N-(1,3,4-Oxadiazol-2-yl)phenylcarboxamides as Herbicides

Abstract

The present invention relates to benzoic acid amides as herbicides represented by the general formula (I), in which X, R and Z represent groups such as alkyl and halogen. [Formula 1] TIFF2024525526000085.tif28155

Description

[Technical field]

[0001] The present invention relates to the technical field of herbicides, in particular to the technical field of herbicides for selectively controlling broadleaf weeds and grass weeds in useful plants. [Background technology]

[0002] Among the subjects described in WO2012 / 126932A1, WO2017 / 144402A1 and WO2018 / 177871A1 are herbicidal benzamides bearing an optionally substituted 1,3,4-oxadiazole on the nitrogen atom of the amide group. WO2021094505A1 describes herbicidal benzamides bearing a haloalkoxy group at the 4-position of the phenyl ring, and a substituted 1,3,4-oxadiazole is one of the substituents on the nitrogen atom of the amide group. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] WO2012 / 126932A1 [Patent Document 2] WO2017 / 144402A1 [Patent Document 3] WO2018 / 177871A1 [Patent Document 4] WO2021094505A1 Summary of the Invention [Problem to be solved by the invention]

[0004] However, the benzamides known from these documents do not always have sufficient herbicidal activity and / or compatibility with crop plants. [Means for solving the problem]

[0005] In benzamide, having an unsubstituted 1,3,4-oxadiazole on the nitrogen atom of the amide group; having a haloalkoxy group at the 4-position of the phenyl ring; and · The 5- and 6-positions of the phenyl ring are unsubstituted; It has been found that said benzamides have superior properties to those known from the prior art.

[0006] Thus, the present invention relates to a compound of formula (I) [ka] wherein the symbols and indices are defined as follows: X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl or (C1-C6)-alkyl-(O). n S; Z is halo-(C1-C6)-alkoxy; R is (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C3-C6)-cycloalkyl; n is 0, 1 or 2. or a salt thereof.

[0007] In formula (I) and all the following formulae, the alkyl radicals having 3 or more carbon atoms can be linear or branched. The alkyl radicals are, for example, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, t-butyl or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, the alkenyl radicals are, 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. The alkynyl radicals are, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl and the like. The multiple bond can be present in any position of the respective unsaturated radical. Cycloalkyl is a carbocyclic saturated ring system having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Alkyl substituted with halogen means linear or branched alkyl groups in which some or all of the hydrogen atoms can be replaced by halogen atoms, such as C1-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.

[0008] Halogen represents fluorine, chlorine, bromine or iodine.

[0009] Heterocyclic radicals (heterocyclyl) are 5- or 6-membered ring radicals containing, in addition to carbon atoms, at least one heteroatom selected from the group N, O, S, where the ring radical may be saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, in which case the attachment site is on a ring atom. Examples of heterocyclic radicals are: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrol-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3 ,6-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-1- or 2- or 3- or 4-yl; 2,3-dihydropyridine-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-pyra 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2- or 3- or 4-oxepanyl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophene-2- or 3-yl; tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl;3,6-Dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl;2H-thiopyran-2- or 3- or 4- or 5- or 6-yl;4H-thiopyran-2- or 3- or 4-yl;1- or 2- or 3- or 4-pyrazolidinyl;4,5-Dihydro-3H-pyrazol-3- or 4- or 5-yl;4,5-Dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl;2,3-Dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl;1- or 2- or 3- or 4-imidazolidinyl;2,3-Di Hydro-1H-imidazol-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazin-1- or 3 - or 4- or 5- or 6-yl;3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl;4,5-dihydropyridazin-3- or 4-yl;3,4-dihydropyridazin-3- or 4- or 5- or 6-yl;3,6-dihydropyridazin-3- or 4-yl;1,6-dihydropyridazin-1- or 3- or 4- or 5- or 6-yl;hexahydropyrimidin-1- or 2- or 3- or 4-yl;1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1,2,5,6-tetrahydropyrimidin 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl;1,2,3,6-Tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl;1,2,3,4-Tetrahydropyrazine-1- or 2- or 3- or 4- or 5- or 6-yl;1,2-Dihydropyrazine-1- or 2- or 3- or 5- or 6-yl;1,4-Dihydropyrazine-1- or 2- or 3-yl;2,3-Dihydropyrazine-2- or 3- or 5- or 6-yl;2,5-Dihydropyrazine-2- or 3-yl;1,3-Dioxolane-2- or 4- or 5-yl;1,3-Dioxol-2- or 4-yl;1,3-Di oxan-2- or 4- or 5-yl;4H-1,3-dioxin-2- or 4- or 5- or 6-yl;1,4-dioxan-2- or 3- or 5- or 6-yl;2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl;1,4-dioxin-2- or 3-yl;1,2-dithiolan-3- or 4-yl;3H-1,2-dithiol-3- or 4- or 5-yl;1,3-dithiolan-2- or 4-yl;1,3-dithiol-2- or 4-yl;1,2-dithian-3- or 4-yl;3,4-dihydro-1,2-dithi 3,6-dihydro-1,2-dithiin-3- or 4-yl;1,2-dithiin-3- or 4-yl;1,3-dithiane-2- or 4- or 5-yl;4H-1,3-dithiin-2- or 4- or 5- or 6-yl;isoxazolidine-2- or 3- or 4- or 5-yl;2,3-dihydroisoxazol-2- or 3- or 4- or 5-yl;2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl;4,5-dihydroisoxazol-3- or 4- or 5-yl;1,3- oxazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,3-oxazin-2- or 4- or 5- or 6-yl;5,6-dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl;2H-1,3-oxazin-2- or 4- or 5- or 6-yl;6H-1,3-oxazin-2- or 4- or 5- or 6-yl;4H-1,3-oxazin-2- or 4- or 5- or 6-yl;morpholin-2- or 3- or 4-yl;3,4-dihydro -2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl;2H-1,4-oxazin-2- or 3- or 5- or 6-yl;4H-1,4-oxazin-2- or 3-yl;isothiazolidine-2- or 3- or 4- or 5-yl;2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl;2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl;4,5-dihydroisothiazol-3- or 4- or 5-yl 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 1,3-thiazinane-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 6H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4,2-dioxazolidin-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl.;

[0010] Depending on the type of substituents and their bonding, the compounds of general formula (I) may exist as stereoisomers. For example, when one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers may exist. Stereoisomers may also exist when n is 1 (sulfoxide). Stereoisomers may be obtained by conventional separation methods from the mixtures obtained in the preparation, for example by chromatographic separation processes. It is also possible to selectively prepare stereoisomers by using stereoselective reactions using optically active starting materials and / or auxiliaries. The present invention also relates to all stereoisomers and mixtures thereof that are encompassed by general formula (I) but not specifically defined.

[0011] The compounds of formula (I) can form salts. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and also ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and hydrogen carbonates, in particular sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate. These salts are also available from compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example salts of the formula [NRRR'R''R'''] + wherein R to R''' are each independently an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also useful are alkylsulfonium salts and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium salts and (C1-C4)-trialkylsulfoxonium salts. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Preferred are compounds of general formula (I) in which the symbols and indices have the following meanings: X is halogen, (C1-C6)-alkyl, CF3, (C1-C6)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl or (C1-C6)-alkylthio; Z is halo-(C1-C6)-alkoxy; R is (C1-C6)-alkyl or cyclopropyl; n is 0, 1 or 2. It is a compound represented by the formula:

[0013] Particularly preferred are compounds of the general formula (I) in which the symbols and indices have the following meanings: X is halogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl or (C1-C6)-alkylthio; Z is halo-(C1-C2)-alkoxy; R is (C1-C6)-alkyl n is 0, 1 or 2. It is a compound represented by the formula:

[0014] Very particular preference is given to compounds of the general formula (I) in which the symbols and indices are defined as follows: X is F, Cl, Br, Me, Et, MeO, EtO, MeOCH2 or MeS; Z is HFCO or FCO; R is Me or Et; n is 0, 1 or 2. It is a compound represented by the formula:

[0015] The compounds of the present invention can be prepared, for example, by the methods specified in WO2012 / 126932A1, WO2017 / 144402A1, WO2018 / 177871A1 and WO2021094505A1. The corresponding benzoyl chlorides, benzoic acid esters or their parent benzoic acids are known in principle and can be prepared, for example, by the methods described in WO2021094505A1. The methods of preparation of the compounds of the present invention are further illustrated by the examples described below.

[0016] The work-up of the respective reaction mixtures is generally carried out by known methods, for example by crystallization, aqueous-extractive work-up, by chromatographic methods or by a combination of these methods.

[0017] The collection of compounds of formula (I) and / or their salts that can be synthesized by the above reactions can also be prepared in parallel, which can be carried out manually, partially automated or fully automated. For example, it is possible to automate the carrying out of the reactions, work-up or purification of the products and / or intermediates. Generally, this is understood to mean, for example, the method described by D. Tiebes in "Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999", pages 1-34.

[0018] The compounds of the present invention represented by formula (I) (and / or salts thereof) (hereinafter collectively referred to as "compounds of the present invention") exhibit excellent herbicidal activity against a wide range of economically important monocotyledonous and dicotyledonous annual harmful plants.

[0019] The present invention therefore also provides a method for controlling undesirable plants or regulating plant growth, preferably in crop plants, in which one or more compounds according to the invention are applied to the plant (e.g., a harmful plant, such as a monocotyledonous or dicotyledonous weed, or an undesirable crop plant) or to a seed (e.g., a grain, a seed, or a vegetative propagation organ, such as a tuber or a shoot part having a bud) or to an area in which the plant is growing (e.g., an arable land). The compounds of the present invention can be used, for example, before planting (and, if appropriate, by incorporation into the soil), before emergence or after emergence. Specific examples of some representative monocotyledonous and dicotyledonous weed floras that can be controlled by the compounds of the present invention are as follows, but such listing is not intended to be limited to a particular species.

[0020] Monocotyledonous harmful plants of the following genera:: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, The genera Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.

[0021] Dicotyledonous weeds of the following genera:: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirrus sium), Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium dium), Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, and Rotala), Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica,Viola, Xanthium.

[0022] When the compounds of this invention are applied pre-emergence to the soil surface, emergence of weed seedlings is either completely prevented or the weeds grow until they reach the cotyledon stage and then cease growth.

[0023] If the active ingredients are applied post-emergence to the green parts of the plants, growth stops after the treatment and the harmful plants either remain in the growth stage present at the time of application or die completely after a certain period of time, so that in this way competition with weeds which are harmful to the crop plants is eliminated very early and permanently.

