[go: up one dir, main page]

EP1115700A1 - N-aryle-o-aryloxyalkyle-carbamates substitues a activite optique - Google Patents

N-aryle-o-aryloxyalkyle-carbamates substitues a activite optique

Info

Publication number
EP1115700A1
EP1115700A1 EP99969407A EP99969407A EP1115700A1 EP 1115700 A1 EP1115700 A1 EP 1115700A1 EP 99969407 A EP99969407 A EP 99969407A EP 99969407 A EP99969407 A EP 99969407A EP 1115700 A1 EP1115700 A1 EP 1115700A1
Authority
EP
European Patent Office
Prior art keywords
cyano
phenyl
substituted
methyl
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Withdrawn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
EP99969407A
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Ernst Rudolf F. Gesing
Johannes Rudolf Jansen
Joachim Kluth
Rolf Grosser
Mark Wilhelm Drewes
Dieter Feucht
Rolf Pontzen
Ingo Wetcholowsky
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 AG
Original Assignee
Bayer 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 AG filed Critical Bayer AG
Publication of EP1115700A1 publication Critical patent/EP1115700A1/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Withdrawn legal-status Critical Current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
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring

Definitions

  • the invention relates to new optically active substituted N-aryl-O-aryloxyalkyl carbamates, processes for their preparation and their use as herbicides.
  • Arl for an optionally substituted, monocyclic or bicyclic, carbocyclic or heterocyclic grouping from the series phenyl, naphthyl, tetralinyl, furyl, benzofuryl, thienyl, benzothienyl, pyridinyl,
  • A is optionally substituted by halogen alkanediyl having 1 to 3 carbon atoms, and where the possible substituents are preferably selected from the following list: cyano, nitro, halogen, each optionally substituted by halogen alkyl, alkoxy, alkylthio, alkylsulfinyl , Alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl each having up to 5 carbon atoms,
  • Ar2 for optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or by (in each case optionally by cyano, halogen, C, -C 4 alkoxy, C, -C 4 alkylthio, C, -C 4 - alkylsulfinyl or C r C 4 -alkylsulfonyl-substituted) alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl each having up to 4 carbon atoms in the alkyl groups, substituted aryl having 6 or 10 carbon atoms,
  • R 1 represents alkyl which has 1 to 4 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, and
  • R 2 represents hydrogen or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, halogen or C r C 4 alkoxy,
  • hydrocarbon chains such as alkyl
  • the hydrocarbon chains are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.
  • Arl preferably represents one of the abovementioned groups, where A represents methyl which is optionally substituted by fluorine and / or chlorine. len or dimethylene (ethane-l, 2-diyl), and where the possible substituents are preferably selected from the following list: cyano, nitro, fluorine, chlorine, bromine, each optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propy
  • AJ2 preferably represents in each case optionally through nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or through (in each case optionally through cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted) methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • R 1 preferably represents methyl, ethyl, n- or i-propyl.
  • R 2 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
  • Ar * particularly preferably represents phenyl, which in the 3-position is a substituent from the series cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or Contains i-propyl, chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, methoxy, ethoxy, fluoromethoxy, difluoromethoxy, chlorofluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy and optionally contains a further substituent in a different position according to the preceding list.
  • Ar-2 particularly preferably represents optionally by nitro, cyano, fluorine, chlorine, bromine or by (in each case optionally substituted by fluorine or chlorine) methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i- Propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl or substituted phenylaminocarbon.
  • R 1 particularly preferably represents methyl or ethyl.
  • R 2 particularly preferably represents hydrogen, methyl or ethyl.
  • Ar 2 has, for example, the meanings given below: 2-chloro-3-fluorophenyl, 2,3-dichlorophenyl, 2-chloro-3-bromophenyl, 2-chloro-3-methylphenyl, 2- Chloro-3-ethyl-phenyl, 2-chloro-3-trifluoromethyl-phenyl, 2-chloro-3-cyano-phenyl, 2-chloro-3-methoxy-phenyl, 2-chloro-3-ethoxy-phenyl, 2- Chloro-4-fluorophenyl, 2,4-dichlorophenyl, 2-chloro-4-bromophenyl, 2-chloro-4-methylphenyl, 2-chloro-4-ethylphenyl, 2 -Chlor-4-trifluoromethyl-phenyl, 2-chloro-4-cyano-phenyl, 2-chloro-4-methoxy-phenyl, 2-chloro-4-ethoxy-phenyl, 2-
  • Fluoro-6-bromophenyl 2-fluoro-6-methylphenyl, 2-fluoro-6-ethylphenyl, 2-fluoro-6-trifluoromethylphenyl, 2-fluoro-6-cyano-phenyl, 2- Fluoro-6-methoxy-phenyl, 2-fluoro-6-ethoxy-phenyl;
  • Ethyl-6-bromophenyl 2-ethyl-6-methylphenyl, 2,6-diethylphenyl, 2-ethyl-6-trifluoromethylphenyl, 2-ethyl-6-cyano-phenyl, 2- Ethyl 6-methoxyphenyl, 2-ethyl-6-ethoxyphenyl;
  • Trifluoromethyl-4-ethoxyphenyl 2-trifluoromethyl-5-fluorophenyl, 2-trifluoromethyl-5-chlorophenyl, 2-trifluoromethyl-5-bromophenyl, 2-trifluoromethyl-5-methylphenyl, 2- Trifluoromethyl-5-ethyl-phenyl, 2,5-bis-trifluoromethyl-phenyl, 2-trifluoromethyl-5-cyano-phenyl, 2-trifluoromethyl-5-methoxy-phenyl, 2-trifluoromethyl-5-ethoxy-phenyl, 2-trifluoromethyl-6-fluorophenyl, 2-trifluoromethyl-6-chlorophenyl, 2-trifluoromethyl-6-bromophenyl, 2-trifluoromethyl-6-methylphenyl, 2-trifluoromethyl-6-ethyl- phenyl, 2,6-bis-trifluoromethyl-phenyl, 2-trifluoromethyl-6-cyano-pheny
  • Methoxy-4-ethoxyphenyl 2-methoxy-5-fluorophenyl, 2-methoxy-5-chlorophenyl, 2-methoxy-5-bromophenyl, 2-methoxy-5-methylphenyl, 2- Methoxy-5-ethyl-phenyl, 2-methoxy-5-trifluoromethyl-phenyl, 2-methoxy-5-cyano-phenyl, 2,5-dimethoxy-phenyl, 2-methoxy-5-ethoxy-phenyl, 2-methoxy- 6-fluorophenyl, 2-methoxy-6-chlorophenyl, 2-methoxy-6-bromophenyl, 2-methoxy-6-methylphenyl, 2-methoxy-6-ethylphenyl, 2-methoxy- 6-trifluoromethyl-phenyl, 2-methoxy-6-cyano-phenyl, 2,6-dimethoxy-phenyl, 2-methoxy-6-ethoxy-phenyl;
