N-(1,3,4-oxadiazole-2-yl)phenylcarboxamide as a herbicide

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, and more particularly 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 having a substituted 1,3,4-oxadiazole on the nitrogen atom of the amide group. WO2021094505A1 describes a herbicidal benzamide having a haloalkoxy group at the 4-position of the phenyl ring, and the substituted 1,3,4-oxadiazole is one of the substituents on the nitrogen atom of that 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 [Overview of the project] [Problems that the invention aims to solve]

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

[0005] In benzamide, • The amide group has an unsubstituted 1,3,4-oxadiazole on the nitrogen atom; • It has a haloalkoxy group at the 4-position of the phenyl ring; and, • The 5th and 6th positions of the phenyl ring are unsubstituted; It was found that the aforementioned benzamides possess superior properties compared to benzamides known from the prior art.

[0006] Therefore, the present invention relates to formula (I) [ka] [In the formula, symbols and subscripts are defined as follows: X is a 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 is; Z is a halo-(C1-C6)-alkoxy; R is (C1-C6)-alkyl, halo-(C1-C6)-alkyl, or (C3-C6)-cycloalkyl; n is 0, 1, or 2. The present invention provides benzamide or a salt thereof represented by the following:

[0007] In formula (I) and all the following formulas, alkyl radicals having three or more carbon atoms can be linear or branched. Examples of alkyl radicals include 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, examples of alkenyls include allyl, 1-methylpropa-2-en-1-yl, 2-methylpropa-2-en-1-yl, buta-2-en-1-yl, buta-3-en-1-yl, 1-methylbuta-3-en-1-yl, and 1-methylbuta-2-en-1-yl. Examples of alkynyls include propargyl, buta-2-in-1-yl, buta-3-in-1-yl, and 1-methylbuta-3-in-1-yl. Multiple bonds can be present at any position on each unsaturated radical. Cycloalkyls are carbocyclic saturated ring systems having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Halogen-substituted alkyls refer to linear or branched alkyl groups in which some or all of the hydrogen atoms in their groups can be replaced by halogen atoms, such as C1-C2-haloalkyls, for example 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-trifluoropropane-2-yl.

[0008] Halogens represent fluorine, chlorine, bromine, or iodine.

[0009] A heterocyclic radical (heterocyclyl) is a five- or six-membered cyclic radical containing, in addition to a carbon atom, at least one heteroatom selected from the group N, O, and S, where the cyclic radical is saturated, unsaturated, partially saturated, or heteroaromatic, and may or may not be substituted, in which case the binding site is on the ring atom. Examples of heterocyclic radicals are: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2- or 3-yl, 2,3-dihydro-1H-pyrrole-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrole-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridine-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-pyran n-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophen-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophen-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-pyrazole-3- or 4- or 5-yl; 4,5-Dihydro-1H-pyrazole-1- or 3- or 4- or 5-yl; 2,3-Dihydro-1H-pyrazole-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-Di Hydro-1H-imidazole-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; hexahydropyridazine-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazine-1- or 3- - or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3- or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3- or 4-yl; 1,6-dihydropyridazine-1- or 3- or 4- or 5- or 6-yl; hexahydropyrimidine-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidine Limidine-1- or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidine-2- or 4- or 5-yl; 4,5-dihydropyrimidine-4- or 5- or 6-yl; 1,4-dihydropyrimidine-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-dioxolan-2- or 4- or 5-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-dithio In-3- or 4- or 5- or 6-yl; 3,6-dihydro-1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; 1,3-dithian-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-dihydroisoxazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisoxazole-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazole-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-oxazinane-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazine-3- or 4- or 5- or 6-yl; 4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 1,3-oxazinane-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 6H-1,3-oxazine-2- or 4- or 5- or 6-yl; 4H-1,3-oxazine-2- or 4- or 5- or 6-yl; morpholine-2- or 3- or 4-yl; 3,4-dihydro -2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 4H-1,4-oxazine-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 Lu; 1,3-thiazolidinedione-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazole-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-thiazole-2- or 4- or 5-yl; 4,5-dihydro-1,3-thiazole-2- or 4- or 5-yl; 1,3-thiadinane-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-thiadin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-thiadin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,3-thiazine-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-thiazine-2- or 4- or 5- or 6-yl; 2H-1,3-thiazine-2- or 4- or 5- or 6-yl; 6H-1,3-thiazine-2- or 4- or 5- or 6-yl; 4H-1,3-thiazine-2- or 4- or 5- or 6-yl; 4,2-dioxazolidine-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-dioxazine-3- or 5- or 6-yl; 1,4,2-dioxazine-3- or 5- or 6-yl.

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

[0011] Compounds represented by formula (I) may form salts. Suitable bases include, for example, organic amines, such as trialkylamines, morpholine, piperidine, or pyridine, and furthermore, hydroxides, carbonates, and bicarbonates of ammonium, alkali metals, or alkaline earth metals, particularly sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, such as metal salts, particularly alkali metal salts or alkaline earth metal salts, particularly sodium salts and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example, of formula [NRR'R''R'''] + The salt is a cation represented by the formula [wherein R~R''' is independently an organic radical, particularly alkyl, aryl, aralkyl, or alkylaryl]. Similarly useful are alkylsulfonium salts and alkylsulfoxonium salts, for example, (C1-C4)-trialkylsulfonium salts and (C1-C4)-trialkylsulfoxonium salts. [Modes for carrying out the invention]

[0012] The preferred general formula is (I) [wherein the formula, the symbols and subscripts have the following meanings: X is a halogen, (C1-C6)-alkyl, CF3, (C1-C6)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, or (C1-C6)-alkylthio; Z is a halo-(C1-C6)-alkoxy; R is (C1-C6)-alkyl or cyclopropyl; n is 0, 1, or 2. It is a compound represented by [formula].

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

[0014] Of particular preference is general formula (I) [wherein the formula, the symbols and subscripts are defined as follows: X is F, Cl, Br, Me, Et, MeO, EtO, MeOCH2, or MeS; Z is either HF2CO or F3CO; R is either Me or Et; n is 0, 1, or 2. It is a compound represented by [formula].

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

[0016] The post-treatment of each reaction mixture is generally carried out by known methods, such as crystallization, aqueous extraction, chromatography, or a combination of these methods.

[0017] Collects of compounds represented by formula (I) and / or their salts that can be synthesized by the above reaction can be prepared in parallel, in which case this can be carried out manually, partially automated, or fully automated. For example, the reaction, workup, or purification of the product and / or intermediates can be automated. Generally, this is understood to mean the method described by D. Tiebes, for example, on pages 1-34 of "Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999".

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

[0019] The present invention also provides a method for controlling or regulating the growth of undesirable plants, preferably within crop plants, wherein one or more compounds according to the present invention are applied to the plant (e.g., harmful plants, e.g., monocotyledonous or dicotyledonous weeds, or undesirable crop plants), or to the seeds (e.g., grains, seeds, or vegetative reproductive organs, e.g., tubers, or shoot portions with buds), or to the area where the plant is growing (e.g., cultivated land). The compounds of the present invention can be used, for example, before planting (and, where appropriate, further by mixing into the soil), before emergence, or after emergence. Specific examples of some representative monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds of the present invention are listed below, but such enumerated examples are not intended to be limited to specific 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, Na Genus 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: Genus Abutilon, Amaranthus, Ambrosia, Anoda, Chamomile, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium 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 Rhododendron ( Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica,Viola and Xanthium genera.

[0022] When the compound of the present invention is applied to the soil surface before germination, the emergence of weed seedlings is completely prevented, or the weeds grow until they reach the cotyledon stage, after which their growth stops.

[0023] When the active ingredient is applied to the green parts of a plant after it has grown, its growth stops after treatment, and the harmful plant either remains at the growth stage at the time of application or dies completely after a certain period of time. As a result, competition with weeds harmful to crop plants is eliminated very early and sustainably.

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

[0025] These active ingredients can also be used to control harmful plants in known or future genetically modified crops due to their herbicidal and plant growth regulating properties. Generally, transgenic plants are characterized by specific advantageous properties, such as resistance to certain active ingredients used in the pesticide industry (especially certain herbicides), or resistance to plant diseases or pathogens of plant diseases (e.g., certain insects or microorganisms, such as fungi, bacteria, or viruses). Other specific properties relate to, for example, the quantity, quality, storability, composition, and specific components of the harvested product. For example, there are known transgenic plants with increased starch content or altered starch quality, or known transgenic plants with different fatty acid compositions in the harvested product. Further specific properties include tolerance or resistance to abiotic stressors, such as heat, cold, drought, salinity, and ultraviolet radiation.

[0026] Preferably, the compound of the present invention represented by formula (I) or a salt thereof is used in economically important transgenic crops of useful plants and ornamental plants.

[0027] The compound represented by formula (I) can be used as a herbicide in crops of useful plants that are resistant to the plant toxicity of the herbicide or have been made resistant through genetic engineering.

[0028] Conventional methods for producing novel plants with modified characteristics compared to existing plants include, for example, conventional cultivation methods and the generation of mutants. Alternatively, novel plants with altered characteristics can be produced using recombinant DNA (see, for example, EP 0221044 and EP 0131624). For example, the following are some of the cases described: Genetic modification of crop plants intended to modify starch synthesized within the plant body (e.g., WO 92 / 011376A, WO 92 / 014827A, WO 91 / 019806A); Transgenic crop plants, e.g., Optimum, that exhibit resistance to specific glufosinate-type (cf. e.g., EP 0242236A, EP 0242246A), glyphosate-type (WO 92 / 000377A), or sulfonylurea-type (EP 0257993A, US 5,013,659) herbicides, or that exhibit resistance to combinations or mixtures of these herbicides by "gene stacking". TM GAT TM Transgenic crop plants having the trade name or designation (glyphosate ALS resistant), such as maize or soybean; Transgenic crop plants (e.g., cotton) that can produce Bacillus turingiensis toxin (Bt toxin), which makes plants resistant to specific pests (EP 0142924A, EP 0193259A); • Transgenic crop plants with modified fatty acid compositions (WO 91 / 013972A); • Genetically modified crop plants containing novel components or secondary metabolites (e.g., novel phytoalexins that improve disease resistance) (EP 0309862A, EP 0464461A); • Genetically modified plants with reduced photorespiration that exhibit higher yields and greater stress tolerance (EP 0305398A); • Transgenic crop plants that produce pharmaceutically or diagnostically important proteins ("molecular pharming"); • Transgenic crop plants characterized by higher yields or superior quality; • For example, transgenic crop plants ("gene stacking") that are distinguished by the combination of novel characteristics described above.

