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WO2009007014A1 - Concentrés solubles dans l'eau de tétramates 3-(2-alcoxy-4-chloro-6-alkyl-phényl)-substitués et leurs énols correspondants - Google Patents

Concentrés solubles dans l'eau de tétramates 3-(2-alcoxy-4-chloro-6-alkyl-phényl)-substitués et leurs énols correspondants Download PDF

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Publication number
WO2009007014A1
WO2009007014A1 PCT/EP2008/005186 EP2008005186W WO2009007014A1 WO 2009007014 A1 WO2009007014 A1 WO 2009007014A1 EP 2008005186 W EP2008005186 W EP 2008005186W WO 2009007014 A1 WO2009007014 A1 WO 2009007014A1
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Prior art keywords
formula
water
composition according
radical
formulas
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PCT/EP2008/005186
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German (de)
English (en)
Inventor
Udo Bickers
Frank Sixl
Erwin Hacker
Annika Franz
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Bayer Cropscience Ag
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Priority claimed from EP07112052A external-priority patent/EP2014169A1/fr
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Publication of WO2009007014A1 publication Critical patent/WO2009007014A1/fr

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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings

Definitions

  • the present invention relates to novel water-soluble concentrates (SL formulations) of 3- (2-alkoxy-4-chloro-6-alkyl-phenyl) -substituted tetramates and their enols, to processes for preparing these formulations and to their use as herbicides.
  • SL formulations novel water-soluble concentrates of 3- (2-alkoxy-4-chloro-6-alkyl-phenyl) -substituted tetramates and their enols
  • EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-arylpyrrolidine-2,4-diones), of which, however, no herbicidal, insecticidal or acaricidal action has become known.
  • Unsubstituted, bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355 599, EP-A-415 211 and JP-A-12-053 670 are known to have herbicidal, insecticidal or acaricidal activity and substituted monocyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077).
  • EP-A-442 073 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
  • EP-A-456 063 EP-A-521 334, EP-A- 596 298, EP-A-613 884, EP-A-613 885, WO 94/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96 / 35,664, WO 97/01 535, WO 97/02 243, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/24437, WO 99/43649 , WO 99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249, WO 03
  • ketalsubstituted 1-H-arylpyrrolidine-2,4-diones from WO 99/16748 and (spiro) - ketalsubstituted N-alkoxy-alkoxy-substituted aryl-pyrrolidindione from JP-A-14 205 984 and Ito M. et. al Bioscience, Biotechnology and Biochemistry 67, 1230-1238, (2003).
  • 3- (2-alkoxy-4-chloro-6-alkyl-phenyl) -substituted tetramic acids are known from WO 2004/080962.
  • WO 04/080962 are as concentrated formulations of the below-mentioned drugs only EC formulations disclosed (Emulsifiable concentrates). These are then diluted in water for use. A concentrated aqueous formulation is not disclosed.
  • X is methoxy or ethoxy
  • W is methyl or ethyl
  • n 1, 2 or 3
  • n 1, 2 or 3
  • a and D together represent a C 1 -C 4 -alkylidenyl group
  • G is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
  • ammonium ion is an ammonium ion, in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups hydrogen, C 1-C 5 -alkyl, C 1 -C 5 -IsOaIlCyI or C 3 -C 7 - Cycloalkyl, which may each be mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy or interrupted by one or more oxygen or sulfur atoms, replaced, or continue
  • a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated 1,4-diazabicyclo [2.2.2] octane (DABCO) or 1,5-diazabicyclo [4.3.0] undecarboxylic acid 7-en (DBU), stands, or continues
  • heterocyclic ammonium cation for example in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, Pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate, stands or remains
  • compositions comprising at least one solvent and at least one compound of the formula (I-A) or (I-B) in dissolved form.
  • the present invention also provides processes for the preparation of water-soluble concentrates comprising at least one compound of the formula (I-A) or (I-B).
  • compositions comprising a phase comprising at least one compound of the formula (I-A) or (I-B) in dissolved form for controlling undesired plant growth.
  • G is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminum or an ion equivalent of a transition metal.