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Group 6
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Group 9
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Group 13
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Group 20
  • Ar 2 has, for example, the meanings given above in Group 1.
  • Ar 2 has, for example, the meanings given above in Group 1.
  • the new substituted N-aryl-O-alkyl-carbamates of the general formula (I) are notable for their strong and selective herbicidal activity.
  • Ar 2 has the meaning given above,
  • Ar and R have the meaning given above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
  • Formula (II) provides a general definition of the arylamines to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I).
  • Ar and R 2 preferably have 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 or particularly preferred for Ar 2 and R 2 .
  • the starting materials of the general formula (II) are known organic synthetic chemicals.
  • Formula (III) provides a general definition of the chloroformate esters to be used further as starting materials in process (a) according to the invention.
  • Ar 1 and R 1 preferably have those meanings which have already been given as preferred or particularly preferred for Ar 1 and R 1 in connection with the description of the compounds of the general formula (I) according to the invention.
  • the starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,399,545).
  • Formula (IV) provides a general definition of the aryl isocyanates to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I).
  • Ar 2 preferably has the meaning which has already been given as preferred or particularly preferred for Ar 2 in connection with the description of the compounds of the general formula (I) according to the invention.
  • the starting materials of the general formula (IV) are known organic synthetic chemicals.
  • Formula (V) provides a general definition of the substituted alkanols to be used further as starting materials in process (b) according to the invention.
  • Ar 1 and R 1 preferably have those meanings which have already been given above as preferred or particularly preferred for Ar 1 and R 1 in connection with the description of the compounds of the general formula (I) according to the invention. - lo -
  • the starting materials of the general formula (V) are known and / or can be prepared by processes known per se (cf. US Pat. No. 5,099,059, US Pat. No. 5,152,827, US Pat. No. 5,399,545).
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries for processes (a) and (b). These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, 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 methanolate, ethanolate, -n- or -i-propanolate, - n-, -i-, -s- or -t-butanolate; basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyl dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5- Ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piper
  • Inert organic solvents are particularly suitable as diluents for carrying out processes (a) and (b) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated
  • Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide;
  • Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
  • reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0J 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 large excess.
  • the reaction is generally carried out in a suitable diluent, if appropriate in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers 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 be used, for example, in the following plants:
  • the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth.
  • the active compounds according to the invention for combating weeds in permanent crops for example forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, used on ornamental and sports turf and pasture land and for selective weed control in annual crops become.
  • 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 decotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • These formulations are prepared in a known manner, e.g. B. by
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include 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, for example petroleum fractions, mineral and vegetable oils , Alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenz
  • 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, are suitable as solid carriers for granules Question: eg broken and fractionated natural rocks such as calcite,
  • Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • 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 0J 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 for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), am tryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azim-sulfurone, benazoline (- ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzopenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime, bromoxynil, butachlor, butroxydim, butylate, cafenstrole,
  • Clomazone Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam- (-methyl), Cumyluron, Cyanazines, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB , 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Difluefenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid,
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. 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. They can also be worked into the soil before sowing.
  • 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.
  • racemate was separated at room temperature (approx. 20 ° C) by HPLC (High Performance Liquid Chromatography) on the chiral stationary silica gel phase Chiracel OD ® using a mixture of n-heptane and isopropanol as eluent and photometric detection.
  • HPLC High Performance Liquid Chromatography
  • 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.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amount of active compound is applied in 1000 liters of water per hectare.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts 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.

