EP0790984A1 - Urees de phenylsulfonyle substituees par soufre; leurs procedes de preparation et leur utilisation comme herbicides et regulateurs de croissance pour vegetaux - Google Patents

Urees de phenylsulfonyle substituees par soufre; leurs procedes de preparation et leur utilisation comme herbicides et regulateurs de croissance pour vegetaux

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Publication number
EP0790984A1
EP0790984A1 EP95937842A EP95937842A EP0790984A1 EP 0790984 A1 EP0790984 A1 EP 0790984A1 EP 95937842 A EP95937842 A EP 95937842A EP 95937842 A EP95937842 A EP 95937842A EP 0790984 A1 EP0790984 A1 EP 0790984A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
formula
radicals
substituted
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.)
Withdrawn
Application number
EP95937842A
Other languages
German (de)
English (en)
Inventor
Gerhard Schnabel
Lothar Willms
Klaus Bauer
Hermann Bieringer
Christopher Rosinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Hoechst Schering Agrevo 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
Application filed by Hoechst Schering Agrevo GmbH filed Critical Hoechst Schering Agrevo GmbH
Publication of EP0790984A1 publication Critical patent/EP0790984A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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

  • Plant growth regulators in particular herbicides for the selective control of weeds and weeds in crops of useful plants.
  • heterocyclically substituted phenylsulfonylureas which carry an amino or a functionalized amino group or a sulfur substituent on the phenyl ring have herbicidal and plant growth-regulating properties (EP-A-1515; EP-A-7687; EP-A-30138; US -A-4,892,946; US-A-4,981,509; US-A-4,664,695; US-A-4,632,695; EP-A-116518;
  • Plant growth regulators are particularly well suited.
  • the present invention relates to compounds of the formula (I) and their salts,
  • W is an oxygen atom or a sulfur atom
  • n 0, 1 or 2
  • R H OH, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy, each of the latter 6 radicals being unsubstituted or substituted, or phenyl which is unsubstituted or substituted, or
  • R ', R "independently of one another are hydrogen, alkyl, alkenyl or alkynyl, each of the latter 3 radicals being unsubstituted or substituted by alkoxy, alkylthio or halogen, or together (C 2 -C 4 ) alkylene or (C 2 -C 4 ) Alkenylene,
  • R 1 is hydroxy, amino, mono- or disubstituted amino, hydroxylamino, substituted hydroxylamino, hydrazino, substituted hydrazino, an aliphatic hydrocarbon or hydrocarbonoxy radical or aryl, heteroaryl, aryloxy or heteroaryloxy, where each of the 6th
  • R 2 is halogen, CN, NO 2 , amino, mono- or disubstituted amino, alkyl or alkoxy, each of the latter two radicals being unsubstituted or substituted,
  • R 3 is hydrogen, hydroxy, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl, each of the latter 4 radicals being unsubstituted or is substituted by halogen, preferably F, Cl or Br,
  • X, Y independently of one another hydrogen, hydroxy, amino, mono- or
  • Z is CH, N or, where R ° is halogen, cyano, alkyl, alkoxy,
  • the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the carbon skeleton can each be straight-chain or branched.
  • the lower carbon skeletons e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl etc., mean e.g.
  • Alkynyl means e.g. Propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
  • Halogen means, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkyl, alkenyl and alkynyl mean partly or completely by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
  • a hydrocarbon residue is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic Hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl;
  • Aryl here means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl;
  • a hydrocarbon radical is preferably alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl; the same applies to a hydrocarbon residue in one
  • heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; it preferably contains one or more
  • Hetero units in the ring preferably from the group N, O, S, SO, SO 2 ;
  • heterocyclic residue can e.g. be a heteroaromatic residue or ring (heteroaryl), e.g.
  • Hetero ring atoms which can exist in different oxidation states, e.g. at N and S, occur.
