EP2265121A1 - Sels sélectionnés du 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-n-[(4,6-diméthoxypyrimidin-2-yl)carbamoyl]pyridin-2-sulfonamide, leur procédé de fabrication, ainsi que leur utilisation en tant qu'herbicides et régulateurs de la croissance des végétaux - Google Patents

Sels sélectionnés du 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-n-[(4,6-diméthoxypyrimidin-2-yl)carbamoyl]pyridin-2-sulfonamide, leur procédé de fabrication, ainsi que leur utilisation en tant qu'herbicides et régulateurs de la croissance des végétaux

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Publication number
EP2265121A1
EP2265121A1 EP09723433A EP09723433A EP2265121A1 EP 2265121 A1 EP2265121 A1 EP 2265121A1 EP 09723433 A EP09723433 A EP 09723433A EP 09723433 A EP09723433 A EP 09723433A EP 2265121 A1 EP2265121 A1 EP 2265121A1
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EP
European Patent Office
Prior art keywords
ion
alkyl
compounds
alkoxy
radicals
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP09723433A
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German (de)
English (en)
Inventor
Christian Waldraff
Hansjörg Krähmer
Martin Jeffrey Hills
Klaus-Helmut Müller
Ulrich Philipp
Ernst Rudolf Gesing
Dieter Feucht
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Bayer CropScience AG
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Bayer CropScience AG
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Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP09723433A priority Critical patent/EP2265121A1/fr
Publication of EP2265121A1 publication Critical patent/EP2265121A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • This invention relates to selected salts of the 3- (5,6-dihydro-1, 4,2-dioxazin-3-yl) -N - [(4,6-dimethoxypyrimidin-2-yl) carbamoyl] pyridine-2-sulfonamide, Process for their preparation and their use as herbicides, in particular as herbicides for the selective control of unwanted harmful plants in legumes, or for non-selective control in non-crop or plantation crops, and as plant growth regulators alone, or with safeners and / or in combination with other herbicides, their use for controlling undesirable weeds (such as weeds / grass weeds) in particular crops or as plant protection regulators, with simultaneous and / or sequential application, either as a ready-to-use formulation or as a tank mix.
  • herbicides in particular as herbicides for the selective control of unwanted harmful plants in legumes, or for non-selective control in non-crop or plantation crops, and as plant growth regulators alone,
  • US Pat. No. 5,476,936 discloses certain herbicidally active N-azinyl-N'- (Het) -arylsulfonylureas which also contain the group of 3- (5,6-dihydro-1,2,2-dioxazin-3-yl) - N- [pyrimidin-2-yl) carbamoyl] pyridine-2-sulfonamides.
  • 5,476,936 also describes Na salts of some of the compounds mentioned therein, including Na salts of individual 3- (5,6-dihydro-1,2,2-dioxazin-3-yl) -N- [pyrimidin-2-yl) carbamoyl] pyridine-2-sulfonamides such as 3- (5,6-dihydro-1,2,2-dioxazin-3-yl) -N- [4,6-dimethoxypyrimidinopyrimidin-2-yl) carbamoyl] pyridine-2 -sulfonamids.
  • the effectiveness of these herbicides against harmful plants is at a high level, but generally depends on the application rate, the particular form of preparation, each to be controlled harmful plants or the Harmful plant spectrum, the climate and soil conditions, etc. from. Another criterion is the duration of the action or the degradation rate of the herbicide. It may also be necessary to take account of changes in the susceptibility of harmful plants, which may occur with prolonged use of the herbicides or geographically. Losses of activity in individual plants can only be compensated to a limited extent by higher application rates of the herbicides, for example because this reduces the selectivity of the herbicides or does not result in an improvement in activity even at a higher application rate.
  • WO 2005/092104 already discloses the non-selective use of some of the herbicidally active N-azinyl-N '- (Het) arylsulfonylureas described in US Pat. No. 5,476,963, in particular from the group of 3- (5,6-dihydro-1, 4,2-dioxazin-3-yl) -N- [pyrimidin-2-yl) carbamoyl] pyridine-2-sulfonamides, as well as their selective use for weed control in legumes.
  • the present invention thus relates to certain agrochemically active salts of S ⁇ ⁇ . ⁇ -dihydro-M ⁇ -dioxazin-S-yO-N - ⁇ . ⁇ -dimethoxypyrimidin- 2-yl) carbamoyl] pyridine-2-sulfonamide.
