocotyledonous and dicotyledonous weeds and crops are placed in sandy loam pots within wood fiber pots and covered with soil. Compounds of the present invention, formulated in the form of a wetting powder (WP) or an emulsion concentrate (EC), are applied to the covered soil surface as an aqueous suspension or emulsion at a water application rate of 600 to 800 l / ha while adding 0.2% wetting agent. After treatment, the pots are placed in a greenhouse and maintained under favorable growth conditions for the test plants. Damage to the test plants is visually assessed after a test period of 3 weeks compared to an untreated control group (herbicidal effect (%): 100% effect = plant death, 0% effect = similar to control plants). Many compounds of the present invention have shown very favorable action against numerous important harmful plants. The following table illustrates the herbicidal effect of the compounds of the present invention after budding in an exemplary manner, and the herbicidal effect is expressed in percentages.

[0464] Table C-1: Pre-emergence effect (%) of ZEAMX at 20 g / ha

[0465]

[0466] Table C-2: Pre-emergence effect (%) of ZEAMX at 80 g / ha

[0467]

[0468] Table C-3: Pre-emergence effect (%) of TRZAS at 20 g / ha

[0469]

[0470] Table C-4: Pre-emergence effect (%) of TRZAS at 80 g / ha

[0471]

[0472] Table C-5: Pre-emergence effect (%) of GLXMA at 20 g / ha

[0473]

[0474] Table C-6: Pre-emergence effect (%) of ABUTH at 20 g / ha

[0475]

[0476] Table C-7: Pre-emergence effect (%) of ABUTH at 80 g / ha

[0477]

[0478] Table C-8: Pre-emergence effect (%) of ALOMY at 20 g / ha

[0479]

[0480] Table C-9: Pre-emergence effect (%) of ALOMY at 80 g / ha

[0481]

[0482] Table C-10: Pre-emergence effect (%) at 20 g / ha for AMARE

[0483]

[0484] Table C-11: Pre-emergence effect (%) at 80 g / ha for AMARE

[0485]

[0486] Table C-12: Pre-emergence effect (%) of DIGSA at 20 g / ha

[0487]

[0488] Table C-13: Pre-emergence effect (%) of DIGSA at 80 g / ha

[0489]

[0490] Table C-14: Pre-emergence effect (%) of ECHCG at 20 g / ha

[0491]

[0492] Table C-15: Pre-emergence effect (%) of ECHCG at 80 g / ha

[0493]

[0494] Table C-16: Pre-emergence effect (%) of LOLRI at 20 g / ha

[0495]

[0496] Table C-17: Pre-emergence effect (%) of LOLRI at 80 g / ha

[0497]

[0498] Table C-18: Pre-emergence effect (%) of MATIN at 20 g / ha

[0499]

[0500] Table C-19: Pre-emergence effect (%) of MATIN at 80 g / ha

[0501]

[0502] Table C-20: Pre-emergence effect (%) of PHBPU at 80 g / ha

[0503]

[0504] Table C-21: Pre-emergence effect (%) of POLCO at 20 g / ha

[0505]

[0506] Table C-22: Pre-emergence effect (%) of POLCO at 80 g / ha

[0507]

[0508] Table C-23: Pre-emergence effect (%) of SETVI at 20 g / ha

[0509]

[0510] Table C-24: Pre-emergence effect (%) of SETVI at 80 g / ha

[0511]

[0512] Table C-25: Pre-emergence effect (%) of VERPE at 20 g / ha

[0513]

[0514] Table C-26: Pre-emergence effect (%) of VERPE at 80 g / ha

[0515]

[0516] Table C-27: Pre-emergence effect (%) of VIOTR at 20 g / ha

[0517]

[0518] Table C-28: Pre-emergence effect (%) of VIOTR at 80 g / ha

[0519]

[0520] Table C-29: Pre-emergence effect (%) at 20 g / ha on KCHSC

[0521]

[0522] Table C-30: Pre-emergence effect (%) at 80 g / ha on KCHSC

[0523]

[0524] 2. Post-emergence herbicidal action against harmful plants

[0525] Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam soil in wood-fiber pots, covered with soil, and grown in a greenhouse under favorable growth conditions. Two to three weeks after sowing, test plants were treated at the one-leaf stage. Compounds of the present invention, formulated as wettable powders (WP) or emulsion concentrates (EC), were sprayed onto the green parts of the plants in the form of aqueous suspensions or emulsions at water application rates of 600 to 800 l / ha while adding a 0.2% wetting agent. After allowing the test plants to stand in a greenhouse under optimal growth conditions for about three weeks, the action of the formulations was visually evaluated by comparing them to an untreated control group (herbicidal effect (%): 100% effect = plant death, 0% effect = similar to control plants). Many compounds of the present invention showed very favorable action against numerous important harmful plants. The following table illustrates the herbicidal effect of the compound of the present invention after budding in an exemplary manner, and the herbicidal effect is described in percentages.