  • Substituted residues such as substituted hydrocarbon residues e.g. Substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl or heteroaryl, mean, for example, one of the unsubstituted
  • unsaturated aliphatic radicals corresponding to the saturated hydrocarbon-containing radicals mentioned, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy etc.
  • radicals with carbon atoms those with 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
  • Substituents from the group halogen, for example fluorine and chlorine, (C 1 -C 4 ) alkyl, preferably methyl or ethyl, (C 1 -C 4 ) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy are generally preferred , preferably methoxy or ethoxy, (C 1 -C 4 ) haloalkoxy, nitro and cyano.
  • the substituents methyl, methoxy and chlorine are particularly preferred.
  • Mono- or disubstituted amino means a chemically stable radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred;
  • Aryl is preferably phenyl or substituted phenyl; for acyl the following applies
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyl, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4- Trifluoro- and -Trichlorphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and
  • An acyl residue means the residue of an organic acid, for example the residue of a carboxylic acid and residues of acids derived therefrom, such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the residue of
  • Carbonic acid monoesters optionally N-substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
  • Acyl means, for example, formyl, alkylcarbonyl such as (C 1 -C 4 alkyl) carbonyl,
  • Phenylcarbonyl where the phenyl ring may be substituted, e.g. as shown above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of
  • the invention also relates to all stereoisomers which are encompassed by formula (I) and mixtures thereof.
  • Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not indicated separately in the general formula (I).
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of
  • the compounds of formula (I) can form salts in which the hydrogen of the -SO 2 -NH group is replaced by a cation suitable for agriculture.
  • These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts or salts with organic amines.
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts or salts with organic amines.
  • Methylaminocarbonylamino dimethylaminocarbonylamino, preferably H or (C 1 -C 4 ) alkyl,
  • X 1 is an oxygen atom
  • X 2 is an oxygen atom
  • R ', R "independently of one another are (C 1 -C 4 ) alkyl.
  • R 1 OH, NR 4 R 5 , (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 6 ) alkoxy, (C 2 -C 6 ) alkenoxy, (C 2 -C 6 ) alkynoxy, (C 3 -C 7 ) cycloalkyl,
  • R 2 halogen, (C 1 -C 3 ) alkyl, (C 1 -C 3 ) haloalkyl, (C 1 -C 5 ) alkoxyalkyl, NO 2 ,
  • NR 11 R 12 CN, (C 1 -C 3 ) alkoxy or (C 1 -C 3 ) haloalkoxy, R 3 H, OH, (C 1 -C 3 ) alkyl, (C 2 -C 3 ) alkenyl, (C 2 -C3) alkynyl or (C 1 -C 3 ) alkoxy, preferably H or (C 1 -C 4 ) Alkyl,
  • R 4 H OH, NH 2 , mono- and di - [(C 1 -C 3 ) alkyl] amino, (C 1 -C 4 ) alkyl,
  • R 5 H (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, [(C 1 -C 4 ) alkyl] carbonyl, [(C 2 -C 4 ) alkenyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl,
  • NR 4 R 5 together form a heterocyclic radical which, in addition to the N atom, contains further hetero units from the group O, N, S, SO or SO 2 im
  • R 6 H (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, ( C 2 -C 4 ) haloalkynyl, OH, (C 1 -C 3 ) alkoxy or
  • R 7 H (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, ( C 2 -C 4 ) haloalkynyl, CO-H, CO 2 CH 3 , CO-CH 3 , CO-NH 2 , CO-NHCH 3 or CON (CH 3 ) 2 ,
  • NR 6 R 7 together form a heterocyclic radical which, in addition to the N atom, contains further hetero units from the group O, N, S, SO or SO 2 im May contain ring structure and which is unsubstituted or by one or more radicals from the group halogen, OH, NH 2 , NO 2 , CONHCH 3 , CONH 2 , NHCH 3 , N (CH 3 ) 2 , CN, CO 2 CH 3 , CON ( CH 3 ) 2 , COCH 3 , CO-H, (C 1 -C 3 ) alkyl, (C 1 -C 3 ) haloalkyl, (C 1 -C 3 ) alkoxy, (C 1 -C 3 ) haloalkoxy and oxo function is
  • R 8 H (C 1 -C 3 ) alkyl, (C 1 -C 3 ) haloalkyl, (C 1 -C 3 ) alkoxy, (C 1 -C 3 ) haloalkoxy, (C 1 -C 3 ) alkylthio, ( C 1 -C 3 ) haloalkylthio, NH 2 , NHCH 3 , N (CH 3 ) 2 or OH,