[0024] The compounds of the invention can be selective among useful plant crops and can also be used as non-selective herbicides.

[0025] The active ingredients can also be used to control harmful plants in crops of known or to be developed transgenic plants by their herbicidal and plant growth regulating properties. In general, transgenic plants are characterized by certain advantageous properties, such as resistance to certain active ingredients (particularly certain herbicides) used in the agrochemical industry, resistance to plant diseases or pathogens of plant diseases (e.g., certain insects or microorganisms, such as fungi, bacteria or viruses). Another specific property relates, for example, to the quantity, quality, storability, composition and specific components of the harvest. For example, there are known transgenic plants with increased starch content or modified starch quality, or with different fatty acid composition in the harvest. A further specific property is tolerance or resistance to abiotic stress factors, such as heat, low temperature, drought, salinity and UV light.

[0026] Preferably, the compounds of formula (I) or salts thereof are used in economically important transgenic crops of useful and ornamental plants.

[0027] The compounds of formula (I) can be used as herbicides in crops of useful plants which are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides in question.

[0028] Conventional methods for generating new plants with modified properties compared to existing plants are, for example, conventional cultivation methods and the generation of mutants. Alternatively, new plants with altered properties can be generated using recombinant methods (see, for example, EP 0221044, EP 0131624). For example, several cases have been described relating to the genetic modification of crop plants with the aim of modifying the starch synthesized in the plant (for example WO 92 / 011376A, WO 92 / 014827A, WO 91 / 019806A); transgenic crop plants, e.g. Optimum β-lactam ... TM GAT TM (Glyphosate ALS Tolerant) trade name or designation, such as corn or soybean; · transgenic crop plants (e.g. cotton) capable of producing Bacillus thuringiensis toxins (Bt toxins) that render the plants resistant to certain pests (EP 0142924A, EP 0193259A); · Transgenic crop plants with altered fatty acid composition (WO 91 / 013972A); · Genetically modified crop plants with novel components or secondary metabolites (e.g. novel phytoalexins that improve disease resistance) (EP 0309862A, EP 0464461A); · Transgenic plants with reduced photorespiration with higher yields and higher stress tolerance (EP 0305398A); · Transgenic crop plants producing proteins of pharma- ceutical or diagnostic importance ("molecular pharming"); · Transgenic crop plants characterized by higher yields or better quality; · Transgenic crop plants, distinguished by combinations of novel properties, e.g. as described above ("gene stacking").

[0029] Many molecular biological techniques are known in principle that can be used to generate new transgenic plants with modified properties; see, for example, 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.

[0030] For such genetic manipulation, nucleic acid molecules that allow sequence changes by mutagenesis or recombination of DNA sequences can be introduced into plasmids. Using standard methods, for example, base exchanges can be performed, subsequences can be removed, or natural or synthetic sequences can be added. Adapters or linkers can be added to DNA fragments to link them together; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd edition, 1996.

[0031] 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 by expressing a sense RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of said gene product. For this purpose, it is possible to use DNA molecules that contain the entire coding sequence of the gene product, including all possible flanking sequences, and also to use DNA molecules that contain only parts of the coding sequence, in which case these parts must be long enough to have an antisense effect in the cell. Furthermore, DNA sequences that are highly homologous to the coding sequences of the gene products, but are not completely identical to them, can also be used.

[0032] When expressing a nucleic acid molecule in a plant body, the synthesized protein can be localized in any desired compartment of the plant cell. However, to localize in a specific compartment, it is possible, for example, to link the coding region to a DNA sequence that ensures localization in a specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Furthermore, such nucleic acid molecules can be expressed in organelles of plant cells.

[0033] The transgenic plant cells can be regenerated by known techniques to give rise to whole plants. In principle, the transgenic plants can be of any desired plant species, i.e., not only can they be monocotyledonous, but also dicotyledonous.

[0034] In this way, transgenic plants can be obtained which have properties altered by overexpression, suppression or inhibition of a homologous (= natural) gene or gene sequence or by expression of a heterologous (= foreign) gene or gene sequence.

[0035] The compounds (I) of the present invention can be preferably used in transgenic crops resistant to growth regulators (e.g. 2,4-D, dicamba) or to herbicides inhibiting essential plant enzymes (e.g. acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD)), or in transgenic crops resistant to herbicides selected from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and similar active ingredients, or in transgenic plants resistant to any desired combination of these active ingredients.

[0036] The compounds of the invention can be particularly preferably used in transgenic crop plants which are resistant to combinations of glyphosates and glufosinates, or to combinations of glyphosates and sulfonylureas or imidazolinones. Most preferably, the compounds of the invention are used in combination with, for example, Optimum TM GAT TM The gene may be used in transgenic crop plants (eg, corn or soybean) bearing the trade name or designation (Glyphosate ALS Tolerance).

[0037] The use of the active ingredients of the invention in transgenic crops not only results in the effects against harmful plants observed in other crops, but in many cases also in effects specific to the application in a particular transgenic crop, such as a modified or especially expanded spectrum of weeds that can be controlled, modified application rates that can be used for said application, preferably better combinability with herbicides to which the transgenic crop is resistant, as well as effects on the growth and yield of the transgenic crop plants.

[0038] The present invention therefore also relates to the use of the compounds of formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

[0039] The compounds of the present invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in conventional formulations.Thus, the present invention also provides herbicidal compositions and plant growth regulating compositions comprising the compounds of the present invention.

[0040] The compounds of the invention can be formulated in various ways depending on the biological and / or physicochemical parameters required. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water emulsions and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for broadcast and granules for soil application, granules in the form of microgranules (GR), spray granules, absorption granules and impregnated granules. granules), water dispersible granules (WG), water-soluble granules (SG), microspray formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in Winnacker-Kuchler, “Chemische Technologie” [Chemical Technology], 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.

[0041] The necessary formulation auxiliaries, such as inert substances, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell NJ; Hv Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, NY; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, NY 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood NJ; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., NY 1964; Schonfeldt, “Grenzflachenaktive Athylenoxidaddukte” [Interface-active Ethylene Oxide Winnacker-Kuchler, “Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th ed. 1986”.

[0042] On the basis of these formulations, it is also possible to prepare combinations with further active ingredients (e.g. insecticides, acaricides, herbicides, fungicides) and also with safeners, fertilizers and / or growth regulators, for example in the form of finished formulations or as tank mixes.

[0043] Combination partners which can be used for the compounds of general formula (I) in mixed formulations or tank mixes are, for example, known active ingredients which are based on inhibiting, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, or act as plant growth regulators, as known, for example, from 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 references cited therein.

[0044] Examples of known herbicides or plant growth regulators which can be combined with the compounds of general formula (I) include the following active ingredients, which are indicated by their "common name" or by their chemical name or by their code number according to the International Organization for Standardization (ISO), and which always include all use forms (e.g. acids, salts, esters) and all isomers (e.g. stereoisomers and optical isomers). These include, by way of example, single use forms, but in some cases, multiple use forms: Acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-dimethylammonium, Aminopyralid-trypromine, Amitrole, Ammonium sulfamate, Anilofos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azafenidine, Azimsulfuron, Beflubutamid, (S)-(-)-Beflubutamid, Beflubutamid-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-potassium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulide, Bentazon, Bentazon-sodium, Benzobicyclon, Benzofenap, Bicyclo Ropyrone, Bifenox, Biranaphos, Biranaphos-sodium, Bipyrazone, Bispyribac, Bispyribac-sodium, Bixlozone, Bromacil, Bromacil-lithium, Bromacil-sodium, Bromobutide, Bromophenoxime, Bromoxynil, Bromoxynil-butyrate, Bromoxynil-potassium, Bromoxynil-heptanoate and Bromoxynil-octanoate, Busoxinon, Butachlor, Butafenacil, Butamiphos, Butenachlor, Butralin, Butroxydim, Butyrate, Caffeine carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim,Chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, symmetryn, exo-(+)-symmetryn, i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)-symmetryn, i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, [2.2.1] Heptane, cinosulfuron, clasifos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-methyl, clopyralid-olamine, clopyralid-potassium, clopyralid-trypomine, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranyl, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop bromobutyryl, cyprazine, 2,4-D (and their ammonium salts, butotyl, butyl, choline, diethylammonium, dimethylammonium, diolamine, doboxyl, dodecylammonium, ethexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, meptyl, methyl, potassium, tetradecylammonium, triethylammonium, triisopropyl, isopropylammonium ... isopropanol ammonium salt, tryptomine salt and trolamine salt), 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dalapon-calcium, dalapon-magnesium, dalapon-sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl pyrazolate (DTP), dicamba and its salts (e.g., dicamba biproamine, dicamba N,N-bis(3-aminopropyl)methylamine, dicamba butotyl, dicamba choline,Dicamba diglycolamine, dicamba dimethyl ammonium, dicamba diethanolamine ammonium, dicamba diethyl ammonium, dicamba isopropyl ammonium, dicamba methyl, dicamba monoethanolamine, dicamba olamine, dicamba potassium, dicamba sodium, dicamba triethanolamine), dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-di Methyl-1,2-oxazolidin-3-one, Dichlorprop, Dichlorprop-butotyl, Dichlorprop-dimethylammonium, Dichlorprop-ethexyl, Dichlorprop-ethylammonium, Dichlorprop-isooctyl, Dichlorprop-methyl, Dichlorprop-potassium, Dichlorprop-sodium, Dichlorprop-P, Dichlorprop-P-dimethylammonium, Dichlorprop-P-ethexyl, Dichlorprop-P-potassium, Dichlorprop- Sodium, Diclofop, Diclofop-Methyl, Diclofop-P, Diclofop-P-Methyl, Diclosulam, Difenzoquat, Difenzoquat-Methyl Sulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-Sodium, Dimefuron, Dimepiperate, Dimethasulfazate, Dimethachlor, Dimethamethrin, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb, Dinoterb-Acetate, Diphenamide, Diquat, Diquat-Dibromide, Diquat dichloride, dithiopyr, diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, endothal, endothal-diammonium, endothal-dipotassium, endothal-disodium, epirifenacil (S-3100), EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyphene, ethoxyphene-ethyl, ethoxysulfuron, etobenzanide, F-5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1yl]phenyl]ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, Fenquinotrion, fentrazamide, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpi Flu-ethyl, Flumetsulam, Flumicrac, Flumicrac-pentyl, Flumioxazin, Fluometuron, Flurenol, Flurenol-butyl, -dimethylammonium and -methyl, Fluoroglycofen, Fluoroglycofen-ethyl, Flupropanate, Flupropanate-sodium, Flupyrsulfuron, Flupyrsulfuron-methyl, Flupyrsulfuron-methyl-sodium, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-butmethyl, Fluroxypyr-meptyl, Flurtamone, Fluthiaset, Flu Luciaset-methyl, Fomesafen, Fomesafen-sodium, Foramsulfuron, Foramsulfuron-sodium, Fosamine, Fosamine-ammonium, Glufosinate, Glufosinate-ammonium, Glufosinate-sodium, L-Glufosinate-ammonium, L-Glufosinate-sodium, Glufosinate-P-sodium, Glufosinate-P-ammonium, Glyphosate, Glyphosate-ammonium, Glyphosate-isopropylammonium, Glyphosate-diammonium, Glyphosate-dimethylammonium,Glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium and glyphosate-trimesium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropyl phosphoramidothioate, haloxifen, haloxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, haloxyfop-sodium, hexazinone, HNPC-A8169, i.e., prop-2-yn-1-yl(2S)-2-{3-[(5-tert-butylpyridin-2-yl)-2-propan-1-yl )oxy]phenoxy}propanoate, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, hydantocidin, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazaquin-methyl, imazethapyr, imazethapyr-ammoni um, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil, ioxynil-lithium, -octanoate, -potassium and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl ]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, ketospiradox-potassium, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -butyl, -dimethylammonium, -diolamine, -2-ethylhexyl, -ethyl, -isobutyl, isooctyl, -isopropyl, -isopropylammonium, -methyl, -olamine, -potassium, -sodium and -trolamine, MCPB,MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethexyl, mecoprop-ethadyl, mecoprop-isooctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mefluidide-diolamine, mefluidide-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron-sodium, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metoslam, methoxuron, metribuzin, 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-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo-[4,3- a]pyridine-8-carboxamide, nebulon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat-dichloride, paraquat-dimethyl sulfate, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petroleum, phenmedipham, phenmedipham-ethyl, picloram, picrolam loram-dimethylammonium, picloram-ethexyl, picloram-isooctyl, picloram-methyl, picloram-olamine, picloram-potassium, picloram-triethylammonium, picloram-tryplomine, picloram-trolamine, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone,Propoxycarbazone-sodium, Propyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolinate (pyrazolate), Pyrazosulfuron, Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-isopropyl, Pyribambenz-propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-sodium, Pyroxasulfone, Pyroxisulam, Quinclorac, Quinclorac-dimethylammonium , quinclorac-methyl, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201, i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, such as TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, takstmin, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron,Thifensulfuron-methyl, thiobencarb, thiaphenacyl, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate sulfate), vernolate, XDE-848, ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]ethyl acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl 5-Chloropyrimidin-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazin-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl propane-1-sulfonate,4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate cyanomethyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate prop-2-yn-1-yl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate methyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate methyl, 4-amino-3- Chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid benzyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid ethyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxamide Methyl 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylate, methyl 4-amino -3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate potassium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate sodium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate butyl, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one,3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-( 2-Methylphenyl)quinazoline-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-1-ium salt (as appropriate) salts with suitable anions (e.g., chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salts (salts with suitable anions (e.g., chloride, acetate or trifluoroacetate)), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salts (salts with suitable anions (e.g., chloride, acetate or trifluoroacetate)), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salts (salts with suitable anions (e.g., chloride, acetate or trifluoroacetate)), ) pyridazin-1-ium salts (salts with appropriate anions (e.g., chloride, acetate, or trifluoroacetate)), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salts (salts with appropriate anions (e.g., chloride, acetate, or trifluoroacetate)), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salts (salts with appropriate 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-dihydropyrimidin-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)-2-(trifluoromethyl)benzaldehyde O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxime, 2-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino, -3,5-Dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid.