[0526] Table C-31: Post-budding effect (%) of ZEAMX at 20 g / ha

[0527]

[0528] Table C-32: Post-emergence effect (%) on TRZAS at 20 g / ha

[0529]

[0530] Table C-33: Post-emergence effect (%) of TRZAS at 80 g / ha

[0531]

[0532] Table C-34: Post-budding effect (%) of ABUTH at 20 g / ha

[0533]

[0534] Table C-35: Post-budding effect (%) of ABUTH at 80 g / ha

[0535]

[0536] Table C-36: Post-budding effect (%) at 20 g / ha on ALOMY

[0537]

[0538] Table C-37: Post-emergence effect (%) on ALOMY at 80 g / ha

[0539]

[0540] Table C-38: Post-emergence effect (%) on AMARE at 20 g / ha

[0541]

[0542] Table C-39: Post-emergence effect (%) on AMARE at 80 g / ha

[0543]

[0544] Table C-40: Post-emergence effect (%) of DIGSA at 20 g / ha

[0545]

[0546] Table C-41: Post-emergence effect (%) of DIGSA at 80 g / ha

[0547]

[0548] Table C-42: Post-budding effect (%) of LOLRI at 20 g / ha

[0549]

[0550] Table C-43: Post-budding effect (%) of LOLRI at 80 g / ha

[0551]

[0552] Table C-44: Post-budding effect (%) of MATIN at 20 g / ha

[0553]

[0554] Table C-45: Post-budding effect (%) of MATIN at 80 g / ha

[0555]

[0556] Table C-46: Post-budding effect (%) of PHBPU at 20 g / ha

[0557]

[0558] Table C-47: Post-budding effect (%) of PHBPU at 80 g / ha

[0559]

[0560] Table C-48: Post-budding effect (%) of POLCO at 80 g / ha

[0561]

[0562] Table C-49: Post-budding effect (%) of SETVI at 20 g / ha

[0563]

[0564] Table C-50: Post-budding effect (%) of SETVI at 80 g / ha

[0565]

[0566] Table C-51: Post-budding effect (%) of VERPE at 20 g / ha

[0567]

[0568] Table C-52: Post-budding effect (%) of VERPE at 80 g / ha

[0569]

[0570] Table C-53: Post-budding effect (%) of VIOTR at 20 g / ha

[0571]

[0572] Table C-54: Post-budding effect (%) of VIOTR at 80 g / ha

[0573]

[0574] Table C-55: Post-budding effect (%) at 20 g / ha on KCHSC

[0575]

[0576] Table C-56: Post-budding effect (%) at 80 g / ha on KCHSC

[0577]

[0578] 3. Comparative Experiment

[0579] In the following experiments, the herbicidal activity of many compounds of the present invention and structurally similar compounds known in WO2012 / 28579 and WO2019 / 25540 was compared under the conditions specified above through pre-emergence and post-emergence methods. The example numbers provided in the table relate to the compounds of the present invention of this application, and each comparative compound is disclosed in the cited literature but not specifically mentioned (Compounds V-1 to V-6) and is identified by their IUPAC names below:

[0580] V-1: 3-acetyl-2-chloro-4-methoxy-N-(1-methyl-1H-tetrazole-5-yl)benzamide

[0581] V-2: 2-chloro-4-methoxy-N-(1-methyl-1H-tetrazole-5-yl)-3-propionylbenzamide

[0582] V-3: 2-chloro-3-(cyclopropylcarbonyl)-4-methoxy-N-(1-methyl-1H-tetrazole-5-yl)benzamide

[0583] V-4: 3-acetyl-2-chloro-N-(1-ethyl-1H-tetrazole-5-yl)-4-methoxybenzamide

[0584] V-5: 2-chloro-N-(1-ethyl-1H-tetrazole-5-yl)-4-methoxy-3-propionylbenzamide

