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WO1994013619A1 - Benzoylcyclohexenones, leur procede de preparation et leur utilisation comme herbicides et regulateurs de croissance des vegetaux - Google Patents

Benzoylcyclohexenones, leur procede de preparation et leur utilisation comme herbicides et regulateurs de croissance des vegetaux Download PDF

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Publication number
WO1994013619A1
WO1994013619A1 PCT/EP1993/003385 EP9303385W WO9413619A1 WO 1994013619 A1 WO1994013619 A1 WO 1994013619A1 EP 9303385 W EP9303385 W EP 9303385W WO 9413619 A1 WO9413619 A1 WO 9413619A1
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Prior art keywords
formula
compounds
alkyl
halogen
alkoxy
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PCT/EP1993/003385
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German (de)
English (en)
Inventor
Stephan Müller
Rainer SCHÜTZE
Klaus Bauer
Hermann Bieringer
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Hoechst Schering Agrevo Gmbh
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Filing date
Publication date
Application filed by Hoechst Schering Agrevo Gmbh filed Critical Hoechst Schering Agrevo Gmbh
Priority to EP94902660A priority Critical patent/EP0673359A1/fr
Priority to JP6513740A priority patent/JPH08504414A/ja
Priority to KR1019950702368A priority patent/KR950704233A/ko
Priority to BR9307631A priority patent/BR9307631A/pt
Priority to AU56949/94A priority patent/AU5694994A/en
Publication of WO1994013619A1 publication Critical patent/WO1994013619A1/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
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/48—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —S—C≡N groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C261/00—Derivatives of cyanic acid
    • C07C261/02—Cyanates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/06—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • Benzoylcyclohexenones process for their preparation and their use as herbicides and plant growth regulators
  • the invention lies in the technical field of plant treatment agents, which are preferably used against monocotyledonous and dicotyledonous weeds
  • agricultural crops n can be used.
  • the invention relates to the use of compounds of the formula (I)
  • n is an integer from 0 to 6
  • halogen CN, OCN, SCN, C 2 -C 4 alkynyl or CHR 5 R 6 , where R 5 and R 6 independently of one another CN, NO 2 , formyl, (C 1 - C 4 alkyl) carbonyl or ( C 1 -C 4 alkoxy) carbonyl, in which the latter two radicals are unsubstituted or substituted by one or more halogen atoms, or phenylcarbonyl which is unsubstituted or substituted,
  • R 1 is the same or different substituents from the group C 1 -C 4 alkyl, or C 3 -C 6 cycloalkyl, the two latter radicals being unsubstituted or substituted by one or more halogen atoms, or phenyl which is unsubstituted or substituted,
  • R 2 halogen, CN, NO 2 , C 1 -C 3 alkyl, C 1 - C 3 alkoxy, C 1 - C 3 haloalkyl,
  • R 3 H halogen, OH, C 1 - C 3 alkyl, C 1 -C 3 alkoxy, C 1 - C 3 haloalkyl, C 1 - C 3 - haloalkoxy or (C 1 -C 3 alkoxy) - carbonyl and
  • Halogenalkoxy each be straight-chain or branched.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, alkylcarbonyl etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl.
  • Alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, such as 1-propynyl, 2-propynyl, 1-, 2- or 3-butynyl.
  • Halogen means fluorine, chlorine, bromine or iodine.
  • Optionally substituted phenyl is unsubstituted phenyl or substituted phenyl usual in herbicides;
  • Substituted phenyl is, for example, phenyl which is substituted one or more times, preferably up to three times by the same 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, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3- Dichlorophenyl, o-, m- and p-methoxyphenyl.
  • substituted phenyl radicals in composite meanings, such as phenylcarbonyl.
  • Some compounds of the formula (I) contain one or more asymmetric carbon atoms, which are not specified separately in the general formula (I).
  • the possible stereoisomers such as enantiomers, diastereomers, as well as their mixtures defined by their specific spatial shape, are all encompassed by the formula (I).
  • halogen CN, OCN, SCN, C 2 -C 4 alkynyl or CHR 5 R 6 , where R 5 and R 6 independently of one another CN, NO 2 , formyl, (C 1 -C 2 alkyl) carbonyl, ( C 1 -C 4 alkoxy) carbonyl or phenylcarbonyl, wherein the three
  • Halogen atoms are substituted
  • R 1 are identical or different substituents from the group C 1 -C 3 alkyl, C 4 -C 6 cycloalkyl or phenyl, the three last-mentioned radicals being unsubstituted or substituted by one or more halogen atoms,
