EP0000002A1 - Dérivés du tétrahydrofuranne, leurs procédés de préparation et leur utilisation comme herbicides - Google Patents

Dérivés du tétrahydrofuranne, leurs procédés de préparation et leur utilisation comme herbicides Download PDF

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Publication number
EP0000002A1
EP0000002A1 EP78100007A EP78100007A EP0000002A1 EP 0000002 A1 EP0000002 A1 EP 0000002A1 EP 78100007 A EP78100007 A EP 78100007A EP 78100007 A EP78100007 A EP 78100007A EP 0000002 A1 EP0000002 A1 EP 0000002A1
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EP
European Patent Office
Prior art keywords
tetrahydrofuran
alkyl
phenyl
atoms
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.)
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EP78100007A
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German (de)
English (en)
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EP0000002B1 (fr
Inventor
Thomas Dr. Schmidt
Wilfried Dr. Draber
Ludwig Dr. Eue
Robert Rudolf Dr. Schmidt
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Bayer AG
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Bayer AG
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Publication of EP0000002A1 publication Critical patent/EP0000002A1/fr
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Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
    • F01D—NON-POSITIVE DISPLACEMENT MACHINES OR ENGINES, e.g. STEAM TURBINES
    • F01D1/00—Non-positive-displacement machines or engines, e.g. steam turbines

