EP2205091A2 - Sels de 2-iodo-n-[(4-méthoxy-6-méthyl-1,3,5-triazine-2-yle)carbamoyl]benzolsulfonamide, procédés de production et utilisation en tant qu'herbicides et régulateurs de croissance végétale - Google Patents

Sels de 2-iodo-n-[(4-méthoxy-6-méthyl-1,3,5-triazine-2-yle)carbamoyl]benzolsulfonamide, procédés de production et utilisation en tant qu'herbicides et régulateurs de croissance végétale

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Publication number
EP2205091A2
EP2205091A2 EP08841543A EP08841543A EP2205091A2 EP 2205091 A2 EP2205091 A2 EP 2205091A2 EP 08841543 A EP08841543 A EP 08841543A EP 08841543 A EP08841543 A EP 08841543A EP 2205091 A2 EP2205091 A2 EP 2205091A2
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EP
European Patent Office
Prior art keywords
ion
alkyl
methyl
radicals
alkoxy
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
EP08841543A
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German (de)
English (en)
Inventor
Christian Waldraff
Klaus-Helmut Müller
Ernst Rudolf Gesing
Jan Dittgen
Dieter Feucht
Hansjörg Krähmer
Martin Jeffrey Hills
Georg Bonfig-Picard
Martin Hess
Dominique Schreiber
Christopher Hugh Rosinger
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Bayer CropScience AG
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Bayer CropScience AG
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Publication date
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Priority to EP08841543A priority Critical patent/EP2205091A2/fr
Publication of EP2205091A2 publication Critical patent/EP2205091A2/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Withdrawn legal-status Critical Current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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/65—N-sulfonylisocyanates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom

Definitions

  • This invention relates to salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide, to a process for their preparation and to their use as herbicides, in particular as Herbicides for the selective control of undesired weed plants in crops, permanent crops or non-crops, as well as plant growth regulators alone, or with safeners and / or in combination with other herbicides, their use for controlling unwanted weeds (such as weeds / grass weeds) in specific crops or known as crop protection regulators is, with simultaneous and / or sequential application, either as a ready-made formulation or as a tank mix.
  • substituted phenylsulfonylureas have herbicidal properties. These are e.g. phenyl derivatives which are monosubstituted or polysubstituted (for example US 4127405, WO 9209608, BE 853374, WO 9213845, EP 84020, WO 9406778, WO 02072560, US 4169719, US 4629494, DE 4038430). From WO 2006/114220 it is furthermore known that sulphonamides iodinated on the phenyl ring have herbicidal properties.
  • salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide are particularly advantageously suitable as herbicides and / or plant growth regulators ,
  • the present invention thus provides agrochemically active salts of 2-iodo-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) carbamoyl] benzenesulfonamide.
  • the preferred subject matter of the present invention are compounds of the general formula (I)
  • cation (M + ) (a) is an ion of the alkali metals, preferably lithium, sodium, potassium, or
  • transition metals preferably manganese, copper, zinc and iron, or
  • a sulfonium ion preferably tri - ((C 1 -C 4 ) alkyl) sulfonium, or (g) an oxonium ion, preferably tri - ((C 1 -C 4 ) -alkyl) -oxonium, or (h) a saturated or unsaturated / aromatic N-, optionally mono- or polysubstituted and / or (C 1 -C 4 ) -alkyl-substituted containing heterocyclic ionic compound having 1-10 C atoms in the ring system.
  • transition metals preferably manganese, copper, zinc and iron
  • ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the group CJ) -alkyl, hydroxy- (C 1 -C 4 ) -alkyl, (C 3 -C 4 ) -cycloalkyl, (C 1 -C 2 ) -alkoxy- (C 1 -C 2 ) -alkyl, hydroxy- ( CrC 2 ) alkoxy- (Ci-C 2 ) -alkyl, (dC 2 ) -Mercaptoalkyl, phenyl or benzyl are substituted, the aforementioned
  • Radicals optionally substituted by one or more identical or different radicals from the group halogen, such as F, Cl, Br or I, nitro, cyano, azido, (dC ⁇ alkyl, (C r C 2) -haloalkyl, (C 3 - C 4 ) -cycloalkyl, (C 1 -C 2 ) -alkoxy, (C r C 2 ) -haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N-
  • DBU 1,8-diazabicyclo [5.4.0] undec-7-ene
  • Imidazolium ion a morpholinium ion, a 1,8-diazabicyclo [5.4.0] undec-7-enium-ion.
  • cation (M + ) is a sodium ion, a potassium ion, a magnesium ion, a calcium ion, or an NH 4 + ion.
  • 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 means a carbocyclic saturated ring system preferably having 3-6 C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • the compounds of the formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). For example, if one or more alkenyl groups are present, then
  • Diastereomers (Z and E isomers) occur. For example, if one or more asymmetric carbon atoms are present, then enantiomers and Diastereomers occur.
  • Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, 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 no longer specified with their specific stereoform, and their mixtures.
  • 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 the preparation of the salts according to the invention, in particular of compounds of the general formula (I).