[0045] Examples of plant growth regulators as possible mixing partners are: Abscisic acid and related analogues [e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid, methyl (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, methyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid, methyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid], acibenzolar, acibenzolar-S-methyl, S-adenosylhomocysteine, allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g., (isopropylidene)aminooxyacetic acid 2-(methoxy)-2-oxoethyl ester, (isopropylidene)aminooxyacetic acid 2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)aminooxyacetic acid-2-(isopropyloxy)-2-oxoethyl ester], 1-aminocycloprop-1-yl carboxylic acid N-Methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives (as described in DE 3335514, EP 30287, DE 2906507 or US 5123951), 1-aminocyclopropyl-1-hydroxamic acid, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl , L-canaline, catechol and catechols (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chitooligosaccharides (CO; COs differ from LCOs in that they do not have the fatty acid side chains characteristic of LCOs. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units but do not themselves form chitin molecules [(CH. 13 No. 5) n , CAS No. 1398-61-4] and chitosan molecule [(C 11 No. 4) n, CAS-No.9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet-sodium, n-decanol, dikegluc, dikegluc-sodium, endothal, endothal-dipotassium (dipo tassum), -disodium and mono(N,N-dimethylalkylammonium), ethephon, 1-ethylcyclopropene, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonate esters or other derivatives (e.g., jasmonate methyl ester, jasmonate ethyl ester), lipochitooligosaccharides (LCOs, sometimes referred to as symbiotic nodulation signals (Nod or Nod factors) or Myc factors, are composed of an oligosaccharide backbone consisting of β-1,4-linked N-acetyl-D-glucosamine residues ("GlcNAc") with N-linked fatty acid side chains condensed at the non-reducing end.As can be inferred from the literature, LCOs differ in the number of GlcNAc units in their backbone structure, in the length and saturation of the fatty acid chains, and in the substitution of reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic acid hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydro furan-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one and related lactones (described in EP 2248421), 2-(1-naphthyl)acetamide, 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, prohydrojasmone, rhizobitoxin, 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, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine.

[0046] Safeners which can be used in combination with the compounds of the invention of formula (I) and, optionally, with further active ingredients (e.g. the fungicides, herbicides, acaricides, insecticides mentioned above) are preferably selected from the group consisting of:

[0047] (S1) Equation (S1) [ka] wherein the symbols and indices have the following meanings: n A is a natural number from 0 to 5, preferably a natural number from 0 to 3; R A 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl; W A is an unsubstituted or substituted divalent heterocyclic radical selected from the group of partially unsaturated or aromatic 5-membered heterocycles having 1 to 3 ring heteroatoms selected from the group of N and O, in which at least one nitrogen atom and at most one oxygen atom are present in the ring, preferably (W A 1 )~(W A 4 ) [ka] is a radical selected from the group m A is 0 or 1; R A 2 OR A 3 , S.R. A 3 Or NR A 3 R A 4or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms, preferably selected from the group consisting of O and S, which is linked to the carbonyl group in (S1) via a nitrogen atom and which is unsubstituted or substituted with a radical selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably of the formula OR A 3 , formula NHR A 4 or a radical of the formula N(CH3)2, in particular of the formula OR A 3 is a radical represented by: R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms; R A 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or unsubstituted phenyl; R A 5 is H, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, cyano or COOR A 9 (where 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); R A 6 , R A 7 , R A 8are the same or different and are selected from hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C 12 )-cycloalkyl or substituted or unsubstituted phenyl. A compound represented by the formula: Preferably: (a) Compounds of the type dichlorophenylpyrazoline-3-carboxylic acid (S1 a ), preferably compounds such as: 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) ("mefenpyr-diethyl") and related compounds, which are described in WO-A-91 / 07874; (b) Derivatives 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, which are described in EP-A-333131 and EP-A-269806; (c) Derivatives 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 related compounds (which are described, for example, in EP-A-268554); (d) Triazole carboxylic acid type compounds (S1 d), preferably compounds such as: fenchlorazole (-ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7) and related compounds (which are described in EP-A-174562 and EP-A-346620); (e) Compounds of the type 5-benzyl-2-isoxazoline-3-carboxylic acid or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the type 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e ), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds, which are described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), which are described in patent application WO-A-95 / 07897.

[0048] (S2) Formula (S2) [ka] wherein the symbols and indices have the following meanings: R B 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl; n B is a natural number from 0 to 5, preferably a natural number from 0 to 3; R B 2 OR B 3, S.R. B 3 Or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms, preferably selected from the group O and S, which is linked to the carbonyl group in (S2) via a nitrogen atom and which is unsubstituted or substituted with a radical selected from the group (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably of the formula OR B 3 , formula NHR B 4 or a radical of the formula N(CH3)2, in particular of the formula OR B 3 is a radical represented by: R B 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms; R B 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy or substituted or unsubstituted phenyl; T B is a (C1 or C2)-alkanediyl chain, which is unsubstituted or substituted by one or two (C1-C4)-alkyl radicals or by [(C1-C3)-alkoxy]carbonyl; A quinoline derivative represented by the formula: Preferably: (a) Compounds of the 8-quinolineoxyacetic acid type (S2 a ), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate ("cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy)acetic acid (1,3-dimethyl-but-1-yl) (S2-2), (5-chloro-8-quinolinoxy)acetic acid 4-allyloxybutyl (S2-3), (5-chloro-8-quinolinoxy)acetic acid 1-allyloxyprop-2-yl (S2-4), (5-chloro-8-quinolinoxy)ethyl acetate (S2-5), (5-chloro-8-quinolinoxy)methyl acetate (S2-6), (5-chloro-8-quinolinoxy)allyl acetate (S2-7), 2-(2-propylideneiminooxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds, which are described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366, and also (5-chloro-8-quinolinoxy)acetic acid (S2-10), its hydrates and salts, for example its lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, which are described in WO-A-2002 / 34048; (b) (5-chloro-8-quinolinoxy)malonic acid type compounds (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methylethyl (5-chloro-8-quinolinoxy)malonate and related compounds, which are described in EP-A-0582198.

[0049] (S3) Equation (S3) [ka] wherein the symbols and indices are defined as follows: R C 1is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl; R C 2 , R C 3 are identical or different and are 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 or substituted or unsubstituted phenyl or R C 2 and R C 3 together form a substituted or unsubstituted heterocyclic ring (preferably an oxazolidine ring, a thiazolidine ring, a piperidine ring, a morpholine ring, a hexahydropyrimidine ring or a benzoxazine ring). A compound represented by the formula: Preferably: Active ingredients of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-acting safeners), e.g. "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) [supplied by Stauffer] (S3-2), "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) [supplied by Stauffer] (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (supplied by PPG Industries) (S3-5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) [supplied by Sagro-Chem] (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) [supplied by Nitrokemia or Monsanto] (S3-7), "TI-35" (1-dichloroacetylazepane) [supplied by TRI-Chemical RT] (S3-8), "diclonon" (dicyclonone) or "BAS 145138" or "LAB 145138" (S3-9), ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) [supplied by BASF], "Furilazol" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10) and its (R)-isomer (S3-11).