  • G is an ammonium ion in which optionally one, two, three or all four hydrogen atoms are represented by identical or different radicals from the groups hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkyl 5 -isoalkyl or C 3 -C 7 -cycloalkyl, each of which may be substituted one or more times by fluorine, chlorine, bromine, cyano, hydroxy or interrupted by one or more oxygen or sulfur atoms.
  • G is lithium, sodium, potassium, magnesium, calcium, barium, copper, zinc, aluminum, ammonium, trimethyl or triethylsulfonium.
  • Particularly useful are compounds of formula (I-B) in which G is lithium, sodium, potassium.
  • compositions comprising a phase containing at least one compound of the formulas (I-A) or (I-B) in dissolved form can be increased by the addition of certain surfactants.
  • Suitable surfactants are, for example, sulfates, sulfonates, phosphates and phosphonates of hydrocarbons, which may optionally contain alkylene oxide units.
  • the sulfates, sulfonates, phosphates and phosphonates may be in the form of the acids or as salts.
  • Anionic surfactants of the following formula (H) are preferred:
  • Q is -O- SO 3 M, -SO 3 M, -0-PO 3 HM or -PO 3 HM,
  • M is hydrogen or a cation, in particular a metal cation such as an alkali metal ion or alkaline earth metal ion, or an ammonium ion,
  • R is an unsubstituted or substituted Ci-C 3 o-hydrocarbon radical, optionally via
  • Alkylene oxide units may be bonded, or R is an alkylene oxide unit.
  • alkylene oxide units in particular units of C 2 -C O - alkylene oxides such as ethylene oxide, propylene oxide or butylene understood, the units may be arranged differently and thereby randomly mixed or in blocks within the surfactant same or different.
  • R is a C, -C 2 o-alkyl radical (eg, methyl, ethyl, propyl, butyl) or a C 6 -C 24 aryl radical (eg, phenyl, biphenyl, naphthyl), which may optionally carry one or more radicals, for example from the group Ci-C 20 alkyl (for example, linear or branched Ci-C2o-alkyl such as sec.
  • Ci-C 20 alkyl for example, linear or branched Ci-C2o-alkyl such as sec.
  • butyl or dodecyl which comprises one or more radicals such as C 6 -C 20 aryl radicals (such as phenyl, biphenyl, naphthyl) and C 6 -C 20 -aryl (eg phenyl, biphenyl or naphthyl), which may optionally carry one or more radicals such as C r Ci 0 alkyl (eg, methyl, ethyl, propyl, butyl), or
  • R is a radical R'O- (AO) W , wherein w is an integer from 1 to 100, and AO is an alkylene oxide moiety, eg (EO) X (PO) Y (BO) Z , where EO is an ethylene oxide moiety, PO a propylene oxide unit, BO is a butylene oxide unit, x is an integer from 0-100, y is an integer from 0-100, z is an integer from 0 to 100 and the sum x + y + z is at least 1, and the alkylene oxide unit, eg (EO) X (PO) Y (BO) Z , randomly mixed or block-structured, and R 1 is H, a C r C 2 o-alkyl radical (for example methyl, ethyl, propyl, butyl) or a C 6 -C 24 -aryl radical (for example phenyl, biphenyl, naphthyl), which may optionally carry one or more radicals, for example
  • alkylaryl sulfonates such as dodecyl benzene sulfonates, e.g. Erdalkalidodecylbenzolsulfonate such as calcium dodecylbenzenesulfonates (eg Phenylsulfonat® CaIOO from Clariant), Alkylarylpolyglykolethersulfate and sulfonates, in particular Arylalkylarylpolyglykolethersulfate as Tristyrylphenolpolyglykolethersulfate, in particular the alkali or ammonium or triethanolamine salts (eg Soprophore® series of Rhodia), alkyl ether sulfates and their salts (eg Genapol® LRO from Clariant), alkyl sulfates and alkyl sulfonates (eg, such as the Hostapur® series from Clariant), alkyl polyglycol ether phosphat
  • Alkylaryl polyglycol ether phosphates in particular in the form of the alkali metal salts.
  • the salts are generally preferably metal salts such as alkali or alkaline earth metal salts or ammonium or trialkylamine salts.