  • R * is a substituted or unsubstituted (CrC 2 O) hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C r C4) alkyl,
  • R ** is a substituted or unsubstituted (CrC 2 O) hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (Ci-C 4) -alkyl,
  • the base heterocycle of formula (V) is first base catalysed with a carbonic acid ester, e.g. Diphenyl carbonate, reacted and the intermediate formed in a one-pot reaction with 2-iodobenzenesulfonamide (II) (see variant a)) (see JP1989221366), or
  • Hal is a halogen atom, preferably chlorine (Villa), or fluorine (VIIIb), or bromine (VIIIc), with a cyanate, for example a metal cyanate, in particular an alkali metal cyanate, such as sodium cyanate, to the isocyanate of the formula (VI) or a solvated ( stabilized) derivative thereof, and then reacted with the amino heterocycle of formula (V) implements,
  • a cyanate for example a metal cyanate, in particular an alkali metal cyanate, such as sodium cyanate
  • R * is a substituted or unsubstituted (C 1 -C 2 0 ) hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C 1 -C 4 ) -alkyl (see WO 96/22284),
  • Carbonic acid esters e.g. Diphenylcarbamat
  • the reaction of the compounds of the formulas (II) and (III) according to variant a) is preferably carried out under base catalysis in an inert organic solvent such as dichloromethane, acetonitrile, dioxane or THF at temperatures between 0 0 C and the boiling point of the solvent, preferably at room temperature
  • DBU 1,8-diazabicyclo [
  • 2-iodobenzenesulfonyl isocyanate is a novel compound which, as well as its preparation and its use for the preparation of compounds of formula (I), are the subject of the present invention.
  • 2-iodobenzenesulfonamide (II) can be e.g. as shown in the following Schemes 1 to 7.
  • 2-nitroaniline can, for example by diazotization of the amino group with an alkali metal nitrite, such as. As sodium nitrite, in the presence of hydrochloric acid at temperatures between -1O 0 C and 10 0 C and subsequent exchange of the resulting diazo z. B. with sulfur dioxide in the presence of a diluent, such as. For example, dichloromethane, 1, 2-dichloroethane or acetic acid, and in the presence of a catalyst such.
  • an alkali metal nitrite such as sodium nitrite
  • hydrochloric acid at temperatures between -1O 0 C and 10 0 C and subsequent exchange of the resulting diazo z.
  • sulfur dioxide in the presence of a diluent, such as.
  • a diluent such as.
  • N-tert-butyl-2-nitrobenzenesulfonamide (X) can be obtained.
  • the sulfonamide is, for example, in inert solvents such as dichloromethane, tetrahydrofuran (THF), dioxane, toluene or dimethylformamide (DMF) at temperatures between -70 0 C to the boiling point of the solvent used, preferably carried out at 25 0 C.
  • inert solvents such as dichloromethane, tetrahydrofuran (THF), dioxane, toluene or dimethylformamide (DMF)
  • THF tetrahydrofuran
  • DMF dimethylformamide
  • Aniline (XI) can be diazotised under standard conditions for diazotization reactions and then converted into N-tert-butyl-2-iodobenzenesulfonamide (XII).
  • the diazotization takes place in the presence of the acid H + X " , where X " is preferably Cl “ , I “ or HSO 4 " , in aqueous solution, if appropriate using an organic solvent which is inert under the reaction conditions, with a nitrite an alkali metal nitrite such as NaNO 2 (sodium nitrite) in amounts of from 1.0 to 1.2 mol of nitrite, preferably from 0.01 to 1.05 mol of nitrite, per mole of aniline (XI)
  • Suitable acids are mineral acids or strong organic acids, preferably hydrochloric acid or sulfuric acid.
  • the solvent is water or a mixture of water and an inert organic solvent under the reaction conditions.
  • the reaction temperature is generally between -5 0 C and 5O 0 C, preferably 1O 0 C to 2O 0 C.
  • the reaction of the diazonium salts obtained for iodine compound (XII) is usually carried out without isolation and is carried out in the same aqueous or aqueous-organic solvent or solvent mixture as the diazotization.
  • alkali metal iodide preferably sodium iodide or potassium iodide.
  • the amount of iodide is, for example, 1.1 to 1.5 moles of iodide per mole of originally used aniline (XI).
  • the reaction temperature amounts to here generally 1O 0 C to 4O 0 C, preferably 15 0 C to 3O 0 C (see. This example, DE 19625831 and Bioorg. Med. Chem. 2004, 12, 2079) (Scheme 3).
  • the cleavage of the tert-butyl protecting group in (XII) to give 2-iodobenzenesulfonamide (II) takes place, for example, by treatment with a strong acid (see WO 89/10921).
  • strong acids are mineral acids, such as H 2 SO 4 or HCl, or strong organic acids, such as trifluoroacetic acid.
  • the reaction takes place for example at temperatures from -20 0 C to the respective reflux temperature of the reaction mixture, preferably at 0 C to 40 0 C.
  • the reaction can be in bulk or in an inert solvent such as dichloromethane or trichloromethane, are carried out (Scheme 4).