Landscapes

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

Abstract

L'invention concerne de nouveaux N-aryle-O-aryloxyalkyle-carbamates substitués à activité optique de la formule (I) dans laquelle Ar1 désigne un groupement monocyclique ou bicyclique, carbocyclique ou hétérocyclique, éventuellement substitué dans chaque cas, de la série comprenant phényle, naphtyle, tétralinyle, furyle, benzofuryle, thiényle, benzothiényle, pyridinyle, quinolinyle, isoquinolinyle ou le groupement suivant (a) éventuellement substitué, où A désigne alcandiyle éventuellement substitué par halogène et ayant entre 1 et 3 atomes de carbone, les substituants possibles étant dans chaque cas sélectionnés de préférence dans l'énumération suivante: cyano, nitro, halogène, et dans chaque éventuellement substitué par halogène, alkyle, alcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle, alkylcarbonyle, alcoxycarbonyle, ayant dans chaque cas jusqu'à 5 atomes de carbone; Ar2 désigne aryle ayant entre 6 et 10 atomes de carbone et éventuellement substitué par nitro, cyano, carboxy, carbamoyle, thiocarbamoyle, halogène ou par alkyle, alcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle, alkylamino, dialkylamino, alyklcarbonyle, alcoxycarbonyle, alkylaminocarbonyle ou dialkylaminocarbonyle ayant chacun jusqu'à 4 atomes de carbone dans les groupes alkyle (dans chaque cas éventuellement substitué par cyano, halogène, alcoxy C¿1?-C4, alkylthio C1-C4, alkylsulfinyle C1-C4 ou alkylsulfonyle C1-C4); R?1¿ désigne alkyle ayant entre 1 et 4 atomes de carbone, éventuellement substitué par cyano, halogène ou alcoxy C¿1?-C4, et R?2¿ désigne hydrogène ou alkyle ayant entre 1 et 4 atomes de carbone, éventuellement substitué par cyano, halogène ou alcoxy C¿1?-C4. Les substituants qui se trouvent sur l'atome de carbone auquel R?1¿ est lié sont disposés de manière que le plan de polarisation de la lumière polarisée soit tourné vers la gauche. L'invention concerne en outre des procédés permettant de préparer lesdits composés et leur utilisation comme herbicides.
EP99969407A 1998-09-24 1999-09-13 N-aryle-o-aryloxyalkyle-carbamates substitues a activite optique Withdrawn EP1115700A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19843763 1998-09-24
DE19843763A DE19843763A1 (de) 1998-09-24 1998-09-24 Optische aktive substituierte N-Aryl-O-aryloxyalkyl-carbamate
PCT/EP1999/006754 WO2000017157A1 (fr) 1998-09-24 1999-09-13 N-aryle-o-aryloxyalkyle-carbamates substitues a activite optique