Definitions

  • the present invention relates to new tetrahydrofuran derivatives, several processes for their preparation and their use as herbicides, in particular as selective herbicides.
  • chloroacetanilides such as, for example, 2-ethyl-6-methyl-N- (l'-methyl-2'-methoxyethyl) chloroacetanilide
  • DT-OS 2 328 340 grass-like weeds
  • the tetrahydrofuran derivatives according to the invention are superior to the known herbicides, such as, for example, 2-ethyl-6-methyl-N- (1'-methyl-2'-methoxyethyl) chloroacetanilide, and also have a significantly better action Selectivity in important crops.
  • the active compounds according to the invention thus represent a substantial enrichment of the herbicidal compositions, in particular the grass herbicides.
  • Formula (II) provides a general definition of the alcoholates of 2-hydroxymethyl tetrahydrofuran derivatives to be used as starting materials for process variant (a).
  • R 1 to R different 6 same or different and preferably represent hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, halogenoalkyl with up same to 2 carbon atoms and up to three or different halogen atoms, preferred halogens being fluorine, chlorine and bromine, alkoxyalkyl having 1 or 2 carbon atoms in each alkyl part, and optionally substituted phenyl and benzyloxyalkyl having 1 to 2 carbon atoms in the alkyl part, the preferred substituents being: halogen, alkyl and alkoxy each having 1 or 2 carbon atoms and haloalkyl up to 2 carbon atoms and up to three identical or different halogen atoms, such as in particular fluorine and chlorine.
  • R 'and R 6 also preferably together represent a
  • R 7 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkenyl and alkynyl each having 2 to 4 carbon atoms, alkoxyalkyl having 1 or 2 carbon atoms in each alkyl part and optionally substituted phenyl and benzyloxyalkyl with 1 to 2 carbon atoms in the alkyl part, the substituents which are preferably those already mentioned for R 'to R 6 .
  • R 8 and R 9 are the same or different and are preferably hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkenyl and alkynyl each having 2 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms and for optionally substituted phenyl, benzyl or benzyloxy, preferably as the substituents in question preferably already mentioned for R 1 to R. 6
  • M preferably represents the alkali metals sodium and potassium as well as for 1 equivalent of the alkaline earth metals magnesium and calcium.
  • the alcoholates of the formula (II) are known or can be prepared by known methods. They are obtained, for example, by reacting the corresponding 2-hydroxymethyl-tetrahydrofuran derivatives with suitable strong bases, such as, for example, alkali or alkaline earth amides, hydrides or hydroxides, in an inert solvent.
  • suitable strong bases such as, for example, alkali or alkaline earth amides, hydrides or hydroxides
  • suitable strong bases such as, for example, alkali or alkaline earth amides, hydrides or hydroxides
  • Formula (III) provides a general definition of the compounds to be used as starting materials for process variant (a).
  • R 10 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, alkenyl and alkynyl each having 2 to 4 carbon atoms, haloalkyl having up to 2 carbon and up to three identical or different halogen atoms, the halogens in particular Fluorine, chlorine and bromine as well as optionally substituted phenyl, the substituents which are preferably those which are preferably mentioned at R 'to R 6 in the starting materials of the formula (II).
  • Y preferably represents optionally substituted aryl having 6 to 10 carbon atoms, in particular phenyl and naphthyl, which can carry one or more identical or different substituents.
  • Preferred substituents are the halogens fluorine, chlorine or bromine; Alkyl and alkexy of 1 to 4 carbon atoms; Haloalkyl, haloalkoxy and haloalkylthio with up to 4 carbon atoms and up to 5 halogen atoms, in particular with up to 2 carbon atoms and up to 3 identical or different halogen atoms, halogen, in particular fluorine, chlorine and bromine; phenyl, phenoxy or phenoxycarbonyl optionally substituted by halogen, in particular fluorine, chlorine or bromine, alkyl and alkoxy each having 1 to 2 carbon atoms and haloalkyl having up to 2 carbon and up to 3 identical or different halogen atoms, such as in particular fluorine and chlorine; Alk