  • R 9 (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 5 ) alkoxyalkyl, (C 2 -C 4 ) alkenyl,
  • R 10 (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 5 ) haloalkyl,
  • R 1 1 H, (C 1 -C 3 ) alkyl, (C 1 -C 3 ) haloalkyl, (C 1 -C 3 ) alkoxy, (C 1 -C 3 ) haloalkoxy or OH and
  • R 12 H (C 1 -C 3 ) alkyl, (C 1 -C 3 ) haloalkyl, CHO, COCH 3 , CO 2 CH 3 , CO 2 C 2 H 5 , SO 2 CH 3 or CN,
  • NR 11 R 12 together form a heterocyclic radical which, in addition to the N atom, contains further hetero units from the group O, N, S, SO or SO 2 im
  • X, Y independently of one another H, halogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy,
  • Preferred compounds of the formula (I) and their salts are those in which
  • R 1 (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 1 -C 4 ) alkoxy, each of the latter 4 radicals being unsubstituted or by one or more Radicals from the group halogen, (C 1 -C 4 ) alkoxy and (C 1 -C 4 ) alkylthio, or (C 3 -C 6 ) cycloalkyl, benzyl, phenyl, thienyl, pyridyl, each of the latter 5 radicals unsubstituted or by one or more radicals from the group halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, CN, NO 2 and OH is substituted, or NH
  • n 0, 1 or 2.
  • R 2 is (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or halogen and m is 0, 1, 2 or 3, preferably 0 or 1 mean.
  • one of the radicals X and Y is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, mono- or di - [(C 1 -C 4 ) alkyl] amino and the other of the radicals X and Y (C 1 -C 4 ) alkyl, (C 1 -C 4 ) Alkoxy or (C 1 -C 4 ) haloalkoxy mean.
  • the present invention further provides processes for the preparation of the compounds of the formula (I) according to the invention or their salts, characterized in that a) a compound of formula (II)
  • R ** means unsubstituted or substituted phenyl or (C 1 -C 4 ) alkyl, or
  • a cyanate for example an alkali metal cyanate such as sodium or potassium cyanate, or c) a sulfonamide of the formula (II) (see a) in succession with a cyanate
  • a cyanate for example an alkali metal cyanate such as sodium or potassium cyanate
  • a sulfonamide of the formula (II) see a) in succession with a
  • Ar-O-CO-CI (VI) in which Ar is an unsubstituted or substituted aryl radical and is reacted with a heterocyclic amine of the formula (V) (see b), or
  • R * CH (X 1 R ') (X 2 R ") derivatizes the obtained formyl compound to the formyl equivalent of the formula (I) or
  • the bases used are, for example, organic amine bases such as 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), triethylamine or else
  • Chlorinating agents - such as PCI 3 , POCI 3 or SOCI 2 - lead to the sulfochloride of the formula (X).
  • This reaction takes place in bulk or in inert solvents such as dichloromethane, sulfolane, acetonitrile or in a solvent mixture of inert components.
  • inert solvents such as dichloromethane, sulfolane, acetonitrile or in a solvent mixture of inert components.
  • solvents such as, for example, dimethylformamide, N, N-dimethylacetic acid amide or N-methylpyrrolidinone
  • suitable bases such as, for example, sodium or potassium carbonate .
  • suitable oxidizing agents eg potassium peroxomonosulfate, ® Oxone
  • R tert-butyl
  • the tert-butyl group is split off from the aromatics of the formula (XIV) by reaction with strong acids to give the sulfonamides of the formula (IIIa).
  • strong acids are mineral acid, such as H 2 SO 4 or HCl, or strong organic acids, such as CF 3 COOH.
  • the compounds of formula (VII) at temperatures between -10 ° C and 70 ° C, preferably 0 to 40 ° C in an inert solvent such as e.g. Dichloromethane, trichloromethane, dimethylformamide or
  • Formylating agents e.g. the mixed anhydride from ant and
  • Aryl chloroformates (VI) and heterocyclic amines of the formula (V) also lead to the compounds of the formula (I).
  • the (thio) isocyanates of the formula (VIII) can be obtained by processes known from the literature (EP-A-232067, EP-A-166516).
  • the reaction of the (thio) isocyanates (VIII) with compounds (II) takes place at -10 ° C. to 100 ° C., preferably 20 to 100 ° C., in an inert aprotic solvent, such as acetone or acetonitrile, in the presence of a suitable one Base, for example N (C 2 H 5 ) 3 or K 2 CO 3 .