  • R 2 halogen, CN, NO 2 , C 1 -C 2 alkyl, C 1 -C 2 alkoxy, C 1 - C 2 haloalkyl,
  • R 7 is C 1 - C 2 alkyl and m is zero, one or two, R 3 H, halogen, OH, C 1 - C 2 alkyl, C 1 - C 2 alkoxy, C 1 - C 2 haloalkyl,
  • R 4 H halogen, CN, NO 2 , C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy or R 8 S (O) p -, where R 8 is C 1 -C 3 alkyl and p is zero, one or two are mean.
  • n is preferably an integer from 0 to 3;
  • X is preferably fluorine, chlorine, bromine, iodine, cyano, cyanato, thiocyanato, ethynyl, 1-propynyl, CH (CN) 2 , CH (CN) COOC 2 H 5 , CH (CN) COOCH 3 , CH (COCH 3 ) COOCH 3 , CH (COCH 3 ) COOC 2 H 5 , CH (COCH 3 ) NO 2 ,
  • R 1 is preferably methyl, ethyl, i-propyl, cyclopentyl, cyclohexyl or phenyl;
  • R 2 is preferably fluorine, chlorine, cyano, nitro, methyl, methoxy,
  • R 3 is preferably hydrogen, hydroxy, chlorine, methyl, methoxy,
  • R 4 is preferably hydrogen, chlorine, bromine, cyano, nitro, trifluoromethyl, difluoromethoxy, trifluoromethoxy, methylsulfonyl or ethylsulfonyl. Uses according to the invention of compounds of the formula (I) which have a combination of the abovementioned preferred features are also preferred.
  • R 1 , R 2 , R 3 , R 4 and n are as defined in formula (I), with suitable halogenating reagents, such as, for example
  • Compounds (I) according to variant a) are preferably prepared in aprotic solvents, in particular halogenated hydrocarbons such as e.g. Dichloromethane, trichloromethane and 1, 2-dichloroethane at -20 ° C to the boiling point of the reaction mixture, especially at room temperature.
  • aprotic solvents in particular halogenated hydrocarbons such as e.g. Dichloromethane, trichloromethane and 1, 2-dichloroethane at -20 ° C to the boiling point of the reaction mixture, especially at room temperature.
  • the compounds (I) are prepared according to variants b) and c)
  • the compounds of the formula (II) required for the preparation of the compounds of the formula (I) according to variant a) can be synthesized by or analogously to known processes, see e.g. US-A-4 780 127, EP-A-502 492.
  • 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
  • Alopecurus Phalaris, Echinochloa, Digitaria, Setaria as well as Cyperus species from the annual group and on the part of the perennial species Agropyron,
  • 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
  • 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 to regulate the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of 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
  • CS capsule suspensions
  • DP dusts
  • pickling agents granules for spreading and soil application
  • granules GR
  • WG water-dispersible granules
  • SG water-soluble granules
  • Microcapsules and waxes are Microcapsules and waxes.
  • 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 Diluent 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, C.
  • Manufacture herbicides, fungicides, safeners, fertilizers and / or growth regulators e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (wetting agents, dispersants), for example polyoxyethylated ones Alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines,
  • the herbicidal active ingredients are used, for example, in customary 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
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
  • Fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as, for. B. sorbitan fatty acid esters or polyoxethylene sorbitan esters such. B.
  • 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 z. B. above with the others
  • EW oil-in-water emulsions
  • 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 usually contain 0.1 to 99
  • active compound of the formula (I) % By weight, in particular 0.1 to 95% by weight, of active compound 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, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions about 0.05 to 80, preferably 2 to 50% by weight.
  • 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.
  • Active substances can be used, as in e.g. from Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Brackneil, England, and the literature cited therein.
  • herbicides known from the literature which can be combined with the compounds of formula (I), z.
  • the following active substances are to be mentioned (note: the compounds are identified either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name, possibly together with a usual code number):
  • BAS 516 H ie 5-fluoro-2-phenyl-4H-3, 1-benzoxazin-4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl;
  • benzthiazuron bialaphos; bifenox; bromacil; bromobutide; bromofenoxim;