  • alkyl ether sulfates and their salts e.g., such as Genapol® LRO ex Clariant.
  • Suitable surfactants are, for example, also alkanol alkoxylates into consideration.
  • Surfactants according to the invention are alkanol alkoxylates of the formula (III)
  • R 2 is straight-chain or branched alkyl having 4 to 20 carbon atoms
  • AO stands for an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and
  • n stands for numbers from 2 to 20.
  • a preferred group of surfactants are alkanol alkoxylates of the formula (DI-a)
  • R 2 is branched alkyl having 8 to 15 carbon atoms
  • b stands for numbers from 4 to 18.
  • surfactants are cationic surfactants derived from primary fatty alcohol amines. These may e.g. represented by the formula (IV):
  • R 3 represents straight-chain or branched alkyl having 14 to 20 carbon atoms and the sum of p and q is 15 to 25.
  • the above-mentioned surfactants may be present as a mixture of different substances which fall under the general formulas (II), (III) and (FV).
  • the values given for m, b, p and q are averages.
  • Particularly preferred surfactants are those of the formula (II).
  • the present invention accordingly also relates to compositions comprising in addition at least one phase containing at least one compound of the formulas (IA) or (I-B) in dissolved form and at least one surfactant selected from the surfactants of the formulas (II), (DI) and (IV).
  • Suitable solvents in the compositions according to the invention are all water-miscible solvents conventionally used in agrochemical formulations in which the active compounds of the formulas (IA) and (IB) are dissolved in the concentrations used here.
  • examples which may be mentioned are water, alcohols such as methanol, ethanol or isopropanol, ethers or polyethers such as 1,4-dioxane, tetrahydrofuran or dimethoxyethane, amides such as formamide, Acetamide, N, N-dimethylformamide, N, N-dimethylacetamide or Hallcomid® (mixture of 50-60% N, N-dimethyloctanamide and 35-45% N, N-dimethyldecanamide), sulfoxides / sulfones such as dimethyl sulfoxide or sulfolane and lactones / Lactams such as N-methylpyrrolidone and gamma-butyrol
  • Preferred solvents are water, methanol, ethanol, isopropanol, 1,4-dioxane, tetrahydrofuran, dimethoxyethane, Hallcomid® (mixture of 50-60% N, N-dimethyloctanamide and 35-45% N, N-dimethyldecanamide), dimethyl sulfoxide, sulfolane , N-methylpyrrolidone and gamma-butyrolactone.
  • the solvent is water.
  • Suitable bases are in principle all organic and inorganic bases, as far as their use is harmless for agricultural purposes.
  • metal hydroxides such as lithium, sodium and potassium hydroxide, magnesium and calcium hydroxide, aluminum hydroxide, zinc hydroxide or
  • metal oxides such as lithium, sodium and potassium oxide or alumina
  • R 1 , R 2 and R 3 may be the same or different and each represents hydrogen, CpCs-alkyl, Ci-C 5 -isoalkyl or C 3 - C 7 -cycloalkyl, which in turn in each case one or more times with fluorine, chlorine , Bromine, cyano,
  • Hydroxy substituted or interrupted by one or more oxygen or sulfur atoms Hydroxy substituted or interrupted by one or more oxygen or sulfur atoms.