  • N-tert-butyl-2-iodobenzenesulfonic acid amide (XII) can also be obtained by reacting N-tert-butyl-benzenesulfonic acid amide (XIV), which is prepared by reacting commercially available benzenesulfonyl chloride (XIII) with tert-butylamine (see Scheme 1) can be obtained with an organometallic compound, such as alkyl or aryllithium, preferably ⁇ - or sec-butyllithium in hexane, optionally in the presence of a (further) inert diluent, such as tetrahydrofuran, and under an inert gas atmosphere, such as under argon or nitrogen, at temperatures between -70 0 C and 2O 0 C metallated - ie replaced in (XIV) in ortho position to S ⁇ 2 NH-tert-butyl group replaced by a metal atom - and then in the same reaction medium with
  • 2-iodobenzenesulfonamide (II) can also be obtained (Scheme 6) by dissolving 2-iodobenzenesulfonyl chloride (Villa) by diazotizing the amino group in 2-iodoaniline (XV) and then replacing the resulting diazo group with a chlorosulfonyl group (as in Scheme 1 described in more detail) is produced, reacted with ammonia.
  • ammonia gas is introduced in inert solvent, preferably dichloromethane or tetrahydrofuran, until no more ammonia is absorbed.
  • 2-iodobenzenesulfonyl chloride Villa
  • XII N-tert-butyl-2-iodobenzenesulfonamide
  • tert-butylamine analogous to Schemes 1 and 5
  • the tert-butyl protective group is then removed by means of acid (analogous to Scheme 4) to obtain 2-iodobenzenesulfonamide (II).
  • the aminoheterocycles of formula (V) are known, in part commercially available synthetic chemicals.
  • the reaction of the sulfonylcarbamates of the formula (IV) with the aminoheterocycles of the formula (V) is carried out by known processes (cf., for example, WO 2003 091228) (Scheme 7).
  • 2-iodobenzenesulfonyl isocyanate of the formula (VI) is a novel compound and is therefore also the subject of this invention. It can be prepared by processes known per se from 2-iodobenzenesulfonamide (II) (cf., DE 3208189, EP 23422, EP 64322, EP 44807, EP 216504).
  • the sulfonyl isocyanate of the formula (VI) is obtained when 2-iodobenzenesulfonamide (II) with phosgene, diphosgene or thiophosgene, if appropriate in the presence of an alkyl isocyanate, such as butyl isocyanate, optionally in the presence of a reaction auxiliary, such as a tertiary amine, preferably a diazabicyclo [2.2.2] octane, and in the presence of a Verkowsmiteis, such as toluene, XyIoI or chlorobenzene, at temperatures between 80 0 C and 150 0 C reacted and after the completion of the reaction, if appropriate, the volatile components distilled off under reduced pressure (Scheme 8 ).
  • an alkyl isocyanate such as butyl isocyanate
  • a reaction auxiliary such as a tertiary amine, preferably a diazabicyclo [
  • the isocyanates of the general formula (VII) are obtained, for example, from the aminoheterocycles of the type (V) by treatment with oxalyl chloride or phosgene (in analogy to Angew. Chem. 1971, 83, p. 407, EP 388 873).
  • the reaction of the isocyanate of type (VII) with 2-iodobenzenesulfonamide (II) takes place, for example, in analogy to variant c) (Scheme 10).
  • 2-iodobenzenesulphonic acid fluoride (VIIIb) can be prepared by various methods known from the literature: i) from 2-iodobenzenesulphonamide (II) by diazotization with alkali metal nitrite, for example sodium nitrite, and subsequent reaction with hydrogen fluoride (J.Am.Chem. Soc. 1951, 73, 1857 ); ii) reaction of 2-iodobenzenesulfonyl chloride (Villa) with potassium fluoride (J. Chem. Soc, Perkin Trans.
  • reaction mixture obtained by reaction of the sulfonic acid halide (VIII) with a cyanate is used directly for the coupling with the aminotriazine of the formula (V) for the synthesis of the precursor (neutral compound) of the formula (I) (cf. WO 2003 091228 and US 5550238).
  • the salts according to the invention can be selected from the neutral form of the sulphonylurea or sulphonylurea metal salts, in particular alkali metal salts (see for example EP-A-30138, EP-A-7687) or also starting from sulphonamide salts e.g. in the following way:
  • the sulfonylurea of the formula (I) is dissolved or suspended in an inert solvent or solvent mixture and reacted with one equivalent of M + B " at temperatures between -2O 0 C and 100 0 C, preferably between -10 0 C and 5O 0 C. ,
  • alkali metal salts such as NaCl
  • the neutral Sulfonalharnstoff (XX) is dissolved in an inert solvent or solvent mixture and reacted with one equivalent of the reagents M + X ' and MetB.
  • the by-produced metal salt in particular alkali metal salt (eg NaCl) can be separated off by filtration.
  • R is a (CrC 2 o) -carbon radical such as (C 1 -C 4) -alkyl
  • R 'and R are identical or different and are hydrogen or (C 1 -C 30) -hydrocarbon radicals such as (C 1 -C 10) -alkyl
  • m is an integer of 0 to 100.