  • bromoxynil bromuron; buminafos; busoxinone; butachlor; butamifos;
  • chlorazifop-butyl pirifenop-butyl; chlorbromuron; chlorobufam; chlorfenac;
  • chlorflurecol-methyl chloridazon; chlorimuron ethyl; chloronitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlororthal dimethyl; chlorothiamide;
  • clopyralid cyanazine; cycloate; cycloxydim; cycluron; cyperquat; cyprazine; cyprazole; 2,4-DB; dalapon; desmediphan; desmetryn; di-allate; dicamba;
  • dichlobenil dichlorprop; diclofop-methyl; diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethazone, clomazone; dimethipin; dimetrasulfuron, cinosulfuron; dinitramine; dinoseb; dinoterb;
  • glufosinate glyphosate; halosates; haloxyfop and its ester derivatives;
  • napropamide ; naptalam; NC 310, i.e. H. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitraline; nitrofen;
  • procyazine prodiamine; profluralin; proglinazine-ethyl; prometon; prometryn; propachlor; propanil; propaquizafop and its ester derivatives; propazine;
  • propham propyzamide; prosulfalin; prosulfocarb; prynachlor; pyrazolinates;
  • pyrazone pyrazosulfuron-ethyl; pyrazoxyfen; pyridate; quinclorac; quinmerac; quinofop and its ester derivatives, quizalofop and its ester derivatives;
  • terbucarb terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, i.e. H. N, N-Diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1 H-1, 2,4-triazole-1-carboxamide; thiazafluron; thifensulfuron-methyl; thiobencarb; tiocarbazil; tralkoxydim;
  • the invention also relates to a method for combating
  • 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.
  • Plant growth can be regulated in a direct or indirect manner.
  • Formulations e.g. in the form of granules, microcapsules or as
  • Irrigation water solution in irrigation water, especially in rice cultivation.
  • Oxalyl bromide are placed in 30 ml of dichloromethane and mixed with 0.2 ml of dimethylformamide. The mixture is stirred at room temperature for 5 hours. The reaction mixture is washed neutral with saturated sodium bicarbonate solution and then with water. The organic phase is dried and the solvent is evaporated. The oily
  • a readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of formula (I) with 6 parts by weight of alkylphenol polyglycol ether (Triton ® X 207), 3 wt. parts by
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I), 75 parts by weight of cyclohexanone as
  • Emulsifier e) A water-dispersible granulate is obtained by:
  • a water-dispersible granulate is also 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. in the
  • Compounds according to the invention 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.
  • the compounds of Examples 5, 6, 8, 9, 13, 25, 28, 31, 35, 38, 45, 47, 50, 51, 57, 76, 86, 103, 107, 132, 140, 149, 150 from Table 1 good to very good herbicidal activity against harmful plants such as Alopecurus myosuroides, Amaranthus retroflexus, Poa annua, Setaria pumila, Sinapis alba, Stellaria media, Echinochloa crus-galli and Lolium multiflorum in the pre-emergence process at an application rate of 0.3 kg to 0.005 kg of active ingredient per hectare. 2.
  • 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. Weeds found in rice cultivation are grown in pots in which water is up to 2 cm above the surface of the soil and cultivated during the trial phase. Three weeks after sowing, the test plants are treated at the three-leaf stage.
  • the compounds according to the invention formulated as wettable powder or as emulsion concentrates are available in various
  • the agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, even after emergence.
  • the compounds of Examples 5, 6, 8, 9, 13, 25, 28, 31, 35, 38, 45, 47, 50, 51, 57, 76, 86, 103, 107, 132, 140, 149, 150 from Table 1 good to very good herbicidal activity against harmful plants such as Alopecurus myosuroides,
  • pots are immediately as in 1. Treated described, the rest set up in the greenhouse until the plants have developed two to three real leaves and then with the active compounds according to the invention and in
  • Water rice is partly applied by pouring the active ingredients or their formulation into the irrigation water.
  • the active compounds according to the invention leave different cultures undamaged in the pre- and post-emergence process, even with high active compound doses. They protect Gramineae crops such as barley, wheat, rye, sorghum and especially corn and rice.
  • the active compounds according to the invention thus have a high selectivity when used to combat undesirable plant growth
  • the active ingredients are suitable for being able to effectively reduce herbicide damage to crop plants, especially rice.