  • Formula (IV) provides a general definition of the diols to be used as starting materials for process variant (b).
  • R 'to R 9 preferably represent the radicals which have already been mentioned as preferred for the alcoholates of the formula (II).
  • R 10 and Y preferably represent the radicals which have already been mentioned as preferred for the compounds of the formula (III).
  • R 'to R' preferably represent the radicals which have already been mentioned as preferred for the alcoholates of the formula (II).
  • R 10 and Y preferably represent the radicals which have already been mentioned as preferred for the compounds of the formula (III).
  • Formula (VI) provides a general definition of the furan derivatives to be used as starting materials for process variant (d).
  • R 2 , R 3 , R ', R 5 and R 9 preferably represent the radicals which have already been mentioned as preferred for the alcoholates of the formula (II).
  • R 10 and Y preferably represent the radicals which have already been mentioned as preferred for the halides of the formula (III).
  • the alcoholates of the formulas (VIIa), (VIIb), (VIIc) and (VIII) are known or can be prepared by known methods. They are obtained, for example, by reacting the corresponding 2-hydroxymethyl-dihydrofuran derivatives or 2-hydroxymethyl-furan derivatives with suitable strong bases, such as, for example, alkali metal or alkaline earth metal amides, hydrides or hydroxides, in an inert solvent.
  • suitable strong bases such as, for example, alkali metal or alkaline earth metal amides, hydrides or hydroxides.
  • the 2-hydroxymethyl derivatives mentioned are also known or can be prepared by known methods (see, inter alia, H. Kröper in Houben-Weyl, 'Methods of Organic Chemistry', Volume 6/3, pp. 519ff (1965) and the one cited therein Literature).
  • Inert organic solvents are preferably suitable as diluents for the reaction according to process variant (a) according to the invention.
  • These preferably include ethers such as diethyl ether, tetrahydrofuran or dioxane, aromatic hydrocarbons such as benzene or toluene, and in individual cases also chlorinated hydrocarbons such as chloroform, methylene chloride or carbon tetrachloride.
  • reaction temperatures can be varied within a substantial range. In general, one works between 0 and 120 ° C, preferably at 20 to 100 ° C.
  • the process variant (a) according to the invention is preferably carried out in molar amounts. However, it is also possible to use the alcoholates of the formula (II) or the compounds of the formula (III) in excess of up to 1 mol.
  • water is added to the reaction mixture, the organic phase is separated off and worked up and purified in the customary manner. In individual cases, the end product can also be distilled off from the reaction product directly after the solvent.
  • the procedure is advantageously carried out in such a way that a 2-hydroxymethyl-tetrahydrofuran derivative is used, the latter converted into the alkali metal alcoholate of the formula (II) in a suitable inert solvent using alkali metal hydride or amide, and the latter without Isolation is immediately reacted with a compound of the formula (III) and the compounds of the formula (I) according to the invention are thus obtained in one operation.
  • the compound of formula (III) can also be added to the reaction mixture before the alcoholate is prepared.
  • the preparation of the alcoholate of the formula (II) and the reaction according to the invention by process (a) are advantageously carried out in a two-phase system, such as aqueous sodium or potassium hydroxide solution / toluene or methylene chloride, with the addition of a phase transfer catalyst, such as, for example, ammonium or phosphonium compounds.
  • a phase transfer catalyst such as, for example, ammonium or phosphonium compounds.
  • reaction according to process variant (b) according to the invention is preferably carried out without a solvent.
  • the reaction according to the invention in process variant (b) is carried out in the presence of an acid catalyst.
  • an acid catalyst can be used. These preferably include organic acids, such as p-toluenesulfonic acid, inorganic acids, such as hydrochloric acid and sulfuric acid, and metal halides, such as aluminum chloride.
  • reaction temperatures in process variant (b) can be varied within a substantial range. Generally one works between 80 and 250 ° C, preferably between about 100 and 220 ° C.