  • the neutral sulfonylurea (XX) is reacted with a zwitterionin, as indicated, for example, in Scheme 14, in an inert solvent such as methanol, tetrahydrofuran or methylene chloride or solvent mixture at temperatures between -2O 0 C and 100 0 C, preferably -1O 0 C and 8O 0 C reacted in equimolar ratios.
  • a zwitterionin as indicated, for example, in Scheme 14
  • the reaction takes place in an inert solvent or solvent mixture - such as. B. tetrahydrofuran - at temperatures between -2O 0 C and 100 0 C, preferably between -1O 0 C and 7O 0 C, by reacting the isocyanate (VII) equimolar with the sulfonic acid amide salt of the formula (IIa).
  • the sulfonic acid amide salt of the formula (IIa) can be used directly or be formed in situ - z.
  • the reaction is carried out in an inert solvent (or solvent mixture) - such as tetrahydrofuran - at temperatures between -2O 0 C and 100 0 C, preferably between -1O 0 C and 70 0 C by reacting the carbamate of the formula (III) equimolar with with the sulfonic acid amide salt of the formula (IIa).
  • the sulfonic acid amide salt of the formula (IIa) can be used directly or formed in situ - z.
  • Haloalkoxy and phenyl are substituted, and wherein in each case two substituents on the N atom together optionally form an unsubstituted, optionally a substituted ring, or
  • (C) a possibly singly or multiply fused and / or (C 1 -C 4 ) alkyl substituted saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1-10 carbon atoms in the ring system correspond
  • This reaction takes place between temperatures of -2O 0 C to 100 0 C, preferably between -1O 0 C and 5O 0 C, in inert solvent, such as.
  • inert solvent such as tetrahydrofuran, methylene chloride or methanol or mixtures of solvents instead.
  • inert solvents denoted in the above process variants are meant in each case solvents which are inert under the respective reaction conditions, but need not be inert under any reaction conditions.
  • Collections of salts according to the invention in particular those of the formula (I) which can be synthesized after the abovementioned reactions, can also be prepared in a parallelized manner, this being manual, in part automated or completely automated way. 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 an approach as described, for example, by SH DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity:"
  • a microwave oven e.g. Model "Discover” by the company CEM GmbH Microwave Analysis, Carl-Friedrich-Gauss-Str. 9, 47475 Kamp-Lintfort be used.
  • 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 salts according to the invention, in particular of compounds of the general formula (I) can be carried out completely or partially by methods supported by solid phases.
  • 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, eg 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, US 4,631,211; Houghten et al., Proc Natl Acad. Sei, 1985, 82, 5131-51305
  • 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 salts according to the invention in particular compounds of the formula (I), 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 is It does not matter whether the substances are applied in pre-sowing, pre-emergence or post-emergence procedures.
  • salts according to the invention in particular compounds of the formula (I) are applied to the surface of the earth before germination, then 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 expiration from three to four weeks completely off.
  • active ingredients are applied to the green parts of the plants postemergence, a drastic growth stop also occurs very rapidly after the treatment, and the weed plants remain in the position reached at the time of application
  • the salts according to the invention in particular the compounds of the formula (I), have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, e.g. Wheat, barley, rye, oats, rice, maize, sugarcane, flax and other plantation crops are marginally or not at all damaged.
  • crops of economically important crops e.g. Wheat, barley, rye, oats, rice, maize, sugarcane, flax and other plantation crops are marginally or not at all damaged.
  • the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops.
  • salts according to the invention in particular compounds of the formula (I) have very advantageous properties with regard to the behavior in the environment, in particular with respect to the reproduction behavior, i. towards the compounds according to the invention of the formula (I) otherwise sensitive cultures, such as sugar beet, sunflower or Cruciferen, such as rapeseed, mustard and turnip rape.
  • the salts according to the invention in particular the compounds of the formula (I), have excellent growth-regulatory properties in crop plants. They regulate in the plant's own Metabolism and can thus be used for the targeted influencing of plant ingredients and to facilitate harvesting, such as by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented.
  • the active compounds 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 relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • the active compounds can also be used to control harmful plants in crops of known or yet to be developed mutant-selected plants.
  • the salts according to the invention in particular of compounds of the formula (I), in economically important transgenic or mutant-selected crops of useful and ornamental plants, eg.
  • crops of useful and ornamental plants eg.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or even crops of rapeseed, potato, tomato, pea and other vegetables.
  • the salts according to the invention, in particular the compounds of the formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant, or obtained by mutant selection.
  • the salts according to the invention in particular the compounds of the formula (I), can likewise be used as herbicides in crops which represent a cross product of genetically resistant plants and plants obtained by mutant selection, as described, for example, in WO 2007/024782.
  • 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.
  • z For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments.