  • the present invention thus relates to compounds of the general formula (I)
  • cation M (a) is a lithium or potassium ion, or
  • transition metals preferably manganese, copper, zinc and iron, or
  • transition metals preferably manganese, copper, zinc and iron, or
  • an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group consisting of (C 1 -C 4 ) -alkyl, hydroxy (C 1 -C 4 ) -alkyl, acylated hydroxy (Ci-C 4) alkyl, (C 3 -C 4) cycloalkyl, (Ci-C2) alkoxy- (Ci-C2) alkyl, hydroxy (CrC ⁇ alkoxy-CCRC ⁇ alkyl, (C r C 2 ) -mercaptoalkyl, phenyl or benzyl, where the abovementioned radicals are optionally substituted by one or more, identical or different radicals from the group halogen, such as F, Cl, Br or I 1 nitro, cyano, azido, (C r C 2 ) alkyl, (C r C 2 ) haloalkyl, (C 3 -
  • a quaternary phosphonium ion preferably tetra - ((C- ⁇ -C 4) - alkyl) phosphonium and tetraphenyl phosphonium, wherein the (Ci-C 4) alkyl radicals and the phenyl radicals optionally monosubstituted or polysubstituted by identical or different Radicals from the group halogen, such as F, Cl, Br or I, (C 1 - C 2) alkyl, (Ci-C 2) -haloalkyl, (C 3 -C 4) -cycloalkyl, (C 1 -C 2 ) - alkoxy and (CrC 2 ) -haloalkoxy, or
  • a tertiary sulfonium ion preferably tri - ((C- ⁇ -C 4) alkyl) - or sulfonium triphenyl sulfonium, wherein the (C 1 -C 4) -
  • Alkyl radicals and phenyl radicals optionally monosubstituted or polysubstituted by identical or different radicals from the group halogen, such as F, Cl, Br or I, (C 1 -C 2) - alkyl, (Ci-C 2) -haloalkyl, (C 3 - C 4) -cycloalkyl, (C 1 -C 2) - alkoxy and (CrC 2) haloalkoxy groups, or
  • halogen such as F , Cl, Br or I
  • n corresponds to a number 1, 2 or 3.
  • the cation M is a potassium ion, a lithium ion, a magnesium ion, a calcium ion, an NH 4 + -IOn, a (2-hydroxyeth-1-yl) ammonium -lon, a bis-N, N- (2-hydroxyeth-1-yl) ammonium ion, a tris-N, N, N- (2-hydroxyeth-1-yl) ammonium ion, a methyl ammonium ion, a dimethylammonium ion, a trimethylammonium ion, a tetramethylammonium ion, Ion an ethylammonium ion, a diethylammonium ion, a triethylammonium ion, a tetraethylammonium ion, an isopropylammonium ion, a diiso
  • cation M is a potassium ion, a lithium ion, a magnesium ion, a calcium ion, or an NH 4 + ion.
  • cation M is a potassium ion, a lithium ion or an NH 4 + ion
  • n corresponds to a number 1 or 2.
  • the carbon-containing radicals such as alkyl, alkoxy may each be straight-chain or branched, e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl.
  • Cycloalkyl is a carbocyclic, saturated ring system preferably having 3-6 C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • the invention also relates to all stereoisomers which are comprised by compounds of the formula (I) according to the invention and mixtures thereof.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I).
  • stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods.
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • radicals or ranges of radicals which fall under the general terms such as "alkyl” are not exhaustive.
  • the general terms also include the definitions given below for residue regions in groups of preferred compounds, in particular residue regions which comprise specific residues from the table examples.
  • the present invention also provides processes for preparing the salts according to the invention, in particular compounds of the general formula (I), characterized in that the corresponding free acid (neutral compound) to the general formula (I), wherein the group N ' M + by NH is replaced with a corresponding base is implemented.
  • the salts of the formula (I) according to the invention can be prepared in the above-mentioned manner by processes known per se, cf. for this purpose, the process steps described in EP 521500 and WO 2000/044227 (p.24 to 27) are produced,
  • the reaction is carried out, for example, in the presence of solvents which are inert under the reaction conditions.
  • solvents are inorganic solvents such as water or organic solvents, for example alcohols, such as methanol or ethanol, halogenated hydrocarbons such as dichloromethane, ethers such as tetrahydrofuran or dioxane, ketones such as acetone or MIBK (methyl isobutyl ketone), amides such as DMF, nitriles such as acetonitrile and sulfoxides, such as DMSO.
  • the reaction temperatures are generally between 0 0 C and the boiling point of the solvent.
  • the products of general formula (I) can be isolated in practically quantitative yield and good purity in some cases directly by filtration or, if readily soluble, after distillative removal of the solvents.
  • Collections of compounds of the formula (I) according to the invention which can be synthesized after the abovementioned reactions can also be prepared in a parallelized manner, which can be done in a manual, partially automated or completely automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood as a procedure as described, for example, by S.H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", Volume 1, published by Escom 1997, pages 69 to 77.