  • reaction mixture is distilled in vacuo and then the water is separated off in the customary manner.
  • inert organic solvents are preferably suitable when using a diluent.
  • a diluent preferably include alcohols, such as methanol and ethanol, and ethers, such as diethyl ether and tetrahydrofuran.
  • the reactions according to the invention in process variants (c) and (d) are carried out in the presence of a catalyst.
  • a catalyst You can use all commonly used hydrogenation catalysts. These preferably include noble metal, noble metal oxide (or noble metal hydroxide) catalysts or so-called 'Raney catalysts', such as in particular platinum, platinum oxide, nickel, rhodium, rhodium oxide, ruthenium, palladium and osmium.
  • reaction temperatures can be varied over a wide range in process variants (c) and (d).
  • I n generally between 20 and 200 ° C, preferably at 80 to 150 ° C.
  • the reactions according to process variants (c) and (d) can be carried out under normal pressure, but also under elevated pressure, preferably at 1 to 200 atm.
  • the compounds of the formula (I) according to the invention can optionally be present in different geometric isomers which can be obtained in different proportions. They are also available as optical isomers. The case may arise that certain isomers have a greater activity than others, so that it may be expedient to prepare or isolate the more active components. All isomers are claimed according to the invention.
  • the active compounds according to the invention influence plant growth and can therefore be used as defoliants, desiccants, haulm killers, germ inhibitors and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up 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.
  • Monocot crops of the genera Rice (Oryza), Maize (Zea), Wheat (Triticum), Barley (Hordeum), Oats (Avena), Rye (Secale), Black Millet (Sorghum), Millet (Panicum), Sugar Cane (Saccharum), Pineapple (pineapple), asparagus (asparagus), leek (allium).
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops can e.g. Forestry, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weeding. fighting in annual crops.
  • the active compounds according to the invention have, in particular, strong herbicidal effects against grasses, without damaging various crop plants. They can therefore preferably be used for selective weed control.
  • the following crops are particularly suitable: beets, soybeans, beans, cotton, rapeseed, peanuts, vegetables, corn and rice.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are manufactured in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene, benzene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B.
  • Liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and pressure, e.g. B.
  • aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane; as solid carriers: natural rock flour, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates; as an emulsifier; nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • the active compounds according to the invention as such or in their formulations for strengthening and supplementing their spectrum of action, can be combined with other herbicidal active compounds, depending on the intended use, finished formulation or tank mix being possible.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90 percent by weight.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the usual way, e.g. by spraying, spraying, dusting, scattering and pouring.
  • the active compounds according to the invention can be applied both after and in particular before emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can fluctuate in larger areas. It essentially depends on the type of effect you want. In general, the application rates are between 0.1 and 10 kg of active ingredient per ha, preferably between 0.2 and 6 kg / ha.
  • the active compounds according to the invention not only have herbicidal properties, but also a fungicidal and insecticidal activity.
  • 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.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP78100007A 1977-06-01 1978-06-01 Dérivés du tétrahydrofuranne, leurs procédés de préparation et leur utilisation comme herbicides Expired EP0000002B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772724675 DE2724675A1 (de) 1977-06-01 1977-06-01 Tetrahydrofuran-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2724675 1977-06-01