[0029] Many molecular biological techniques are known in principle that can be used to produce novel transgenic plants with modified characteristics; 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] Regarding such genetic manipulation, nucleic acid molecules that enable mutagenesis or sequence modification by DNA recombination can be introduced into plasmids. Using standard methods, for example, base exchanges can be performed, partial sequences 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 gene product activity 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 the gene product. For this purpose, it is possible to first use a DNA molecule containing the entire coding sequence of the gene product, including all possible flanking sequences, and furthermore, to use a DNA molecule containing only a portion of the coding sequence (in this case, these portions must be long enough to have an antisense effect in the cell). Furthermore, it is also possible to use DNA sequences that are highly homologous to the coding sequence of the gene product, but not identical to them.

[0032] When nucleic acid molecules are expressed within a plant, the synthesized protein can be localized to any desired compartment of the plant cell. However, to localize it to a specific compartment, it is possible, for example, to ligate the coding region to a DNA sequence that guarantees localization to that 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", and "Sonnewald et al., Plant J. 1 (1991), 95-106"). Furthermore, such nucleic acid molecules can also be expressed within organelles of plant cells.

[0033] Transgenic plant cells can be regenerated using known techniques for producing complete plants. In principle, transgenic plants can be any desired plant species, that is, they can be monocots as well as dicots.

[0034] In this way, transgenic plants can be obtained that have altered characteristics due to the overexpression, suppression, or inhibition of homologous (=natural) genes or gene sequences, or the expression of non-homologous (=foreign) genes or gene sequences.

[0035] Compound (I) of the present invention can preferably be used in transgenic crops resistant to growth regulators (e.g., 2,4-D, dicamba), or in transgenic crops resistant to herbicides that inhibit essential plant enzymes (e.g., acetolactic acid 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 benzoyl isoxazoles and similar active ingredients, or in transgenic plants resistant to any desirable combination of these active ingredients.

[0036] The compounds of the present invention can be used, in particular, in transgenic crop plants that exhibit resistance to combinations of glyphosates and glufosinates, or combinations of glyphosates and sulfonylureas or imidazolinones. Most preferably, the compounds of the present invention can be used, for example, in Optimum TM GAT TM It can be used in transgenic crop plants (e.g., maize or soybean) that have the trade name or designation (glyphosate ALS resistant).

[0037] When the active ingredient of the present invention is used in a transgenic crop, not only are the effects on harmful plants observed in other crops produced, but often effects specific to the application in a particular transgenic crop, such as a modified or particularly expanded spectrum of controllable weeds, modified application rates that can be used for such application, preferably good compatibility with herbicides to which the transgenic crop is resistant, and effects on the growth and yield of the transgenic crop plant.

[0038] Accordingly, the present invention also relates to the use of the compound represented by formula (I) as a herbicide for controlling harmful plants in transgenic crop plants.

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

[0040] The compounds of the present invention can be formulated in various ways depending on the required biological and / or physicochemical parameters. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsions (EC), emulsions (EW), such as oil-in-water emulsions and water-in-oil emulsions, sprayable solutions, suspension formulations (SC), oil or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, broadcast granules and soil application granules, granules in the form of fine particles (GR), spray granules, absorption granules, and adsorption granules. These include granules, wettable granules (WG), water-soluble granules (SG), micro-spray formulations, microencapsulated formulations, and waxes. The types of these individual formulations are generally known 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", and "K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd. London".

[0041] Necessary formulation aids such as inert substances, surfactants, solvents, and further additives are also known and described, for example, in the following: "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] Based on these formulations, it is also possible to manufacture combinations with other active ingredients (e.g., insecticides, acaricides, herbicides, fungicides), and further combinations with phytotoxicity reducers, fertilizers and / or growth regulators, for example, in the form of finished formulations or as tank mixes.

[0043] Possible adjuncts for use in mixed formulations or tank mixes with compounds represented by general formula (I) include, for example, known active ingredients that inhibit acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvirshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, or protoporphyrinogen oxidase, or that act as plant growth regulators, as known from, for example, "Weed Research 26 (1986) 441-445" or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the literature cited therein.