  • a microwave device eg "Discover" model from CEM GmbH Microwave-Analysentechnik, Carl-Fhedrich-Gauss-Str. 9, 47475 Kamp-Lintfort can be used.
  • Discover model from CEM GmbH Microwave-Analysentechnik, Carl-Fhedrich-Gauss-Str. 9, 47475 Kamp-Lintfort
  • a number of commercially available devices can be used, as for example by the company Stern Corporation, Woodrolfe road, Tollesbury, Essex, England, H + P Laboratory GmbH, Bruckmannring 28, 85764 Oberschl affectheim, Germany or the company Radleys, Shirehill, Saffron Waiden, Essex, CB 11 3AZ, England.
  • chromatographic apparatuses are available, inter alia, for example the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems may be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.
  • the preparation of the compounds of the general formula (I) according to the invention can be carried out completely or partially by solid phase-assisted methods.
  • solid phase-assisted methods For this purpose, individual intermediates or all intermediates of the synthesis or adapted for the appropriate approach synthesis are bound to a synthetic resin.
  • Solid phase assisted synthetic methods are well described in the literature, e.g. Barry A. Bunin in The Combinatorial Index, Academic Press, 1998.
  • solid-phase assisted synthesis methods allows a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the "teabag method” Houghten, U.S. 4,631,211; Houghten et al., Proc. Natl. Acad. Sei, 1985, 82, 5131-5135) with products from IRORI, 11149 North Torrey Pines Road, La JoIIa, CA 92037, USA.
  • the automation of solid-phase assisted parallel synthesis succeeds, for example, by equipment of the companies Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.
  • the preparation according to the processes described herein provides the salts according to the invention, in particular compounds of the formula (I), in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of the invention, in particular compounds of formula (I).
  • the compounds of the formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.
  • the compounds of the formula (I) according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented, or the weeds grow up to the cotyledon stage, but then cease their growth and finally die after three to three weeks four weeks completely off.
  • the compounds of the formula (I) according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, some crops of economically important crops, such as leguminous plants, are insignificantly or not at all damaged.
  • the present compounds of the formula (I) according to the invention have an excellent selectivity in legumes, and surprisingly, even at low doses of active ingredient, an outstanding action against the harmful plants typically occurring in leguminous plants is retained.
  • leguminous crops often difficult to control, such as species of the genera Amaranthus, Echinochloa, Sorghum, Ipomoea, Pharbitis, Solanum, Setaria, Brachiaria, Lolium, Euphorbia and Abutilon are very effectively controlled.
  • the present compounds of the formula (I) according to the invention are very well suited for the selective control of undesired plant growth in legumes but also for non-selective control of undesired plant growth, e.g. in permanent and plantation crops or on roadsides, squares, industrial plants, airfields or railway facilities or in the burn-down application.
  • the compounds of formula (I) according to the invention have excellent growth-regulatory properties in some crops. They regulate the plant's metabolism and can thus be used to specifically influence plant ingredients and facilitate harvesting, eg by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented. Because of their herbicidal and plant growth-regulating properties, the compounds of the formula (I) according to the invention can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • the active compounds can also be used to control harmful plants in cultures of known or yet to be developed mutant selection plants.
  • the compounds of the formula (I) according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the compounds of the formula (I) according to the invention or have been made genetically resistant or were obtained by mutant selection.
  • the compounds of the formula (I) according to the invention can be used as herbicides in crops representing a cross-product of genetically-resistant plants and plants obtained by mutant selection, as described, for example, in WO 2007/024782.
  • Well-known routes for the production of new plants which have modified properties compared to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
  • new plants with altered properties can be produced by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
  • genetic modifications of cultivated plants have been described for the purpose of modifying the starch synthesized in the plants (eg WO 92/11376, WO 92/14827, WO 91/19806), transgenic crop plants which are resistant to certain glufosinate-type herbicides (US Pat.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
  • standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • connection of the DNA fragments with each other can be made to the fragments adapters or linkers.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell.
  • the coding region is linked to DNA sequences which ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • the compounds of the formula (I) according to the invention can be used in transgenic or mutant selection cultures or crosses / hybrids thereof, which are resistant to herbicides from the group of sulfonylureas, glufosinate-ammonium or glyphosate isopropylammonium and analogous active ingredients.
  • the effects for application in the respective transgenic or by mutant selection cultures or Crosses thereof are specific, for example, a modified or specially extended weed spectrum that can be combated, changing rates that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of transgenic crops.