  • the salts of the compounds of formula (I) are preferably in inert polar solvents such as e.g. Water, methanol, acetone, dichloromethane, tetrahydrofuran, in individual cases also in non-polar solvents such as toluene or heptane, at temperatures from 0 to 100 ° C.
  • inert polar solvents such as e.g. Water, methanol, acetone, dichloromethane, tetrahydrofuran, in individual cases also in non-polar solvents such as toluene or heptane, at temperatures from 0 to 100 ° C.
  • Suitable bases for the preparation of the salts according to the invention are, for example
  • Alkali carbonates such as potassium carbonate, alkali and alkaline earth metal hydroxides, for example NaOH, KOH or Ca (OH) 2 , ammonia or a suitable amine base from the group of primary, secondary and tertiary amines, such as triethylamine or
  • Ethanolamine Suitable acids for salt formation are, for example, HCl, HBr, H 2 SO 4 or HNO 3 .
  • U * denotes NH 2 , Cl, mono- or disubstituted amino, such as alkylamino, in particular t-butylamino, or aryloxycarbonylamino, and R * , R 1 , R 2 , n and m are as defined in formula (I).
  • Solvents "mean solvents which are inert under the respective reaction conditions, but not under any
  • the compounds of formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Even difficult to fight
  • Post-emergence also occurs very rapidly after the treatment and the weed plants remain in the growth stage at the time of application or die completely after a certain time, so that one for the
  • Crops harmful weed competition is eliminated very early and sustainably.
  • Cultivated plants of economically important crops such as Wheat, barley, rye, rice, corn, sugar beet, cotton and soy are only slightly or not at all damaged.
  • the present compounds are suitable from these
  • the substances according to the invention have excellent growth-regulating properties in crop plants. They intervene regulating the plant's own metabolism and can therefore be used to influence plant constituents in a targeted manner and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and
  • Inhibiting unwanted vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many mono- and dicotyledon crops, as this can reduce or completely prevent storage.
  • 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 relates to herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I).
  • the compounds of formula (I) can be formulated in different ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • sprayable solutions emulsions
  • SC Suspension concentrates
  • Oil-miscible solutions capsule suspensions (CS), dusts (DP), mordants, granules for sprinkling 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 are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Kunststoff, 4th Edition 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY , 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.
  • the necessary 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, “Solvent Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, “Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976; Winnacker-kuchler, "Chemical Technology", Volume 7,
  • 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, dispersing agents), e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines,
  • the herbicides are used Active ingredients, for example in conventional equipment such as hammer mills,
  • Blower mills and air jet mills are finely ground and mixed simultaneously or subsequently with the formulation auxiliaries.
  • 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.
  • surfactants of ionic and / or nonionic type emulsifiers
  • Alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters,
  • Alkylaryl polyglycol ether fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, alkyl polyether, sorbitan esters such as e.g.
  • Sorbitan fatty acid esters or polyoxethylene sorbitan esters such as e.g.
  • 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. upstairs with the others
  • Emulsions for example oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Emulsions can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as those already listed above for the other types of formulation.
  • Granules can either by spraying the active ingredient
  • adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • Water-dispersible granules are usually made according to the usual
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active ingredient of the formula (I).