[0585] V-6: 2-chloro-3-(cyclopropylcarbonyl)-N-(1-ethyl-1H-tetrazole-5-yl)-4-methoxybenzamide

[0586] Pre-emergence weed control effect:

[0587] inv. = According to the present invention

[0588]

[0589]

[0590]

[0591]

[0592]

[0593]

[0594]

[0595]

[0596]

[0597]

[0598]

[0599]

[0600]

[0601]

[0602]

[0603]

[0604]

[0605]

[0606]

[0607]

[0608]

[0609]

[0610] Weed control effect after germination:

[0611] inv. = Compound of the present application according to the present invention

[0612]

[0613]

[0614]

[0615]

[0616]

[0617]

[0618]

[0619]

[0620]

[0621]

[0622]

Claims

Claim 1 3-acylbenzamide of the following chemical formula (I) or a salt thereof: (In the formula, the symbol and the exponent are defined as follows: R x is (C1-C6)-alkyl, X is a halogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl, Y is a halo-(C1-C6)-alkoxy, Z is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl, and (C3-C6)-cycloalkyl is R 1 It is substituted with a radical, and R 1 is a halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C1-C6)-alkyl-O, and m is 0, 1, 2 or 3). Claim 2 In paragraph 1, the symbol is 3-acylbenzamide or its salt:R, which is defined as follows. x is (C1-C6)-alkyl, X is a halogen, (C1-C6)-alkyl, or (C3-C6)-cycloalkyl, Y is OCF3, OCHF2, OCH2CHF2, or OCF2Me, Z is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, or (C3-C6)-cycloalkyl-(C1-C6)-alkyl, and (C3-C6)-cycloalkyl is R 1 Substituted with a radical, and R 1 is a halogen, (C1-C6)-alkyl or halo-(C1-C6)-alkyl, and m is 0, 1, or 2. Claim 3 In paragraph 1, the symbol is 3-acylbenzamide or its salt:R, which is defined as follows. x is Me, Et, X is chlorine, bromine, methyl, ethyl, or cyclopropyl, Y is OCF3, OCHF2, or OCH2CHF2, and Z is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, vinyl, allyl, ethinyl, prop-1-in-1-yl, methoxymethyl, chloromethyl, cyclopropylmethyl, 1-methylcyclopropyl, or difluoromethyl. Claim 4 A herbicide composition comprising at least one 3-acylbenzamide according to any one of claims 1 to 3 mixed with a formulation adjuvant. Claim 5 A herbicide composition according to claim 4, comprising at least one additional insecticidal active substance from the group of insecticides, miteicides, herbicides, fungicides, emphysicators, and growth regulators. Claim 6 A control method for unwanted plants, characterized by applying an effective amount of 3-acylbenzamide according to at least one of claims 1 to 3 or a herbicide composition according to claim 4 or 5 to the site of unwanted plants or to the plants. Claim 7 Use of 3-acylbenzamide of formula (I) according to any one of claims 1 to 3 or a herbicide composition according to claim 4 or 5 for the control of unwanted plants. Claim 8 In claim 7, 3-acylbenzamide of formula (I) is used for controlling unwanted plants among crops of useful plants. Claim 9 In paragraph 8, the use is characterized in that the useful plant is a genetically modified useful plant. Claim 10 Compound of the following chemical formula (II): (In the formula, the symbol and exponent are defined as follows: L is a halogen or R 2 O is O, X is a halogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl, Y is halo-(C1-C6)-alkoxy, Z is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl or (C3-C6)-cycloalkyl-(C1-C6)-alkyl, and (C3-C6)-cycloalkyl is R 1 Substituted with a radical, and R 1 is a halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C1-C6)-alkyl-O, and R 2 is hydrogen or (C1-C6)-alkyl). Claim 11 A compound of formula (II), wherein L is chlorine, methoxy or hydroxyl, X is chlorine, bromine, methyl, ethyl or cyclopropyl, Y is OCF3, OCHF2 or OCH2CHF2, and Z is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, vinyl, allyl, ethinyl, prop-1-in-1-yl, methoxymethyl, chloromethyl, cyclopropylmethyl, 1-methylcyclopropyl or difluoromethyl.

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