[0050] (S4) Equation (S4) [ka] wherein the symbols and indices are defined as follows: A D is SO2-NR D 3 -CO or CO-NR D 3 -SO2; X D is CH or N; R D 1 is CO-NR D 5 R D 6 or NHCO-R D 7and; R D 2 is halogen, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl; R D 3 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl; R D 4 is halogen, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C3-C6)-cycloalkyl, phenyl, (C1-C4)-alkoxy, cyano, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl; R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl or 3-6 membered heterocyclyl, where the heterocyclyl is selected from the group consisting of nitrogen, oxygen and sulfur. D 4 heteroatoms), in which the last seven radicals are selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl and phenyl, and in the case of cyclic radicals are additionally selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, D is substituted with a substituent; R D 6is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, where the last three mentioned radicals are selected from the group consisting of halogen, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio. D or R D 5 and R D 6 together with the nitrogen atom bearing them form a pyrrolidinyl or piperidinyl radical; R D 7 is hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the last two mentioned radicals are selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio, and in the case of cyclic radicals are additionally selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, v D is substituted with a substituent; n D is 0, 1 or 2; m D is 1 or 2; v D is 0, 1, 2 or 3. N-acylsulfonamides represented by the following formula (I) and salts thereof; Among these, for example, those known from WO-A-97 / 45016, for example those of the formula (S4 a ) [ka] [During the ceremony, R D 7is (C1-C6)-alkyl or (C3-C6)-cycloalkyl, where the last two mentioned radicals are selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio, and in the case of cyclic radicals are additionally selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, v D is substituted with a substituent; R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy or CF3; m D is 1 or 2; v D is 0, 1, 2 or 3. Preferred are compounds of the N-acylsulfonamide type represented by and, For example, compounds of the formula (S4 b ) [ka] For example, in the above formula, R D 5 = cyclopropyl, and (R D 4 ) = 2-OMe ("cyprosulfamide", S4-1); R D 5 = cyclopropyl, and (R D 4 ) = 5-Cl-2-OMe (S4-2); R D 5 = ethyl, and (R D 4 )=2-OMe(S4-3); R D 5 = isopropyl, and (R D 4 ) = 5-Cl-2-OMe (S4-4); and R D 5 = isopropyl, and (R D 4 )=2-OMe(S4-5); Also preferred are and, For example, the compound of the formula (S4 c ) [ka] [During the ceremony, R D 8 and R D 9 is independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl or (C3-C6)-alkynyl; R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m D is 1 or 2. Compounds of the N-acylsulfamoylphenylurea type represented by the formula: 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea ("methocamiphen", S4-6); 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea; 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; Also preferred are: and, For example, the compound of formula (S4 d ) [ka] For example, N-phenylsulfonyl terephthalamide represented by the above formula: R D 4is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m D is 1 or 2; R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl; N-phenylsulfonyl terephthalamide and the like are also preferred.

[0051] (S5) Active ingredients (S5) selected from the class of hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, such as, for example, 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 (which are described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001).

[0052] (S6) Active ingredients (S6) selected from the class of the 1,2-dihydroquinoxalin-2-ones, such as 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one (which are described in WO-A-2005 / 112630).

[0053] (S7) Formula (S7) (which is described in WO-A-1998 / 38856) [ka] wherein the symbols and indices are defined as follows: R E1 , R E 2 are independently halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, nitro; A E COOR E 3 or COSR E 4 and; R E 3 , R E 4 are independently hydrogen, (C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl, (C1-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium; n E 1 is 0 or 1; n E 2 , n E 3 are independently 0, 1 or 2. A compound represented by the formula: Preferably: Diphenyl methoxy acetic acid, Ethyl diphenylmethoxyacetate, Methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).

[0054] (S8) Formula (S8) (which is described in WO-A-98 / 27049) [ka] [During the ceremony, X F is CH or N; n F X F =N is an integer from 0 to 4; and n F X FWhen =CH, it is an integer from 0 to 5; R F 1 is 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; R F 2 is hydrogen or (C1-C4)-alkyl; R F 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, each of which is unsubstituted or substituted with one or more (preferably up to three) identical or different radicals selected from the group consisting of halogen and alkoxy. or a salt thereof; Preferably, in the above formula: X F is CH; n F is an integer between 0 and 2; R F 1 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy; R F 2 is hydrogen or (C1-C4)-alkyl; R F 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, each of which is unsubstituted or substituted with one or more (preferably up to three) identical or different radicals selected from the group consisting of halogen and alkoxy; A compound or a salt thereof.

[0055] (S9) An active ingredient (S9) selected from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones, such as 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), which are described in WO-A-1999 / 000020.

[0056] (S10) Formula (S10 a ) or formula (S10 b ) (these are described in WO-A-2007 / 0237190 and WO-A-2007 / 023764) [ka] [During the ceremony, R G 1 is halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3; Y G , Z G represent, independently of each other, O or S; n G is an integer from 0 to 4; R G 2 is (C1-C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl, benzyl, halobenzyl; R G 3 is hydrogen or (C1-C6)-alkyl. A compound represented by the formula:

[0057] (S11) Active ingredients of the oxyimino compound type (S11) (these are known as seed dressing agents), e.g. "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for foxtail millet / sorghum against injury by metolachlor; "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed dressing safener for foxtail millet / sorghum against injury by metolachlor; and "Siometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is a known seed dressing safener for foxtail millet / sorghum against injury by metolachlor.

[0058] (S12) Active ingredients (S12) selected from the class of isothiochromanones, such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds (WO-A-1998 / 13361).

[0059] (S13) One or more compounds selected from the following group: "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against injury by thiocarbamate herbicides; "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice; "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for foxtail millet and sorghum against injury by alachlor and metolachlor; "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) (supplied by American Cyanamid), which is known as a safener for corn against injury by imidazolinones; "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) [supplied by Nitrokemia] (known as a safener for corn); "MG 838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) [Supplied by: Nitrokemia]; "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7); "Dietholate" (O,O-diethyl O-phenylphosphorothioate) (S13-8); “Mephenate” (4-chlorophenyl methylcarbamate) (S13-9).

[0060] (S14) Active ingredients that have a herbicidal effect against harmful plants and also a phytotoxicity reducing effect against crop plants such as rice, e.g. "Dimepyrate" or "MY 93" (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), known as a safener for rice against injury by the herbicide molinate; "Dymron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolyl urea), known as a safener for rice against injury caused by the herbicide imazosulfuron; "Cumyluron" = "JC 940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea; see JP-A-60087254) (which is known as a safener for rice against injury by some herbicides); "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone) (which is known as a safener for rice against injury caused by some herbicides); "CSB" (1-Bromo-4-(chloromethylsulfonyl)benzene) [Supplied by: Kumiai] (CAS Reg. No. 54091-06-4), which is known as a safener for injury by some herbicides in rice.

[0061] (S15) Formula (S15) (which is described in WO-A-2008 / 131861 and WO-A-2008 / 131860) [ka] [During the ceremony, R H 1 is a (C1-C6)-haloalkyl radical; and R H 2 is hydrogen or halogen; and R H 3 , R H 4 are independently hydrogen, (C1-C 16 )-Alkyl, (C2-C 16 )-alkenyl or (C2-C 16)-alkynyl, in which the last three radicals are each unsubstituted or substituted by one or more radicals selected from the group of halogen, hydroxyl, 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, in which the cycloalkyl is fused on one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl, which is fused to one side of the ring to a 4-6-membered saturated or unsaturated carbocyclic ring, in which the last four radicals mentioned are each unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, 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; Or, R H 3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy; and R H 4is hydrogen or (C1-C4)-alkyl; or R H 3 and R H 4 is, together with the nitrogen atom to which it is directly attached, a 4-8 membered heterocyclic ring which, in addition to the nitrogen atom, can also contain further ring heteroatoms (preferably up to two further ring heteroatoms selected from the group N, O and S) and which is unsubstituted or substituted with one or more radicals selected from the group halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio. or a tautomer thereof.

[0062] (S16) Active ingredients that are primarily used as herbicides but also have a phytotoxicity-reducing effect 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); 3,6-Dichloro-2-methoxybenzoic acid 1-(ethoxycarbonyl)ethyl (lactidichlor-ethyl).

[0063] Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, dichlormid and metcamifen.

[0064] Wettable powders are preparations capable of being homogeneously dispersed in water, which contain, in addition to the active ingredient and apart from diluents or inert substances, further surfactants of ionic and / or nonionic type (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoyl methyl taurate. To prepare wettable powders, the herbicidal active ingredient is pulverized in conventional equipment, such as hammer mills, blower mills and air jet mills, and simultaneously or subsequently mixed with formulation auxiliaries.

[0065] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (such as butanol, cyclohexanone, dimethylformamide, xylene or aromatic substances or hydrocarbons with relatively high boiling points) or a mixture of such organic solvents and adding one or more surfactants (emulsifiers), ionic and / or non-ionic. Examples of emulsifiers that can be used are: calcium alkylarylsulfonates, such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensates, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0066] Dusting products are obtained by grinding the active ingredient with finely distributed solid matter, such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0067] Suspension formulations can be aqueous or oil-based. They can be prepared, for example, by wet-milling using a commercial bead mill, and optionally with the addition of a surfactant (such as those already mentioned above for the different formulation types).

[0068] Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, for example, using aqueous organic solvents and, optionally, surfactants (e.g. those already mentioned above for the other formulation types), using stirrers, colloid mills and / or static mixers.

[0069] Granules can be prepared by spraying the active ingredient onto the surface of an adsorbent granular inert material, or by applying an active ingredient concentrate onto the surface of a carrier material (e.g., sand, kaolinite, or granular inert material) with an adhesive (e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oil). It is also possible to granulate suitable active ingredients (as a mixture with fertilizer, if necessary) in a manner customary for producing fertilizer granules.

[0070] Water dispersible granules are generally prepared by conventional methods such as spray drying, fluid bed granulation, pan granulation, mixing with high speed mixers, and extrusion without solid inert materials.

