WO2000044226A1 - Formulation d'herbicides - Google Patents

Formulation d'herbicides Download PDF

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Publication number
WO2000044226A1
WO2000044226A1 PCT/EP2000/000470 EP0000470W WO0044226A1 WO 2000044226 A1 WO2000044226 A1 WO 2000044226A1 EP 0000470 W EP0000470 W EP 0000470W WO 0044226 A1 WO0044226 A1 WO 0044226A1
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WO
WIPO (PCT)
Prior art keywords
substituted
alkyl
unsubstituted
alkoxy
halogen
Prior art date
Application number
PCT/EP2000/000470
Other languages
German (de)
English (en)
Inventor
Gerhard Schnabel
Detlev Haase
Thomas Maier
Julio Martinez De Una
Jochen Würtz
Original Assignee
Aventis Cropscience Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE1999103064 external-priority patent/DE19903064A1/de
Priority claimed from DE1999163395 external-priority patent/DE19963395A1/de
Application filed by Aventis Cropscience Gmbh filed Critical Aventis Cropscience Gmbh
Priority to AU45217/00A priority Critical patent/AU4521700A/en
Publication of WO2000044226A1 publication Critical patent/WO2000044226A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to the technical field of the formulation of herbicides and plant growth regulators, in particular herbicides for controlling undesired plant growth, e.g. of weeds and grasses in crops.
  • sulfonylureas have herbicidal and plant growth-regulating properties.
  • the sulfonylureas are usually formulated for use in the agrochemical sector.
  • the chemical stability and the active ingredient concentration in the formulation are important for their effectiveness.
  • the present invention therefore relates to formulations, in particular agrochemical, e.g. herbicidal formulations containing a sulfonylurea salt of the formula (Ia),
  • R 2 is a substituted or unsubstituted C 1 -C 2 -hydrocarbon radical such as substituted or unsubstituted (Ci-C ⁇ J-alkyl), substituted or unsubstituted (C 2 -C 6 ) alkenyl), substituted or unsubstituted (C 2 -C 6 ) alkynyl) is substituted or unsubstituted (C3-C7) cycloalkyl,
  • R 3 is a substituted or unsubstituted C ⁇ -C2o hydrocarbon radical, such as substituted or unsubstituted (C ⁇ -C6) alkyl), substituted or unsubstituted (C 2 -C 6) alkenyl), substituted or unsubstituted (C2-C ⁇ ) - alkynyl ), substituted or unsubstituted (C3-C7) cycloalkyl
  • R 4 is halogen such as F, Cl, Br, I or a substituted or unsubstituted C ⁇ -C2o hydrocarbon radical, or C ⁇ -C 2 o- ohlenwasserstoffoxyrest such as (Ci-C ⁇ ) - alkyl, (C 2 -C 6) alkenyl) , (C 2 -C 6 ) alkynyl), (CrC 6 ) alkoxy), (C 3 -C 6 ) alkenyloxy), (C 3 -Ce) alkynyloxy), the
  • R 5 is H, halogen such as F, Cl, Br, I or a substituted or unsubstituted C ⁇ -C2o hydrocarbon radical, or C ⁇ -C 2 o-hydrocarbon oxy group such as (Ci-C ⁇ ) - alkyl substituted by one or more radicals from the Halogen group such as F, CI, Br or J or (-C-C3) alkoxy can be substituted or (-C-C5) alkoxy, which by one or more radicals from the group halogen (F, CI, Br, I) or (-C-C 3 ) alkoxy may be substituted
  • R 7 H halogen such as F, Cl, Br or J, OH, NR X R Y , in which R x and R ⁇ are H or (d-Ca ⁇ - alkyl, or R 7 N- (-C-C 3 ) - Alkyl-N-acylamino, N-acylamino, or a substituted or unsubstituted C 1 -C 2 -hydrocarbon radical or hydrocarbonoxy radical such as (dC 3 ) alkyl, (C 1 -C 3 ) haloalkyl, halogen, (C1-C3) - alkyl - (N- (-C-C 3 ) -alkyl-N-acylamino), (C ⁇ -C 3 ) -alkyl- (N-acylamino) or (C1-C3) - alkoxy,
  • R 6 is a substituted or unsubstituted C ⁇ -C2o hydrocarbon radical, such as substituted or unsubstituted (C ⁇ -C6) alkyl, substituted or unsubstituted (C 3 -C 6) alkenyloxycarbonyl, substituted or unsubstituted (C 3 -C 6) Cycloalkyl, substituted or unsubstituted (C 3 -C 7 ) alkynyl, substituted or unsubstituted (C 4 -C 8 ) cycloalkylalkyl, R 7 is halogen such as F, Cl, Br or J, OH, NR X R Y , where R x and R ⁇ are H or (C 1 -C 3 ) alkyl, or R 7 ' N- (CrC 3 ) alkyl N-acylamino or a substituted or unsubstituted C ⁇ -C2o hydrocarbon radical, or -C 2 o-stoffoxyrest