[0044] Examples of known herbicides or plant growth regulators that can be combined with compounds represented by general formula (I) include the following active ingredients (where the compounds are indicated by their "generic names" according to the International Organization for Standardization (ISO), their chemical names, or their code numbers), and these always encompass all forms of use (e.g., acids, salts, esters) and all isomers (e.g., stereoisomers and optical isomers). These include, for example, a single form of use, but in some cases, multiple forms of use: Acetochlor, aciflorphen, aciflorphen-methyl, aciflorphen-sodium, acroniphen, alachlor, alidocrol, alloxidim, alloxidim-sodium, ametrine, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralide, aminopyralide-dimethylammonium, Aminopyralide-tripromine, amitorol, ammonium sulfamate, anirophos, aslam, aslam-potassium, aslam-sodium, atrazine, azaphenidine, azimusulfuron, beflubutamide, (S)-(-)-beflubutamide, beflubutamide-M, benazoline, benazoline-ethyl, benazoline-dimethylammonium, benazoline-potassium, benfluralin, benfresate, bensulfuron, bensulfuron-methyl, benslid, bentazon, bentazon-sodium, benzobicyclon, benzofenap, bisic Ropiron, Bifenox, Viranafos, Viranafos-sodium, Bipirazone, Bispiribac, Bispiribac-sodium, Bixlozone, Bromacil, Bromacil-lithium, Bromacil-sodium, Bromobutide, Bromophenoxime, Bromoxynil, Bromoxynil-butyrate, Bromoxynil-potassium, Bromoxynil-heptanoate and Bromoxynil-octanoate, Busoxinon, Butachlor, Butaphenacil, Butamiphos, Butenaclor, Buttraline, Butroxidime, Butyrate, Caffeine Nstrol, Cambendichlor, Carbetamide, Carfentrazone, Carfentrazone-ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamine, Chloramben-methyl, Chloramben-methylammonium, Chloramben-sodium, Chlorbromulone, Chlorfenac, Chlorfenac-ammonium, Chlorfenac-sodium, Chlorfenprop, Chlorfenprop-methyl, Chlorflurenol, Chlorflurenol-methyl, Chloridazone, Chlorimurone, Chlorimurone-ethyl, Chlorophthalim,Chlorotolurone, chlorsulfuron, chlortal, chlortal-dimethyl, chlortal-monomethyl, synidone, synidone-ethyl, symmetrin, exo-(+)-symmetrin, i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)-symmetrin, i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo [2.2.1] Heptane, cinosulfurone, clasiphos, cretodym, clodinahop, clodinahop-ethyl, clodinahop-propargyl, chromazon, clomeprop, clopyralide, clopyralide-methyl, clopyralide-olamine, clopyralide-potassium, clopyralide-tripomin, chloranslam, chloranslam-methyl, cumylon, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamurone, cycloxidym, cyhalofop, cyha Rohop-butyl, cyprazine, 2,4-D (and its ammonium salts, butotyl salt, butyl salt, choline salt, diethylammonium salt, dimethylammonium salt, diolamin salt, doboxyl salt, dodecylammonium salt, etexyl salt, ethyl salt, 2-ethylhexyl salt, heptylammonium salt, isobutyl salt, isooctyl salt, isopropyl salt, isopropylammonium salt, lithium salt, meptyl salt, methyl salt, potassium salt, tetradecylammonium salt, triethylammonium salt, tori Sopropanolammonium salt, tripromine 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), darapon, darapon-calcium, darapon-magnesium, darapon-sodium, dazomet, darapon-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedifam, detosyl pyrazolate (DTP), dicamba and its salts (e.g., dicamba biproamine, dicamba N,N-bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline,Dicanba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolamineammonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolamine, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine), diclobenyl, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidine-3-one, 2-(2,5-dichlorobenzyl)-4,4-di Methyl-1,2-oxazolidine-3-one, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-ethoxyl, dichlorprop-ethylammonium, dichlorprop-isooctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-ethoxyl, dichlorprop-P-potassium, dichlorprop- Sodium, diclohop, diclohop-methyl, diclohop-P, diclohop-P-methyl, diclothram, diphenzocort, diphenzocort-methylsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimeflon, dimepiperate, dimesulfazet, dimethachlor, dimethametrin, dimethenamide, dimethenamide-P, dimethrasulfuron, dinitramine, dinoterb, dinoterb-acetate, diphenamide, diquat, diquat-dibromide, diquat To-dichloride, dithiopyr, diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, endotal, endotal-diammonium, endotal-dipotassium, endotal-disodium, epiriphenacil (S-3100), EPTC, esprocarb, ethalfluralin, etamethosulfuron, etamethosulfuron-methyl, ethidine, etofumesate, 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-benzimidazole-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, phenoxaprop, phenoxaprop-P, phenoxaprop-ethyl, phenoxaprop-P-ethyl, phenoxasulfone, fenpyrazone, Fenquinotrione, Fentrazamide, Flamprop, Flamprop-isopropyl, Flamprop-methyl, Flamprop-M-isopropyl, Flamprop-M-methyl, Flazasulfuron, Floraslam, Florpyrauxifen, Florpyrauxifen-benzyl, Fluadifop, Fluadifop-butyl, Fluadifop-methyl, Fluadifop-P, Fluadifop-P-butyl, Flucarbazone, Flucarbazone-sodium, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpir, Flufenpi Lu-ethyl, flumetsuram, flumicrolac, flumicrolac-pentyl, flumioxazine, fluomethron, flurenol, flurenol-butyl,-dimethylammonium and-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupropanate-sodium, flupyrusulfuron, flupyrusulfuron-methyl, flupyrusulfuron-methyl-sodium, flulidone, flulochloridone, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-meptyl, flulutamone, fluthiaset, flu Luthiaset-methyl, homesaphen, homesaphen-sodium, horamsulfuron, horamsulfuron-sodium, hosamin, hosamin-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-p-sodium, glufosinate-p-ammonium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium,Glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium and glyphosate-trimethium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidethioate, halaxifen, halaxifen-methyl, halosaphene, halosulfuron, halosulfuron-methyl, haloxyhop, haloxyhop-P, haloxyhop-ethoxyethyl, haloxyhop-P-ethoxyethyl, haloxyhop-methyl, haloxyhop-P-methyl, haloxyhop-sodium, hexazinone, HNPC-A8169, i.e., propa-2-in-1-yl(2S)-2-{3-[(5-tert-butylpyridine-2-yl )Oxy]phenoxy}propanoate, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy)acetate, hydantocidin, imazametabenz, imazametabenz-methyl, imazamox, imazamox-ammonium, imazapick, imazapick-ammonium, imazapyr, imazapyr-isopropylammonium, imazakine, imazakine-ammonium, imazakine-methyl, imazetapir, imazetapir-ammonium Um, Imazosulfuron, Indanophan, Indadiflame, Iodosulfuron, Iodosulfuron-methyl, Iodosulfuron-methyl-sodium, Ioxynyl, Ioxynyl-lithium, -octanoate, -potassium and -sodium, Ipfencarbazone, Isoproturone, Isouron, Isoxaben, Isoxaflutol, Carbutyrate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-yl ]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, ketospiradox-potassium, lactofen, 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, Mu, Mefenacet, Mefluidide, Mefluidide-Diolamine, Mefluidide-Potassium, Mesosulfuron, Mesosulfuron-Methyl, Mesosulfuron-Sodium, Mesotrione, Metabenzthiazulon, Metam, Metamihop, Metamitron, Metazachlor, Metazosulfuron, Metabenzthiazulon, Methiopyrsulfuron, Methiozoline, Methyl Isothiocyanate, Metobromulone, Metrachlor, S-Metrachlor, Metoslam, Metoxlon, Metrivudine, Metosulfuron, Metosulfur N-methyl, molinate, monolinurone, monosulfuron, monosulfuron-methyl, MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, NC-656, i.e., 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazole-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo-[4,3- a] Pyridine-8-carboxamide, Nebulon, Nicosulfuron, Nonanoic acid (pelargonic acid), Norflurazone, Oleic acid (fatty acid), Olbencarb, Orthosulfamurone, Oryzalin, Oxaziargyl, Oxadiazone, Oxasulfuron, Oxadiclomephone, Oxyfluorphene, Paraquat, Paraquat-dichloride, Paraquat-dimethyl sulfate, Pebrate, Pendimethalin, Penoxuslam, Pentachlorophenol, Pentoxazone, Petoxamide, Petroleum, Fenmedifame, Fenmedifame-ethyl, Pichloram, Picloram Loram-dimethylammonium, picloram-etexyl, picloram-isooctyl, picloram-methyl, picloram-olamine, picloram-potassium, picloram-triethylammonium, picloram-tripromine, picloram-troramine, picolinafene, pinoxadene, piperofos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, prophoxidyme, prometon, promethrin, propacrol, propanil, propaxafop, propazine, profam, propisochlor, propoxycarbazone,Sodium propoxycarbazone, propyrisulfuron, propizamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfolol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyrifthalide, pyriminovac, pyriminovac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxislam, quinchlorac, quinchlorac-dimethylammonium , quinchlorac-methyl, quinmelac, quinoclamin, quizalopop, quizalopop-ethyl, quizalopop-P, quizalopop-P-ethyl, quizalopop-P-tefuryl, QYM201, i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazole-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidine-2-one, limsulfuron, saflufenacil, cethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfenthrazone, sulfomethane, sulfomethane-methyl, sulfosulfuron, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobuta-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(propa-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazine-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g., TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiurone, tefuryltrione, tembotrione, tepraloxidim, terbasil, terbucarb, terbumetone, terbutyrazine, terbutrin, tetoflupyrrolimet, taxomin, tenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron,Thiafensulfuron-methyl, thiobencarb, thiafenacil, torpylate, topramezon, tralcoxidime, triafamone, trialate, triasulfuron, triaziflame, tribenulon, tribenulon-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr-ethyl, triclopyr-triethylammonium, trietadine, 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-dimethoxypyrimidine-2-yl)oxy]benzyl}aniline, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidine-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate ethyl ester, [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}pyridine-2-yl)oxy]ethyl acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl 5-Chloropyrimidine-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohexa-1-en-1-yl)carbonyl]-6-methylpyridazine-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridine-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazole-4-yl)(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophene-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophene-5-yl)carbonyl]-1H-pyrazole-5-ylpropane-1-sulfonate,4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazole-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazole-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate cyanomethyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate prop-2-in-1-yl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate methyl, 4-amino-3- Chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylic acid, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylic acid benzyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylic acid ethyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indole-6-yl)pyridine-2-carboxylic acid Methyl carboxylate, 6-(1-acetyl-7-fluoro-1H-indole-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate methyl, 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indole-6-yl]-5-fluoropyridine-2-carboxylate methyl, 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indole-6-yl]pyridine-2-carboxylate methyl, 4-amino -3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate potassium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate sodium, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate butyl, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridine-2-yl]imidazolidin-2-one,3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidined-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridine-2-yl]-4-hydroxy-1-methylimidazolidined-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridine-2-yl]imidazolidined-2-one, 6-[(2-hydroxy-6-oxocyclohexa-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-oxocyclohexa-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholine-4-ylmethyl)benzoyl]-3-hydroxycyclohexa-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidine-2-yl)pyridazine-1-ium salt (appropriate) Salts with suitable anions (e.g., chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salt (salts with suitable anions (e.g., chloride, acetate, or trifluoroacetate)), 4-(pyrimidine-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (salts with suitable anions (e.g., chloride, acetate, or trifluoroacetate)), 4-(pyridazin-3-yl)-1-(2-sulfoethyl ) Pyridazine-1-ium salt (salt with a suitable anion (e.g., chloride, acetate or trifluoroacetate)), 1-(2-carboxyethyl)-4-(1,3-thiazole-2-yl)pyridazine-1-ium salt (salt with a suitable anion (e.g., chloride, acetate or trifluoroacetate)), 1-(2-carboxyethyl)-4-(1,3-thiazole-2-yl)pyridazine-1-ium salt (salt with a suitable anion (e.g., chloride, acetate or trifluoroacetate)),Methyl (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)-2-(trifluoromethyl)benzaldehyde O-{2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy]benzoyl}oxime, 2-fluoro-N-(5-methyl-1,3,4-oxadiazole-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino, -3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid.

[0045] Examples of plant growth regulators that can be used as mixing partners are as follows: Abscisic acid and related analogues [e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohexa-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohexa-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohexa-2-en-1-yl)penta-2,4-dienoate, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl (Tyl-4-oxocyclohexa-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, methyl(2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohexa-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.0) (Hepta-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-aminocyclopropane-1-carboxylic acid N-methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1-aminocyclopropane-1-carboxylic acid derivatives (described in DE3335514, EP30287, DE2906507 or US5123951), 1-aminocyclopropyl-1-hydroxamic acid, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, L-canavanine, catechol and catechols (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chito-oligosaccharides (CO; COs are different from LCOs in that they do not have the fatty acid side chains that are characteristic of LCOs. COs are sometimes also referred to as N-acetylchito-oligosaccharides and are similarly composed of GlcNAc units, but they themselves are chitin molecules [(C8H. 13 NO5) n , CAS No. 1398-61-4] and chitosan molecules [(C5H 11 NO4) n(Having a side chain that distinguishes it from [CAS-No.9012-76-4]), chitin-like compounds, chlormecoat-chloride, cloprop, cyclanilide, 3-(cyclopropa-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamide]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamide]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet-sodium, n-decanol, dikeglac, dikeglac-sodium, endotar, endotar-dipotassium (dipo Tassum), disodium and mono(N,N-dimethylalkylammonium), etephon, 1-ethylcyclopropene, flumetraline, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyrate, isoprothiolane, probenazole, jasmonic acid, jasmonic acid ester or other derivatives (e.g., methyl jasmonate, ethyl jasmonate), lipochytooligosaccharide (LCO, sometimes also called symbiotic nodulation signal (Nod or Nod factor) or Myc factor, and composed of an oligosaccharide skeleton consisting of a β-1,4-linked N-acetyl-D-glucosamine residue ("GlcNAc") having an N-linked fatty acid side chain condensed at the non-reducing end.As can be inferred from the literature, LCOs differ in the number of GlcNAc units in their skeletal structure, in the length and saturation of the fatty acid chain, and in the substitutions in reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic acid hydrazide, mepicote chloride, mepicote pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinoline-6-yl)methanesulfonamide and related substitutions (tetrahydroquinoline-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydro [Fran-2-yl]oxymethylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one and related lactones (as described in EP2248421), 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, 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-phenylphthalamidic acid, prohexadione, prohexadione-calcium, 1-n-propylcyclopropene, putrescine, prohydrojasmon, rhizobitoxin, salicylic acid and methyl salicylate, sarcosine, sodium Cyclopropane-1-en-1-yl acetate, sodium Cyclopropane-2-en-1-yl acetate, sodium 3-(cyclopropane-2-en-1-yl)propanoate, sodium 3-(cyclopropane-1-en-1-yl)propanoate, sidefungin, spermidine, spermine, strigolactone, technazene, tidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine.

[0046] A phytotoxicity reducing agent that can be used in combination with the compound of the present invention represented by formula (I), and optionally in combination with further active ingredients (for example, the fungicides, herbicides, acaricides, and insecticides listed above), is preferably selected from the group consisting of the following.