[0071] For the preparation of bread granules, fluid bed granules, extrusion granules and spray granules, reference is made, for example, to the methods described in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; "Agglomeration", J.E. Browning, Chemical and Engineering 1967, pages 147 ff.; and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

[0072] For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0073] The agrochemical preparations generally contain 0.1% to 99% by weight, in particular 0.1% to 95% by weight, of the compound of the invention. In wettable powders, the concentration of the active ingredient is, for example, about 10% to 90% by weight, the remainder up to 100% by weight being made up of conventional formulation ingredients. In emulsifiable concentrates, the concentration of the active ingredient can be about 1% to 90% by weight, preferably 5% to 80% by weight. Formulations in the form of powders contain 1% to 30% by weight of active ingredient, preferably usually 5% to 20% by weight; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredient. In the case of wettable powders, the content of the active ingredient depends in part on whether the active compound is present in liquid or solid form, and in part on what granulation aids, fillers, etc. are used. In the water dispersible granule, the content of the active ingredient is, for example, 1 to 95% by weight, or preferably 10 to 80% by weight.

[0074] In addition, the above formulations of the active ingredients optionally contain the respective customary adhesives, wetting agents, dispersing agents, emulsifying agents, penetrating agents, preservatives, antifreeze agents, as well as solvents, extenders, carriers, as well as dyes, antifoaming agents, evaporation retardants, and agents for influencing pH and viscosity.

[0075] On the basis of these formulations, it is also possible to prepare combinations with other pesticidal active substances (e.g. insecticides, acaricides, herbicides, fungicides) and also with safeners, fertilizers and / or growth regulators, for example in the form of finished formulations or as tank mixes.

[0076] For application, the commercial formulations are, where appropriate, diluted in the customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water dispersible granules. Dust-type preparations, granules for soil application or broadcast granules and sprayable solutions are usually not further diluted with other inert substances before application.

[0077] The required application rate of the compounds of formula (I) and their salts varies depending on the external conditions (such as, inter alia, temperature, humidity and the type of herbicide used). It can vary within a wide range, for example, within the range of 0.001 to 10.0 kg / ha or more of active substance. However, it is preferably 0.005 to 5 kg / ha, more preferably 0.01 to 1.5 kg / ha, more preferably 0.05 to 1 kg / ha. This applies both to pre-emergence and post-emergence application.

[0078] A carrier is a natural or synthetic organic or inorganic substance that is mixed or combined with the active ingredient to improve applicability, especially for application to plants or plant parts or seeds. Such carriers can be solid or liquid, but should generally be inert and suitable for use in agriculture.

[0079] Useful solid or liquid carriers include, for example, ammonium salts, and natural rock flours, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as micronized silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohol, in particular butanol, organic solvents, mineral oils and vegetable oils, and derivatives thereof. Mixtures of such carriers may also be used. Useful solid carriers for granules include, for example, crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic meal, and also granules of organic materials, such as sawdust, coconut shells, corn cobs and tobacco stems.

[0080] Suitable liquefied gas extenders or carriers are liquids that are gases at standard temperature and atmospheric pressure, such as aerosol propellants, for example, halogenated hydrocarbons, or butane, propane, nitrogen, and carbon dioxide.

[0081] In the above formulations, tackifiers can be used, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders or granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids, etc. Further additives can be mineral and vegetable oils.

[0082] When the extender used is water, for example, organic solvents can also be used as auxiliary solvents.Useful liquid solvents are essentially the following: aromatic compounds, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or dichloromethane, aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions, mineral oils and vegetable oils, alcohols, such as butanol or glycols and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and also water.

[0083] The compositions of the present invention may additionally contain further ingredients, such as, for example, surfactants. Useful surfactants are emulsifiers and / or foam formers, dispersants or wetting agents having ionic or non-ionic properties, or mixtures of such surfactants. Examples of these are: salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and fatty alcohols or fatty acids or polycondensates of ethylene oxide and fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of said compounds containing sulfate, sulfonate and phosphate anions, such as alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite waste liquors and methylcellulose. If one of the active ingredients and / or one of the inert carriers is water-insoluble and application is carried out in water, it is necessary to have a surfactant present. The proportion of the surfactant is 5 to 40% by weight of the composition of the present invention. Colorants such as inorganic pigments, such as iron oxide, titanium oxide, and Prussian Blue, as well as organic dyes, such as alizarin dyes, azo dyes, and metal phthalocyanine dyes, as well as trace nutrients, such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts, and zinc salts, can be used.

[0084] If appropriate, additional other ingredients may also be present, such as protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrating agents, stabilizers, sequestering agents, complexing agents, etc. In general, the active ingredient can be combined with any solid or liquid additive commonly used for formulation purposes. In general, the compositions and formulations of the present invention contain 0.05% to 99% by weight, 0.01% to 98% by weight, preferably 0.1% to 95% by weight, more preferably 0.5% to 90% by weight, and most preferably 10% to 70% by weight of the active ingredient. The active ingredients or compositions of the invention can be used as they are or in the form of their formulations or in the use forms prepared therefrom, depending on their individual physical and / or chemical properties, such as, for example, aerosols, capsule suspensions, cold-fogging concentrates, warm-fogging concentrates, encapsulated granules, fine granules, seed treatment flowables, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, large granules, fine granules, oil-dispersible powders, oil-miscible flowables, oil-miscible liquids, foams, pastes, pesticide-coated seeds, suspension concentrates, suspoemulsions, soluble concentrates, suspensions, sprayable powders, soluble powders. powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, natural products and synthetic substances impregnated with the active ingredient, and also those microencapsulated in polymeric substances and in coating substances for seeds, and also ULV cold-fogging formulations and ULV warm-fogging formulations.

[0085] The formulations can be prepared in a manner known per se, for example by mixing the active ingredient with at least one customary extender, solvent or diluent, emulsifier, dispersant and / or binder or fixative, wetting agent, water repellent, optionally drying agents and UV stabilizers, and optionally dyes and pigments, defoamers, preservatives, secondary thickeners, tackifiers, gibberellins and further processing aids.

[0086] The compositions of the present invention include not only formulations which are ready for use and can be applied to plants or seeds using appropriate equipment, but also commercial concentrates which require dilution with water before use.

[0087] The active ingredient of the present invention may be present on its own or in its (commercially standard) formulation or in a use form prepared from such a formulation, as a mixture with other (known) active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners or semiochemicals.

[0088] The treatment of plants and plant parts according to the invention with the active ingredients or compositions is carried out by customary treatment methods, for example directly by immersion, spraying, spraying, irrigation, vaporization, dusting, fume, broadcasting, foaming, painting, spreading-on, watering (drenching), drip irrigation, etc., or by applying the active ingredients or compositions to the surroundings, habitat or storage space of the plants and plant parts, and also, in the case of propagation material, in particular seeds, by dry seed treatment, by wet seed treatment, by slurry treatment, by incrustation, by coating with one or more layers. Furthermore, the active ingredients can also be deployed by ultra-low volume methods or the active ingredient preparations or the active ingredients themselves can be injected into the soil.

[0089] The active ingredients of the present invention are suitable for protecting plants and plant organs, for increasing yield, and for improving the quality of harvested crops, when they show good compatibility with plants, have desirable toxicity to homeotherms, and have good compatibility with the environment.They can preferably be used as crop protection compositions.They show activity against normal sensitive and resistant species, and also show activity against all or specific developmental stages.

[0090] Plants which can be treated according to the invention include the following main crop plants: corn, soybean, cotton, Brassica oil seeds, such as Brassica napus (e.g. canola), Brassica rapa, B. juncea (e.g. (field) mustard) and Brassica carinata, rice, wheat, sugar beet, sugar cane, oats, rye, barley, millet and sorghum, triticale, flax, grapes, as well as various fruits and vegetables belonging to different botanical taxa, such as Rosaceae sp. (e.g. pome fruits, such as apple and pear, as well as stone fruits, such as apricot, cherry, almond and peach, and berries, such as strawberry), Ribesioidae sp. sp.), Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g. banana trees and plantations), Rubiaceae sp. (e.g. coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (e.g. lemons, oranges and grapefruit); Solanaceae sp. (e.g., tomato, potato, pepper, eggplant), Liliaceae sp., Compositae sp. (e.g., lettuce, artichoke, and chicory (which includes root chicory, endive, or common chicory)), Umbelliferae sp.) (e.g. carrot, parsley, celery and celeriac), Cucurbitaceae sp. (e.g. cucumber (which includes gherkin), pumpkin, watermelon, gourd and melon), Alliaceae sp. (e.g. leek and onion), Cruciferae sp. (e.g. white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, Chinese cabbage, kohlrabi, radish, horseradish, cress and Chinese cabbage), Leguminosae sp. (e.g. peanut, pea and Phaseolus vulgaris (e.g. common bean and fava bean)), Chenopodiaceae sp. sp. (e.g. Swiss chard, fodder beet, spinach, beetroot), Malvaceae (e.g. okra), Asparagaceae (e.g. asparagus); useful and ornamental plants in gardens and forests; and, in each case, genetically modified versions of these plants.

[0091] As stated above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species and plant cultivars or plant species and cultivars obtained by conventional biological breeding methods such as crossing or protoplast fusion, as well as their parts, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, where appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated. The terms "parts" or "parts of plants" or "plant parts" have been explained above. Particularly preferred according to the invention is the treatment of plants of the respective plant cultivars that are commercially conventional or in use. Plant cultivars are understood to mean plants with new properties ("traits") that have been cultivated by conventional breeding or by mutagenesis or recombinant DNA techniques. They can be cultivars, varieties, biotypes and genotypes.

[0092] The treatment method of the invention can also be used to treat genetically modified organisms (GMOs), such as plants or seeds. A genetically modified plant (or transgenic plant) is a plant in which a heterologous gene has been stably integrated into its genome. The term "heterologous gene" essentially means a gene, supplied or constructed outside the plant, which, when introduced into the nuclear, chloroplast or mitochondrial genome, confers new or improved agronomic properties or other traits to the transformed plant, either by expressing a protein or polypeptide of interest, or by down-regulating or switching off another gene or genes present in the plant (e.g. using antisense, co-suppression or RNAi technology [RNA interference], etc.). A heterologous gene present in the genome is also called a transgene. A transgene, defined by its specific presence in the plant genome, is called a transformation or transgenesis event.

[0093] Depending on the plant species or plant varieties, their growing location and growing conditions (soil, climate, growing season, nutrients (diet)), the treatment of the present invention may also produce effects that are more than additive ("synergistic effects"). For example, the following effects beyond the actual expected effects are possible: reduced application rate and / or broadening of the activity spectrum and / or increased efficacy of the active ingredients and compositions that can be used according to the present invention, improved plant growth, improved resistance to high or low temperatures, improved resistance to drought or salts contained in water or soil, improved flowering ability, improved ease of harvesting, accelerated maturation, increased yield, increased fruit size, increased plant height, improved green leaf color, earlier flowering, improved quality and / or increased nutritional value of harvested products, increased sugar content in fruits, improved storage stability and / or improved processability of harvested products.