  • R 6 halogen such as F, Cl, Br or J or a substituted or unsubstituted C 1 - C 2 o-carbon-containing radical such as (Ci-C ⁇ J-alkyl, which is replaced by one or more radicals from the group halogen (F, Cl, Br, I) or (C ⁇ -C3) alkoxy can be substituted, (Ci-C ⁇ ) - alkoxy, which by one or more radicals from the group halogen (F, Cl, Br, J) or (C- ⁇ -C3) - Alkoxy can be substituted, substituted or unsubstituted alkoxycarbonyl, (Ci-C ⁇ J-mono- or dialkylamino, N- (-C-C 6 ) -alkyl-N-acylamino or N-acyiamino, is,
  • Y substituted or unsubstituted (Ci-C ⁇ J-alkyl, substituted or unsubstituted (Ci-C ⁇ J-alkoxyl, halogen such as F, Cl, Br or J, substituted or unsubstituted (Ci-C ⁇ J-mercapto-alkyl or (C ⁇ -C3) mono - or (C 1 -C 3) - dialkylamino, and Z is C-halogen such as CF, CCI, CBr or CJ, CH, or N and
  • alkyl, alkoxy, haloaikyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the carbon skeleton can each be straight-chain or branched.
  • Me methyl
  • Et ethyl
  • Pr propyl
  • Bu butyl
  • n Pr n-propyl
  • 'Pr iso-propyl
  • c Pr cyclopropyl
  • n Bu n- Butyl
  • 'Bu iso-butyl
  • s Bu secondary butyl
  • l Bu tertiary butyl
  • c Bu cyclobutyl
  • Ph phenyl.
  • ammonium ions also includes "quaternized" nitrogen systems with an sp 2 -hybridized N atom, such as pyridinium ions.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic and unsubstituted or substituted; it preferably contains one or more heteroatoms in the ring, preferably from the group N, O and S; it is preferably an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms and contains 1, 2 or 3 heteroatoms.
  • the heterocyclic residue can e.g. be a heteroaromatic residue or ring (heteroaryl), e.g.
  • Substituted radicals such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heteroaryl, a substituted bicyclic radical or ring or a substituted bicyclic radical, optionally with aromatic constituents, mean, for example, a substituted one derived from the unsubstituted basic body Radical, where the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and Dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alky
  • Mono- and disubstituted amino means e.g. B. alkylamino, dialkylamino, acylamino, arylamino, N-aryl-N-alkylamino.
  • Acyl means, for example, formyl, alkylcarbonyl such as (-CC 4 -alkyl) -carbonyl, phenylcarbonyl, where the phenyl ring can be substituted, for example as shown above for phenyl, or alkyloxycarbonyl, phenyioxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1 -iminoalkyl and other residues of organic acids.
  • the formula (Ia) also includes all stereoisomers of the formula (Ia) and their mixtures.
  • Such compounds of the formula (Ia) contain one or more asymmetric carbon atoms or else double bonds which are not specified separately in the general formula (IA).
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (Ia) and can be obtained by conventional methods from mixtures of the stereoisomers or by stereoselective reactions in combination with the use of stereochemically pure starting materials can be produced.
  • R 2 (-C 3 ) alkyl or (-C 3 ) haloalkyl, especially Me and Et,
  • R 4 (-C-C ⁇ ) -alkyl, (C ⁇ -C ⁇ ) -haloalkyl or (dC 6 ) -alkoxy, in particular Me, Et, OMe, OEt or CF 3 ,
  • R 5 H halogen such as F, Cl, Br or J, OMe, OEt, Me, CF 3 , the radicals R 5 in formula (III) which are different from W Waasssseerrssttooffff vveerrsscch preferably being in the 5-position on the phenyl ring,
  • R 7 H Me, Et, CF 3 , F, Cl, Br, J, N [(dC 3 ) -alkyl] -R 8 , NH-R 9 , CH 2 N [(-C-C 3 ) -alkyl] - R 10 , CH 2 NH-R 11 , CH 2 CH 2 N [(-CC 3 ) alkyl] -R 12 , CH 2 CH 2 NH-R 13 , where the radicals R 7 other than hydrogen in the formula ( IVa) are preferably in the 5-position on the phenyl ring, and the radicals R 8 to R 13 H, (-CC 6 ) -alkyl, (d-C ⁇ ) - haloaikyl, CHO, COO (dC 6 ) -alkyl, COO (-CC 6 ) -haloalkyl, SO 2 - (-C-C 6 ) alkyl, SO 2 - (dC 6 ) - haloalkyl, CO-
  • COOEt COO ⁇ Pr, COO'Pr, unsubstituted or substituted NH- (-C-C 6 ) -alkyl-acyl, unsubstituted or substituted NH- (C3-C 7 ) -cycloalkyl, unsubstituted or substituted (C 4 -C 8 ) -Cycloalkylalkyl, unsubstituted or substituted N- (C 3 -C 7 ) -