  • 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. Also possible is the use of DNA sequences encoding a high degree of homology to the ones
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Be. USA 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 salts according to the invention in particular compounds of the formula (I), can preferably be employed in transgenic or mutant-selected cultures or crosses / hybrids thereof which are resistant to herbicides from the group of sulfonylureas, glufosinate-ammonium or glyphosate isopropylammonium and analogous active substances.
  • the active compounds according to the invention in addition to the effects observed in other cultures on harmful plants, effects which are specific for the application in the respective transgenic or mutant selection-derived cultures or crosses thereof are often present, For example, a modified or specially extended weed spectrum that can be controlled, changed application rates that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of transgenic crops.
  • the invention therefore also relates to the use of the salts according to the invention, in particular of compounds of the formula (I), as herbicides for controlling harmful plants in transgenic or mutant-selected crop plants 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).
  • the salts according to the invention in particular the compounds of the formula (I), 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 powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water dispersible
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC oil or water
  • WG Granules
  • SG water-soluble granules
  • ULV formulations microcapsules and waxes.
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agent, dispersing agent) in addition to the active ingredient, apart from a diluent or inert substance.
  • surfactants of the ionic and / or nonionic type (wetting agent, dispersing agent) in addition to the active ingredient, apart from a diluent or inert substance.
  • 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, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
  • Propylene oxide-ethylene oxide condensation products alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
  • Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding by means of commercial bead mills and, if appropriate, addition of surfactants, as already listed above, for example, in the other formulation types.
  • Emulsions e.g. 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 described e.g. listed above for the other formulation types.
  • Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on 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 from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, particularly preferably from 0.5 to 90% by weight of active ingredient of the salts according to the invention, in particular of the compounds of the formula (I) ,
  • 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% by weight, preferably between 10 and 80% by weight.
  • 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: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules: For example, broken 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: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and
  • adhesives such as carboxymethyl cellulose, natural and synthetic powdery, gromige or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural
  • Phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • the herbicidal activity of the herbicidal combinations according to the invention may be e.g. also be improved by surface-active substances, preferably by wetting agents from the series of fatty alcohol polyglycol ethers.
  • the fatty alcohol preferably by wetting agents from the series of fatty alcohol polyglycol ethers.
  • 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 may be nonionic, or ionic, e.g. in the form of fatty alcohol polyglycol ether sulfates, e.g. as alkali salts (e.g., sodium and potassium salts) or ammonium salts, or as alkaline earth salts such as
  • Magnesium salts can be used, such as C 2 / C 4 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 to 20, preferably 3 to 15,
  • Genapol ® X series such 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 components A and B with the previously mentioned 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 may be present nonionically or ionically (for example as fatty alcohol polyglycol ether sulfates).
  • 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 may be present nonionically or ionically (for example as fatty alcohol polyglycol ether sulfates).
  • Genapol ® X series such as Genapol ® X-030, Genapol ® X - C 2 / Ci4-fatty alcohol diglycol ether sulfate sodium (Genapol ® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3 are preferably 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) as a penetration aid and enhancer for a number of other herbicides, including for
  • Herbicides from the series of imidazolinones are suitable (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 refers to 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 their transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.
  • the vegetable oils are preferably esters of C1 -C22- 0, preferably C12-C-20 fatty acids.
  • the C O -C 2 2-fatty acid ester are, for example, esters of unsaturated or saturated Cio-C 22 fatty acids, especially with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and in particular C-
  • C 10 -C 22 fatty acid esters are esters obtained by reacting glycerol or glycol with the C O -C 22 fatty acids, as they are, for example, in oils from oil-plant species, or -C 2 o alkyl -CioC22 fatty acid esters, as for example, by transesterification of the aforementioned glycerol or glycol Ci 0 -C 22 fatty acid esters with CrC 2 o-alcohols (eg, methanol, ethanol, propanol or
  • Butanol can be obtained.
  • the transesterification can be carried out by known methods, such as e.g. are described in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.
  • Preferred as CrC 2 o-alkyl-Cio-C 22 fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters.
  • Preferred glycol- and glycerol-Cio-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 8 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
  • the present invention comprises combinations with the abovementioned vegetable oils, such as rapeseed oil, preferably in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil, such as Hasten® (Victorian Chemical Company, Australia, below Hasten mentioned, main ingredient: rapeseed oil ethyl ester), Actirob ® B (Novance, France, hereinafter ActirobB called Main Ingredient: (rapeseed oil), Renol ®: Rapsölmethylester), Rako-Binol ® (Bayer AG, Germany, termed Rako-Binol, main ingredient , hereinafter referred Stefes, Germany Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ® (Stefes, Germany, termed Mero called main ingredient: Rapsölmethylester).
  • Hasten® Victorian Chemical Company, Australia, below Hasten mentioned, main ingredient: rapeseed oil
  • Dyes such as inorganic pigments, e.g. 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 salts according to the invention in particular the compounds of the formula (I), can be used as such or in the form of their formulations (formulations) with other pesticide-active substances, such as.
  • pesticide-active substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators
  • insecticides e.g. B. as a ready-made formulation or as tank mixes.
  • Suitable combination partners for the salts according to the invention are, for example, known, preferably herbicidal active ingredients 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.