Publications (2)

Publication Number Publication Date
EP0000002A1 true EP0000002A1 (fr) 1978-12-20
EP0000002B1 EP0000002B1 (fr) 1981-08-26

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100007A Expired EP0000002B1 (fr) 1977-06-01 1978-06-01 Dérivés du tétrahydrofuranne, leurs procédés de préparation et leur utilisation comme herbicides

Country Status (10)

Country Link
EP (1) EP0000002B1 (fr)
JP (1) JPS543057A (fr)
BR (1) BR7803476A (fr)
DD (1) DD137320A5 (fr)
DE (2) DE2724675A1 (fr)
DK (1) DK242578A (fr)
IL (1) IL54802A0 (fr)
IT (1) IT7823999A0 (fr)
PT (1) PT68098A (fr)
ZA (1) ZA783090B (fr)

Cited By (27)

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EP0013581A1 (fr) * 1979-01-08 1980-07-23 Shell Internationale Researchmaatschappij B.V. Dérivés du tétrahydrofuranne, un procédé pour leur préparation, compositions herbicides les contenant et leur utilisation dans une méthode pour maîtriser la croissance de plantes indésirables
DE3101461A1 (de) * 1980-01-21 1982-01-07 Shell Internationale Research Maatschappij B.V., 2596 's-Gravenhage Ungesaettigte alkohole und ihre verwendung zur herstellung von oxolanen
EP0064306A1 (fr) * 1981-05-01 1982-11-10 Shell Internationale Researchmaatschappij B.V. Tétrahydrofurannes substitués herbicides
US4400198A (en) * 1980-01-21 1983-08-23 Shell Oil Company Herbicidal tetrahydrofuran derivatives
EP0081893A3 (en) * 1981-12-16 1984-02-08 Shell Internationale Research Maatschappij B.V. Oxabicycloalkane herbicides
US4439225A (en) * 1982-06-14 1984-03-27 Shell Oil Company Herbicidal cyano-tetrahydrofuranylmethyl ether and cyano-tetrahydropyranylmethyl ether derivatives
US4493936A (en) * 1982-06-14 1985-01-15 Shell Oil Company 2-Cyano-tetrahydrofuran-5-methanols
US4497649A (en) * 1983-08-18 1985-02-05 Chevron Research Company 5-O-Acyl-5-C-alkyl-3-O-arylmethyl or substituted arylmethyl-1,2-O-alkylidene-αD-gluco-pentofuranose and β-L-ido-pentofuranose herbicides
US4579582A (en) * 1982-08-18 1986-04-01 Chevron Research Company 5-deoxy-3-O-arylmethyl or substituted arylmethyl-1,2-O-alkylidene-α-D-xylofuranose herbicide derivatives
EP0183650A1 (fr) * 1984-11-27 1986-06-04 Ciba-Geigy Ag Phénylhydrazines, procédé pour leur préparation et leur utilisation dans la lutte contre les organismes nuisibles
US4594094A (en) * 1983-04-04 1986-06-10 Shell Oil Company Oxacycloalkane-alpha-(thio)carboxylic acid derivatives and use as plant growth regulators and herbicides
AT387931B (de) * 1987-08-13 1989-04-10 Iag Ind Automatisierungsges M Heisspresse zum herstellen von scheibenbremsbelaegen
AT390413B (de) * 1988-07-20 1990-05-10 Steinbach Gerhard Ludwig Selbstklebende folie fuer kraftwagen-karosserien
AT392238B (de) * 1987-04-16 1991-02-25 Jenbacher Werke Ag Einrichtung zur steuerung von druckluftgesteuerten bremsen an schienenfahrzeugen
AT392965B (de) * 1986-10-15 1991-07-25 Erba Farmitalia Verfahren zur herstellung von azetidinonen
AT394978B (de) * 1986-08-20 1992-08-10 Erlau Ag Eisen Drahtwerk Reifenkette
AT396897B (de) * 1990-12-21 1993-12-27 Haltmeier Georg Mittel zum imprägnieren von holz
AT397333B (de) * 1988-06-20 1994-03-25 Elin Union Ag Einrichtung zur befestigung von bauteilen
AT398158B (de) * 1992-07-16 1994-10-25 Attrezzature Meccanismi Minute Spannvorrichtung
AT398199B (de) * 1992-11-27 1994-10-25 Chemie Linz Gmbh Verfahren zur herstellung von arylhydantoinen
AT399074B (de) * 1991-12-23 1995-03-27 Lenhard Ges M B H Vorrichtung zum halten von leiterplatten
AT399414B (de) * 1989-03-21 1995-05-26 Rudolf Dipl Ing Winkler Vorrichtung zur abstandsmessung für kraftfahrzeuge
EP1621111A1 (fr) * 2004-07-28 2006-02-01 Compin Siège pour véhicule de transport en commun
WO2016053320A1 (fr) 2014-09-30 2016-04-07 Hewlett-Packard Development Company, L.P. Manipulation gestuelle d'images tridimensionnelles
EP2420223B1 (fr) 2008-03-17 2017-07-19 Novartis Ag Compositions pharmaceutiques aqueuses contenant des complexes de borate-polyol
US11032035B2 (en) 2000-09-13 2021-06-08 Qualcomm Incorporated Signaling method in an OFDM multiple access system
WO2024108053A1 (fr) 2022-11-17 2024-05-23 Sanofi Conjugués anticorps-médicaments de ceacam5 et leurs méthodes d'utilisation

