EP1478621A2 - Arylcetones substituees - Google Patents

Arylcetones substituees

Info

Publication number
EP1478621A2
EP1478621A2 EP03742453A EP03742453A EP1478621A2 EP 1478621 A2 EP1478621 A2 EP 1478621A2 EP 03742453 A EP03742453 A EP 03742453A EP 03742453 A EP03742453 A EP 03742453A EP 1478621 A2 EP1478621 A2 EP 1478621A2
Authority
EP
European Patent Office
Prior art keywords
cyano
chlorine
fluorine
optionally
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Withdrawn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
EP03742453A
Other languages
German (de)
English (en)
Inventor
Hans-Georg Schwarz
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
Monika Schmitt
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
Bayer CropScience AG
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 Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1478621A2 publication Critical patent/EP1478621A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • 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
    • C07C2601/14—The ring being saturated
    • 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

  • the invention relates to new substituted aryl ketones, processes for their preparation and their use as plant treatment agents, in particular as herbicides.
  • n represents the numbers 0, 1 or 2
  • R represents in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • X ' for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio,
  • n the numbers 0 to 6
  • R 1 stands for hydrogen, halogen or for optionally substituted alkyl, alkylthio or aryl, or - if m stands for the numbers 2 to 6 - optionally also together with a second radical R 1 stands for oxygen or alkanediyl (alkylene) .
  • R represents hydroxy, formyloxy, halogen, or for each optionally substituted alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxyalkyloxy arylcarbonyloxyalkyloxy, Arylalkylsulfinyl, arylalkylsulfonyl or heterocyclyl bonded via nitrogen, R 3 represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfony
  • R 4 stands for hydrogen or for optionally substituted alkyl, alkenyl,
  • R 5 for hydroxy, formyloxy, or for optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy,
  • hydrocarbon chains such as alkyl or alkanediyl
  • the invention includes the respective possible tautomeric or stereoisomeric forms.
  • n is preferably the number 0 or 2.
  • R preferably represents optionally cyano-, halogen-, C 1 -C 4 alkoxy, C ⁇ - C alkylthio, alkylsulfinyl or CrC 4 -C 4 - alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, for alkenyl or alkynyl, each optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C 1 -C alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 Carbon atoms in
  • the alkyl moiety or represents in each case optionally substituted by nitro, cyano, halogen, -C 4 - alkyl, -C 4 - haloalkyl, C ⁇ -C 4 -alkoxy or C 1 -C 4 haloalkoxy substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
  • X preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally substituted by cyano, halogen, dC 4 -alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfmyl or C1-C4-alkylsulfonyl
  • m preferably represents the numbers 0, 1, 2 or 3.
  • R 1 preferably represents hydrogen, halogen, each optionally substituted by cyano, halogen, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfmyl or CrC - alkylsulfonyl substituted alkyl or alkylthio, each with 1 to 6 Carbon atoms, or for phenyl, or - if m is 2 or 3 - optionally together with a second radical R 1 for oxygen or alkanediyl (alkylene) having 3 to 5 carbon atoms.
  • R> 2 preferably represents hydroxyl, formyloxy, halogen, for alkoxy, alkylthio, alkylsulfmyl, each optionally substituted by cyano, halogen, .C ⁇ -C 4 alkoxy, CrC - alkoxycarbonyl, C ⁇ -C alkylthio, C ⁇ -C 4 alkylsulfinyl or C ⁇ -C 4 alkylsulfonyl, Alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms, for alkenyloxy or alkynyloxy each optionally substituted by halogen, each having 3 to 6 carbon atoms, each optionally containing nitro, cyano, halogen, C 1 -C 4 -alkyl, -C-C 4 - haloalkyl, CrC 4 -alk
  • R 3 preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, in each case optionally substituted by cyano, halogen, CrC 4 alkoxy, CrC - alkylthio, C 1 -C 4 -alkylsulfinyl or CrC 4 - alkylsulfonyl ' alkyl, alkoxy, alkylthio, Alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, or for optionally substituted by cyano, halogen or C 1 -C 4 alkyl
  • R 4 preferably represents hydrogen, represents optionally cyano-, halogen. dC 4 - alkoxy, -CC 4 -alkylthio, -C-C 4 - alkylsulfinyl or -C-C 4 - alkylsulfonyl substituted alkyl with 1 to 6
  • the alkyl moiety or represents in each case optionally substituted by nitro, cyano, halo, C ⁇ -C 4 - alkyl, C ⁇ -C - haloalkyl, 'C ⁇ -C 4 -alkoxy, C haloalkoxy, dC 4 alkylthio, C ⁇ -C 4 - Haloalkylthio, -C-C 4 - alkylsulfinyl, C 1 -C -haloalkylsulfinyl, C ⁇ -C 4 - alkylsulfonyl or C ⁇ -C 4 -haloalkylsulfonyl substituted aryl or arylalkyl, each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
  • R 5 preferably represents hydroxy, formyloxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or dC 4 -alkoxy, for alkenyl optionally substituted by cyano or halogen - oxy or alkinyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally substituted by nitro, cyano, halogen, Ci-C 4 - alkyl, dC 4 - haloalkyl, C ⁇ -C4 alkoxy, -C 4 -haloalkoxy, C 1 -C 4 -Alkylthio, dC 4 - haloalkylthio, dd-alkylsulfinyl, -C-C 4 -haloalkyls
  • n particularly preferably stands for the number 2.
  • R particularly preferably represents in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl and / or n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, for each optionally Ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl,
  • X particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy,
  • R 1 particularly preferably represents the numbers 0, 1 or 2.