  • herbicidal active ingredients 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.
  • salts also include those which are formed by replacement of a hydrogen atom on the sulfonamide group by a cation.
  • Ester derivatives e.g., butyl ester, DEH-112; cyperquat; cyprazine; cyprazole; daimuron;
  • SAN-582H dimethenamide-P; dimethylarsinic acid; dimethipin; dimetrasulfuron; dimexyflam; dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat salts; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.
  • 310 i. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazol; neburon; nicosulfuron; nipyraclofen; nitralin; nitrofen; nitrophenolate mixture; nitrofluorfen; nonanoic acid; norflurazon; orbencarb; orthosulfamuron; oxabetrinil; oryzalin; oxadiargyl
  • 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;
  • ICI-A0224 sulfosulfuron; TCA (-sodium); tebutam (GCP-5544); tebuthiuron; tecnacene; tefuryltrione; tembotrione; tepraloxydim; terbacil; terbucarb; terbuchlor; terbumeton; Terbuthylazine; terbutryn; TFH 450, i.
  • trimeturon trinexapac; tritosulfuron; tsitodef; Uniconazole; vernolate; WL
  • salts according to the invention in particular the compounds of the formula (I) already have very good to sufficient selectivity in many cultures, phytotoxicities on the crop plants can in principle in some cultures and above all also in the case of mixtures with other herbicides which are less selective occur.
  • the safeners which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg. B. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.
  • the safeners are preferably selected from the group consisting of:
  • ⁇ A is a natural number from 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (CrC 4) alkyl, (dC 4) -alkoxy, nitro or (C r C 4) -haloalkyl; WA is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero-ring atoms of the type N or O, at least one N-atom and at most one O-atom in the ring, preferably a radical from the group (W A 1 ) to (W A 4 ),
  • RA 2 is ORA 3 , SR A 3 or NR A 3 R A 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, which is connected via the N-atom with the carbonyl group in (SI) and is unsubstituted or substituted by radicals from the group (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or optionally substituted phenyl, preferably a radical of the formula OR A 3 , NHR A 4 or N (CH 3 ) 2> in particular of the formula OR A 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having in total 1 to 18 carbon atoms;
  • RA 4 is hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H, (CrC 8) alkyl, C r C 8 (haloalkyl), (Ci-C 4) alkoxy (CrC 8) -alkyl, cyano or COOR 9, wherein R A 9 is hydrogen, (C r C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 4 ) -
  • RA 6 , RA 7 , RA 8 are identical or different hydrogen, (C 1 -C 8 ) -alkyl,
  • a) compounds of the type dichlorophenylpyrazoline-3-carboxylic acid preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (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, (dC 4) alkyl, (C 1 -C 4 J -alkoxy, nitro or (C r C 4) -haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3;
  • Radicals from the group (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or optionally substituted phenyl preferably a radical of the formula ORB 3 , NHRB 4 or N (CH 3 ) 2 , in particular of the formula ORB 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 ) -alkyl, (C 1 -C 6 ) -alkoxy or substituted or unsubstituted phenyl.
  • TB 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 3 ) -alkoxy] -carbonyl;
  • S2 8-quinolinoxyacetic acid
  • Rc 1 is (C r C4) alkyl, (C r C4) -haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 -C 7 ) -cycloalkyl, preferably dichloromethyl;
  • Rc 2, rc 3 is identical or different hydrogen, (C r C4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -alkynyl, (C r C4) -haloalkyl, (C 2 -C 4) haloalkenyl, (dC ⁇ O-alkylcarbamoyl (Ci-C 4) alkyl, (C 2 -C 4) -Alkenylcarbamoyl- (Ci-C 4) alkyl, (C r C4) alkoxy- (Ci-C4) alkyl
  • active agents of the dichloroacetamide type preferably: active agents of the dichloroacetamide type, often as pre-emergence safeners
  • R-29148 S-dichloroacetyl ⁇ . ⁇ -trimethyl-I .S-oxazolidine from Stauffer
  • R-28725" 3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine from Stauffer
  • Benoxacor see Pestic. Man.