  • ammonia methylamine, dimethylamine, triethylamine, ethylamine, diethylamine, triethylamine, isopropylamine, ethanolamine, diethanolamine, triethanolamine, 2-diethylaminoethanol, diisopropylamine, cyclohexylamine, dicyclohexylamine, d) mono-, bi- or tricyclic amines such as, for example, morpholine, thiomorpholine, piperidine, pyrrolidine, 1,4-diazabicyclo [2.2.2] octane (DABCO) or 1,5-diazabicyclo [4.3.0] un-decane 7-en (DBU),
  • diamines such as N, N-bis (2-hydroxyethyl) -C 8 -C 8 -alkylamines, lentetramin hexamethylene, N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine, 2 Diethylaminoethylamine, NNN'.N'-tetraethylethylenediamine, N, N, N ', N'-tetramethylethylenediamine, 2- (2-aminoethylamino) ethanol or lysine,
  • diamines such as N, N-bis (2-hydroxyethyl) -C 8 -C 8 -alkylamines, lentetramin hexamethylene, N, N, N ', N'-tetrakis (2-hydroxypropyl) ethylenediamine, 2 Diethylaminoethylamine, NNN'.N'-tetraethylethylenediamine
  • aromatic amines such as pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, Pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate,
  • g) carbonates such as, for example, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, magnesium carbonate, calcium carbonate, copper carbonate, zinc carbonate or lithium carbonate,
  • sulphites such as, for example, sodium, potassium, lithium or zinc sulphite
  • phosphates such as lithium potassium, sodium, calcium and magnesium phosphate, lithium, potassium, sodium, calcium and magnesium hydrogen phosphate or potassium and sodium dihydrogen phosphate,
  • alcoholates such as, for example, sodium and potassium methylate or ethylate
  • ammonium hydroxides such as, for example, trimethyl, triethyl, tripropyl or tributylammonium hydroxide, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetraethanolammonium hydroxide or methyltriethylammonium hydroxide,
  • amidines and guanidines each of which may optionally be substituted, for example acetamidine, formamidine, guanidine, 1,1,3,3-tetraaminoguanides, aminoguanidine or arginine,
  • m) basic carboxylic acid salts preferably acetates such as lithium, sodium or potassium acetate, oxalates such as sodium or potassium oxalate, tartrates such as sodium or potassium tartrate, and citrates such as sodium or potassium citrate,
  • n) strongly or weakly basic anion exchangers loaded with hydroxide ions for example, those commercially available under the names AMBERLITE®, AMBERLYST®, DUOLITE®, DOWEX® or LEWATITE®.
  • the base can in principle also be used in immobilized form, it being possible for the carrier material to be separated off after preparation of the concentrate according to the invention, for example by filtration.
  • Preferred as basic auxiliaries are lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and ammonia, alkylamines and hydroxyalkylamines.
  • the formulations according to the invention contain further additives from the groups of the foam-inhibiting agents, the antioxidants and / or the dyes.
  • Suitable foam-inhibiting substances are all substances customarily usable for this purpose in agrochemical compositions. Preference is given to polydimethylsiloxanes, silicone oils and magnesium stearate.
  • antioxidants are all commonly used for this purpose in agrochemical agents substances into consideration. Preference is given to butylhydroxytoluene (2,6-di-t-butyl-4-methylphenol, BHT).
  • Suitable dyes are all substances customarily usable for this purpose in agrochemical compositions. Examples include titanium dioxide, carbon black, zinc oxide and blue pigments as well as permanent red FGR.
  • the content of active compound of the formula (IA) or (IB) is generally from 0.1 to 50% by weight, preferably 0 , 2 to 50 wt .-%, particularly preferably 1 to 25 wt .-%, most preferably 2 to 20 wt .-%.
  • the content of surfactant is generally from 5 to 50% by weight and preferably from 10 to 30% by weight.
  • the content of surfactant is generally 0.1 to 10 g / l, preferably 0.3 to 3 g / l.
  • the surfactant is generally applied at a rate of from 20 to 1000 g ai / ha, preferably from 100 to 300 g ai / ha.
  • Compositions according to the invention may additionally comprise, in addition to at least one compound of the formula (IA) or (IB), at least one further herbicidal active ingredient, preferably from the group consisting of acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (- sodium), ametryne, Amicarbazone, amidochlor, amidosulfuron, aminopyralid, anilofos, asulam, atrazine, azafenidine, azimsulfuron, beflubutamide, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, bencarbazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl ), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxime, Bromoxyn
  • compositions of the invention may also contain herbicidal safeners.
  • herbicidal safeners are Benoxacor, Cloquintocet-mexyl, Cumyluron, Dymron, Dimepiperate, Cyprosulfamide, Cyometrinil, Dichlormid, Dicyclonon, Dietholate, Fenchlorazole, Fenchlorazolethyl, Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen, Isoxadifen-ethyl, Mefenpyr, Mefenpyr diethyl, mephenate, naphthalic anhydride, oxabetrinil
  • Preferred safeners are mefenpyr-diethyl and isoxadifen-ethyl
  • compositions comprising as herbicidal active substances
  • compositions according to the invention are also those comprising at least one compound of the formulas (IA) or (IB), fenoxaprop-P-ethyl and mefenpyr-diethyl and compositions containing at least one compound of the formulas (IA) or (IB), fenoxaprop-P-ethyl and isoxadifen-ethyl.