[0094] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that may be treated according to the invention are herbicide-tolerant plants, i.e. plants that have been made tolerant to one or more given herbicides. Such plants can be obtained by genetic transformation or by selecting plants that contain a mutation that confers resistance to the herbicide in question.

[0095] Herbicide-resistant plants are, for example, glyphosate-resistant plants, i.e. plants that have been made tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant to glyphosate by various methods. Thus, for example, glyphosate-resistant plants can be obtained by transforming plants with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutation CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the EPSPS-encoding gene of Petunia (Shah et al., 1986, Science 233, 478-481), the EPSPS-encoding gene of tomato (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or the EPSPS-encoding gene of Eleusine (WO 01 / 66704). It can be a mutant EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally occurring mutations of the above genes. Plants expressing an EPSPS gene that confers glyphosate tolerance have already been described. Plants expressing another gene (e.g. a decarboxylase gene) that confers glyphosate tolerance have already been described.

[0096] Another herbicide-resistant plant is, for example, a plant that has been made tolerant to herbicides that inhibit the enzyme glutamine synthase (e.g., bialaphos, phosphinothricin or glufosinate). Such plants can be obtained by expressing an enzyme that detoxifies the herbicide in question or by expressing a mutant glutamine synthase enzyme that is resistant to inhibition. One example of such an effective detoxifying enzyme is an enzyme that codes for phosphinothricin acetyltransferase (e.g., the bar or pat proteins from Streptomyces species). Plants expressing exogenous phosphinothricin acetyltransferase have been described.

[0097] Further herbicide-resistant plants are also plants that are made tolerant to herbicides that inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). Hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants that are resistant to HPPD inhibitors can be transformed with a gene that codes for a naturally occurring resistant HPPD enzyme, or with a gene that codes for a mutant or chimeric HPPD enzyme, as described in WO 96 / 38567, WO 99 / 24585, WO 99 / 24586, WO 2009 / 144079, WO 2002 / 046387 or US 6,768,044. Resistance to HPPD inhibitors can also be obtained by transforming plants with a gene that codes for a specific enzyme that can form homogentisate despite the inhibition of the native HPPD enzyme by HPPD inhibitors. Such plants are described in WO 99 / 34008 and WO 02 / 36787. The resistance of plants to HPPD inhibitors can also be improved by transforming the plant with a gene encoding a prephenate dehydrogenase enzyme in addition to a gene encoding an HPPD resistance enzyme, as described in WO 2004 / 024928. Furthermore, plants can be made more resistant to HPPD inhibitors by inserting into their genome a gene encoding an enzyme that metabolizes or degrades HPPD inhibitors (e.g., a CYP450 enzyme) (see WO 2007 / 103567 and WO 2008 / 150473).

[0098] Another herbicide-resistant plant is a plant that is made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylurea herbicides, imidazolinone herbicides, triazolopyrimidine herbicides, pyrimidinyloxy(thio)benzoate herbicides, and / or sulfonylaminocarbonyltriazolinone herbicides. Various mutations in the ALS enzyme (also known as "acetohydroxyacid synthase (AHAS)") are known to confer tolerance to various herbicides and groups of herbicides, as described, for example, in Tranel and Wright (Weed Science 2002, 50:700-712). The creation of sulfonylurea-resistant and imidazolinone-resistant plants has been described. Further sulfonylurea-resistant and imidazolinone-resistant plants have also been described.

[0099] Further plants which are resistant to imidazolinones and / or sulfonylureas can be obtained by induced mutagenesis, by selection in cell culture in the presence of the herbicides or by mutation breeding (cf. e.g. US 5,084,082 for soybean, WO 97 / 41218 for rice, US 5,773,702 and WO 99 / 057965 for sugar beet, US 5,198,599 for lettuce or WO 01 / 065922 for sunflower).

[0100] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by specific target insects. Such plants can be obtained by genetic transformation or by selecting plants containing a mutation that confers such insect resistance.

[0101] In the context of the present invention, the term "insect-resistant transgenic plant" includes any plant that contains at least one transgene that includes a coding sequence that codes for: (1) Insecticidal crystal proteins derived from Bacillus thuringiensis or insecticidal portions thereof, e.g., the Bacillus thuringiensis crystal protein disclosed in the online publication "Bacillus thuringiensis" edited by Crickmore et al. (Microbiology and Molecular Biology Reviews 1998, 62, 807-813) and published by Crickmore et al. (2005) at http: / / www.lifesci.sussex.ac.uk / Home / Neil_Crickmore / Bt / . thuringiensis toxin nomenclature, such as a protein or a portion thereof that exhibits insecticidal activity of the Cry protein family (Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb) (e.g., EP-A 1999141 and WO 2007 / 107302), or a protein encoded by a synthetic gene, such as that described in U.S. Patent Application Serial No. 12 / 249,016; or (2) A crystal protein or a portion thereof derived from Bacillus thuringiensis, which exhibits insecticidal activity in the presence of a second crystal protein or a portion thereof other than Bacillus thuringiensis, such as a binary toxin composed of Cy34 crystal protein and Cy35 crystal protein (Nat. Biotechnol. 2001, 19, 668-72; Applied Environm. Microbiol. 2006, 71, 1765-1774), or a binary toxin composed of Cry1A or Cry1F protein and Cry2Aa or Cry2Ab or Cry2Ae protein (U.S. Patent Application Serial No. 12 / 214,022 and EP 08010791.5); or (3) an insecticidal hybrid protein comprising portions of two different insecticidal crystal proteins derived from Bacillus thuringiensis, such as a hybrid of the proteins described in (1) above, or a hybrid of the proteins described in (2) above, such as the Cry1A.105 protein produced in corn event MON89034 (WO 2007 / 027777); or (4) Any one of the above proteins (1) to (3) in which some amino acids (particularly 1 to 10 amino acids) have been replaced with other amino acids in order to obtain a stronger insecticidal activity against the target insect species and / or to expand the range of the affected target insect species and / or due to changes introduced into the coding DNA during cloning or transformation, such as the Cry3Bb1 protein in corn event MON863 or MON88017, or the Cry3A protein in corn event MIR604; or (5) An insecticidal secretory protein or a part thereof exhibiting insecticidal activity derived from Bacillus thuringiensis or Bacillus cereus, for example, a vegetative insecticidal protein (VIP) listed in "http: / / www.lifesci.sussex.ac.uk / Home / Neil_Crickmore / Bt / vip.html", for example, a protein of the VIP3Aa protein family; or (6) a secreted protein from Bacillus thuringiensis or Bacillus cereus, which exhibits insecticidal activity in the presence of a second secreted protein from Bacillus thuringiensis or Bacillus cereus, such as a binary toxin composed of the VIP1A protein and the VIP2A protein (WO 94 / 21795); or (7) An insecticidal hybrid protein containing a portion of a different secreted protein derived from Bacillus thuringiensis or Bacillus cereus, for example, a hybrid of the protein of (1) above or a hybrid of the protein of (2) above; or (8) In any one of the above items (5) to (7), some amino acids (particularly 1 to 10 amino acids) are replaced with other amino acids in order to obtain a stronger insecticidal activity against the target insect species and / or to expand the range of the target insect species affected, and / or due to changes induced in the coding DNA during cloning or transformation (still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT102; or (9) Bacillus thuringiensis or Bacillus cereus secretory proteins that exhibit insecticidal activity in the presence of crystal proteins derived from Bacillus thuringiensis, such as binary toxins composed of the proteins VIP3 and Cry1A or Cry1F (U.S. Patent Application No. 61 / 126083 and U.S. Patent Application No. 61 / 195019), or binary toxins composed of the VIP3 protein and the Cry2Aa protein, Cry2Ab protein, or Cry2Ae protein (U.S. Patent Application No. 12 / 214,022 and EP 08010791.5); or (10) In the protein according to item (9) above, some amino acids (in particular 1 to 10 amino acids) have been replaced by other amino acids in order to obtain a stronger insecticidal activity against the target insect species and / or to expand the range of the target insect species affected and / or due to changes induced in the coding DNA during cloning or transformation (which still encodes an insecticidal protein).

[0102] Of course, the term "insect-resistant transgenic plant" as used herein also encompasses any plant that contains a combination of genes encoding any one of the proteins in the above classes (1) to (10). In one embodiment, the insect-resistant plant contains two or more transgenes encoding any one of the proteins in the above classes (1) to (10) in order to expand the range of target insect species that are affected, or to delay the development of insect resistance to the plant by using different proteins that have insecticidal activity against the same target insect species but different mechanisms of action (e.g., binding to different receptor binding sites in the insect).

[0103] In the context of the present invention, "insect-resistant transgenic plant" also includes any plant that contains at least one transgene that contains a sequence that produces double-stranded RNA that prevents the growth of pests after they ingest the food.

[0104] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are resistant to abiotic stress factors. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such stress resistance. Particularly useful stress-tolerant plants include: (a) a plant comprising a transgene capable of reducing the expression and / or activity of a poly(ADP-ribose) polymerase (PARP) gene in a plant cell or in the plant; (b) a plant comprising a stress tolerance enhancing transgene capable of reducing the expression and / or activity of a PARG-encoding gene in the plant or plant cell; (c) a plant comprising a stress tolerance enhancing transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including nicotinamidase, nicotinic acid phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase, or nicotinamide phosphoribosyltransferase.

[0105] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention exhibit modified quantity, quality and / or storage stability of the harvested product and / or modified characteristics of certain components of the harvested product, for example: (1) transgenic plants which synthesize modified starches whose physicochemical properties, in particular the amylose content or amylose / amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscous behavior, the gelling strength, the starch granule size and / or the starch granule morphology, are altered compared to the starch synthesized in wild-type plant cells or plants, making them more suitable for certain applications; (2) transgenic plants which synthesize non-starch carbohydrate polymers or which synthesize non-starch carbohydrate polymers with altered properties compared to the non-genetically modified wild-type plants (examples are plants which produce polyfructose (in particular inulin- and levan-type polyfructose), plants which produce α-1,4-glucans, plants which produce α-1,6-branched α-1,4-glucans, and plants which produce alternan); (3) transgenic plants producing hyaluronan; (4) Transgenic or hybrid plants having properties such as "high soluble solids content," "low pungency" (LP) and / or "long shelf life" (LS), e.g., onion.