[0047] (S1) Equation (S1) [ka] [In the formula, the symbols and subscripts have the following meanings: n A is a natural number between 0 and 5, preferably a natural number between 0 and 3; R A 1 These are halogens, (C1-C4)-alkyls, (C1-C4)-alkoxys, nitros, or (C1-C4)-haloalkyls; 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 (where the ring contains at least one nitrogen atom and at most one oxygen atom), preferably (W A 1 )~(W A 4 ) [ka] A radical selected from the group; m A is either 0 or 1; R A 2 is OR A 3 , SR A 3 Or NR A 3 R A 4Either or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms (preferably heteroatoms selected from the group consisting of O and S) (where the heterocycle is bonded to the carbonyl group in (S1) via the nitrogen atom, and the heterocycle is either 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 represented by formula N(CH3)2, in particular, formula OR A 3 It is a radical represented by; R A 3 is either hydrogen, or an unsubstituted or substituted (preferably having a total of 1 to 18 carbon atoms) aliphatic hydrocarbon radical; R A 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, or substituted or unsubstituted phenyl; R A 5 This refers to H, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, cyano, or COOR A 9 (Here, R A 9 These include hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-hydroxyalkyl, (C3-C 12 It is a cycloalkyl or tri-(C1-C4)-alkylsilyl; R A 6 , R A 7 , R A 8They are either the same or different, and hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C 12 )-Cycloalkyl, or substituted or unsubstituted phenyl. A compound represented by; Preferably: (a) Compounds of the type dichlorophenylpyrazoline-3-carboxylic acid (S1 a Preferably, the following compounds: 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid ethyl (S1-1) ("mefenpyr-diethyl") and related compounds (these are described in WO-A-91 / 07874); (b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1 b Preferably, the following compounds: 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate ethyl (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate ethyl (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate ethyl (S1-4) and related compounds (these are described in EP-A-333131 and EP-A-269806); (c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c Preferably, the following compounds: 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate ethyl (S1-5), 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate methyl (S1-6), and related compounds (these are described, for example, in EP-A-268554); (d) Compounds of the type of triazolecarboxylic acid (S1 dPreferably, the following compounds: fenchlorazole (-ethyl ester), i.e., 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate ethyl (S1-7) and related compounds (these 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 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e Preferably, the following compounds: 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate ethyl (S1-8) or 5-phenyl-2-isoxazoline-3-carboxylate ethyl (S1-9) and related compounds (these are described in WO-A-91 / 08202), or 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-10) or 5,5-diphenyl-2-isoxazoline-3-carboxylate ethyl (S1-11) ("isoxadifen-ethyl") or 5,5-diphenyl-2-isoxazoline-3-carboxylate n-propyl (S1-12) or 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate ethyl (S1-13) (these are described in patent application WO-A-95 / 07897).

[0048] (S2) Formula (S2) [ka] [In the formula, the symbols and subscripts have the following meanings:] R B 1 These are halogens, (C1-C4)-alkyls, (C1-C4)-alkoxys, nitros, or (C1-C4)-haloalkyls; n B is a natural number between 0 and 5, preferably a natural number between 0 and 3; R B 2 is OR B 3, SR B 3 Or NR B 3 R B 4 Either or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms (preferably heteroatoms selected from the group O and S) (where the heterocycle is bonded to the carbonyl group in (S2) via the nitrogen atom, and the heterocycle 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 represented by formula N(CH3)2, in particular, formula OR B 3 It is a radical represented by; R B 3 is either hydrogen, or an unsubstituted or substituted (preferably having a total of 1 to 18 carbon atoms) aliphatic hydrocarbon radical; R B 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, or substituted or unsubstituted phenyl; T B [The alkanediyl chain is either unsubstituted, substituted with one or two (C1-C4)-alkyl radicals, or substituted with a [(C1-C3)-alkoxy]carbonyl group] A quinoline derivative represented by; Preferably: (a) Compounds of the type 8-quinoline oxyacetic acid (S2 a ), preferably, (5-chloro-8-quinolineoxy)acetic acid 1-methylhexyl ("Croquintoset-mexyl") (S2-1), (5-chloro-8-quinolineoxy)acetic acid (1,3-dimethylbuta-1-yl)(S2-2), (5-chloro-8-quinolineoxy)acetate 4-allyloxybutyl(S2-3), (5-chloro-8-quinolineoxy)acetate 1-allyloxypropane-2-yl(S2-4), (5-chloro-8-quinoline oxy)ethyl acetate (S2-5), (5-chloro-8-quinolineoxy)methyl acetate (S2-6), (5-chloro-8-quinolineoxy)allyl acetate (S2-7), (5-chloro-8-quinolineoxy)acetic acid 2-(2-propyrideniminoxy)-1-ethyl (S2-8), (5-chloro-8-quinolineoxy)acetic acid 2-oxopropa-1-yl (S2-9) and related compounds (these are described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366), and further, (5-chloro-8-quinolineoxy)acetic acid (S2-10), its hydrates and salts, such as its lithium salt, sodium salt, potassium salt, calcium salt, magnesium salt, aluminum salt, iron salt, ammonium salt, quaternary ammonium salt, sulfonium salt or phosphonium salt (these are described in WO-A-2002 / 34048); (b) Compound of the type (5-chloro-8-quinolineoxy)malonic acid (S2 b Preferably, the following compounds: (5-chloro-8-quinolineoxy) diethyl malonate, (5-chloro-8-quinolineoxy) diallyl malonate, (5-chloro-8-quinolineoxy) methyl ethyl malonate and related compounds (these are described in EP-A-0582198).

[0049] (S3) Equation (S3) [ka] [In the formula, symbols and subscripts 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 the same 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 phenyl which is substituted or unsubstituted, or R C 2 and R C 3 together form a substituted or unsubstituted heterocyclic ring (preferably an oxazolidine ring, thiazolidine ring, piperidine ring, morpholine ring, hexahydropyrimidine ring or benzoxazine ring)] a compound represented by; Preferably: Active ingredients of the type of dichloroacetamide often used as a pre-emergence phytotoxicity reducing agent (soil-acting phytotoxicity reducing agent), for example, "Dichloromid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) [Supplier: Stauffer] (S3-2), "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) [Supplier: 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) [Supplier: PPG Industries] (S3-5), 「DKA-24」(N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) [Supplier: Sagro-Chem] (S3-6), 「AD-67」or「MON 4660」(3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) [Supplier: Nitrokemia, or, Monsanto] (S3-7), 「TI-35」(1-dichloroacetylazepane) [Supplier: TRI-Chemical RT] (S3-8), 「diclonon」(dicyclonon) or「BAS 145138」or「LAB 145138」(S3-9), ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) [Supplier: BASF], 「furilazole」or「MON 13900」((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10) and its (R)-isomer (S3-11).

[0050] (S4) Formula (S4) <�

Chemical formula

【In the formula, the symbols and subscripts 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 These are halogens, (C1-C4)-haloalkyls, (C1-C4)-haloalkoxys, nitros, (C1-C4)-alkyls, (C1-C4)-alkoxys, (C1-C4)-alkylsulfonyls, (C1-C4)-alkoxycarbonyls, or (C1-C4)-alkylcarbonyls; R D 3 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, or (C2-C4)-alkynyl; R D 4 These are halogens, nitros, (C1-C4)-alkyls, (C1-C4)-haloalkyls, (C1-C4)-haloalkoxys, (C3-C6)-cycloalkyls, phenyls, (C1-C4)-alkoxys, cyanos, (C1-C4)-alkylthios, (C1-C4)-alkylsulfinyls, (C1-C4)-alkylsulfonyls, (C1-C4)-alkoxycarbonyls, or (C1-C4)-alkylcarbonyls; R D 5 This includes hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl, or a 3- to 6-membered heterocycline (where the heterocycline is selected from the group consisting of nitrogen, oxygen, and sulfur). D (containing a number of heteroatoms) (where the last seven radicals are selected from the group consisting of halogens, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, and phenyl, and in the case of cyclic radicals, they are also selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, v D Substituting with the substituent); R D 6The radicals are hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, or (C2-C6)-alkynyl (where the last three radicals are selected from the group consisting of halogen, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy, and (C1-C4)-alkylthio). D Substituted with radicals of); or, R D 5 and R D 6 These, together with the nitrogen atoms that possess them, form a pyrrolidinyl radical or a piperidinyl radical; R D 7 These are hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C6)-alkyl, and (C3-C6)-cycloalkyl (where the last two 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, they are also selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, v D Substituting with the substituent); n D is 0, 1, or 2; m D is either 1 or 2; v D [is 0, 1, 2, or 3] N-acyl sulfonamides and their salts represented by the same name; Among these, for example, known from WO-A-97 / 45016, for example, the following formula (S4 a ) [ka] [During the ceremony, R D 7is (C1-C6)-alkyl or (C3-C6)-cycloalkyl (where the last two radicals are selected from the group consisting of halogens, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio, and in the case of cyclic radicals, they are further selected from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl, v D Substituting with the substituent); R D 4 These are halogens, (C1-C4)-alkyls, (C1-C4)-alkoxys, or CF3; m D is either 1 or 2; v D [is 0, 1, 2, or 3] A compound of the type N-acylsulfonamide represented by is preferred. And further, For example, as seen in WO-A-99 / 16744, for example, the following formula (S4 b ) [ka] Acyl sulfamoyl benzamide represented by the above formula, 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); Those that are also preferred, And further, For example, the following formula (S4) is known from EP-A-365484. c ) [ka] [During the ceremony, R D 8 and R D 9 These are independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, or (C3-C6)-alkynyl; R D 4 These are halogens, (C1-C4)-alkyls, (C1-C4)-alkoxys, and CF3; m D [is 1 or 2] Compounds of the type N-acylsulfamoylphenylurea represented by, for example, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea ("methcamifen", S4-6); 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea; 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; These are also preferable, And further, For example, the formula (S4) is known from CN 101838227. d ) [ka] N-phenylsulfonyl terephthalamide represented by the above formula, for example, in the above formula, R D 4However, these are halogens, (C1-C4)-alkyls, (C1-C4)-alkoxys, and CF3; m D However, it is either 1 or 2; R D 5 These are hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, and (C5-C6)-cycloalkenyl; N-phenylsulfonyl terephthalamide is also preferred.