  • the active ingredient concentration in wettable powders is, for example, about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components.
  • 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 compound, 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.
  • active ingredient formulations mentioned may contain the usual adhesive, wetting, dispersing, emulsifying, penetrating,
  • Preservatives Preservatives, antifreeze and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents that influence pH and viscosity.
  • Mixture formulations or in the tank mix can be used, for example, known active ingredients, such as those found in e.g. from Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Bracknell, England, and the literature cited therein.
  • Herbicides known from the literature which can be combined with the compounds of the formula (I) are, for example The following active substances are to be named (note: the compounds are either identified with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name, if necessary together with a common code number):
  • acetochlor acifluorfen; aclonifen; AKH 7088, i.e. [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidenes] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim; ametryn;
  • chlorimuron ethyl Chlorine nitrofen; chlorotoluron; chloroxuron; chlorpropham;
  • clethodim clethodim
  • clodinafop and its ester derivatives e.g. clodinafop-propargyl
  • clomazone clomeprop; cloproxydim; clopyralid; cumyluron (JC 940); cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (e.g. butyl ester, DEH-112); cyperquat; cyprazine;
  • diclofop-methyl diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethazone, clomazone; dimethipin; dimetrasulfuron, dinitramine; dinoseb; dinoterb;
  • diphenamide dipropetryn; diq ⁇ at; dithiopyr; diuron; DNOC; eglinazine-ethyl;
  • EL 177 i.e. 5-cyano-1- (1, 1-dimethylethyl) -N-methyl-1H-pyrazole-4-carboxamide; endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; F5231, i.e. N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1 H-tetrazol-1-yl] phenyl] ethanesulfonamide; ethoxyfen and its esters (e.g.
  • ethyl ester HN-252
  • etobenzanide HW 52
  • fenoprop fenoxan, fenoxaprop and fenoxaprop-P and their esters, e.g. fenoxaprop-P-ethyl and fenoxaprop-ethyl
  • fenoxydim fenuron
  • flamprop-methyl flazasulfuron
  • fluazifop and fluazifop-P and their esters e.g. fluazifop-butyl and fluazifop-P-butyl;
  • fluchloralin flumetsulam; flumeturon; flumiclorac and its esters (e.g.
  • Pentyl ester S-23031); flumioxazin (S-482); flumipropyn; flupoxam (KNW-739); fluorodifen; fluoroglycofen-ethyl; flupropacil (UBIC-4243); fluridone;
  • flurochloridone fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen;
  • glufosinate giyphosate
  • halosates halosulfuron and its esters
  • Methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P ( R-haloxyfop) and its ester; hexazinone; imazamethabenz-methyl;
  • imazapyr imazaquin and salts such as the ammonium salt; imazethamethapyr; imazethapyr; imazosulfuron; ioxynil; isocarbamide; isopropaline; isoproturon;
  • met.zthiazuron metham; methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron; metobromuron; metolachlor; metosulam
  • monalide monocarbamide dihydrogen sulfates; monolinuron; monuron; MT 128, i.e. 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazinamine;
  • naproanilide napropamide; naptalam
  • NC 310 i.e. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitraline;
  • nitrofen nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone;
  • propargyl esters quinclorac; quinmerac; quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives e.g. quizalofop-ethyl; quizalofop-P-tefuryl and ethyl; renriduron; rimsulfuron
  • terbuthylazine terbutryn
  • TFH 450 ie N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1, 2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiazafluron; thizopyr (Mon-13200); thidiazimin (SN-124085);
  • Formulations optionally diluted in the usual way e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible
  • Granules using water Granules using water. Dust-like preparations, soil or
  • Scatter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • Compounds of formula (I) can fluctuate within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but it is preferably between 0.005 and 5 kg / ha.