  • R 1 particularly preferably represents hydrogen, fluorine, chlorine or bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, Methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-Butylthio, or for phenyl, or - if m is 2 - optionally also together with a second radical R 1 for oxygen,
  • R 2 particularly preferably represents hydroxyl, formyloxy, fluorine or chlorine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,
  • R 3 particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio , n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl,
  • Propoxycarbonyl or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl.
  • R 4 particularly preferably represents hydrogen, " • in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by cyano, fluorine, chlorine and / or bromine, for each optionally by Cyano, fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycl
  • R particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each optionally chlorine by cyano, fluorine and / or
  • R very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i- or s-, each optionally substituted by fluorine and / or chlorine.
  • X very particularly preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or for each optionally substituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl and / or ethylsulfonyl, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl or dim dimethylaminosulfonyl.
  • n very particularly preferably stands for the number 0.
  • R, ⁇ ' very particularly preferably represents hydrogen, each methyl optionally substituted by fluorine or chlorine,
  • R 2 very particularly preferably represents hydroxyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, each optionally substituted by fluorine or chlorine, Acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propyl for propenyloxy, butenyloxy, propynyloxy or butynyloxy each optionally substitute
  • R very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-, each optionally substituted by fluorine or chlorine. or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for cyclopropyl which is optionally substituted by fluorine, chlorine or methyl.
  • R 4 very particularly preferably represents hydrogen, in each case methyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine, chlorine and / or bromine, for each optionally by fluorine, Chloro or methyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl
  • R) 5 very particularly preferably represents hydroxy, for in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by fluorine, chlorine and / or bromine or for each optionally by nitro,
  • X most preferably represents fluorine, chlorine, bromine, iodine, methoxy, methylthio, methylsulfonyl or trifluoromethyl.
  • R most preferably represents methyl, ethyl, n-propyl, i-propyl, n-butyl, i-
  • R 1 most preferably represents hydrogen or methyl.
  • R most preferably represents hydroxy, chlorine or n-pyrazolyl.
  • R 3 most preferably represents hydrogen or methyl.
  • R 4 most preferably represents methyl or ethyl.
  • R 5 most preferably represents hydroxy, propargyloxy, n-propylsulfonyloxy, tosyloxy, (benzoyl) methoxy, (ethoxycarbonyl) methoxy, or benzyloxy optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl.
  • R represents methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, benzyl or phenyl which is optionally substituted by fluorine, chlorine, nitro, cyano .
  • X represents fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl or nitro
  • n 0 or 2
  • X is trifluoromethyl, n is 2 and
  • X is bromine, n is 2 and
  • n, X, R, R 3 and R 4 have the meanings given above.
  • n, X and R have the meanings given above.
  • n, X and R have the meanings given above, and
  • R 2 has the meanings given above for R 2 with the exception of hydroxy.
  • the new substituted aryl ketones of the formula (I) are notable for strong and selective herbicidal activity.
  • n, R and X have the meaning given above - or reactive derivatives thereof, such as corresponding acid halides, acid cyanides or esters -
  • Formula (II) provides a general definition of the carboxylic acids to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • n, R and X have preferably those meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred, very particularly preferred or most preferred for n, R and X.
  • Formula (III) provides a general definition of the compounds to be used further as starting materials in the process according to the invention for the preparation of compounds of the general formula (I).
  • Z preferably has the meaning which has already been given for Z in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred, very particularly preferred or most preferred .
  • the starting materials of the general formula (III) are known organic synthetic chemicals.
  • reaction auxiliaries The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal, acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide , Sodium or potassium, methanol,
  • the process according to the invention is optionally carried out using a dehydrating agent.
  • a dehydrating agent The usual chemicals suitable for binding water come into consideration here.
  • Examples of these are dicyclohexylcarbodumide, carbonyl-bis-imidazole and propanephosphonic anhydride.
  • Dicyclohexylcarbodumide and propanephosphonic anhydride may be mentioned as particularly suitable dehydrating agents.
  • Formula (I) is preferably carried out using one or more diluents.
  • Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane,
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours.
  • the work-up is carried out using customary methods (cf. the manufacturing examples).
  • n and R have the meanings given above are new and the subject of the present application.
  • X is CF 3 , n is 0, 1 or 2 and R is methyl
  • X is bromine, n is 0, 1 or 2 and
  • R represents methyl
  • X stands for CF 3
  • R 6 represents alkyl, benzyl or AUyl
  • R has the meanings given above
  • X stands for CF 3