  • Cycloalkyl-aryl unsubstituted or substituted N- (C 4 -C 8 ) -cycloalkylalkyl-acyl, preferably
  • R 7 F, Cl, Me, Et, CF 3 , OCH 3 , OEt, OCH 2 CF 3 ,
  • R 14 to R 16 are the same or different H or substituted or unsubstituted (-C-C 3 o) -alkyl , substituted or unsubstituted (C ⁇ -C ⁇ o) alkyl (hetero) aryl, substituted or unsubstituted (C 3 -C 3 o) - (oligo) alkenyl, substituted or unsubstituted (C 3 -do) - (oligo) - Alkenyl (hetero) aryl, substituted or unsubstituted (C 3 -C 3 o) - (oligo) alkynyl, substituted or unsubstituted (C3-C10) - (oligo) alkynyl (hetero) aryl, substituted or unsubstituted (Heter
  • R 17 and R 25 substituted or unsubstituted (-C-C 3 o) -alkyl, substituted or unsubstituted (C ⁇ -C ⁇ o) -alkyl- (hetero) -aryl, substituted or unsubstituted (C3- C 3 o) - (oligo) - Alkenyl, substituted or unsubstituted (C 3 -C ⁇ o) - (oligo) alkenyl- (hetero) aryl, substituted or unsubstituted (C 3 -C 3 o) - (oligo) alkynyl, substituted or unsubstituted (C 3 -C ⁇ o ) - (Oligo) alkynyl (hetero) aryl, substituted or unsubstituted (hetero) aryl and where two radicals R 14 / R 15 and R 16 / R 17 together can form an unsubstituted or substituted ring,
  • Suitable cations M are cyclic cations such as [Py-R ⁇ ] + or the formula
  • Preferred ammonium cations M ⁇ are characterized in that
  • R 14 substituted or unsubstituted (dC 3 o) alkyl, substituted or unsubstituted (C ⁇ -C ⁇ o) alkyl- (hetero) -aryl, substituted or unsubstituted (C 3 -C 3 o) - (oligo) -alkenyl, substituted or unsubstituted (C3-C ⁇ o) - (oligo) -alkenyl- (hetero) -aryl, substituted or unsubstituted (C 3 -C3o) - (oligo) -alkynyl, substituted or unsubstituted (C 3 -C 10 ) - (oligo) - Alkynyl (hetero) aryl, substituted or unsubstituted (hetero) aryl,
  • R 16 substituted or unsubstituted (dC 3 o) alkyl, substituted or unsubstituted (C ⁇ -C ⁇ o) alkyl- (hetero) -aryl, substituted or unsubstituted (C 3 -C 3 o) - (oligo) -alkenyl, substituted or unsubstituted (C 3 -C ⁇ o) - (oligo) alkenyl (hetero) aryl, substituted or unsubstituted (C 3 -C 3 o) - (oligo) alkynyl, substituted or unsubstituted (C3-C ⁇ o) - (oligo) alkynyl (hetero) aryl, substituted or unsubstituted (hetero) aryl or H,
  • x is an integer from 1-40
  • R 25 (-CC 22 ) -alkyl, unsubstituted or substituted by one or more radicals of the group (-C-C 5 ) -alkyl, (-C-C 5 ) -alkoxy, (d-Cs) -haloalkoxy, halogen, such as Fluorine, chlorine, bromine and iodine, O- (CH 2 -CH 2 -O) x H, O- (CH 2 -CH 2 -O) ⁇ - (-C ⁇ -C 3 ) alkyl, O- (CH 2 - CH 2 -O) x - (COHC ⁇ -C 3 ) alkyl or O- (CH 2 -CH 2 -O) ⁇ - (CO) - (C ⁇ -C 3 ) alkoxy, phenyl, unsubstituted or substituted by one or several radicals of the group (-C 5 -C) alkyl, (-C 5 -C) alkoxy, (dC
  • x is an integer from 1 to 40
  • R 14 to R 17 and R 25 are identical or different from one another (-C 22 ) alkyl, unsubstituted or substituted by one or more radicals from the group (C1-C5) - alkyl, (Ci-CsJ-alkoxy, (C ⁇ -Cs ) -Haloalkoxy, halogen, such as fluorine, chlorine, bromine and iodine, O- (CH 2 -CH 2 -O) x H, O- (CH 2 -CH 2 -O) x - (-C-C 3 ) alkyl , O- (CH 2 -CH 2 -O) x - (CO) - (d-C3) - alkyl or O- (CH 2 -CH 2 -O) x - (CO) - (C ⁇ -C 3 ) - alkoxy,
  • Phenyl unsubstituted or substituted by one or more radicals of the group (-CC 5 ) alkyl, (-C-C 5 ) -alkoxy, (-C-C 5 ) -haloalkoxy, halogen, such as fluorine, chlorine, bromine and iodine, O- (CH 2 -CH 2 -O) x H, O- (CH 2 -CH 2 -O) x - (-C ⁇ -C 3 ) alkyl, O- (CH 2 -CH 2 -O) x - ( CO) - (dC 3 ) -alkyl, O- (CH 2 -CH 2 -O) ⁇ - (CO) - (-C ⁇ -C 3 ) -alkoxy, dC 10 -alkyl, which is likewise replaced by one of the radicals O- ( CH 2 -CH 2 ) ⁇ -OH, O- (CH 2 -CH 2 ) x -O-
  • sulfonylurea salts preferably of the formula (Ia), in combination with auxiliaries and additives, are suitable for the production of formulations, in particular for the production of EC formulations.
  • Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator - and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC dispersions based on oil or water
  • Formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic and / or nonionic surfactants (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonate sulfates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, and alkyl benzene sulfonates , 2,2 , -Dinaphthylmethane-6
  • Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as those e.g. already listed above for the other types of formulation.
  • Emulsions e.g. Oil-in-water emulsions (EW) can be used, for example, with stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as those e.g. already listed above for the other formulation types.
  • EW Oil-in-water emulsions
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying Active ingredient concentrates using adhesives, such as sugar and pentoses and hexoses or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • adhesives such as sugar and pentoses and hexoses or mineral oils
  • Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the auxiliaries of the formula (XVIII) or (XIX) can be used as pure substance or in the form of a solid or liquid mixture.
  • the indices w, x, y, z can independently assume an integer value from 0 to 50, preferably 0 to 20, particularly preferably 1 to 10.
  • the radical R is an unsubstituted or substituted Cs-C 4 o-hydrocarbon radical such as a C 8 -C 4 o-alkyl radical. This can be saturated or unsaturated, linear or branched. Examples of suitable substituents are F, Cl, Br or I or a hydroxyl or amino group.
  • EO means ethoxy unit
  • PO means propoxy unit when R ', R ", R'" are substituted or unsubstituted C ⁇ -C ⁇ oo hydrocarbon radicals such as d-doo-alkyl radicals, where the radicals can be saturated or unsaturated, linear or branched.
  • suitable substituents are F, Cl, Br or I or a hydroxyl or amino group. This definition also includes the substitution of one carbon atom of the alkyl chain by one or more oxygen or nitrogen atoms.
  • Known herbicides which can be combined with the sulfonylurea salts are, for example, the following active substances (note: the compounds are either with the "common name" according to the International Organization for Standardization (ISO) or with the chemical name, if appropriate together with a common code number): acetochlor; acifluorfen; aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim; ametryn; amidosulfuron; amitrole; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azafenidin; azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 5
  • the formulations present in the commercial form are optionally diluted in the customary manner, for example for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • the formulations according to the invention generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active compound, preferably a sulfonylurea salt of the formula (Ia).
  • active compound preferably a sulfonylurea salt of the formula (Ia).
  • the active ingredient concentration in wettable powders is, for example, about 10 to 90% by weight, the remainder being 100% by weight of conventional Formulation ingredients.
  • the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight.
  • Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • Dust-like formulations, soil or scatter granules as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the EC formulations according to the invention are characterized in that the proportion of sulfonylurea salts is generally 0.01-70% by weight, preferably 0.1-70% by weight, particularly preferably 0.1-50% by weight.
  • further agrochemicals from the field of crop protection - ZBHerbizide, fungicides, insecticides, growth regulators, safeners or fertilizers - can be contained between 0 and 70% by weight. It can also contain between 1 and 40% by weight, preferably 2-40% by weight, of a surfactant system.
  • the surfactant system can be composed, for example, of a) one or more nonionic surfactants, b) one or more betaine surfactants, c) one or more anionic surfactants, d) one or more cationic surfactants, or e) a mixture of the below a) -d) Put together the surfactants mentioned.
  • the EC formulations can contain between 0 and 95% by weight, preferably between 5 and 95% by weight, of a solvent system.