  • the reaction mixture was concentrated in a high vacuum.
  • the backlog is in
  • Acetonitrile is distilled off, the residue is taken up in water and washed with diethyl ether. After acidifying the aqueous phase with
  • Trifluoroacetic acid distilled off. The backlog is left with little
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207) and 3 parts by weight
  • Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range e.g. approx. 255 to above 277 ° C) are mixed and ground in a friction ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I), 75 parts by weight of cyclohexanone
  • Emulsifier e) A water-dispersible granulate is obtained by:
  • the spray tower is atomized and dried using a single-component nozzle.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants are placed in sandy loam in plastic pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders or emulsion concentrates are then applied as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l / ha in different dosages to the surface of the covering earth.
  • the pots are placed in the greenhouse and kept under good growth conditions for the weeds.
  • the visual assessment of the damage to the plants or the soiling occurs after the soiling
  • Compounds according to the invention have a good herbicidal pre-emergence activity against a broad spectrum of grasses and weeds.
  • Examples Nos. 1-26, 2-26, 3-1, 3-13, 3-16, 3-26, 3-51, 3-76, 3-101 and 3-103 see Tables 1 and 3) very good herbicidal activity against
  • Harmful plants such as Sinapis alba, Chrysanthemum segetum, Avena sativa, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Setaria spp., Abutilon theophrasti, Amaranthus retroflexus and Panicum miliaceum im
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are placed in sandy loam soil in plastic pots, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants are treated at the three-leaf stage.
  • Compounds according to the invention are sprayed onto the green parts of the plant in various dosages with a water application rate of the equivalent of 600 to 800 l / ha. After the test plants have stood in the greenhouse for about 3 to 4 weeks under optimal growth conditions, the effect of the preparations is assessed visually in comparison to untreated controls.
  • the agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, even after emergence. For example, Examples Nos. 1-26, 2-26, 3-1, 3-13, 3-16, 3-26, 3-51, 3-76, 3-101 and 3-103 (see Tables 1 and 3) very good herbicidal activity against harmful plants such as Sinapis alba, Stellaria media,
  • Echinochloa crus-galli Lolium multiflorum, Chrysanthemum segetum, Setaria spp., Abutilon theophrasti, Amaranthus retroflexus, Panicum miliaceum and Avena sativa in the post-emergence process with an application rate of 0.3 kg and less active substance per hectare. 3. Crop tolerance
  • Cultures such as Leave soy, cotton, rapeseed, sugar beet and potatoes undamaged in the pre- and post-emergence process, even with high active ingredient doses. Some substances also protect Gramineae crops such as Barley, wheat, rye, sorghum, corn or rice.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Les composés de la formule (I) et leurs sels s'utilisent comme herbicides et régulateurs de croissance pour végétaux. Dans cette formule, R*, R?1, R2, R3¿, X, Y, Z, W, n et m ont la notation mentionnée dans la revendication 1 et spécialement R* désigne un équivalent formyle de la formule CHO, -CH=NR ou CH(X1R')(X2R'). La préparation s'effectue de manière similaire aux procédés connus, en partie à l'aide d'intermédiaires de la formule (XVII) où U* = NH¿2?, Cl, amino (subst.).
EP95937842A 1994-11-07 1995-10-25 Urees de phenylsulfonyle substituees par soufre; leurs procedes de preparation et leur utilisation comme herbicides et regulateurs de croissance pour vegetaux Withdrawn EP0790984A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4439676A DE4439676A1 (de) 1994-11-07 1994-11-07 Schwefelsubstituierte Phenylsulfonylharnstoffe, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE4439676 1994-11-07
PCT/EP1995/004182 WO1996014303A1 (fr) 1994-11-07 1995-10-25 Urees de phenylsulfonyle substituees par soufre; leurs procedes de preparation et leur utilisation comme herbicides et regulateurs de croissance pour vegetaux