  • R represents methyl, ethyl, allyl or benzyl
  • the new compounds of the formulas (II) and (VI) are suitable for the preparation of active compounds for pharmaceutical, biological and agricultural purposes.
  • R 6 represents alkyl (in particular methyl or ethyl), benzyl or allyl, and
  • X I represents halogen (especially chlorine or bromine), with mercapto compounds of the general formula (N),
  • alkali metal salts such as sodium or potassium salts
  • reaction aids e.g. Potassium carbonate, triethylamine or sodium hydride
  • diluents e.g. Tetrahydrofuran, acetonitrile or N, N-dimethylformamide
  • oxygenating agents such as hydrogen peroxide
  • one or more diluents such as acetic acid and / or water
  • the esters thus obtained by customary methods, for example by reaction with aqueous sodium hydroxide and then converted into the carboxylic acids of the formula (II) using hydrochloric acid (cf. the preparation examples).
  • diluents such as acetic acid and / or water
  • the active compounds according to the invention can be used as defoliants, desiccants, herbicides and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the active compounds according to the invention for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm,
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and femst encapsulations in polymers
  • formulations are made in a known manner, e.g. by mixing
  • the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers, are suitable for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers, are suitable for granules: e.g. broken and fractionated natural rocks such as calcite, marble
  • coconut shells, corn cobs and tobacco stalks as emulsifying and or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho- lipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, ready-to-use formulations or tank mixes being possible mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.
  • safeners substances which improve crop tolerance
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium),
  • Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, dichlormid, Dymron, Fenclorim, Fenchlorazol (-ethyl) , Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG-191, Oxabetrinil, PPG-1292, R-29148.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents to improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. You can also dig into the soil before sowing. be working.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained by conventional breeding, by mutagenesis, or else by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention - also in combination with other agrochemicals
  • Active ingredients better growth of crops, increased tolerance of crops to high or low temperatures, increased tolerance of crops to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, received genetic material which contained them Gives plants special beneficial valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value the harvest products, higher shelf life and / or workability of the harvest products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicides
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • the " traits” are particularly emphasized the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), Cry ⁇ A (b) , Cry ⁇ A (c), CrylLA, CrylllA, CryIILB2, Cry9c Cry2Ab, Cry3Bb and CryLF as well as their combinations) are produced in the plants (hereinafter referred to as "Bt plants”).
  • the increased resistance is also particularly emphasized as properties ("traits”) of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins.
  • traits the increased tolerance of the plants to certain herbicidal active substances is particularly emphasized , for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example "PAT” -. gene)
  • Genes conferring traits can also occur in combinations with one another in the transgenic plants. Examples of “Bt plants” are maize varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g.
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinothricin, e.g. rapeseed), IMI® (tolerance against imidazolinones) and
  • STS® tolerance to sulfonylureas e.g. maize.
  • the herbicide-resistant plants include the varieties sold under the name Clearf ⁇ eld® (e.g. maize).
  • Clearf ⁇ eld® e.g. maize.
  • these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated according to the invention particularly advantageously with the compounds of the general formula I or the active compound mixtures according to the invention, the synergistic effects mentioned above occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the mixture is then concentrated under reduced pressure, the residue is stirred with saturated aqueous sodium carbonate solution, diethyl ether is added and the mixture is filtered.
  • the aqueous phase of the filtrate is separated off, acidified with 2N hydrochloric acid and extracted with methylene chloride.
  • the organic extraction solution is washed with water, dried with sodium sulfate and filtered.
  • the filtrate is concentrated under reduced pressure, the residue is digested with diethyl ether / petroleum ether and the crystalline product is isolated by suction.
  • the lambda maximums were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • the melting points given in the tables were determined using standard laboratory methods using a device from Büchi, Melting point B-545, in melting point determination tubes. The melting point is given in ° C.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation so that the desired one
  • Amount of active ingredient is applied per unit area.
  • the active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants with a height of 5 to 15 cm are sprayed with the active substance preparation in such a way that the desired quantities of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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