  • a further embodiment of the formulations according to the invention is characterized in that it is a dispersion, the liquid, homogeneous phase being constructed as described above and in which one or more insoluble compounds are dispersed.
  • the insoluble substances can be agrochemicals such as, for example, herbicides, insecticides, fungicides, safeners or fertilizers, or else formulation auxiliaries, such as tensides, which do not dissolve in the organic phase, such as, for example, Netzer IS (Clariant).
  • the EC formulations according to the invention are preferably characterized in that the proportion of the sulfonylurea salt, in particular of the formula (Ia) or the mixture of sulfonylurea salts, generally 0.1-70.0% by weight, preferably 0.1-50.0 % By weight.
  • Suitable solvents are polar solvents such as gamma-butyrolactone, acetonitrile, propionitrile; their share is 5.0 -95.0% by weight.
  • the finished EC product should have a weight fraction of 2.0-40.0% by weight of a mixture of an anionic and a nonionic surfactant or a mixture of cationic and non- ionic surfactants included.
  • other constituents can optionally be added to the EC formulations: by adding a hydrophobic solvent in the range from 1.0 to 90.0% by weight, the formation of emulsions in aqueous spray mixtures can be advantageously influenced.
  • Suitable solvent components are, for example, rapeseed oil methyl ester, aromatic solvents such as Solvesso, esters of long-chain acids and alcohols, or a mixture of hydrophobic solvents.
  • the content of sulfonylurea salts is generally 0.1-70.0 % By weight, preferably 0.1-50.0% by weight; one or more active ingredients can be included in the formulation
  • a polar solvent e.g. Gamma-butyrolactone, acetonitrile, propionitrile, propylene carbonate, or mixtures thereof are contained
  • sulfonylurea salt After the sulfonylurea salt is completely dissolved, there are 5.0 to 15.0% by weight calcium or sodium salt of dodecylbenzenesulfonic acid or a salt mixture, 5.0 to 15.0% by weight of a (-C 2 -C ⁇ s) - fatty acid polyglycol ester 40 EO and 15.0 to 20.0 wt .-% of a fatty alcohol polyglycol ether with stirring to the solution.
  • a water scavenger, an acid scavenger, a defoamer or a crystallization inhibitor can be used.
  • the sulfonylurea salts contained in the formulations according to the invention can be derived from known sulfonylureas or sulfonylurea metal salts, in particular alkali metal salts (see e.g. EP-A-30138, EP-A-7687) or also starting from sulfonamide salts e.g. Manufacture in the following ways:
  • the sulfonylurea is dissolved in an inert solvent or solvent mixture and reacted with one equivalent each of the reagents M + X " and MetB.
  • the metal salt in particular alkali metal salt (for example NaCl), which is obtained as a by-product, can be separated off.
  • R is a C 1 -C 2 -hydrocarbon radical such as Ci-Cio-alkyl
  • R 'and R are identical or different and hydrogen or C1-C30-hydrocarbon radicals such as Ci-Cio-alkyl and m are an integer from Is 0 to 100.
  • a sulfonyurea for example of the formula XIII, with a zwitterion, as given, for example, in equation (4), is given in an inert solvent, for example MeOH, THF or CH2Cl2 or a solvent mixture at temperatures between
  • N, m and o are integers between 1 and 100.
  • Harmful plants occurring in rice under the specific culture conditions such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus of the active compounds according to the invention also superbly combated. If the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
  • the compounds and formulations according to the invention have excellent herbicidal activity against mono- and dicotyledon weeds, crop plants of economically important crops, such as e.g. Wheat, barley, rye, rice, corn, sugar beet, cotton and soy are only slightly or not at all damaged. For these reasons, the present compounds are very suitable for the selective control of undesired plant growth in agricultural crops or in ornamental crops.
  • B. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