  • PPG-1292 N-allyl-N-KI.S-dioxolane) -y-O-methyl-J-dichloroacetamide from the company
  • DKA-24 N-allyl-N-kallylaminocarbonyO-methyll-dichloroacetamide from Sagro-Chem
  • TI-35 1-dichloroacetyl-azepane from TRI-Chemical RT
  • X 0 is CH or N;
  • R D 1 is CO-NRD 5 RD 6 or NHCO-R 0 7 ;
  • RD 2 is halogen, (C r C4) -haloalkyl, (Ci-C 4) -haloalkoxy, nitro, (CrC 4) alkyl, (C r C4) alkoxy, (Ci-C 4) alkylsulfonyl, (C 1 -C 4 ) alkoxycarbonyl or (C 1 -C 4 ) -alkylcarbonyl;
  • R 0 3 is hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl or (C 2 -C 4 ) -alkynyl;
  • R 0 4 is halogen, nitro, (C r C4) alkyl, (C r C4) -haloalkyl, (C r C 4) -haloalkoxy, (C 3 - C 6) cycloalkyl, phenyl, (CrC 4 ) alkoxy, cyan
  • R 0 6 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl, where the last three radicals mentioned are represented by VD radicals from the group consisting of halogen, hydroxy, (Cr C 4 ) alkyl, (dC 4 ) alkoxy and (dC 4 ) alkylthio substituted, or
  • RD 7 is hydrogen, (C 1 -C 4 ) -alkylamino, di- (C 1 -C 4 ) -alkylamino, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, where the 2 last-mentioned radicals are represented by VD substituents from the group Group halogen, (Ci-C 4 ) alkoxy, halogen (CrC 6 ) alkoxy and (CrC 4 ) alkylthio and in the case of cyclic radicals are also (Ci-C 4 ) alkyl and (CrC 4 ) haloalkyl substituted ;
  • V 0 is 0, 1, 2 or 3;
  • R 0 4 is halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, CF 3; rn D is 1 or 2; v D is 0, 1, 2 or 3;
  • R 0 8 u ⁇ ⁇ n nd A DD R 9 are independently hydrogen, (Ci-C ⁇ ) alkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 6) -alkenyl, (C 3 -C 6) -alkynyl,
  • R 0 4 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3 m D 1 or 2;
  • H) active compounds from the class of 1, 2-Dihydrochinoxalin-2-ones for example 1-methyl-3- (2-thienyl) -1, 2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl ) -1,2-dihydroquinoxaline-2-thione, 1- (2-aminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxalin-2-one-hydro- Chloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydro-quinoxalin-2-one, as described in WO 2005/12630,
  • R ⁇ 1, R K 2 are each independently halo, (Ci -CO-Al kyl, (CrC 4) alkoxy, (Cr C4) -haloalkyl, (C r C4) - Alkylamino, di- (C 1 -C 4 ) -alkylamino, nitro;
  • a ⁇ COORK 3 or COOR K 4 RK 3 are independently halo, (Ci -CO-Al kyl, (CrC 4) alkoxy, (Cr C4) -haloalkyl, (C r C4) - Alkylamino, di- (C 1 -C 4 ) -alkylamino, nitro.
  • RK 4 independently of one another are hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 4 ) -alkynyl, cyanoalkyl, (C 1 -C 4 ) -haloalkyl, phenyl, nitrophenyl, Benzyl, halobenzyl, pyridinylalkyl and alkylammonium, n ⁇ 1 0 or 1 n « 2 , n ⁇ 3 independently of one another 0, 1 or 2
  • RL 1 is halogen, (C r C4) alkyl, (C r C4) -haloalkyl, (C r C4) alkoxy, (C r C4) haloalkoxy,
  • R L 2 is hydrogen or (C r C 4) alkyl
  • R L 3 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, or aryl wherein each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of halogen and alkoxy; or their salts.
  • R N 1 is halogen, (C r C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 Y, Z are each independently O or S, n N is an integer from 0 to 4,
  • RN 2 (CRCI 6) alkyl, (C2 -Ce) -alkenyl, (C 3 -C 6) -cycloalkyl, aryl; Benzyl, halobenzyl, R N 3 is hydrogen, (Ci-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). It can vary within wide limits, e.g. between 0.001 and 10000 g / ha or more of active substance, but is preferably between 0.5 and 5000 g / ha, preferably between 0.5 and
  • the active compounds of the invention may e.g. used in the following plants:
  • the salts according to the invention are also suitable, depending on the concentration, 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 turf and grazing areas and for selective weed control in annual crops are used.
  • the salts according to the invention in particular the compounds of the formula (I), show strong herbicidal activity and a broad spectrum of activity when applied to the soil and above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both preemergence and postemergence, or in sequential use.
  • the salts according to the invention show a favorable influence on subsequent cultures (reproduction behavior), i. there was no or extremely low phytotoxicity (such as in the form of (a) light green to yellow leaf veins, (b) yellowing of whole plants, (c) retarded plant growth, (d) abnormal development of younger plant parts or the whole plant) on different subsequent cultures , which are sensitive to the salts according to the invention, in particular the compounds of formula (I), such as sugar beet, sunflower or Cruciferen, such as oilseed rape, mustard and turnip greens observed.
  • a dust is obtained by mixing 10 parts by weight of a salt according to the invention, in particular a compound of formula (I) and 90 parts by weight of talc as an inert material and comminuted in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a salt according to the invention, in particular a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as inert material,
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a salt according to the invention, in particular a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
  • a salt according to the invention in particular a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a compound according to the invention in particular a compound of the formula (I), 10 parts by weight of calcium lignosulfonate,
  • 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.
  • Table 1 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.
  • compositions according to the invention also have a good herbicidal activity against a broad spectrum of economically important weed grasses and weeds in postemergence.