[0051] (S5) Active ingredient (S5) selected from the class of hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, e.g., ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid (these are described in WO-A-2004 / 084631, WO-A-2005 / 015994, and WO-A-2005 / 016001).

[0052] (S6) An active ingredient selected from the 1,2-dihydroquinoxarin-2-one class (S6), e.g., 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxarin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxarin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxarin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxarin-2-one (these are described in WO-A-2005 / 112630).

[0053] (S7) Equation (S7) (This is described in WO-A-1998 / 38856) [ka] [In the formula, symbols and subscripts are defined as follows: R E1 , R E 2 These are independently halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, and nitro; A E COOR E 3 or COSR E 4 and; R E 3 , R E 4 These 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 either 0 or 1; n E 2 , n E 3 [These are independently 0, 1, or 2.] A compound represented by; Preferably: Diphenylmethoxyacetic acid, Diphenylmethoxyethyl acetate, Diphenylmethoxymethyl acetate (CAS Reg. No. 41858-19-9) (S7-1).

[0054] (S8) Equation (S8) (This is described in WO-A-98 / 27049) [ka] [During the ceremony, X F is either CH or N; n F X F If =N, then it is an integer from 0 to 4; and, n F X FIf =CH, it is an integer between 0 and 5; R F 1 These are halogens, (C1-C4)-alkyls, (C1-C4)-haloalkyls, (C1-C4)-alkoxys, (C1-C4)-haloalkoxys, nitros, (C1-C4)-alkylthios, (C1-C4)-alkylsulfonyls, (C1-C4)-alkoxycarbonyls, optionally substituted phenyls, and optionally substituted phenoxys; R F 2 is hydrogen or (C1-C4)-alkyl; R F 3 [wherein the carbon-containing radical is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl (wherein the carbon-containing radical is either unsubstituted or substituted with one or more (preferably up to three) identical or different radicals selected from the group consisting of halogens and alkoxy)] Compounds represented by or salts thereof; Preferably, in the above formula, X F However, it is CH; n F However, these are integers between 0 and 2; R F 1 However, these are halogens, (C1-C4)-alkyls, (C1-C4)-haloalkyls, (C1-C4)-alkoxys, and (C1-C4)-haloalkoxys; R F 2 However, it is hydrogen or (C1-C4)-alkyl; R F 3 However, the radical is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl (wherein each of the carbon-containing radicals is either unsubstituted or substituted with one or more (preferably up to three) identical or different radicals selected from the group consisting of halogens and alkoxys); A compound or a salt thereof.

[0055] (S9) An active ingredient selected from the 3-(5-tetrazolylcarbonyl)-2-quinolone class, e.g., 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8) (these 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 These are halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, and OCF3; Y G , Z G These represent O or S independently of each other; n G is an integer between 0 and 4; R G 2 (C1-C 16 These are )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl, benzyl, and halobenzyl; R G 3 [is hydrogen or (C1-C6)-alkyl] A compound represented by the formula.

[0057] (S11) Active ingredients of the type of oxyimino compound (S11) (these are known as seed coating agents), for example, "Oxavethrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1) (This is known as a seed powder phytotoxicity mitigating agent for millet / sorghum against damage caused by metrachlor); "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2) (This is known as a seed powder phytotoxicity mitigating agent for millet / sorghum against damage caused by metrachlor); and, "Siometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3) (This is known as a seed powder phytotoxicity mitigating agent for millet / sorghum against damage caused by metrachlor).

[0058] (S12) An active ingredient selected from the isothiochromanone class (S12), for example, [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]methyl 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 (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic acid anhydride) (S13-1) (This is known as a seed coating phytotoxicity mitigating agent for corn against damage caused by thiocarbamate herbicides); "Fenchlorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2) (This is known as a phytotoxicity-reducing agent for pretilachlor in sown rice); "Flurazole" (2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate benzyl) (S13-3) (This is known as a seed powder phytotoxicity mitigating agent for millet and sorghum against damage caused by alachlor and metrachlor); "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) [Supplier: American Cyanamid] (This is known as a phytotoxicity reducer for maize against damage caused by imidazolinones); "MG 191" (CAS Reg. No. 96420-72-3) (2-Dichloromethyl-2-methyl-1,3-Dioxolane) (S13-5) [Supplier: Nitrokemia] (This is known as a phytotoxicity reducer for maize); "MG 838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4,5]decane-4-carboditioate) (S13-6) [Supplier: Nitrokemia]; "Disulfonate" (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 herbicidal effects against harmful plants as well as effects that reduce phytotoxicity to crop plants such as rice, for example, "Dimethylate" or "MY 93" (S-1-methyl 1-phenylethylpiperidine-1-carbothioate) (this is known as a phytotoxicity reducer for rice against damage caused by the herbicide molinate); "Daimlon" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea) (known as a phytotoxicity reducer for rice against damage caused by the herbicide imazosulfuron); "Kumiluron" = "JC 940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea; see JP-A-60087254) (This is known as a phytotoxicity reducer for rice against damage from some herbicides); "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone) (known as a phytotoxicity reducer for rice against damage from certain herbicides); "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) [Supplier: Kumiai] (CAS Reg. No. 54091-06-4) (This is known as a phytotoxicity reducer for damage caused by certain herbicides in rice).

[0061] (S15) Formula (S15) (This 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 Independently, hydrogen, (C1-C 16 )-alkyl, (C2-C 16 )-alkenyl or (C2-C 16)-alkynyl (where the last three radicals are, respectively, unsubstituted or substituted with one or more radicals selected from the group consisting 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 (where the cycloalkyl is condensed on one side of the ring into a 4-6 member saturated or unsaturated carbocyclic ring) (C1-C4)-C6-cycloalkenyl (where the cycloalkenyl is condensed with a 4- to 6-membered saturated or unsaturated carbocyclic ring on one side of the ring) (where the last four radicals are either unsubstituted or substituted with 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 This is a 4-8 membered heterocyclic ring (where the heterocyclic ring may also contain additional ring heteroatoms (preferably up to two additional ring heteroatoms selected from the group N, O, and S) in addition to the nitrogen atom, and the heterocyclic ring is either 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) A compound represented by or its tautomer.

[0062] (S16) Active ingredients that are mainly used as herbicides but also have the effect of reducing phytotoxicity to crops, for example, (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)butyrate (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-methoxybenzoate 1-(ethoxycarbonyl)ethyl (lactidichlor-ethyl).

[0063] Particularly preferred drug-induced harm reduction agents are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, croquintoset-mexyl, benoxacol, dichlormid, and metcamifen.

[0064] The wettable powder is a preparation that can be homogeneously dispersed in water, comprising, in addition to the active ingredient and separately from diluents or inert substances, ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated aliphatic alcohols, polyethoxylated aliphatic amines, aliphatic alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzene sulfonates, sodium lignosulfonates, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To manufacture the wettable powder, the herbicidal active ingredient is finely ground in conventional equipment such as a hammer mill, blower mill, and air jet mill, and then mixed with a formulation aid, either simultaneously or afterward.

[0065] The emulsion is prepared by dissolving the active ingredient in an organic solvent (e.g., butanol, cyclohexanone, dimethylformamide, xylene, or an aromatic substance or hydrocarbon with a relatively high boiling point) or a mixture of such organic solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium alkylaryl sulfonates, e.g., calcium dodecylbenzenesulfonate; or nonionic emulsifiers, e.g., fatty acid polyglycol esters, alkylaryl polyglycol ethers, aliphatic alcohol polyglycol ethers, propylene oxide / ethylene oxide condensates, alkyl polyethers, sorbitan esters, e.g., sorbitan fatty acid esters; or polyoxyethylene sorbitan esters, e.g., polyoxyethylene sorbitan fatty acid esters.

[0066] Dusting products are obtained by grinding the active ingredient together with finely distributed solids (e.g., talc, natural clay, e.g., kaolin, bentonite and pyrophyllite, or diatomaceous earth).

[0067] The suspension formulations may be aqueous or oily. They can be produced, for example, by wet grinding using a commercial bead mill, and optionally with the addition of a surfactant (e.g., the surfactants already mentioned above in relation to other formulations).

[0068] Emulsions, such as oil-in-water emulsions (EWs), can be prepared using, for example, an aqueous organic solvent and optionally a surfactant (for example, a surfactant already mentioned above for other formulations), using a stirrer, a colloidal mill, and / or a static mixer.

[0069] Granules can be produced by spraying the active ingredient onto the surface of an adsorbent granular inert material, or by applying a concentrated active ingredient to the surface of a carrier material (e.g., sand, kaolinite, or granular inert material) using an adhesive (e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oil). Furthermore, suitable active ingredients can also be granulated using conventional methods for producing fertilizer granules (as a mixture with fertilizer, if necessary).

[0070] Granular wettable powders are generally manufactured by conventional methods such as spray drying, fluidized bed granulation, bread granulation, mixing using a high-speed mixer, and extrusion without the use of solid inert substances.

[0071] For the manufacture of bread granules, fluidized bed granules, extruded granules, and spray granules, please refer to the methods described in, for example, “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London, JE Browning, “Agglomeration”, 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, "GC Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96" and "JD Freyer, SA Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103".

[0073] The pesticide preparation generally contains 0.1% to 99% by weight, and particularly 0.1% to 95% by weight, of the compound of the present invention. In wettable powders, the concentration of the active ingredient is, for example, about 10% to 90% by weight, with the remainder up to 100% by weight consisting of conventional formulation components. In emulsions, the concentration of the active ingredient may be about 1% to 90% by weight, preferably 5% to 80% by weight. Formulations in powder form contain 1% to 30% by weight of the 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 the active ingredient. In granular wettable powders, the content of the active ingredient depends in part whether the active compound exists in liquid or solid form, and in part on what granulation aids, fillers, etc., are used. In granular wettable powders, the content of the active ingredient is, for example, 1% to 95% by weight, preferably 10% to 80% by weight.