  • the total content of active substances and optionally safeners generally 0.2 to 50 wt .-%, preferably 1 to 40 wt .-%, particularly preferably 2 to 30 wt .-%.
  • the additionally present herbicidal active ingredient in the solvent used for the active ingredient of the formula (I-A) or (I-B) is soluble in the required concentrations, all active ingredients can be dissolved in one phase.
  • the concentrates of the invention are then (e.g., water-based) soluble concentrates.
  • a phase comprising at least one dissolved active compound of the formulas (I-A) and (I-B) and a further active substance selected from glyphosate, glufosinate or L-glufosinate,
  • the invention therefore particularly preferably contains compositions
  • compositions if they already contain both active ingredients in concentrated form, are more effective than mixtures of identical active ingredients produced by tank mix at the same application rates. Due to the high water solubility of the active ingredients, a dependency on the original type of formulation was not to be expected here as well.
  • the further herbicidal active ingredient such as fenoxaprop-P-ethyl
  • the further active ingredient can be dissolved in another suitable solvent.
  • the two phases can then be mixed, resulting, for example, in an EW formulation (emulsion in water).
  • EW formulation emulsion in water
  • a phase comprising at least one dissolved active compound of the formulas (I-A) or (I-B),
  • a phase comprising at least one dissolved active compound of the formulas (I-A) or (I-B),
  • compositions Accordingly, particular preference is given to containing compositions
  • additives from the groups of emulsifiers, antifoaming agents, antioxidants and / or dyes.
  • Suitable emulsifiers are all customary nonionic, anionic, cationic and zwitterionic substances having surface-active properties which are customarily used in agrochemical compositions. These substances include reaction products of fatty acids, fatty acid esters, fatty alcohols, fatty amines, alkylphenols or alkylarylphenols with ethylene oxide and / or propylene oxide and / or butylene oxide, and their sulfuric acid esters, phosphoric monoesters and phosphoric diesters, also reaction products of ethylene oxide with propylene oxide , furthermore alkyl sulfonates, alkyl sulfates, aryl sulfates, tetra-alkyl ammonium halides, trialkylaryl ammonium halides and alkylamine sulfonates.
  • the emulsifiers can be used individually or in a mixture.
  • reaction products of castor oil with ethylene oxide in a molar ratio of 1:20 to 1:60 Reaction products of C 6 -C 2 o-alcohols with ethylene oxide in a molar ratio of 1: 5 to 1: 50, reaction products of fatty amines with ethylene oxide in a molar ratio of 1: 2 to 1: 25, reaction products of 1 mole of phenol with 2 to 3 moles of styrene and 10 to 50 mol of ethylene oxide, reaction products of C 1 -C 4 -alkylphenols with ethylene oxide in a molar ratio of 1: 5 to 1: 30, alkyl glycosides, C 7 -C 12 -alkylbenzene-sulfonic acid salts, such as, for example, calcium, monoethanolammonium, diethanolammonium and triethanolammonium salts. salts.
  • sapogenate T180 tri-sec-butylphenol ethoxylate, Clariant Fa
  • Alkamuls OR36 castor oil ethoxylate, Fa Rhodia
  • Emulsogen TS54 tristyryl phenol ethoxylate, Clariant
  • compositions according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.
  • the spectrum of activity extends to species such as Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharitis spp. , Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp.
  • compositions according to the invention are applied to the surface of the earth before germination, either the weed seedlings are completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die off completely after three to four weeks.
  • the herbicidal compositions of the invention are characterized by a rapidly onset and long-lasting herbicidal activity.
  • the rainfastness of the active ingredients in the compositions according to the invention is generally favorable.
  • a considerable reduction in the required application rate of the active ingredients is made possible.
  • compositions according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants, including species which are resistant to herbicidal active substances such as glyphosate, glufosinate, atrazine or imidazolinone herbicides.