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

L'invention concerne des formulations contenant a) au moins un sel d'ammonium d'une sulfonylurée, le cation d'ammonium du sel présentant au moins un substituant qui diffère de l'hydrogène, et b) des auxiliaires et additifs classiques.
PCT/EP2000/000470 1999-01-27 2000-01-22 Formulation d'herbicides WO2000044226A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU45217/00A AU4521700A (en) 1999-01-27 2000-01-22 Herbicidal formulation

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19903064.2 1999-01-27
DE1999103064 DE19903064A1 (de) 1999-01-27 1999-01-27 Formulierung von Herbiziden und Pflanzenwachstumsregulatoren
DE19963395.9 1999-12-28
DE1999163395 DE19963395A1 (de) 1999-12-28 1999-12-28 Formulierung von Herbiziden

Publications (1)

Publication Number Publication Date
WO2000044226A1 true WO2000044226A1 (fr) 2000-08-03

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Family Applications (1)

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PCT/EP2000/000470 WO2000044226A1 (fr) 1999-01-27 2000-01-22 Formulation d'herbicides

Country Status (4)

Country Link
AR (1) AR022336A1 (fr)
AU (1) AU4521700A (fr)
CO (1) CO5231144A1 (fr)
WO (1) WO2000044226A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6225260B1 (en) 1996-11-22 2001-05-01 Lonza Inc. Quaternary ammonium salts of a sulfonylurea
WO2001030155A2 (fr) * 1999-10-26 2001-05-03 Aventis Cropscience Gmbh Agents herbicides