[0074] Furthermore, the above-mentioned formulations of the active ingredients may optionally contain their respective conventional adhesives, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreezes, as well as solvents, bulking agents, carriers, dyes, defoaming agents, evaporation inhibitors, and agents that affect pH and viscosity.

[0075] Based on these formulations, it is also possible to manufacture combinations with other biocidal substances (e.g., insecticides, acaricides, herbicides, fungicides), and further, combinations with phytotoxicity reducers, fertilizers and / or growth regulators, for example, in the form of finished formulations or as tank mixes.

[0076] For application, commercially available formulations are diluted by customary methods where appropriate, for example, with water in the case of wettable powders, emulsions, dispersions, and granular wettable powders. Powdered preparations, soil application granules, broadcast granules, and sprayable solutions are not usually further diluted with another inert substance before application.

[0077] The required application rates of the compounds represented by formula (I) and their salts vary depending on external conditions (e.g., temperature, humidity, and the type of herbicide used). It can vary over a wide range, for example, from 0.001 to 10.0 kg / ha or more of the active substance. However, it is preferably 0.005 to 5 kg / ha, more preferably 0.01 to 1.5 kg / ha, and even more preferably 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.

[0078] The carrier is a natural or synthetic organic or inorganic substance that is mixed or combined with the active ingredient to improve its applicability, particularly with respect to application to plants, plant parts, or seeds. Such carriers may 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 powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth, and synthetic rock powders such as finely ground silica, alumina, and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral oils, and vegetable oils, and their derivatives. 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, meerschmitt, and dolomite, and synthetic granules made from coarsely ground inorganic and organic powders, and further granules made from organic materials such as sawdust, coconut shells, corn cobs, and tobacco leaf stalks.

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

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

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

[0083] The composition of the present invention may also optionally contain further components (e.g., surfactants). Useful surfactants are emulsifiers and / or foaming agents, dispersants, or wetting agents having ionic or nonionic properties, or mixtures of such surfactants. These examples include: salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and fatty alcohols or polycondensates of ethylene oxide and fatty acids or polycondensates of ethylene oxide and fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinate esters, taurine derivatives (preferably alkyl taurates), phosphate esters of polyethoxylated alcohols or polyethoxylated phenols, fatty acid esters of polyols, and derivatives of these compounds containing sulfate anions, sulfonate anions and phosphate anions, such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolysates, lignosulfite wastewater, 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, the presence of a surfactant is necessary. The proportion of surfactant is 5 to 40% by weight of the composition of the present invention. Colorants such as inorganic pigments, such as iron oxide, titanium dioxide, and Prussian blue, as well as organic dyes, such as alizarin dyes, azo dyes, and metal phthalocyanine dyes, and micronutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts, and zinc salts can be used.

[0084] Where appropriate, additional components such as protective colloids, binders, adhesives, thickeners, thixotropes, penetrants, stabilizers, metal ion chelating agents, and complexing agents may also be present. Generally, the active ingredient can be combined with any solid or liquid additive commonly used for formulation purposes. Generally, 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 of the active ingredient, and most preferably 10% to 70% by weight of the active ingredient. The active ingredients or compositions of the present invention can be used as is, or, depending on their individual physical and / or chemical properties, can be used in the form of their formulations or in forms of use prepared from such formulations, such as: for example, aerosols, capsule suspensions, cold-fogging concentrates, warm-fogging concentrates, encapsulated granules, fine granules, flowable formulations for seed treatment, ready-to-use solutions, powders, emulsions, oil-in-water emulsions, water-in-oil emulsions, large granules, fine granules, oil-dispersible powders, oil-miscible flowable formulations, oil-miscible liquids, foams, pastes, pesticide-coated seeds, suspension concentrates, suspension emulsions, soluble concentrates, suspensions, sprayable powders, soluble powders Powder), powders and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, natural and synthetic products impregnated with active ingredients, and further, those microencapsulated in polymer materials and those microencapsulated in seed coating materials, and further, ULV cold-fogging formulations and ULV warm-fogging formulations.

[0085] The above-mentioned formulations can be produced by methods known to the extent of the activity, for example, by mixing the active ingredient with at least one conventional bulking agent, solvent or diluent, emulsifier, dispersant and / or binder or fixative, wetting agent, water repellent, optionally drying agent and UV stabilizer, and optionally dyes and pigments, defoamers, preservatives, a second thickening agent, tackifiers, gibberellins, and further, another processing aid.

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

[0087] The active ingredient of the present invention may exist on its own, or in its (commercially standard) formulation, or in a form of use prepared from such formulation, as a mixture with other (known) active ingredients such as insecticides, attractants, sterilizers, bactericidal agents, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, phytotoxicity reducers, or informational chemicals.

[0088] The treatment of plants and plant parts according to the present invention using the above-mentioned active ingredient or composition may be carried out directly by conventional treatment methods, such as immersion, spraying, misting, vaporization, dusting, fogging, scattering, foaming, coating, diffusion (spreading-on), irrigation (drenching), or drip irrigation, or by applying the active ingredient or composition to the surroundings, habitat, or storage space of the plants and plant parts. Furthermore, in the case of propagation material, especially seeds, the treatment may be carried out by coating with one or more layers of film by dry seed treatment, wet seed treatment, slurry treatment, or incrustation. In addition, it is possible to deploy the active ingredient by an ultra-low volume method, or to inject the active ingredient preparation or the active ingredient itself into the soil.

[0089] The active ingredients of the present invention are suitable for protecting plants and plant organs, increasing yields, and improving the quality of harvested crops, provided that the plants show good compatibility, the toxicity to homeothermic animals is at a desirable level, and the plants are well-suited to the environment. They can preferably be used as crop protection compositions. They are active against normally susceptible and resistant species, and are active at all developmental stages or specific developmental stages.

[0090] Plants that can be processed according to the present invention include the following major crop plants: corn, soybeans, cotton, Brassica oil seeds, e.g., Brassica napus (e.g., canola), Brassica rapa, Brassica juncea (e.g., (field) mustard) and Brassica carinata, rice, wheat, sugar beet, sugarcane, oats, rye, barley, millet and sorghum, rye wheat, flax, grapevines, and various fruits and vegetables belonging to various botanical taxa, e.g., Rosaceae sp. (e.g., pome fruits, e.g., apples and pears, as well as drupes, e.g., apricots, cherries, almonds and peaches, and berries, e.g., strawberries), Ribesioidae sp. sp.), various Juglandaceae sp., various Betulaceae sp., various Anacardiaceae sp., various Fagaceae sp., various Moraceae sp., various Oleaceae sp., various Actinidaceae sp., various Lauraceae sp., various Musaceae sp. (e.g., banana trees and plantations), various Rubiaceae sp. (e.g., coffee), various Theaceae sp., various Sterculiceae sp., various Rutaceae sp. (e.g., lemons, oranges and grapefruits); various Solanaceae sp.) (e.g., tomato, potato, chili pepper, eggplant), various Liliaceae sp., various Compositae sp. (e.g., lettuce, Korean thistle and chicory (this includes root chicory, endive or common chicory)), various Umbelliferae sp.)(e.g., carrots, parsley, celery and celeriac), various Cucurbitaceae sp. (e.g., cucumber (which includes gherkins), pumpkin, watermelon, gourd and melon), various Alliaceae sp. (e.g., leeks and onions), various Cruciferae sp. (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, Chinese cabbage, kohlrabi, radish, horseradish, pepper and Chinese cabbage), various Leguminosae sp. (e.g., peas, peas and kidney beans (e.g., common beans and broad beans)), various Chenopodiaceae (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 all cases, genetically modified versions of these plants.

[0091] As described above, all plants and their parts can be processed according to the present invention. In preferred embodiments, wild plant species and varieties, or plant species and varieties obtained by conventional biological breeding methods such as hybridization or protoplast fusion, and their parts are processed. In preferred further embodiments, transgenic plants and varieties (genetically modified organisms) and their parts obtained by genetic engineering methods, where appropriate, in combination with conventional methods are processed. The terms “parts,” “parts of plants,” or “plant parts” have been explained above. Particularly preferred according to the present invention is the processing of each commercially conventional plant variety or each plant variety used. A plant variety is understood to mean a plant having a new trait ("trait") cultivated by conventional breeding or by mutagenesis or recombinant DNA technology. These can be varieties, cultivars, biotypes, and genotypes.

[0092] The processing method of the present invention can also be used to process genetically modified organisms (GMOs), such as plants or seeds. Genetically modified plants (or transgenic plants) are plants in which heterologous genes are stably incorporated into their genome. The term "heterologous gene" essentially means a gene that, when introduced into the nuclear genome, chloroplast genome, or mitochondrial genome, confers a new or improved crop-related characteristic or another trait to the transformed plant by expressing an interesting protein or polypeptide, or by downregulating or switching off one or more other genes present in the plant (for example, by using antisense techniques, cosuppression techniques, or RNAi techniques [RNA interference]). Heterologous genes present in the genome are also called transgenes. A transgene, defined by its specific presence in the plant genome, is called a transformation or gene transfer event.

[0093] Depending on the plant species or variety, their growing location, and growing conditions (soil, climate, growing season, nutrients (diet)), the treatment of the present invention may produce effects beyond additive effects ("synergistic effects"). For example, the following effects exceeding those actually expected are possible: reduction of the application rate of the active ingredients and compositions that can be used according to the present invention and / or expansion of the activity spectrum and / or enhancement of potency; improved plant growth; improved tolerance to high or low temperatures; improved tolerance to drought or salinity in water or soil; improved flowering ability; improved ease of harvesting; accelerated maturation; increased yield; increased fruit size; increased plant height; improved leaf greenness; earlier flowering; improved quality and / or increased nutritional value of harvested produce; increased sugar content in fruit; improved storage stability and / or improved processability of harvested produce.

[0094] The plants or plant varieties that can be treated according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are herbicide-resistant plants, i.e., plants that have been made resistant to one or more given herbicides. Such plants can be obtained by genetic transformation or by selecting plants that contain mutations that confer the herbicide resistance.