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US4356023A (en) 1980-06-30 1982-10-26 Shell Oil Company Certain herbicidal tetrahydrofurans
JPS6234626A (ja) * 1985-08-06 1987-02-14 Kawasaki Steel Corp 電縫管の製造方法
DE102020006104A1 (de) 2020-10-06 2022-04-07 Veronika Eitel Halterung für ein zu untersuchendes Objekt
DE102021107482A1 (de) 2021-03-25 2022-09-29 Verein zur Förderung von Innovationen durch Forschung, Entwicklung und Technologietransfer e.V. (Verein INNOVENT e.V.) Zerstäuberdüse

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NL7712277A (nl) * 1976-11-10 1978-05-12 Shell Int Research Werkwijze ter bereiding van preparaten met her- bicide-eigenschappen.

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Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013581A1 (fr) * 1979-01-08 1980-07-23 Shell Internationale Researchmaatschappij B.V. Dérivés du tétrahydrofuranne, un procédé pour leur préparation, compositions herbicides les contenant et leur utilisation dans une méthode pour maîtriser la croissance de plantes indésirables
DE3101461A1 (de) * 1980-01-21 1982-01-07 Shell Internationale Research Maatschappij B.V., 2596 's-Gravenhage Ungesaettigte alkohole und ihre verwendung zur herstellung von oxolanen
US4400198A (en) * 1980-01-21 1983-08-23 Shell Oil Company Herbicidal tetrahydrofuran derivatives
EP0064306A1 (fr) * 1981-05-01 1982-11-10 Shell Internationale Researchmaatschappij B.V. Tétrahydrofurannes substitués herbicides
EP0081893A3 (en) * 1981-12-16 1984-02-08 Shell Internationale Research Maatschappij B.V. Oxabicycloalkane herbicides
US4439225A (en) * 1982-06-14 1984-03-27 Shell Oil Company Herbicidal cyano-tetrahydrofuranylmethyl ether and cyano-tetrahydropyranylmethyl ether derivatives
US4493936A (en) * 1982-06-14 1985-01-15 Shell Oil Company 2-Cyano-tetrahydrofuran-5-methanols
US4579582A (en) * 1982-08-18 1986-04-01 Chevron Research Company 5-deoxy-3-O-arylmethyl or substituted arylmethyl-1,2-O-alkylidene-α-D-xylofuranose herbicide derivatives
US4594094A (en) * 1983-04-04 1986-06-10 Shell Oil Company Oxacycloalkane-alpha-(thio)carboxylic acid derivatives and use as plant growth regulators and herbicides
US4497649A (en) * 1983-08-18 1985-02-05 Chevron Research Company 5-O-Acyl-5-C-alkyl-3-O-arylmethyl or substituted arylmethyl-1,2-O-alkylidene-αD-gluco-pentofuranose and β-L-ido-pentofuranose herbicides
EP0183650A1 (fr) * 1984-11-27 1986-06-04 Ciba-Geigy Ag Phénylhydrazines, procédé pour leur préparation et leur utilisation dans la lutte contre les organismes nuisibles
AT394978B (de) * 1986-08-20 1992-08-10 Erlau Ag Eisen Drahtwerk Reifenkette
AT392965B (de) * 1986-10-15 1991-07-25 Erba Farmitalia Verfahren zur herstellung von azetidinonen
AT392238B (de) * 1987-04-16 1991-02-25 Jenbacher Werke Ag Einrichtung zur steuerung von druckluftgesteuerten bremsen an schienenfahrzeugen
AT387931B (de) * 1987-08-13 1989-04-10 Iag Ind Automatisierungsges M Heisspresse zum herstellen von scheibenbremsbelaegen
AT397333B (de) * 1988-06-20 1994-03-25 Elin Union Ag Einrichtung zur befestigung von bauteilen
AT390413B (de) * 1988-07-20 1990-05-10 Steinbach Gerhard Ludwig Selbstklebende folie fuer kraftwagen-karosserien
AT399414B (de) * 1989-03-21 1995-05-26 Rudolf Dipl Ing Winkler Vorrichtung zur abstandsmessung für kraftfahrzeuge
AT396897B (de) * 1990-12-21 1993-12-27 Haltmeier Georg Mittel zum imprägnieren von holz
AT399074B (de) * 1991-12-23 1995-03-27 Lenhard Ges M B H Vorrichtung zum halten von leiterplatten
AT398158B (de) * 1992-07-16 1994-10-25 Attrezzature Meccanismi Minute Spannvorrichtung
AT398199B (de) * 1992-11-27 1994-10-25 Chemie Linz Gmbh Verfahren zur herstellung von arylhydantoinen
US11032035B2 (en) 2000-09-13 2021-06-08 Qualcomm Incorporated Signaling method in an OFDM multiple access system
EP1621111A1 (fr) * 2004-07-28 2006-02-01 Compin Siège pour véhicule de transport en commun
EP2420223B1 (fr) 2008-03-17 2017-07-19 Novartis Ag Compositions pharmaceutiques aqueuses contenant des complexes de borate-polyol
WO2016053320A1 (fr) 2014-09-30 2016-04-07 Hewlett-Packard Development Company, L.P. Manipulation gestuelle d'images tridimensionnelles
WO2024108053A1 (fr) 2022-11-17 2024-05-23 Sanofi Conjugués anticorps-médicaments de ceacam5 et leurs méthodes d'utilisation

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DE2860975D1 (en) 1981-11-19
ZA783090B (en) 1979-06-27
JPS543057A (en) 1979-01-11
IT7823999A0 (it) 1978-05-30
EP0000002B1 (fr) 1981-08-26
DE2724675A1 (de) 1978-12-14
DD137320A5 (de) 1979-08-29
IL54802A0 (en) 1978-07-31
BR7803476A (pt) 1979-02-20
PT68098A (de) 1978-06-01
DK242578A (da) 1978-12-02

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