Abstract

L'invention concerne de nouvelles arylcétones de formule (I), dans laquelle Z, X, R et n ont les significations données dans la description. L'invention concerne également un procédé de production des composés de formule (I), leur utilisation comme produits phytosanitaires ainsi que des produits intermédiaires destinés à la production de ces composés.
EP03742453A 2002-02-19 2003-02-12 Arylcetones substituees Withdrawn EP1478621A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10206792A DE10206792A1 (de) 2002-02-19 2002-02-19 Substituierte Arylketone
DE10206792 2002-02-19
PCT/EP2003/001365 WO2003070696A2 (fr) 2002-02-19 2003-02-12 Arylcetones substituees

Publications (1)

Publication Number Publication Date
EP1478621A2 true EP1478621A2 (fr) 2004-11-24

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EP03742453A Withdrawn EP1478621A2 (fr) 2002-02-19 2003-02-12 Arylcetones substituees

Country Status (16)

Country Link
US (1) US7153813B2 (fr)
EP (1) EP1478621A2 (fr)
JP (1) JP2005517736A (fr)
KR (1) KR20040085198A (fr)
CN (1) CN1646488A (fr)
AR (1) AR038551A1 (fr)
AU (1) AU2003210250A1 (fr)
BR (1) BR0307822A (fr)
CA (1) CA2476501A1 (fr)
DE (1) DE10206792A1 (fr)
MX (1) MXPA04008021A (fr)
PL (1) PL372296A1 (fr)
RU (1) RU2004128085A (fr)
UA (1) UA79268C2 (fr)
WO (1) WO2003070696A2 (fr)
ZA (1) ZA200406566B (fr)

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CN103980202B (zh) * 2014-05-27 2017-01-18 青岛清原化合物有限公司 一种具有除草活性的4‑苯甲酰吡唑类化合物
CN105399674B (zh) * 2015-12-31 2017-02-15 青岛清原化合物有限公司 吡唑类化合物或其盐、制备方法、除草剂组合物及用途
CN106588836B (zh) * 2016-12-15 2018-09-18 西华大学 2-环己烯酮衍生物及其在农药中的应用

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US20050119129A1 (en) 2005-06-02
CN1646488A (zh) 2005-07-27
US7153813B2 (en) 2006-12-26
BR0307822A (pt) 2005-02-09
KR20040085198A (ko) 2004-10-07
ZA200406566B (en) 2005-08-29
PL372296A1 (en) 2005-07-11
MXPA04008021A (es) 2004-11-26
DE10206792A1 (de) 2003-08-28
CA2476501A1 (fr) 2003-08-28
AU2003210250A1 (en) 2003-09-09
UA79268C2 (en) 2007-06-11
WO2003070696A3 (fr) 2004-03-25
WO2003070696A2 (fr) 2003-08-28
JP2005517736A (ja) 2005-06-16
AR038551A1 (es) 2005-01-19
RU2004128085A (ru) 2006-02-27

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