[0095] Herbicide-resistant plants are, for example, glyphosate-resistant plants, i.e., plants that have been made resistant to the herbicide glyphosate or its salts. Plants can be made resistant to glyphosate by various methods. Thus, for example, glyphosate-resistant plants can be obtained by transforming plants with a gene encoding the enzyme 5-enolpyruvirshikimic acid-3-phosphate synthase (EPSPS). Examples of such EPSPS genes include: the AroA gene (mutation CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of various Agrobacterium species (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 is also possible that it is a mutant EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding the glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding the glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants containing spontaneous mutations of the above genes. Plants expressing the EPSPS gene that confers glyphosate tolerance have already been described. Plants expressing another gene that confers glyphosate tolerance (e.g., a decarboxylase gene) have already been described.

[0096] Another type of herbicide-resistant plant is one that has been made resistant 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, or by expressing a mutant glutamine synthase enzyme that is resistant to the inhibition. One example of such an effective detoxification enzyme is the enzyme encoding phosphinothricin acetyltransferase (e.g., the bar or pat protein from various Streptomyces species). Plants expressing exogenous phosphinothricin acetyltransferase have been described.

[0097] Further herbicide-resistant plants are those that have been made resistant to herbicides that inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). Hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyrubate (HPP) is converted to homogentisate. Plants that are resistant to HPPD inhibitors can be transformed using genes encoding spontaneously occurring resistant HPPD enzymes, or using genes encoding mutant HPPD enzymes or chimeric HPPD enzymes, 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 using genes encoding specific enzymes that can form homogentisate despite inhibition of the natural HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99 / 34008 and WO 02 / 36787. Plant resistance to HPPD inhibitors can also be improved by transforming the plants 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 even more resistant to HPPD inhibitors by inserting a gene encoding an enzyme that metabolizes or degrades the HPPD inhibitor (e.g., a CYP450 enzyme) into their genome (see WO 2007 / 103567 and WO 2008 / 150473).

[0098] Another type of herbicide-resistant plant is one that has been made resistant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylurea herbicides, imidazolinone herbicides, triazolopyrimidine herbicides, pyrimidinyl oxy(thio)benzoate herbicides, and / or sulfonylaminocarbonyltriazolinone herbicides. Various mutants of the ALS enzyme (also known as "acetohydroxy acid synthase (AHAS)") are known to confer resistance 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 already been described. Further sulfonylurea-resistant and imidazolinone-resistant plants have also already been described.

[0099] Further plants resistant to imidazolinone and / or sulfonylurea herbicides can be obtained by induced mutagenesis, by selection in cell culture in the presence of the herbicide, or by mutation breeding (cf. for example, US 5,084,082 for soybeans, WO 97 / 41218 for rice, US 5,773,702 and WO 99 / 057965 for sugar beets, US 5,198,599 for lettuce, or WO 01 / 065922 for sunflowers).

[0100] Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) that can be similarly treated according to the present invention are insect-resistant transgenic plants, i.e., plants made resistant to attacks by specific target insects. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such insect resistance.

[0101] In relation to the present invention, the term "insect-resistant transgenic plant" encompasses any plant comprising at least one transgene containing a coding sequence that encodes the following: (1) Insecticidal crystalline protein derived from Bacillus thuringiensis or a portion thereof exhibiting insecticidal activity, for example, edited by Crickmore et al. (Microbiology and Molecular Biology Reviews 1998, 62, 807-813) and published online by Crickmore et al. (2005) at http: / / www.lifesci.sussex.ac.uk / Home / Neil_Crickmore / Bt / as "Bacillus thuringiensis" Insecticidal crystalline proteins or portions thereof exhibiting insecticidal activity, updated in the "Toxin Nomenclature of thuringiensis," for example, Cry proteins (Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb) or portions thereof exhibiting insecticidal activity (e.g., EP-A 1999141 and WO 2007 / 107302), or proteins encoded by synthetic genes described, for example, in U.S. Patent Application No. 12 / 249,016; or (2) A crystalline protein or portion thereof derived from Bacillus thuringiensis that exhibits insecticidal activity in the presence of a second crystalline protein or portion thereof other than that of Bacillus thuringiensis, for example, a binary toxin composed of Cy34 crystalline protein and Cy35 crystalline 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 (US Patent Application No. 12 / 214,022 and EP 08010791.5); or (3) An insecticidal hybrid protein comprising a portion of two different insecticidal crystalline proteins derived from Bacillus thuringiensis, for example, a hybrid of the protein in (1) above, or a hybrid of the protein in (2) above, for example, the Cry1A.105 protein (WO 2007 / 027777) produced in the maize event MON89034; or (4) Any one of the proteins in (1) to (3) above, in order to obtain stronger insecticidal activity against target insect species and / or to expand the range of target insect species affected and / or, due to changes introduced into the encoding DNA during cloning or transformation, several amino acids (in particular, 1 to 10 amino acids) are replaced with other amino acids, for example, the Cry3Bb1 protein in maize events MON863 or MON88017, or the Cry3A protein in maize event MIR604; or, (5) Insecticidal secretory proteins derived from Bacillus thuringiensis or Bacillus cereus, or portions thereof exhibiting insecticidal activity, for example, vegetative insecticidal proteins (VIPs) listed at "http: / / www.lifesci.sussex.ac.uk / Home / Neil_Crickmore / Bt / vip.html", such as VIP3Aa proteins; or, (6) A secretory protein derived from Bacillus thuringiensis or Bacillus cereus that exhibits insecticidal activity in the presence of a second secretory protein derived from Bacillus thuringiensis or Bacillus cereus, for example, a binary toxin (WO 94 / 21795) composed of VIP1A protein and VIP2A protein; or (7) Insecticidal hybrid proteins comprising a portion of different secreted proteins derived from Bacillus thuringiensis or Bacillus cereus, for example, a hybrid of the proteins in (1) above, or a hybrid of the proteins in (2) above; or (8) In any one of the proteins in items (5) to (7) above, several amino acids (in particular, 1 to 10 amino acids) have been replaced with other amino acids in order to obtain stronger insecticidal activity against target insect species and / or to expand the range of target insect species affected and / or due to changes induced in the encoding DNA during cloning or transformation (which still encode an insecticidal protein), for example, the VIP3Aa protein in cotton vent COT102; or, (9) Secretory proteins derived from Bacillus thuringiensis or Bacillus cereus that exhibit insecticidal activity in the presence of crystalline proteins derived from Bacillus thuringiensis, for example, binary toxins composed of protein 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 VIP3 protein and Cry2Aa protein, Cry2Ab protein, or Cry2Ae protein (U.S. Patent Application No. 12 / 214022 and EP 08010791.5); or (10) In the protein of item (9) above, several amino acids (in particular, 1 to 10 amino acids) have been replaced with other amino acids in order to obtain stronger insecticidal activity against target insect species and / or to expand the range of target insect species affected and / or due to changes induced in the encoding DNA during cloning or transformation (which still encode an insecticidal protein).

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

[0103] In connection with the present invention, the term "insect-resistant transgenic plant" further includes any plant comprising at least one transgene comprising a sequence that produces double-stranded RNA that prevents the growth of the pest after the pest has ingested food.

[0104] Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) that can be similarly treated according to the present invention exhibit resistance to abiotic stressors. 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 the following: (a) Plants containing a transgene capable of reducing the expression and / or activity of the poly(ADP-ribose) polymerase (PARP) gene within plant cells or within the plant body; (b) Plants containing transgenes that enhance stress tolerance, which can reduce the expression and / or activity of PARG-coding genes in plants or plant cells; (c) A plant containing a transgene that enhances stress tolerance by encoding a plant-functional enzyme in the nicotinamide adenine dinucleotide salvage biosynthesis pathway, including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinate mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase, or nicotinamide phosphoribosyltransferase.

[0105] Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) that can be similarly treated according to the present invention exhibit modified quantities, quality and / or storage stability of harvested products, and / or modified properties of specific components of harvested products. For example: (1) Transgenic plants that synthesize modified starch more suitable for specific uses, having altered physicochemical properties (particularly amylose content or amylose / amylopectin ratio, degree of branching, mean chain length, side chain distribution, viscosity behavior, gelling strength, starch particle size and / or starch particle morphology) compared to starch synthesized in wild-type plant cells or plants; (2) Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers having modified properties compared to non-genetically modified wild-type plants [examples include plants that produce polyfructose (especially inulin-type and levan-type polyfructose), plants that produce α-1,4-glucans, plants that produce α-1,6-branched α-1,4-glucans, and plants that produce alternans]; (3) Transgenic plants that produce hyaluronan; (4) Transgenic or hybrid plants having characteristics such as "high soluble solids content," "low spiciness" (LP), and / or "long shelf life" (LS), such as onions.

[0106] Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) that can be similarly treated according to the present invention are plants having modified fiber properties (e.g., cotton plants). Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such modified fiber properties. Examples of such plants include: (a) Plants containing modified forms of the cellulose synthase gene (e.g., cotton plants); (b) Plants containing modified forms of rsw2 homologous nucleic acids or rsw3 homologous nucleic acids (e.g., cotton plants), e.g., cotton plants with 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 gate control is altered (e.g., via downregulation of fiber-selective β-1,3-glucanase) (e.g., cotton plants); (e) Plants having fibers whose reactivity has been modified (for example, via the expression of an N-acetylglucosamine transferase gene containing nodC and the expression of a chitin synthase gene) (e.g., cotton plants).

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

[0108] Plants or plant varieties (which can be obtained by plant biotechnology methods such as genetic engineering) that can be similarly treated according to the present invention include potatoes exhibiting virus resistance [e.g., resistance to potato virus Y (SY230 and SY233 events, Tecnoplant, Argentina)], potatoes exhibiting resistance to diseases (e.g., potato blight) (e.g., RB gene), potatoes exhibiting reduced cold-induced sweetness (which have the Nt-Inh gene and II-INV gene), or potatoes exhibiting a dwarf phenotype (A-20 oxidase gene).