Publications (1)

Publication Number Publication Date
EP1115700A1 true EP1115700A1 (fr) 2001-07-18

Family

ID=7882058

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99969407A Withdrawn EP1115700A1 (fr) 1998-09-24 1999-09-13 N-aryle-o-aryloxyalkyle-carbamates substitues a activite optique

Country Status (11)

Country Link
EP (1) EP1115700A1 (fr)
JP (1) JP2002526471A (fr)
KR (1) KR20010074841A (fr)
CN (1) CN1316989A (fr)
AR (1) AR020416A1 (fr)
AU (1) AU5977899A (fr)
BR (1) BR9914049A (fr)
CA (1) CA2345073A1 (fr)
DE (1) DE19843763A1 (fr)
PL (1) PL346858A1 (fr)
WO (1) WO2000017157A1 (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996016941A1 (fr) * 1994-12-02 1996-06-06 Novartis Ag Herbicides a base de carbamate
EP1056734A2 (fr) * 1998-02-20 2000-12-06 Bayer Ag Composes d'alcoxycarbonyle substitues

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0017157A1 *

Also Published As

Publication number Publication date
KR20010074841A (ko) 2001-08-09
JP2002526471A (ja) 2002-08-20
AU5977899A (en) 2000-04-10
CA2345073A1 (fr) 2000-03-30
BR9914049A (pt) 2001-06-19
DE19843763A1 (de) 2000-03-30
CN1316989A (zh) 2001-10-10
AR020416A1 (es) 2002-05-08
PL346858A1 (en) 2002-03-11
WO2000017157A1 (fr) 2000-03-30

Similar Documents

Publication Publication Date Title
EP1095027B1 (fr) Phenyluracile substitue
WO2000031066A1 (fr) (thio)amides de l&#39;acide n-pyrazolyl-phenoxynicotinique substitues, utilisables comme herbicides
EP1107955A2 (fr) 3-aryle-pyrazoles substitues
EP0946544B1 (fr) Heterocyclyluraciles
EP1095028B1 (fr) Uraciles d&#39;acylaminophenyle substituees
EP1189893B1 (fr) 2-aryl-1,2,4-triazin-3,5-di(thi)ones substituees
EP1051404B1 (fr) Phenyluraciles substitues a effet herbicide
WO1999065869A1 (fr) N-aryl-o-alkyl-carbamates substitues
EP1037882B1 (fr) 2,4-diamino-1,3,5-triazines substituees
DE19946852A1 (de) Substituierte N-Phenyl-phenoxynicotinsäure-(thio)amide
DE19812879A1 (de) Substituierte 2,4-Diamino-1,3,5-triazine
EP1115700A1 (fr) N-aryle-o-aryloxyalkyle-carbamates substitues a activite optique
EP1066267B1 (fr) Phenyluraciles substituees
EP1204651B1 (fr) 5-chlorodifluoromethyl-1,3-4-thiadiazol-2yl-oxyacetanilides herbicides
DE19803395A1 (de) Substituierte Heteroarylmethylverbindungen
WO2000034257A1 (fr) 2-imino-thiazolines substituees et leur utilisation comme herbicides
WO2001005786A2 (fr) Thienylalkylamino-1,3,5-triazines a activite optique
EP1178956A1 (fr) N-cyano-amidines substituees
WO2000015606A1 (fr) Ferbames n-aryl-o-alkyle substitue
DE19746267A1 (de) Substituierte N-Aryl-O-aryloxyalkyl-carbamate
WO2000047579A1 (fr) Benzo-thiazolyl-alkylamino-1,3,5-triazines substituees utilisees comme herbicides
WO2000010971A1 (fr) N-aryl-o-alkylcarbamates substitues
EP1080077A1 (fr) 1,3-diaza-2-(thi)oxo-cycloalcanes substitues
WO2000042032A1 (fr) 2-imino-thiazolines substituees
WO1999048886A1 (fr) Aminooxyalcancarboxamides substitues

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20010424

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

17Q First examination report despatched

Effective date: 20020507

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20020403