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2609105A1 (de) * 1976-03-05 1977-09-15 Basf Ag Ammonium- und sulfoniumsalze
US4093663A (en) * 1973-11-15 1978-06-06 The Dow Chemical Company Novel onium surfactants
EP0044807A2 (fr) * 1980-07-17 1982-01-27 Ciba-Geigy Ag N-phénylsulfonyl-N'-pyrimidinyl- et -triazinyl urées
EP0521500A1 (fr) * 1991-07-05 1993-01-07 Hoechst Schering AgrEvo GmbH Sel de pyridylsulfonylurées comme herbicides et régulateurs de croissance des plantes, procédé pour leur préparation et leur utilisation
WO1994000982A1 (fr) * 1992-07-01 1994-01-20 Church & Dwight Company, Inc. Compositions de pesticides ecologiques
EP0582021A1 (fr) * 1992-07-30 1994-02-09 Ciba-Geigy Ag Sulfonylurées comme herbicides
CH683341A5 (de) * 1990-03-07 1994-02-28 Vnii Chim Sredstv Zaschity Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel zur Stimulation und Unterdrückung des Pflanzenwachstums auf deren Grundlage.
EP0658307A1 (fr) * 1992-09-04 1995-06-21 Kare Ltd Composition herbicide
WO1995032951A1 (fr) * 1994-06-01 1995-12-07 Hoechst Schering Agrevo Gmbh Urees de phenylsulfonyle comportant des substituants d'azote, leurs procedes de preparation et leur utilisation comme herbicides et comme regulateurs de croissance pour vegetaux
WO1997016969A1 (fr) * 1995-11-07 1997-05-15 Kao Corporation Composition chimique liquide a usage agricole
WO1998021963A1 (fr) * 1996-11-22 1998-05-28 E.I. Du Pont De Nemours And Company Sels d'ammonium quaternaire et leur utilisation dans des formulations a usage agricole

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4093663A (en) * 1973-11-15 1978-06-06 The Dow Chemical Company Novel onium surfactants
DE2609105A1 (de) * 1976-03-05 1977-09-15 Basf Ag Ammonium- und sulfoniumsalze
EP0044807A2 (fr) * 1980-07-17 1982-01-27 Ciba-Geigy Ag N-phénylsulfonyl-N'-pyrimidinyl- et -triazinyl urées
CH683341A5 (de) * 1990-03-07 1994-02-28 Vnii Chim Sredstv Zaschity Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel zur Stimulation und Unterdrückung des Pflanzenwachstums auf deren Grundlage.
EP0521500A1 (fr) * 1991-07-05 1993-01-07 Hoechst Schering AgrEvo GmbH Sel de pyridylsulfonylurées comme herbicides et régulateurs de croissance des plantes, procédé pour leur préparation et leur utilisation
WO1994000982A1 (fr) * 1992-07-01 1994-01-20 Church & Dwight Company, Inc. Compositions de pesticides ecologiques
EP0582021A1 (fr) * 1992-07-30 1994-02-09 Ciba-Geigy Ag Sulfonylurées comme herbicides
EP0658307A1 (fr) * 1992-09-04 1995-06-21 Kare Ltd Composition herbicide
WO1995032951A1 (fr) * 1994-06-01 1995-12-07 Hoechst Schering Agrevo Gmbh Urees de phenylsulfonyle comportant des substituants d'azote, leurs procedes de preparation et leur utilisation comme herbicides et comme regulateurs de croissance pour vegetaux
WO1997016969A1 (fr) * 1995-11-07 1997-05-15 Kao Corporation Composition chimique liquide a usage agricole
WO1998021963A1 (fr) * 1996-11-22 1998-05-28 E.I. Du Pont De Nemours And Company Sels d'ammonium quaternaire et leur utilisation dans des formulations a usage agricole

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6225260B1 (en) 1996-11-22 2001-05-01 Lonza Inc. Quaternary ammonium salts of a sulfonylurea
WO2001030155A2 (fr) * 1999-10-26 2001-05-03 Aventis Cropscience Gmbh Agents herbicides
WO2001030155A3 (fr) * 1999-10-26 2001-10-25 Aventis Cropscience Gmbh Agents herbicides
US6569805B1 (en) 1999-10-26 2003-05-27 Aventis Cropscience Gmbh Herbicidal compositions
AU770910B2 (en) * 1999-10-26 2004-03-04 Bayer Intellectual Property Gmbh Herbicidal agent

Also Published As

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AR022336A1 (es) 2002-09-04
CO5231144A1 (es) 2002-12-27
AU4521700A (en) 2000-08-18

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