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

[0110] Particularly useful transgenic plants that can be processed according to the present invention are plants that include a transformation event or a combination of transformation events and are subject to an application or continuation application for approval with the United States Department of Agriculture (USDA) Animal and Plant Health Inspection Service (APHIS) for non-regulated status within the United States. Relevant information 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 having the following information have been approved by APHIS or are under review by APHIS: - Application: The identification number of the application. Technical descriptions of transformation events can be found in specific application documents available from APHIS on its website, via the application number. Those descriptions are disclosed herein by reference. - Extension of application: A reference to a previous application for which an extension of the scope or period has been requested. - Company: The name of the individual who submitted the application. - Regulated substance: The plant species in question. - Transgenic phenotype: A trait conferred to a plant by a transformation event. - Transformation event or line: The name of one or more events (sometimes also referred to as a line) for which a regulatory exemption is being requested. - APHIS documents: various documents published by APHIS in connection with an application or obtainable from APHIS upon request.

[0111] Particularly useful transgenic plants that can be processed according to the present invention are plants containing one or more genes encoding one or more toxins, for example, 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-tolerant plants that can be mentioned include corn varieties, cotton varieties, and soybean varieties obtainable under the following trade names: Roundup Ready® (tolerance to glyphosates, e.g., corn, cotton, soybean), Liberty Link® (tolerance to phosphinothricin, e.g., rapeseed), IMI® (tolerance to imidazolinones), and SCS® (tolerance to sulfonylureas, e.g., corn). Examples of herbicide-resistant plants (plants bred in a conventional manner with respect to herbicide tolerance) that can be mentioned include varieties sold under the trade name Clearfield® (e.g., corn).

[0112] Particularly useful transgenic plants that can be processed in accordance with the present invention include transformation events or combinations of transformation events, for example, plants described in the databases of regulatory agencies in various countries or regions (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").

Example

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

[0114] Synthesis of 2-chloro-3-(methylsulfanyl)-N-(1,3,4-oxadiazole-2-yl)-4-(trifluoromethoxy)benzamide (Examples No. 1-31)

Chemical

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

[0116] Synthesis of 2-chloro-4-(difluoromethoxy)-3-(methylsulfanyl)-N-(1,3,4-oxadiazole-2-yl)benzamide (Example No. 1-21) [ka] 697 mg (8.19 mmol) of 1,3,4-oxadiazole-2-amine and 2.00 g (7.44 mmol) of 2-chloro-4-(difluoromethoxy)-3-(methylsulfanyl)benzoic acid were added to 50 mL of acetonitrile, to which 2.85 mL (35.73 mmol) of 1-methyl-1H-imidazole was added. The mixture was cooled to a temperature of 0°C to 5°C. 0.97 mL (11.17 mmol) of oxalyl chloride was added in small increments. The reaction mixture was then heated to room temperature and stirred at that temperature for 16 hours. For work-up, the solvent was removed from the reaction mixture 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. A 6 M sodium hydroxide solution was added, and the mixture was then repeatedly washed with dichloromethane. The aqueous phase was then acidified with 6 M hydrochloric acid. The mixture was filtered, and the resulting solid was dried. The solid was then redissolved in dichloromethane and sodium bicarbonate aqueous solutions. After phase separation, the solvent was removed from the organic phase using 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) was isolated.

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

[0118] The examples listed in the table below were prepared in the same manner as described above, or can be obtained in the same manner as described above. These compounds are particularly preferred.

[0119] The abbreviations used have the following meanings: [Table 1] [Table 2] TIFF0007899292000021.tif250161TIFF0007899292000022.tif255165TIFF0007899292 000023.tif250161TIFF0007899292000024.tif254164TIFF0007899292000025.tif52165

[0120] NMR data of the selected example NMR Peak List Method The 1H NMR data of the selected examples are presented in the form of a 1H NMR peak list. For each signal peak, the δ value (ppm) is first described, followed by the signal intensity within parentheses. Pairs of δ value / signal intensity numbers for various signal peaks are described separated from each other by semicolons.

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

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

[0123] To calibrate the chemical shift of the 1H NMR spectrum, tetramethylsilane is used and / or, especially when the spectrum is measured in DMSO, the chemical shift of the solvent is used. Therefore, the peak of tetramethylsilane may be present in the NMR peak list, but does not necessarily have to be present.

[0124] The list of 1H NMR peaks is similar to a conventional 1H NMR printout and thus usually includes all peaks described in the customary interpretation of NMR.

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

[0126] In recording compound signals within the delta range of solvents and / or water, our list of 1H NMR peaks typically shows peaks for common solvents, such as the DMSO peak in DMSO-D6 and the water peak (which usually have high intensities on average).

[0127] The peaks of stereoisomers and / or impurities of the target compound typically have lower intensity on average than the peak of the target compound (e.g., the target compound with a purity of over 90%).

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

[0129] Experts who calculate the peaks of a target compound using known methods (MestreC, ACD simulation, and the use of empirically estimated expectations) can, if necessary, separate the peaks of the target compound using additional intensity filters. This separation would be analogous 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 the compound represented by formula (I) and / or a salt thereof with 90 parts by weight of talc as an inert substance, and then grinding the mixture in a hammer mill.

[0133] (b) A hydrated agent that disperses readily in water is obtained by mixing 25 parts by weight of the compound represented by formula (I) and / or a salt thereof 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 agent and dispersant, and grinding the mixture in a pin disc mill.

[0134] (c) A dispersion concentrate that readily disperses in water is obtained by mixing 20 parts by weight of the compound represented by formula (I) and / or its salt with 6 parts by weight of alkylphenol polyglycol ether (Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8EO), and 71 parts by weight of paraffinic mineral oil (boiling point range: e.g., about 255°C to over 277°C), and then grinding in an attrition ball mill until the powder is less than 5 microns in size.

[0135] (d) The emulsion is obtained from 15 parts by weight of the 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) Granular wettable powders are 75 parts by weight of the compound represented by formula (I) and / or its salt, 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 ingredients, grinding the mixture in a pin disc mill, and then granulating the resulting powder by spraying it with water as a granulating liquid in a fluidized bed.

[0137] (f) The granular wettable powder is further contained in colloid mill, 25 parts by weight of the compound represented by formula (I) and / or its salt, 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 material, then grinding the mixture in a bead mill, and finally 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 weeds and crop plants are placed in sandy loam soil within wood fiber pots, covered with soil, and cultivated in a greenhouse under favorable growing conditions. Two to three weeks after sowing, the test plants are treated at the one-leaf stage. The compound of the present invention, formulated as a wettable powder (WP) or emulsion (EC), is sprayed onto the green parts of the plants as an aqueous suspension or emulsion at a spray volume equivalent to 600-800 L / ha with 0.2% wetting agent added. After the test plants are left to stand in a greenhouse under optimal growing conditions for approximately three weeks, the effect of the preparation is visually evaluated compared to an untreated control (herbicidal effect (%): 100% activity = plant death, 0% activity = same as the control plant).

[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 in the results in Tables 1a / b, 2a / b, 3a / b, 4a / b, 5, 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 post-emerging herbicidal efficacy against a wide range of grass weeds and broadleaf weeds. For example, the described examples show 80-100% activity against Alopecurus myosuroides, Digitaria sanguinalis, Setaria viridis, Veronica persica, and Viola tricolor, in particular, at application rates of 80 / 20 g / ha. Therefore, the compounds of the present invention are suitable for controlling undesirable plant growth by post-emerging methods.

[0168] 2. Pre-emergence herbicide effect and suitability for crops and plants Seeds of monocotyledonous and dicotyledonous weeds and crop plants are placed in sandy loam soil within wood fiber pots and covered with soil. The compound of the present invention, formulated in the form of a wettable powder (WP) or emulsion (EC), is then applied to the surface of the covered soil as an aqueous suspension or aqueous emulsion at a spraying volume equivalent to 600-800 L / ha with 0.2% wetting agent added. After treatment, the pots are placed in a greenhouse and maintained under favorable growing conditions for the test plants. After a 3-week test period, the damage to the test plants is visually evaluated by comparing them to an untreated control (herbicidal activity (%): 100% activity = plant death, 0% activity = same as the control plant).

[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 in 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 efficacy against a wide range of grass weeds and broadleaf weeds. For example, the compound exhibits 80-100% activity against Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Setaria viridis, Amaranthus retroflexus, Viola tricolor, and Veronica persica at an application rate of 80 / 20 g / ha. Therefore, the compound of the present invention is suitable for controlling undesirable plant growth using a pre-emergence method.

Claims

1. Equation (I) 【Chemistry 1】 [In the formula, symbols and subscripts are defined as follows: X is Cl, Br, Me, Et, MeO, EtO, MeOCH ２ or MeS; Z is HF ２ CO or F ３ CO is; R is either Me or Et; n is 0, 1, or 2. Benzamide or a salt thereof, represented by the symbol.

2. A herbicide composition or plant growth regulator composition, characterized in that it contains one or more benzamides represented by formula (I) as described in claim 1 or a salt thereof.

3. The herbicide composition according to claim 2, further comprising a formulation aid.

4. The herbicide composition according to claim 2 or 3, comprising at least one further active ingredient selected from the group consisting of insecticides, acaricides, herbicides, fungicides, phytotoxicity reducers, and / or growth regulators.

5. A herbicide composition according to claim 2 or 3, comprising a phytotoxicity-reducing agent.

6. The herbicide composition according to claim 5, wherein the phytotoxicity reducing agent is selected from the group consisting of mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, croquintoset-mexyl, benoxacol, and dichlormid.

7. A method for controlling undesirable plants, characterized by applying an effective amount of at least one benzamide represented by formula (I) according to claim 1 or the herbicide composition according to claim 2 to the plant or to the growing environment of undesirable vegetation.

8. Use of a benzamide represented by formula (I) according to claim 1 or a herbicide composition according to claim 2 for controlling undesirable plants.

9. The use according to claim 8, characterized in that the benzamide represented by formula (I) is used to control undesirable plants in a crop of useful plants.

10. The use according to claim 9, characterized in that the useful plant is a useful transgenic plant.

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