  • compositions according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous harmful plants, the crop plants are damaged only insignificantly or not at all.
  • compositions of the invention have excellent growth-regulatory properties in the crop plants. They regulate the plant's metabolism and can thus be used to influence the metabolism
  • Stunted growth can be used. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, as crop losses during storage can be reduced or completely prevented.
  • the compositions 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 relate to z. B.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Other special properties may be in a tolerance or resistance to abiotic stressors z. As heat, cold, drought, salt and ultraviolet radiation.
  • compositions according to the invention comprising compounds of the formula (I-A) or (I-B) in economically important transgenic crops of useful and ornamental plants, for.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • compositions containing compounds of the formula (I-A) or (I-B) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • transgenic crop plants which are resistant to certain glufosinate-type herbicides (cf., for example, EP 0242236, EP 242246) or glyphosate (WO 92/00377) or the
  • transgenic crops for example cotton, having the ability Bacillus to produce thuringiensis toxins (Bt toxins) which render the plants resistant to certain pests (EP 0142924, EP 0193259).
  • Bacillus to produce thuringiensis toxins Bacillus to produce thuringiensis toxins (Bt toxins) which render the plants resistant to certain pests (EP 0142924, EP 0193259).
  • transgenic crops characterized by a combination z.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods 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, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. CoId Spring Harbor Laboratory Press, ColD Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
  • 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. 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 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 expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • 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 or compositions according to the invention can be used in transgenic cultures which are resistant to growth substances, such.
  • B. 2,4-D, dicamba or herbicides the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, glyphosate, glufosinates or benzoylisoxazoles and analogues, or resistant to any combination of these agents.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD Hydoxyphenylpyruvat dioxygenases
  • An example of this are transgenic crops such.
  • the compounds or compositions according to the invention can also be used in transgenic crop plants which are resistant to glufosinates, L-glufosinates or glyphosates or a combination of glufosinates or L-glufosinates and glyphosates.
  • effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled
  • Application rates that can be used for the application preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compositions according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the invention also relates to the use of the compositions for controlling harmful plants, preferably in plant crops.
  • herbicidal compositions according to the invention can also be employed non-selectively for controlling unwanted plant growth, for example in plantation crops, on roadsides, squares, industrial plants or railway installations.
  • the active ingredient was mixed with inert material.
  • the powder was ground until an average particle size (d50) of 5 to 10 ⁇ m was reached.
  • a typical composition of a WP20 formulation was:
  • Baykanol® SL 10% by weight
  • the active ingredient was stirred into an aqueous solution of a suitable surfactant.
  • the dispersion was finely ground using standard equipment until an average particle size of less than 5 microns was achieved.
  • a typical composition of an SCl 50 formulation was:
  • the SL formulation was prepared by stirring and dissolving the active ingredient in water.
  • the solutions contained up to 4 g / l active ingredient of the formula (I-A) or up to 100 g / l active ingredient of the formula (I-B).
  • Aqueous solutions of the Li, Na and K salts of the active ingredient can also be prepared by simultaneous stirring of active ingredient (I-A) and an equimolar amount, for example, of LiOH, NaOH or KOH or the corresponding carbonates, acetates or phosphates.
  • a typical composition of an SL formulation was:
  • compositions containing several herbicidal active substances Preparation of compositions containing several herbicidal active substances
  • compositions according to the invention may contain, in addition to at least one active compound of the formulas (IA) and (IB), further herbicidal active compounds or further active compounds and herbicidal safeners. These coformulations are prepared by mixing the individual components.
  • the salt (IB) it is also possible to use a mixture of (IA) and, for example, sodium hydroxide, sodium carbonate, sodium methoxide, sodium acetate, sodium oxalate, sodium oxide or sodium phosphate.
  • the preparation of the EW formulations may require the use of higher shear forces to adequately disperse the organic phase in the aqueous solution. Suitable for this purpose are the known devices, such as tooth colloid mills.
  • Emulsogen® EL 400 1, 00%
  • Glyphosate isopropylammonium 28, .62% ( 337 g / L, equivalent to 250 g / L glyphosate)
  • the spray mixture thus obtained was homogenized by stirring.