  • the invention therefore also relates to the use of the compounds of the formula (I) according to the invention as herbicides for controlling harmful plants in transgenic or mutant selection crops or crosses thereof.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also provides herbicidal and plant growth-regulating agents which contain the compounds of the formula (I) according to the invention.
  • the compounds of the formula (I) according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil-based or water-based dispersions, oil-miscible solutions, capsule suspensions ( CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV- Formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifi
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active ingredient, also contain surfactants, ionic and / or non-diluent or inert nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2 -dinaphthylmethan I-6,6'-disulfonate, sodium dibutylnaphthalene-sulfonate or else sodium oleoylmethyltaurinate contain.
  • surfactants ionic and / or non-diluent or inert nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxye
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • emulsifiers which may be used are alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxethylenesorbitan esters such as polyoxyethylene sorbitan fatty acid esters.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty
  • Dusts are obtained by grinding the active ingredient with finely divided solid
  • Fabrics e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
  • Emulsions for example oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as already listed above for the other formulation types.
  • Granules can either be prepared by spraying the active ingredient onto adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinites or granulated inert material.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying fluidized bed granulation
  • plate granulation mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain 0.1 to 99 wt .-%, preferably 0.1 to 95 wt .-%, particularly preferably 0.5 to 90 wt .-% active ingredient of the compounds of formula (I) according to the invention.
  • the active ingredient concentration is for example about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dusty formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
  • the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin sulphite liquors and methylcellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations.
  • the herbicidal action of the compounds of the formula (I) according to the invention can also be improved, for example, by surface-active substances, preferably by wetting agents from the series of fatty alcohol polyglycol ethers.
  • the fatty alcohol polyglycol ethers preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether section.
  • the fatty alcohol polyglycol ethers can be nonionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates, are present that are, for example, as alkali metal salts (eg sodium and potassium salts) or ammonium salts, or as alkaline earth metal salts are used, such as C 2 / Cu fatty alcohol diglykolethersulfat- sodium (Genapol ® LRO, Clariant GmbH); See, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988).
  • Nonionic fatty alcohol polyglycol ethers are, for example, 2-20, preferably 3-15, ethylene oxide units containing (Ci 0 - Ci 8 ) -, preferably (Cio-Cu) fatty alcohol polyglycol ether (eg isotridecyl alcohol polyglycol ether), for example from the Genapol ® X series as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Clariant GmbH).
  • Genapol ® X series as Genapol ® X-030, Genapol ® X-060, Genapol ® X-080 or Genapol ® X-150 (all from Clariant GmbH).
  • the present invention further comprises the combination of the compounds of the formula (I) according to the invention, with the aforementioned wetting agents from the series of fatty alcohol polyglycol ethers which preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part and nonionic or ionic (eg as fatty alcohol polyglycol ether) may be present.
  • C ⁇ / Cu-fatty alcohol diglycol ether sulfate sodium (Genapol ® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3-15 ethylene oxide units, for example from the Genapol ® X series, such as Genapol ® X-030, Genapol ® X 060, Genapol ® X-080 and Genapol ® X-150 (all from Clariant GmbH).
  • fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (eg fatty alcohol Polyglykolethersulfate) also are suitable as penetration aids and effect enhancers for a number of other herbicides, including for herbicides from the series of imidazolinones (see, for example, EP-A-0502014).
  • fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (eg fatty alcohol polyglycol ether) are also suitable as penetration aids and effect enhancers for a number of other herbicides, including for herbicides from the series of imidazolinones (see for example EP-A -0,502,014).
  • the herbicidal action of the herbicidal combinations according to the invention can also be enhanced by the use of vegetable oils.
  • vegetable oils is understood to mean oils from oil-supplying plant species, such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil or castor oil, in particular rapeseed oil, and
  • Transesterification products e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • the vegetable oils are preferably esters of C10-C22-. preferably C12-C20 fatty acids.
  • the C O -C 22 -fatty acid esters are, for example, esters of unsaturated or saturated C 10 -C 22 fatty acids, especially with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular Cis-fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • Cio-C 22 fatty acid esters are esters which are obtained by reacting glycerol or glycol with the C 10 -C 22 -fatty acids, as contained, for example, in oils from oil-yielding plant species, or C 1 -C 20 -alkyl -CioC 22 fatty acid esters, as can be obtained for example by transesterification of the aforementioned glycerol or glycol Cio-C-22 fatty acid esters with CrC 2 o-alcohols (eg, methanol, ethanol, propanol or butanol).
  • CrC 2 o-alcohols eg, methanol, ethanol, propanol or butanol
  • Preferred glycol and glycerol-C O -C 22 -fatty acid esters the uniform or mixed Glykolester and Glycerinester of Cio-C 22 fatty acids are preferred, in particular fatty acids having an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and, in particular C - ⁇ -fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.