[0106] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that may also be treated according to the invention are plants with modified fiber properties (for example cotton plants). Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such modified fiber properties. Such plants include: (a) a plant (e.g., a cotton plant) that contains an altered form of a cellulose synthase gene; (b) a plant (e.g., a cotton plant) that contains an altered form of an rsw2 homologous nucleic acid or an rsw3 homologous nucleic acid, e.g., a cotton plant having increased expression of sucrose phosphate synthase; (c) plants with increased expression of sucrose synthase (e.g., cotton plants); (d) plants in which the timing of fiber cell-based plasma membrane gating has been altered (e.g., via downregulation of fiber-selective β-1,3-glucanase) (e.g., cotton plants); (e) Plants (eg, cotton plants) having fibers whose responsiveness has been altered (eg, through expression of N-acetylglucosamine transferase genes, including nodC, and expression of chitin synthase genes).

[0107] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that may also be treated according to the invention are plants (e.g. rapeseed plants or related Brassica plants) with altered oil profile characteristics. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such altered oil characteristics. Such plants include: (a) Plants that produce oil with a high oleic acid content (e.g., rapeseed plants); (b) plants that produce oils with low linolenic acid content (e.g., rapeseed plants); (c) Plants that produce oils with low levels of saturated fatty acids (e.g., rapeseed plants).

[0108] Plants or plant cultivars (obtainable by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants such as potato showing resistance to viruses (for example against potato virus Y (SY230 and SY233 events, Tecnoplant, Argentina)) or potato showing resistance to diseases (for example potato late blight) (for example the RB gene) or potato showing reduced cold-induced sweetness (which has the genes Nt-Inh, II-INV) or potato showing a dwarf phenotype (A-20 oxidase gene).

[0109] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that may also be treated according to the present invention are plants (e.g. rapeseed plants or related Brassica plants) with modified seed shattering characteristics. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such modified characteristics. Such plants include plants (e.g. rapeseed plants) in which seed shattering is delayed or reduced.

[0110] Particularly useful transgenic plants that may be treated according to the present invention are plants that contain a transformation event or combination of transformation events that are the subject of a grant or continuing application to the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) for non-regulated status in the United States. Information relating thereto is available at any time from APHIS, 4700 River Road Riverdale, MD 20737, USA, for example via the website "http: / / www.aphis.usda.gov / brs / not_reg.html". As of the filing date of this application, applications bearing the following information have been granted or are pending with APHIS: - Application: The application identification number. A technical description of the transformation event can be found in the specific application documents available from APHIS on its website via the application number. Those descriptions are incorporated herein by reference. - Extension of application: A reference to an earlier application in which an extension in scope or duration is being sought. - Company: the name of the person submitting the application. - Restricted item: the plant species in question. - Transgenic phenotype: The trait conferred to a plant by a transformation event. - Transformation event or line: the name of the event or events (sometimes also referred to as lines) for which a regulatory exemption is being claimed. - APHIS Documents: Various documents that are relevant to the application and have been published by APHIS or are available from APHIS upon request.

[0111] Particularly useful transgenic plants that may be treated according to the present invention are plants that contain one or more genes encoding one or more toxins, such as transgenic plants sold under the following trade names: YIELD GARD® (e.g. corn, cotton, soybean), KnockOut® (e.g. corn), BiteGard® (e.g. corn), BT-Xtra® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (e.g. corn), Protecta® and NewLeaf® (potato). Examples of herbicide-resistant plants that may be mentioned include corn, cotton and soybean varieties available under the following trade names: Roundup Ready (resistant to glyphosates, e.g., corn, cotton, soybean), Liberty Link (resistant to phosphinothricin, e.g., rapeseed), IMI (resistant to imidazolinones) and SCS (resistant to sulfonylureas, e.g., corn). Herbicide-resistant plants (plants bred in a conventional manner for herbicide resistance) that may be mentioned include varieties sold under the trade name Clearfield (e.g., corn).

[0112] Particularly useful transgenic plants that can be treated according to the present invention include a combination of transformation events or transformation events, and are, for example, plants that are listed in the databases of various national or regional regulatory agencies (see, for example, http: / / gmoinfo.jrc.it / gmp_browse.aspx and http: / / cera-gmc.org / index.php?evidcode=&hstIDXCode=&gType=&AbbrCode=&atCode=&stCode=&coIDCode=&action=gm_crop_database&mode=Submit). EXAMPLES

[0113] A. Chemical Examples The following examples illustrate the invention.

[0114] Synthesis of 2-chloro-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide (Example No. 1-31) [ka] To 653 mg (7.68 mmol) of 1,3,4-oxadiazol-2-amine and 2.00 g (6.98 mmol) of 2-chloro-3-(methylsulfanyl)-4-(trifluoromethoxy)benzoic acid in 50 mL of acetonitrile, 2.67 mL (33.49 mmol) of 1-methyl-1H-imidazole were added. The mixture was cooled to a temperature of 0° C.-5° C. 0.91 mL (10.47 mmol) of oxalyl chloride was added in small portions. The reaction mixture was then warmed to room temperature and stirred at that temperature for 3.5 h. For workup, the reaction mixture was freed from the solvent on a rotary evaporator and the residue was dissolved in dichloromethane and water. After phase separation, the organic phase was concentrated and the residue was dissolved in water. 6 M sodium hydroxide solution was added and then the mixture was repeatedly washed with dichloromethane. The aqueous phase was then acidified with 6M hydrochloric acid. The resulting solid was filtered off and dried. The solid was then dissolved again in dichloromethane and aqueous sodium bicarbonate. After phase separation, the organic phase was stripped of solvent on a rotary evaporator. 910 mg of the desired product was isolated with a purity of 85% by weight.

[0115] Synthesis of 2-chloro-3-(methylsulfinyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide (Example No. 1-32) and 2-chloro-3-(methylsulfonyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide (Example No. 1-35) [ka] To 750 mg (85% by weight; 1.80 mmol) of 2-chloro-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide in 25 mL of dichloromethane, 713 mg (77% by weight; 3.18 mmol) of 3-chloroperoxybenzoic acid was added at room temperature. The mixture was stirred at room temperature for 6 days. Then, an additional 119 mg (77% by weight; 0.53 mmol) of 3-chloroperoxybenzoic acid was added and the mixture was stirred at room temperature until monitoring of the reaction showed significant amounts of sulfone and sulfoxide. For workup, aqueous sodium metabisulfite was added. The mixture was stirred for a few minutes and, after phase separation, the organic phase was stripped of solvent on a rotary evaporator. The residue was purified by chromatography to give 112 mg of 2-chloro-3-(methylsulfinyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide (90% purity by weight) and 68 mg of 2-chloro-3-(methylsulfonyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide (90% purity by weight).

[0116] Synthesis of 2-chloro-4-(difluoromethoxy)-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamide (Example No. 1-21) [ka] To 697 mg (8.19 mmol) of 1,3,4-oxadiazol-2-amine and 2.00 g (7.44 mmol) of 2-chloro-4-(difluoromethoxy)-3-(methylsulfanyl)benzoic acid in 50 mL of acetonitrile, 2.85 mL (35.73 mmol) of 1-methyl-1H-imidazole were added. The mixture was cooled to a temperature of 0° C.-5° C. 0.97 mL (11.17 mmol) of oxalyl chloride were added in small portions. The reaction mixture was then warmed to room temperature and stirred at that temperature for 16 h. For workup, the reaction mixture was stripped of solvent on a rotary evaporator and the residue was dissolved in dichloromethane and water. After phase separation, the organic phase was concentrated and the residue was dissolved in water. 6 M sodium hydroxide solution was added and then the mixture was washed repeatedly with dichloromethane. The aqueous phase was then acidified with 6 M hydrochloric acid. The mixture was filtered and the solid obtained was dried. The solid was then dissolved again in dichloromethane and aqueous sodium bicarbonate. After phase separation, the organic phase was stripped of solvent on a rotary evaporator. The residue was stirred with a small amount of dichloromethane and the mixture was then filtered. The solid was dried and 605 mg of the desired product (80% purity by weight) was isolated.

[0117] Synthesis of 2-chloro-4-(difluoromethoxy)-3-(methylsulfonyl)-N-(1,3,4-oxadiazol-2-yl)benzamide (Example No. 1-25) [ka] To 600 mg (80% by weight; 1.43 mmol) of 2-chloro-4-(difluoromethoxy)-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamide in 36 mL of dichloromethane, 1001 mg (77% by weight; 4.47 mmol) of 3-chloroperoxybenzoic acid was added at room temperature. The mixture was stirred at room temperature for 7 days. Then, to complete the reaction, 123 mg (77% by weight; 0.55 mmol) of 3-chloroperoxybenzoic acid and 5 mL of acetonitrile were added twice each. The mixture was stirred at room temperature until monitoring of the reaction showed complete conversion to the sulfone. For workup, an aqueous solution of sodium metabisulfite was added. The mixture was stirred for a few minutes and, after phase separation, the organic phase was stripped of solvent on a rotary evaporator. The residue was dissolved in tert-butyl methyl ether, then the mixture was filtered and the isolated solid was dried. The isolated solid was 427 mg of the desired product (90% pure by weight).

[0118] The examples given in the table below were prepared or can be obtained analogously to the methods described above. These compounds are very particularly preferred.

[0119] The abbreviations used have the following meanings: [Table 1] [Table 2] TIFF2024525526000022.tif250161TIFF2024525526000023.tif255165TIFF2024525526 000024.tif250161TIFF2024525526000025.tif254164TIFF2024525526000026.tif52165

[0120] NMR Data for Selected Examples NMR peak list method The 1H NMR data of selected examples are presented in the form of a 1H NMR peak list. For each signal peak, the δ value (ppm) is listed first, followed by the signal intensity in parentheses. The δ value / signal intensity number pairs for the various signal peaks are listed, separated from each other by semicolons.

[0121] Thus, the peak list for one example takes the following form: δ1(Intensity 1);δ2(Intensity 2);...;δ i (strength i );...;δ n (strength n ).

[0122] The intensity of the sharp signal correlates with the signal height (cm) in the printed example of the NMR spectrum, giving a true ratio of signal intensities. In the case of broad signals, several peaks or the center of the signal and their relative intensities can be shown in comparison to the most intense signal in the spectrum.

[0123] To calibrate the chemical shifts of 1H NMR spectra, tetramethylsilane is used and / or, especially if the spectrum is measured in DMSO, the chemical shifts of the solvent are used, so that in the NMR peak list, the tetramethylsilane peak may be present, but need not be.