  • compounds Nos. 1-1, 1-2, 1-3, 1-4, 1-12, 1-18, 1-19 of Table 1 have very good herbicidal activity against harmful plants such as Amaranthus retroflexus, Lolium multiflorum, abutilon theophrasti, Matricaria inodora, Ipomoea purpurea, Panicum minor, Stellaria media, Solanum nigrum, Veronica persica and Viola tricolor postemergence at an application rate of 0.08 kg and less active ingredient per hectare. 3. Post-emergence weed action - EXPERIMENTAL DESCRIPTION field
  • Table A-1 presents the results obtained which clearly demonstrate the weed control improved by the compounds of formula (I) according to the invention, both with respect to monocot and dicotyledon weeds.
  • Table A-2 shows the results obtained which clearly demonstrate the weed control over the free acid improved by compound I-2 according to the invention.
  • test substances were incorporated into the soil in various dosages. Thereafter, various crops were sown in plastic pots with the treated soil and grown in the greenhouse at a day / night rhythm of 22 ° C / 14 ° C. Four weeks later, the rating was as follows.
  • Tables B1-1 to B1-5 contain the results when sampling sugar beet when using (a) the compound I-2 according to the invention and (b) metsulfuron-methyl at various application rates.
  • Tables B2-1 to B2-5 contain the results of sampling of rape (Brassica napus) in the application of (a) the compound I-2 according to the invention and (b) metsulfuron-methyl at various application rates.
  • Tables B3-1 to B3-5 contain the results when sampling the field bean (Vicia faba) when using (a) the compound I-2 according to the invention and (b) metsulfuron-methyl at various application rates.

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Abstract

L'invention concerne des sels de 2-lodo-N-[(4-méthoxy-6-méthyl-1,3,5-triazine-2-yle)carbamoyl] benzolsulfonamide, des procédés de production associés et leur utilisation en tant qu'herbicides, notamment pour lutter de manière sélective contre des mauvaises herbes dans des cultures de plantes, des cultures pérennes ou sur des sols non cultivés, et en tant que régulateurs de croissance végétale, seuls ou avec des phytoprotecteurs et/ou en combinaison avec d'autres herbicides connus pour leur utilisation dans la lutte contre des mauvaises herbes dans des cultures de plantes spéciales ou en tant que régulateurs phytoprotecteurs, en utilisation simultanée et/ou séquentielle, soit comme formulation prête à l'emploi soit comme mélange extemporané.
EP08841543A 2007-10-24 2008-10-22 Sels de 2-iodo-n-[(4-méthoxy-6-méthyl-1,3,5-triazine-2-yle)carbamoyl]benzolsulfonamide, procédés de production et utilisation en tant qu'herbicides et régulateurs de croissance végétale Withdrawn EP2205091A2 (fr)

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EP08841543A EP2205091A2 (fr) 2007-10-24 2008-10-22 Sels de 2-iodo-n-[(4-méthoxy-6-méthyl-1,3,5-triazine-2-yle)carbamoyl]benzolsulfonamide, procédés de production et utilisation en tant qu'herbicides et régulateurs de croissance végétale

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EP07020807A EP2052604A1 (fr) 2007-10-24 2007-10-24 Sel du 2-lodo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamide, son procédé de fabrication, et son utilisation en tant qu'herbicide et régulateurs de croissance
EP08841543A EP2205091A2 (fr) 2007-10-24 2008-10-22 Sels de 2-iodo-n-[(4-méthoxy-6-méthyl-1,3,5-triazine-2-yle)carbamoyl]benzolsulfonamide, procédés de production et utilisation en tant qu'herbicides et régulateurs de croissance végétale
PCT/EP2008/008947 WO2009053058A2 (fr) 2007-10-24 2008-10-22 Sels de 2-iodo-n-[(4-méthoxy-6-méthyl-1,3,5-triazine-2-yle)carbamoyl]benzolsulfonamide, procédés de production et utilisation en tant qu'herbicides et régulateurs de croissance végétale

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EP2205091A2 true EP2205091A2 (fr) 2010-07-14

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EP08841543A Withdrawn EP2205091A2 (fr) 2007-10-24 2008-10-22 Sels de 2-iodo-n-[(4-méthoxy-6-méthyl-1,3,5-triazine-2-yle)carbamoyl]benzolsulfonamide, procédés de production et utilisation en tant qu'herbicides et régulateurs de croissance végétale

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WO2009053058A3 (fr) 2010-05-20
IL205180A0 (en) 2010-11-30
KR20100088611A (ko) 2010-08-09
ZA201002341B (en) 2010-12-29
CN101932244A (zh) 2010-12-29
CA2703589A1 (fr) 2009-04-30
WO2009053058A2 (fr) 2009-04-30
AU2008315608A1 (en) 2009-04-30
AR068955A1 (es) 2009-12-16
JP2011500745A (ja) 2011-01-06
EP2052604A1 (fr) 2009-04-29
MX2010004531A (es) 2010-07-05
US20100285964A1 (en) 2010-11-11
CO6270189A2 (es) 2011-04-20
BRPI0818390A2 (pt) 2014-10-07
TN2010000174A1 (en) 2011-11-11
MA31791B1 (fr) 2010-10-01
CL2008003142A1 (es) 2009-03-06

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