  • the vegetable oils can be present in the inventive herbicidal compositions, for example in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main ingredient: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter called ActirobB, main ingredient: Rapsölmethylester), Rako-binol ® (Bayer AG, Germany, referred to as Rako-binol called main constituent: rapeseed oil), Renol ® (Stefes, Germany, termed Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ® (Stefes , Germany, hereinafter referred to as Mero, main component: rapeseed oil methyl ester) may be contained.
  • Hasten ® Vanictorian Chemical Company, Australia, hereinbelow termed
  • rapeseed oil preferably commercially available in the form of oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main constituent: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter referred to ActirobB, main component:
  • Rako-Binol ® (Bayer AG, Germany, referred to as Rako-Binol, main ingredient: rapeseed oil), Renol ® (Stefes, hereinafter referred to Germany Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ® (Stefes, Germany, termed Mero called, main component: rapeseed oil methyl ester).
  • Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the compounds of the formula (I) according to the invention as such or in the form of their preparations (formulations) with other pesticidal substances, such as. Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, e.g. as finished formulation or as tank mixes.
  • pesticidal substances such as. Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, e.g. as finished formulation or as tank mixes.
  • combination partners for the compounds of the formula (I) according to the invention in mixture formulations or in the tank mix are known, preferably herbicidal active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase are used.
  • herbicidal active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase are used
  • Ester derivatives e.g., clodinafop-propargyl); clofencet; clomazone; clomeprop; cloprop; cloproxydim; clopyralid; clopyrasulfuron (-methyl); cloransulam (-methyl); cumyluron
  • JC 940 cyanamide; cyanazine; cycloate; Cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (eg, butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D; 2,4-DB; dalapon; daminozide; dazomet; n-decanol; desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; dichlormid; dichlorprop (-P) salts; diclofop and its esters such as diclofop-methyl; diclofop-P (-methyl); diclosulam; diethatyl (-ethyl); difenoxuron; difenzoquat (methylsulfates); diflufenican; diflufenzopyr (-sodium
  • RP-020630 oxadiazon; oxasulfuron; oxaziclomefone; oxyfluorfen; paclobutrazol; paraquat (dichlorides); pebulate; pelargonic acid; pendimethalin; penoxulam; pentachlorophenol; Pentanochlor; pentoxazone; perfluidone; pethoxamid; phenisopham; phenmedipham; picloram; picolinafen; pinoxaden; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron (-methyl); probenazole; procarbazone- (sodium); procyazine; prodi amines; profluralin; profoxydim; Prohexadione (-Calcium); prohydrojasmon; proglinazine (-ethyl); prometon; prometryne; propachlor;
  • Preferred combination partners for use in soybean cultures are compounds which are selective in soy, for example: (a) selective in soybean against monocotyledonous and dicotyledonous harmful plants
  • Herbicides such as trifluralin, metribuzin, clomazone, pendimethalin, metolachlor, flumetsulam, dimethenamid, linuron, ethalfluralin, flufenacet, norflurazon, vernolates, chlorotoluron, chlorotoluron, cloransulam, and esters such as the methyl ester, imazethapyr, imazamox, imazaquin; or
  • herbicides which are selective in soybean against dicotyledonous weeds, for example sulphentrazone, bentazone, thifensulfuron and its esters, especially the methyl esters, oxyfluorfen, lactofen, fomesafen, flumiclorac and its esters such as the pentyl ester, acifluorfen and its sodium salt, 2,4-DB and its esters and salts, flumioxazine, benazoline,
  • herbicides which are selective in soybean monocotyledonous harmful plants, for example sethoxydim, cycloxydim, clethodim, quizalofop-P and its esters such as the ethyl or tefuryl ester, fenoxaprop-P and its
  • Esters such as the ethyl ester, fluazifop-P and its esters such as the butyl ester, Haloxyfop and Haloxyfop-P and their esters such as the methyl or the - etotylester, Propaquizafop, alachlor; or (d) non-selective, eg also usable for specific purposes in soya
  • Herbicides e.g. Glufosinate, glyphosate, paraquat (salts) such as paraquat dichloride,
  • Also preferred combination partners are Benozalin, Fenoxaprop, Lactofen, Chlortoluron, Flufenacet, Metribuzin, Benfuresate, Fentrazamide, Mefenacet, Diclofop, loxynil, Bromoxynil, Amidosulfuron, Flurtamone, Diflufenican, Ethoxysulfuron, Flucarbazone, Propoxycarbazone, Sulcotrione, Mesothone, Isoproturon, Iodosulfuron, Mesosulfuron, Foramsulfuron, anilofos, oxaziclomefones, oxadiargyl, isoxaflutole, linuron.