Publications (1)

Publication Number Publication Date
EP0790984A1 true EP0790984A1 (fr) 1997-08-27

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EP95937842A Withdrawn EP0790984A1 (fr) 1994-11-07 1995-10-25 Urees de phenylsulfonyle substituees par soufre; leurs procedes de preparation et leur utilisation comme herbicides et regulateurs de croissance pour vegetaux

Country Status (8)

Country Link
US (1) US5854179A (fr)
EP (1) EP0790984A1 (fr)
JP (1) JPH10509442A (fr)
AU (1) AU3869495A (fr)
BR (1) BR9509607A (fr)
CA (1) CA2204612A1 (fr)
DE (1) DE4439676A1 (fr)
WO (1) WO1996014303A1 (fr)

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DE19619628A1 (de) * 1996-05-15 1997-11-20 Hoechst Schering Agrevo Gmbh (Hetero)Arylsulfonylharnstoffe mit einer Iminofunktion, ihre Darstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO2012087980A1 (fr) 2010-12-21 2012-06-28 Agraquest, Inc. Mutants « papier de verre » de bacillus et leurs procédés d'utilisation pour stimuler la croissance végétale, promouvoir la santé végétale et lutter contre des maladies et des nuisibles
MX2014002890A (es) 2011-09-12 2015-01-19 Bayer Cropscience Lp Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos.
EP3654968B1 (fr) 2017-07-17 2023-08-16 Merck Sharp & Dohme LLC Inhibiteurs de métallo-bêta-lactamase et leurs méthodes d'utilisation
CN112661704B (zh) * 2020-12-22 2023-09-05 南开大学 单嘧磺隆衍生物及其制备方法、除草剂和除草方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK401978A (da) * 1977-10-06 1979-04-07 Du Pont Herbicide sulfonamider
US4369058A (en) * 1977-10-06 1983-01-18 E. I. Du Pont De Nemours And Company N-(Heterocyclicaminocarbonyl)arylsulfonamides
DK163123C (da) * 1978-05-30 1992-06-09 Du Pont Benzensulfonylurinstoffer til anvendelse som herbicider eller plantevaekstregulatorer, praeparat indeholdende dem samt deres anvendelse
DK259280A (da) * 1979-07-20 1981-01-21 Du Pont Herbicide sulfonamider
US4310346A (en) * 1980-03-14 1982-01-12 E. I. Du Pont De Nemours And Company N(Substituted phenylsulfonyl) N'(substituted cyumidin-2-yl) ureas
US4892946A (en) * 1979-11-30 1990-01-09 E. I. Du Pont De Nemours And Company Agricultural sulfonamides
ZA806970B (en) * 1979-11-30 1982-06-30 Du Pont Agricultural sulfonamides
MA19680A1 (fr) * 1982-01-11 1983-10-01 Novartis Ag N- arylsulfonyl - n' - pyrimidinylurees.
EP0116518B1 (fr) * 1983-02-04 1987-10-28 Ciba-Geigy Ag Urées N-phénylsulfonyl-N'-pyrimidinyl- et -triazinyl
US4981509A (en) * 1984-05-24 1991-01-01 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
CA1226862A (fr) * 1985-02-21 1987-09-15 Donald J. Dumas Sulfonamides herbicides
DE4236902A1 (de) * 1992-10-31 1994-05-05 Hoechst Ag Neue Phenylsulfonylharnstoffe, Darstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren

Non-Patent Citations (1)

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Title
See references of WO9614303A1 *

Also Published As

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CA2204612A1 (fr) 1996-05-17
AU3869495A (en) 1996-05-31
US5854179A (en) 1998-12-29
DE4439676A1 (de) 1996-05-09
JPH10509442A (ja) 1998-09-14
BR9509607A (pt) 1997-10-28
WO1996014303A1 (fr) 1996-05-17

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