[0124] The 1H NMR peak listing resembles a conventional 1H NMR printout and therefore includes all peaks that would normally be listed in the conventional interpretation of NMR.

[0125] Furthermore, they may also show, like a conventional 1H NMR printout, signals of the solvent, signals of stereoisomers of the target compound (which likewise form part of the subject matter of the present invention) and / or signals of impurity peaks.

[0126] In recording compound signals in the delta range of the solvent and / or water, our listing of 1H NMR peaks shows the usual solvent peaks, e.g., the DMSO peak in DMSO-D6, and the water peak (which usually have high intensity on average).

[0127] The peaks of stereoisomers of a target compound and / or the peaks of impurities usually have, on average, lower intensities than the peaks of the target compound (eg, a target compound having a purity of greater than 90%).

[0128] Such stereoisomers and / or impurities may be unique to a particular preparation method and therefore their peaks may help to confirm the reproducibility of our preparation method, in this case with respect to "by-product fingerprints".

[0129] The expert, calculating the peaks of the target compounds by known methods (MestreC, ACD simulations, and also using empirically evaluated expectation values), can separate the peaks of the target compounds, optionally using additional intensity filters, if necessary. This separation would be similar to picking relevant peaks in the conventional interpretation of 1H NMR.

[0130] Further details regarding the 1H NMR peak list can be found in Research Disclosure Database Number 564025.

[0131] [Table 3]

[0132] B. Formulation Examples (a) A dusting product is obtained by mixing 10 parts by weight of a compound of formula (I) and / or a salt thereof with 90 parts by weight of talc as an inert substance and grinding the mixture in a hammer mill.

[0133] (b) A wettable powder which disperses easily in water can be obtained by mixing 25 parts by weight of a compound of formula (I) and / or its salt with 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 and dispersing agent, followed by grinding in a pin disc mill.

[0134] (c) A dispersion concentrate which is easily dispersible in water can be obtained by mixing 20 parts by weight of the compound of formula (I) and / or its salt with 6 parts by weight of an alkylphenol polyglycol ether (Triton X 207®), 3 parts by weight of an isotridecanol polyglycol ether (8EO), and 71 parts by weight of a paraffinic mineral oil (boiling point range: for example, from about 255°C to more than about 277°C) and grinding in an attrition ball mill to a fineness of less than 5 microns.

[0135] (d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound represented by formula (I) and / or a salt thereof, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of oxethylated nonylphenol as an emulsifier.

[0136] (e) Water dispersible granules: 75 parts by weight of a compound represented by formula (I) and / or a salt thereof, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol, and 7 parts by weight of kaolin The powder is obtained by mixing the above, grinding the mixture in a pin disc mill, and granulating the resulting powder in a fluidized bed by spraying water as a granulating liquid.

[0137] (f) Water dispersible granules may also be milled in a colloid mill: 25 parts by weight of a compound represented by formula (I) and / or a salt thereof, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate, and 50 parts by weight of water It can also be obtained by homogenizing and pre-grinding the above-mentioned mixture, then grinding the mixture in a bead mill and spraying and drying the resulting suspension in a spray tower using a one-phase nozzle.

[0138] C. Biological Data The abbreviations used below have the following meanings: [Table 4]

[0139] 1. Post-emergence herbicidal effect against harmful plants Seeds of monocotyledonous and dicotyledonous weed and crop plants are placed in sandy loam in wood fibre pots, covered with soil and cultivated under good growing conditions in a greenhouse. After 2-3 weeks after sowing, the test plants are treated at the one-leaf stage. The green parts of the plants are sprayed with the compounds of the invention, formulated in the form of wettable powders (WP) or as emulsifiable concentrates (EC), as aqueous suspensions or emulsions with an application volume equivalent to 600-800 L / ha with the addition of 0.2% wetting agent. After leaving the test plants in the greenhouse under optimal growing conditions for about 3 weeks, the effectiveness of the preparations is visually assessed in comparison with untreated controls (herbicidal effectiveness (%): 100% activity = death of plants, 0% activity = same as control plants).

[0140] [Table 5]

[0141] [Table 6]

[0142] [Table 7]

[0143] [Table 8]

[0144] [Table 9]

[0145] [Table 10]

[0146] [Table 11]

[0147]

Table 12

[0148]

Table 13

[0149]

Table 14

[0150]

Table 15

[0151]

Table 16

[0152]

Table 17

[0153]

Table 18

[0154]

Table 19

[0155]

Table 20

[0156]

Table 21

[0157]

Table 22

[0158]

Table 23

[0159]

Table 24

[0160]

Table 25

[0161]

Table 26

[0162]

Table 27

[0163]

Table 28

[0164]

Table 29

[0165]

Table 30

[0166]

Table 31

[0167] As shown by the results in Table 1a / b, Table 2a / b, Table 3a / b, Table 4a / b, Table 5, Table 6a / b, Table 7a / b, Table 8a / b, Table 9a / b, Table 10a / b, Table 11a / b, Table 12a / b, Table 13a / b and Table 14a / b, the compounds of the present invention have good post-emergence herbicidal activity against a wide range of grass and broadleaf weeds. For example, the examples described show 80-100% activity at an application rate of 80 / 20 g / ha against, among others, black foxtail (Alopecurus myosuroides), crabgrass (Digitaria sanguinalis), green foxtail (Setaria viridis), Veronica persica and Viola tricolor. Thus, the compounds of the present invention are suitable for controlling undesirable plant growth in a post-emergence manner.

[0168] 2. Pre-emergence herbicidal activity and crop plant compatibility Seeds of monocotyledonous and dicotyledonous weed and crop plants are placed in sandy loam in wood fiber pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsifiable concentrates (EC), are then applied to the surface of the covered soil as aqueous suspensions or emulsions with a spray volume equivalent to 600-800 L / ha with the addition of 0.2% wetting agent. After treatment, the pots are placed in a greenhouse and maintained under good growing conditions for the test plants. After a test period of 3 weeks, the damage to the test plants is visually assessed by comparison with untreated controls (herbicidal activity (%): 100% activity = death of plants, 0% activity = same as control plants).

[0169] [Table 32]

[0170] [Table 33]

[0171] [Table 34]

[0172]

Table 35

[0173]

Table 36

[0174]

Table 37

[0175]

Table 38

[0176]

Table 39

[0177]

Table 40

[0178]

Table 41

[0179]

Table 42

[0180]

Table 43

[0181]

Table 44

[0182]

Table 45

[0183]

Table 46

[0184]

Table 47

[0185]

Table 48

[0186]

Table 49

[0187]

Table 50

[0188]

Table 51

[0189]

Table 52

[0190]

Table 53

[0191]

Table 54

[0192] [Table 55]

[0193] [Table 56]

[0194] [Table 57]

[0195] [Table 58]

[0196] [Table 59]

[0197] As shown by the results in Tables 1a / b, 2a / b, 3a / b, 4a / b, 5a / b, 6a / b, 7a / b, 8a / b, 9a / b, 10a / b, 11a / b, 12a / b, 13a / b and 14a / b, the compounds of the present invention have good pre-emergence herbicidal activity against a wide range of grass weeds and broadleaf weeds. For example, the compounds show 80-100% activity at an application rate of 80 / 20 g / ha against, inter alia, black foxtail (Alopecurus myosuroides), oat (Avena fatua), crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crus-galli), Lolium rigidum, green foxtail (Setaria viridis), redroot pigweed (Amaranthus retroflexus), viola tricolor and persica (Veronica persica).The compounds of the invention are therefore suitable for controlling undesirable plant growth in a pre-emergence manner.

Claims

1. Formula (I) 【Chemical 1】 〔In the formula, the symbols and subscripts are defined as follows: X is halogen, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-alkoxy, halo-(C １ -C ６ )-alkoxy, (C １ -C ４ )-alkoxy-(C １ -C ４ )-alkyl or (C １ -C ６ )-alkyl-(O) ｎ S; Z is halo-(C １ -C ６ )-alkoxy; R is (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl or (C ３ -C ６ )-cycloalkyl; n is 0, 1 or 2〕 The benzamide represented by the formula or a salt thereof.

2. X is halogen, (C １ -C ６ )-alkyl, CF ３ , (C １ -C ６ )-alkoxy, (C １ -C ４ )-alkoxy-(C １ -C ４ )-alkyl or (C １ -C ６ )-alkylthio; Z is halo-(C １ -C ６ )-alkoxy; R is (C １ -C ６ )-alkyl or cyclopropyl; n is 0, 1 or 2; The benzamide according to Claim 1.

3. X is halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-alkoxy, (C １ -C ４ )-alkoxy-(C １ -C ４ )-alkyl or (C １ -C ６ )-alkylthio; Z is halo-(C １ -C ２ )-alkoxy; R is (C １ -C ６ )-alkyl and n is 0, 1 or 2; The benzamide according to Claim 1 or 2.

4. X is F, Cl, Br, Me, Et, MeO, EtO, MeOCH ２ or MeS; Z is HF ２ CO or F ３ is CO; R is Me or Et; n is 0, 1 or 2; The benzamide according to Claim 1.

5. A herbicide composition or a plant growth regulator composition, characterized by containing one or more benzamides represented by the general formula (I) according to Claim 1 or a salt thereof, said herbicide composition or plant growth regulator composition.

6. The herbicide composition according to Claim 5, further containing a formulation adjuvant.

7. The herbicide composition according to Claim 5 or 6, containing at least one additional active ingredient selected from the group consisting of insecticides, acaricides, herbicides, fungicides, phytotoxicity reducers and / or growth regulators.

8. The herbicide composition according to Claim 5 or 6, containing a phytotoxicity reducer.

9. The herbicide composition according to Claim 8, wherein the phytotoxicity reducer is selected from the group consisting of mefenpyr - diethyl, cyprosulfamide, isoxadifen - ethyl, clomazone - methyl, benoxacor and dichlormid.

10. A method for controlling unwanted plants, characterized by applying an effective amount of at least one benzamide represented by the formula (I) according to Claim 1 or the herbicide composition according to Claim 5 to the plants or to the growth environment of the unwanted vegetation, said method.

11. Use of the benzamide represented by the formula (I) according to Claim 1 or the herbicide composition according to Claim 5 for controlling unwanted plants.

12. The use according to Claim 11, characterized in that the benzamide represented by the formula (I) is used for controlling unwanted plants in crops of useful plants.

13. The use according to Claim 12, characterized in that the useful plants are useful transgenic plants.

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