  • suitable non-selective herbicides preferably glufosinates and glyphosates, or their respective salts are suitable as mixing partners.
  • the safeners are preferably selected from the group consisting of: A) compounds of the formula (SI),
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (dC 4) -alkyl, (Ci-C 4) -alkoxy, nitro or (C r C 4) -haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles with 1 to
  • hetero ring atoms of the type N or O wherein at least one N-atom and at most one O-atom is contained in the ring, preferably a radical from the group
  • ITIA is 0 or 1
  • RA 2 is ORA 3 , SR A 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, via the N -
  • Atom is connected to the carbonyl group in (S-I) and unsubstituted or by
  • Radicals from the group (Ci-C 4 ) alkyl, (CrC 4 ) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula ORA 3 , NHR A 4 or N (CH 3 ) 2, in particular the formula ORA 3rd ; RA 3 is hydrogen or an unsubstituted or substituted aliphatic
  • Hydrocarbon radical preferably having a total of 1 to 18 carbon atoms
  • RA 4 is hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy or substituted or unsubstituted phenyl;
  • R A 5 is H, (CrC ⁇ ) alkyl, (C r C 8) haloalkyl, (Ci-C 4) alkoxy (Ci-C 8) alkyl, cyano or COOR A9 wherein R A 9 is hydrogen , (C r C 8 ) -alkyl, (C r C 8 ) -haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) d- C4) alkyl-silyl-alkyl, (d-CeJ-hydroxyalkyl, (C3-Ci2) -cycloalkyl or tri- (
  • RA 6, R 7 A, RA 8 are identical or different hydrogen, (Ci-C 8) -alkyl, (Ci-C ⁇ J -haloalkyl, (C3-Ci2) -cycloalkyl or substituted or unsubstituted phenyl;
  • a) compounds of the type dichlorophenylpyrazoline-3-carboxylic acid preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (S1-1 ) ("Mefenpyr-diethyl", see Pestic.
  • dichlorophenylpyrazolecarboxylic acid preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S1-2), 1- (2,4-dichlorophenyl) -5-isopropyl-pyrazole 3-carboxylic acid ethyl ester (S1-3),
  • RB 1 is halogen, (CrC 4) alkyl, (C 1 -C 4 J -alkoxy, nitro or (dC 4) -haloalkyl, n B is a natural number from 0 to 5, preferably from 0 to 3; RB 2 ORB 3 , SR 8 3 or NRB 3 RB 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N-atom and up to 3 heteroatoms, preferably from the group O and S, via the N atom with the carbonyl group is connected in (S-Il) and is unsubstituted or substituted by radicals from the group (CrC 4) alkyl, (C- ⁇ -C 4) -alkoxy or optionally substituted phenyl, preferably a radical of the formula oR B 3, NHR 8 4 or N (CH 3 ) 2 , in particular of the formula OR B 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (C 1 -C 6 J-AI alkyl, (CrC 6) -alkoxy or substituted or unsubstituted phenyl;
  • T 6 is a (Ci or C 2 ) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C 4 ) -alkyl radicals or by [(C 1 -C 6) -alkoxy] carbonyl;
  • S2 8-quinolinoxyacetic acid
  • Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 -C 7) cycloalkyl , preferably dichloromethyl;
  • Rc2, Rc3 is identical or different hydrogen, (CrC 4) alkyl, (C2-C4) alkenyl, (C 2 -C 4) -alkynyl, (C r C4) -haloalkyl, (C 2 - C 4) haloalkenyl, (Ci-C 4) alkylcarbamoyl (dC 4) alkyl, (C 2 -C 4) -Alkenylcarbamoyl- (C r C 4) alkyl, (CrC 4) alkoxy- (C -C 4) alkyl, dioxolanyl (Ci-C 4) -alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R c 2 and R 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine,
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide from the company
  • TI-35 1-dichloroacetyl-azepane from TRI-Chemical RT
  • diclonone dicyclonone
  • BAS145138 or "LAB145138”
  • MON 13900 3-dichloroacetyl-2,5,5-trimethyl-1, 3-diazabicyclo [4.3.0] nonane from BASF
  • X 0 is CH or N;
  • R 0 1 is CO-NR 0 5 RD 6 or NHCO-RD 7 ;
  • R 0 2 is halogen, (CrC 4) -haloalkyl, (dC 4) -haloalkoxy, nitro, (Ci-C 4) -alkyl, (C 1 - C 4) alkoxy, (CrC 4) alkylsulfonyl, (dC 4 ) alkoxycarbonyl or (C 1 -C 4 ) -alkylcarbonyl;
  • R 0 3 is hydrogen, (C r C4) alkyl, (C 2 -C 4) -alkenyl or (C 2 -C 4) alkynyl;
  • RD 4 is halogen, nitro, (dC ⁇ alkyl, (C r C4) -haloalkyl, (CrC ⁇ -haloalkoxy, (C 3 - C 6)
  • RD 6 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl, where the three last-mentioned radicals are substituted by VD radicals from the group halogen, hydroxy, ( C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy and (C 1 -C 4 ) -alkylthio are substituted, or
  • R 0 5 and R 0 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical
  • R 7 0 is hydrogen, (Ci-C 4) alkylamino, di- (dC 4) alkylamino, (C r C6) alkyl, (C 3 - C 6) -cycloalkyl, where the 2 last-mentioned radicals are substituted by VD Substituents from the group halogen, (CiC 4 ) alkoxy, halogen (CrC 6 ) alkoxy and (CrC 4 ) alkylthio and in the case of cyclic radicals are also (CrC 4 ) alkyl and (CrC 4 ) haloalkyl substituted;
  • R D 4 halogen, (CrC 4) alkyl f (C r C 4) -alkoxy f CF 3;
  • ⁇ TID means 1 or 2;
  • V 0 is 0, 1, 2 or 3;
  • R 0 R 0 8 and 9 are each independently hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 6) -alkenyl, (C 3 -C 6) alkynyl, R 0 4 is halogen, (C r C 4 ) alkyl, (CrC 4 ) alkoxy, CF 3 m D 1 or 2;
  • RK 1 , RK 2 independently of one another are halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 -alkoxy, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkylamino, di- (C 1 -C 4 ) -alkylamino, nitro;
  • R ⁇ 3 , RK 4 independently of one another are hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 6 ) -alkenyl,
  • Halobenzyl, pyridinylalkyl and alkylammonium, n ⁇ 1 0 or 1 n ⁇ 2 , n ⁇ 3 are independently 0, 1 or 2
  • R L 1 is halogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C r C4) alkoxy, (Ci-C 4) -haloalkoxy, nitro, (CrC 4) alkylthio, (Ci-C 4) alkylsulfonyl, (C r C4) -alkoxycarbonyl, optionally substituted.
  • Phenyl, optionally substituted phenoxy, R L 2 is hydrogen or (C r C 4 ) -alkyl
  • R L 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted, or their salts.
  • R N 1 is halogen, (C 1 -C 4 ) -alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 Y, Z independently of one another are O or S, ⁇ N is an integer from 0 to 4, R is N 2 (Ci-Ci 6 ) Alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl, R N 3 is hydrogen, (C r C 6 ) alkyl;
  • a mixture with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners is also possible.
  • Some of the safeners are already known as herbicides and therefore, in addition to the herbicidal effect on harmful plants, also have a protective effect on the crop plants.
  • the weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.
  • the type of herbicide used u.a. varies the required application rate of the compounds of formula (I) according to the invention. It can vary within wide limits, e.g. between 0.001 and 10000 g / ha or more of active substance, but it is preferably between 0.5 and 5000 g / ha, preferably between 0.5 and 1000 g / ha and most preferably between 0.5 and 500 g / ha.
  • the active compounds of the invention may e.g. used in the following plants:
  • the salts according to the invention are also suitable for total weed control, e.g. on industrial and railway tracks and on paths and squares with and without tree cover.
  • the active compounds of the present invention may be used for weed control in permanent crops, e.g. Forest, ornamental, fruit, wine, citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports lawns and grazing land and selective Weed control in one-year crops.
  • the compounds of the formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when applied to the soil and above-ground parts of plants.
  • the preparation and the use of the active compounds according to the invention are evident from the examples below.
  • HPLC 98.5%, 76.7% of theory
  • a dust is obtained by mixing 10 parts by weight of a compound of the formula (I) according to the invention and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of formula (I), 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurine as net and dispersing agent and grinding in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) according to the invention with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3
  • isotridecanol polyglycol ether 8 EO
  • paraffinic mineral oil oil range, for example, about 255 to more than 277 C
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) according to the invention, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granules are also obtained by
  • Plastic pots in sandy loam soil, covered with soil and in the greenhouse under good and defined growth conditions, i. at a day / night rhythm of 22 ° C / 14 ° C, attracted. Thereafter, the plants were treated in the 2-4 leaf stage with an aqueous test solution of various compounds of the invention in the specified dosage. After four weeks, the rating was as follows:
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy soil in cardboard pots and covered with soil.