  • the spray mixture can also be prepared by "tank mixing" of the individual constituents, for example by successively stirring in a commercial glufosinate, glyphosate or fenoxaprop-P-ethyl-containing product and a formulation of the active ingredient (IA) or (IB). whether in the form of WP, SC, SL, EW or WG.
  • g a.i./ha grams of active ingredient / hectare
  • APESV Apera spica venti
  • ECHCG Echinochloa crus galli
  • CYNDA Cynodon dactylon
  • TRZAS Triticum aestivum
  • HORVS Hordeum vulgar
  • the plants were treated on a laboratory spray track with the appropriate spray liquors.
  • the amount of water used for the spray application was 300 l / ha. After treatment, the plants were placed back in the climatic chamber.
  • test plants were sown in the field and grown to the desired application stage.
  • the spray mixtures were applied with a post-emergence spray bar.
  • the amount of water used was 2001 / ha.
  • spray mixtures were prepared starting from WP 20 formulations of the active compound A.3, to which ammonium sulfate was added at a rate of 500 g / ha. 21 days after the application, the efficacy against the weeds was evaluated.
  • the spray mixtures used were prepared from an SC formulation with the active ingredient A.3 or an SL formulation of the corresponding sodium salt (B.6) analogously to the preparation examples.
  • 500 g / ha of ammonium sulfate and 1 l / ha of Genapol LRO were added to the spray mixtures in liquid form.
  • the spray mixtures used were prepared from a WP formulation with the particular active compound of the formula (I-A) or an SL formulation of the corresponding sodium salt of the formula (I-B) analogously to the preparation examples.
  • 500 g / ha of ammonium sulfate and 1 l / ha of Genapol LRO were added to the spray mixtures in liquid form.
  • Table E 1 shows the clear superiority of the A.3-containing SL-finished formulation compared to the pure Liberty® product.
  • spray liquors were prepared by diluting the appropriate formulations (commercially available Liberty® and Mixing Example 2) with water to the concentrations indicated in Table E33.
  • the application was carried out by spraying on the plants AVEFA (Avena fatua), HORVS (Hordeum vulgare) and ZEAMD (Zea mays).
  • the ZEAMD used is a glufosinate-tolerant variety.
  • AVEFA Avena fatua
  • ECHCG Echinochloa crus galli
  • LOLMU Li multiflorum
  • PHACA Phalaris canariensis
  • SETVI Setaria viridis
  • Table E4 shows the superiority of the ready-to-use formulation in controlling the weeds used.
  • the spray liquors were prepared from a commercially available formulation (EW formulation, Puma®, Bayer CropScience) by dilution to the desired concentration and subsequent addition of the stated amount of active compound of the formula (IA) or (IB) (Tank-M ix - procedure).
  • EW formulation Puma®, Bayer CropScience
  • the efficacy was assessed 33 days after application.
  • the result shows the significantly higher effectiveness of the spray liquors containing A.3 in comparison to the sprays containing exclusively fenoxyprop-P-ethyl.
  • the spray liquors were prepared from a commercially available formulation (Roundup Ultra®, Monsanto) or the formulation according to Mixing Example 4 by dilution with water to the desired concentration (Table G)
  • Table G shows the significantly higher effectiveness of the A.3-containing formulation compared to Roundup Ultra®.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
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Abstract

La présente invention concerne de nouveaux concentrés solubles dans l'eau de tétramates 3-(2-alcoxy-4-chloro-6-alkyl-phényl)-substitués et leurs énols, des procédés de fabrication de ces formulations et leur utilisation en tant que pesticides et/ou herbicides.