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

Abstract

L'invention concerne les composés de la formule (I) qui s'utilisent comme herbicides sélectifs ou régulateurs de croissance des végétaux, dans laquelle n vaut entre 0 et 6, X désigne halogène, CN, OCN, SCN, alkynile C2-C4 ou CHR?5R6, R5 et R6¿ désignant indépendamment l'un de l'autre CN, NO¿2?, formyle, carbonyle (alkyle C1-C4) (halosubst.) ou carbonyle (alcoxy C1-C4) (halosubst.) ou phénylcarbonyle (subst.), R?1¿ désigne alkyle C¿1?-C4 (halosubst.), cycloalkyle C3-C6 (halosubst.) ou phényle (subst.), R?2¿ désigne halogène, CN, NO¿2?, alkyle C1-C3, alcoxy C1-C3, halogénure d'alcoyle C1-C3, halogénure d'alcoxy C1-C3 ou R?7S(O)¿m, R7 désignant alkyle C¿1?-C3 et m valant 0, 1 ou 2, R?3¿ désigne H, halogène, OH, alkyle C¿1?-C3, alcoxy C1-C3, halogénure d'alkyle C1-C3, halogénure d'alcoxy C1-C3 ou carbonyle (alcoxy C1-C3) et R?4¿ désigne H, CN, NO¿2?, halogène, halogénure d'alkyle C1-C3, halogénure d'alcoxy C1-C3 ou R?8S(O)¿p-, R8 désignant alkyle C¿1?-C3 et p valant 0, 1 ou 2. Abstraction faite des composés de la formule (I), où X = Cl, ces composés sont nouveaux en tant que tels. Il existe plusieurs manières de préparer des 2-benzoyl-1,3-cyclohexanediones.
PCT/EP1993/003385 1992-12-12 1993-12-02 Benzoylcyclohexenones, leur procede de preparation et leur utilisation comme herbicides et regulateurs de croissance des vegetaux WO1994013619A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP94902660A EP0673359A1 (fr) 1992-12-12 1993-12-02 Benzoylcyclohexenones, leur procede de preparation et leur utilisation comme herbicides et regulateurs de croissance des vegetaux
JP6513740A JPH08504414A (ja) 1992-12-12 1993-12-02 ベンゾイルシクロヘキセノン、それらの製造方法および除草剤および植物生長調整剤としてのそれらの用途
KR1019950702368A KR950704233A (ko) 1992-12-12 1993-12-02 벤조일사이클로헥세논, 이들의 제조방법, 및 이들의 제초제 및 식물생장 조절제로서의 용도(benzoylcyclohexenones, methods of preparing them and their use as herbicides and plant growth regulators)
BR9307631A BR9307631A (pt) 1992-12-12 1993-12-02 Benzoilciclohexenonas processos para a sua prepara-Æo e seu emprego como herbicidas e reguladores do crescimento das plantas
AU56949/94A AU5694994A (en) 1992-12-12 1993-12-02 Benzoylcyclohexenones, methods of preparing them and their use as herbicides and plant-growth regulators