  • the compounds of the invention formulated in the form of wettable powders or emulsion concentrates were then applied to the surface of the cover soil as aqueous suspensions or emulsions having a water application rate of 100 to 800 l / ha in different dosages.
  • compounds Nos. 1-1, 1-2, I-5, 1-14, I-35, I-38, I-39, I-40 of Table 1 also have very good herbicidal activity against harmful plants such as Matricaria inodora, Papaver rhoeas, Stellaria media, and Viola tricolor pre-emergence at an application rate of 0.08 kg and less active ingredient per hectare. 3. crop compatibility

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Abstract

La présente invention porte sur des sels sélectionnés du 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-N-[(4,6-diméthoxypyrimidin-2-yl)carbamoyl]pyridin-2-sulfonamide, sur leur procédé de fabrication, ainsi que sur leur utilisation en tant qu'herbicides, en particulier en tant qu'herbicides pour la lutte sélective contre les mauvaises herbes indésirables dans les légumineuses, ou pour la lutte non sélective contre les mauvaises herbes indésirables dans des terres non cultivées, ainsi qu'en tant que régulateurs de croissance des végétaux, individuellement ou avec des phytoprotecteurs et/ou en combinaison avec d'autres herbicides, dont l'utilisation pour la lutte contre les mauvaises herbes indésirables (comme par exemple les mauvaises herbes et les plantes adventices) est connue dans des cultures spéciales, ou en tant que régulateurs phytosanitaires, dans le cadre d'une utilisation simultanée et/ou séquentielle, en tant que formulation prête à l'emploi ou en tant que mélange en cuve.
EP09723433A 2008-03-19 2009-03-13 Sels sélectionnés du 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-n-[(4,6-diméthoxypyrimidin-2-yl)carbamoyl]pyridin-2-sulfonamide, leur procédé de fabrication, ainsi que leur utilisation en tant qu'herbicides et régulateurs de la croissance des végétaux Withdrawn EP2265121A1 (fr)

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EP09723433A EP2265121A1 (fr) 2008-03-19 2009-03-13 Sels sélectionnés du 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-n-[(4,6-diméthoxypyrimidin-2-yl)carbamoyl]pyridin-2-sulfonamide, leur procédé de fabrication, ainsi que leur utilisation en tant qu'herbicides et régulateurs de la croissance des végétaux

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EP08005143A EP2103216A1 (fr) 2008-03-19 2008-03-19 Sels de 3-(5,6-dihydro-1,4,2-dioxazine-3-yl)-N-[(4,6-diméthoxypyrimidine-2-yl)carbamoyl] pyridine-2-sulfonamide choisis, leur procédé de fabrication et leur utilisation en tant qu'herbicides et régulateurs de croissance des plantes
EP09723433A EP2265121A1 (fr) 2008-03-19 2009-03-13 Sels sélectionnés du 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-n-[(4,6-diméthoxypyrimidin-2-yl)carbamoyl]pyridin-2-sulfonamide, leur procédé de fabrication, ainsi que leur utilisation en tant qu'herbicides et régulateurs de la croissance des végétaux
PCT/EP2009/001822 WO2009115237A1 (fr) 2008-03-19 2009-03-13 Sels sélectionnés du 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-n-[(4,6-diméthoxypyrimidin-2-yl)carbamoyl]pyridin-2-sulfonamide, leur procédé de fabrication, ainsi que leur utilisation en tant qu'herbicides et régulateurs de la croissance des végétaux

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EP09723433A Withdrawn EP2265121A1 (fr) 2008-03-19 2009-03-13 Sels sélectionnés du 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-n-[(4,6-diméthoxypyrimidin-2-yl)carbamoyl]pyridin-2-sulfonamide, leur procédé de fabrication, ainsi que leur utilisation en tant qu'herbicides et régulateurs de la croissance des végétaux

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RS56603B2 (sr) * 2010-10-15 2021-10-29 Bayer Ip Gmbh Upotreba als inhibitora herbicida za kontrolu neželjene vegetacije kod beta vulgaris biljaka tolerantnih na als inhibitore herbicida
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AR070937A1 (es) 2010-05-12
TW201002207A (en) 2010-01-16
BRPI0908703A2 (pt) 2015-07-21
US20110009263A1 (en) 2011-01-13
CN101977508A (zh) 2011-02-16
CL2009000747A1 (es) 2009-07-03
AU2009226680A1 (en) 2009-09-24
KR20100125417A (ko) 2010-11-30
ZA201005784B (en) 2011-04-28
WO2009115237A1 (fr) 2009-09-24
MX2010010207A (es) 2010-10-04
CA2718815A1 (fr) 2009-09-24

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