PCT/EP2008/005186 2007-07-09 2008-06-26 Concentrés solubles dans l'eau de tétramates 3-(2-alcoxy-4-chloro-6-alkyl-phényl)-substitués et leurs énols correspondants WO2009007014A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
EP07112052A EP2014169A1 (fr) 2007-07-09 2007-07-09 Concentré soluble de tétramères 3-(2-alkoxy-4-chlor-6-alkyl-phenyl)-substitués et leurs énols correspondants
EP07112052.1 2007-07-09
EP07113796 2007-08-03
EP07113796.2 2007-08-03
EP07120673.4 2007-11-14
EP07120673 2007-11-14

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
WO2013020985A1 (fr) 2011-08-10 2013-02-14 Bayer Intellectual Property Gmbh Combinaisons de composés actifs comprenant des dérivés spécifiques d'acide tétramique
WO2019197637A1 (fr) * 2018-04-13 2019-10-17 Bayer Aktiengesellschaft Formulations fortement chargées renfermant des insecticides de la classe céto-énol, destinées à être utilisées dans des applications par goutte-à-goutte et par arrosage
CN110463591A (zh) * 2019-08-06 2019-11-19 河南中烟工业有限责任公司 一种抗干旱植物生长调节剂及其应用和植物育苗方法

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DE3513889A1 (de) * 1984-04-23 1985-10-24 Kao Corp., Tokio/Tokyo Biozidzusammensetzung
US5389598A (en) * 1993-12-17 1995-02-14 Monsanto Company Aqueous concentrate formulations having reduced eye irritancy
US6184182B1 (en) * 1996-10-25 2001-02-06 Monsanto Company Composition and method for treating plants with exogenous chemicals
WO2001089300A1 (fr) * 2000-05-19 2001-11-29 Bayer Cropscience Ag Combinaisons de principes actifs aux proprietes insecticides et acaricides
WO2004080962A1 (fr) * 2003-03-14 2004-09-23 Bayer Cropscience Aktiengesellschaft Cetoenols cycliques substitues par 2,4,6-phenyle
US20050209105A1 (en) * 2002-09-05 2005-09-22 Wei Wang Preparation of solid ammonium glyphosate using organic solvent in extraction
WO2006008111A1 (fr) * 2004-07-20 2006-01-26 Bayer Cropscience Ag Insecticides selectifs a base de ceto-enols cycliques substitues et de phytoprotecteurs

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DE3513889A1 (de) * 1984-04-23 1985-10-24 Kao Corp., Tokio/Tokyo Biozidzusammensetzung
US5389598A (en) * 1993-12-17 1995-02-14 Monsanto Company Aqueous concentrate formulations having reduced eye irritancy
US6184182B1 (en) * 1996-10-25 2001-02-06 Monsanto Company Composition and method for treating plants with exogenous chemicals
WO2001089300A1 (fr) * 2000-05-19 2001-11-29 Bayer Cropscience Ag Combinaisons de principes actifs aux proprietes insecticides et acaricides
US20050209105A1 (en) * 2002-09-05 2005-09-22 Wei Wang Preparation of solid ammonium glyphosate using organic solvent in extraction
WO2004080962A1 (fr) * 2003-03-14 2004-09-23 Bayer Cropscience Aktiengesellschaft Cetoenols cycliques substitues par 2,4,6-phenyle
WO2006008111A1 (fr) * 2004-07-20 2006-01-26 Bayer Cropscience Ag Insecticides selectifs a base de ceto-enols cycliques substitues et de phytoprotecteurs

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013020985A1 (fr) 2011-08-10 2013-02-14 Bayer Intellectual Property Gmbh Combinaisons de composés actifs comprenant des dérivés spécifiques d'acide tétramique
US9265252B2 (en) 2011-08-10 2016-02-23 Bayer Intellectual Property Gmbh Active compound combinations comprising specific tetramic acid derivatives
WO2019197637A1 (fr) * 2018-04-13 2019-10-17 Bayer Aktiengesellschaft Formulations fortement chargées renfermant des insecticides de la classe céto-énol, destinées à être utilisées dans des applications par goutte-à-goutte et par arrosage
CN112055537A (zh) * 2018-04-13 2020-12-08 拜耳公司 用于滴注和浸透施用的含酮烯醇类杀虫剂的高负载制剂
US12213484B2 (en) 2018-04-13 2025-02-04 Bayer Aktiengesellschaft Highly loaded formulations with insecticides of the ketoenol class for use in drip and drench applications
CN110463591A (zh) * 2019-08-06 2019-11-19 河南中烟工业有限责任公司 一种抗干旱植物生长调节剂及其应用和植物育苗方法

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