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4241999A DE4241999A1 (de) 1992-12-12 1992-12-12 Benzoylcyclohexenone, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DEP4241999.9 1992-12-12

Publications (1)

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WO1994013619A1 true WO1994013619A1 (fr) 1994-06-23

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EP (1) EP0673359A1 (fr)
JP (1) JPH08504414A (fr)
KR (1) KR950704233A (fr)
AU (1) AU5694994A (fr)
BR (1) BR9307631A (fr)
CA (1) CA2151498A1 (fr)
DE (1) DE4241999A1 (fr)
HU (1) HU9501685D0 (fr)
WO (1) WO1994013619A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024146512A1 (fr) * 2023-01-03 2024-07-11 沈阳万菱生物技术有限公司 Composé de phénylcyclohexène thioéther tri-substitué et son utilisation
WO2024153074A1 (fr) * 2023-01-16 2024-07-25 沈阳万菱生物技术有限公司 Composés de thioéther cyclohexényl(phényltétra-substitué), leur procédé de préparation et leur utilisation

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU672058B2 (en) * 1993-12-30 1996-09-19 Sds Biotech K.K. Substituted benzoyl cyclic enone, process for preparation, and herbicide
IL117940A (en) * 1995-04-19 2003-06-24 Kumiai Chemical Industry Co Benzylsulfide derivatives, process for their production and insecticide compositions containing them
US6372693B1 (en) 1997-05-07 2002-04-16 Basf Aktiengesellschaft Substituted 2-(3-alkenyl-benzoyl)-cyclohexane-1,3-diones
DE19846792A1 (de) * 1998-10-10 2000-04-13 Hoechst Schering Agrevo Gmbh Benzoylcyclohexandione, Verfahren zur ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
JP4608054B2 (ja) * 2000-06-26 2011-01-05 株式会社エス・ディー・エス バイオテック 置換ベンゾイルチオエーテル化合物の製造方法
EP2229813A1 (fr) * 2009-03-21 2010-09-22 Bayer CropScience AG Dérivés de pyrimidine-4-ylpropanedinitrile, leur procédé de fabrication et d'utilisation en tant qu'herbicides et régulateurs de croissance végétale

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0249150A1 (fr) * 1986-06-09 1987-12-16 Stauffer Chemical Company 3-(Thio substitué)-2-benzoyl-cyclohex-2-énones

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0249150A1 (fr) * 1986-06-09 1987-12-16 Stauffer Chemical Company 3-(Thio substitué)-2-benzoyl-cyclohex-2-énones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024146512A1 (fr) * 2023-01-03 2024-07-11 沈阳万菱生物技术有限公司 Composé de phénylcyclohexène thioéther tri-substitué et son utilisation
WO2024153074A1 (fr) * 2023-01-16 2024-07-25 沈阳万菱生物技术有限公司 Composés de thioéther cyclohexényl(phényltétra-substitué), leur procédé de préparation et leur utilisation

Also Published As

Publication number Publication date
DE4241999A1 (de) 1994-06-16
HU9501685D0 (en) 1995-08-28
BR9307631A (pt) 1999-08-24
AU5694994A (en) 1994-07-04
EP0673359A1 (fr) 1995-09-27
KR950704233A (ko) 1995-11-17
JPH08504414A (ja) 1996-05-14
CA2151498A1 (fr) 1994-06-23

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