EP0000002B1 - 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

Info

Publication number
EP0000002B1
EP0000002B1 EP78100007A EP78100007A EP0000002B1 EP 0000002 B1 EP0000002 B1 EP 0000002B1 EP 78100007 A EP78100007 A EP 78100007A EP 78100007 A EP78100007 A EP 78100007A EP 0000002 B1 EP0000002 B1 EP 0000002B1
Authority
EP
European Patent Office
Prior art keywords
tetrahydrofuran
atoms
alkyl
phenyl
formula
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.)
Expired
Application number
EP78100007A
Other languages
German (de)
English (en)
Other versions
EP0000002A1 (fr
Inventor
Thomas Dr. Schmidt
Wilfried Dr. Draber
Ludwig Dr. Eue
Robert Rudolf Dr. Schmidt
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 EP0000002A1 publication Critical patent/EP0000002A1/fr
Application granted granted Critical
Publication of EP0000002B1 publication Critical patent/EP0000002B1/fr
Expired legal-status Critical Current

Links

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 invention relates to 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- (1'-methyl-2'-methoxyethyl) chloroacetanilide
  • grass-like weeds cf. DE-A-2 328 340.
  • selectivity of these compounds is not always satisfactory.
  • tetrahydrofuran derivatives have strong herbicidal, in particular selective herbicidal properties.
  • 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, in their herbicidal action and also show a markedly better selectivity important kulfur plants.
  • the active compounds according to the invention thus represent a significant enrichment of herbicides, especially grass herbicides.
  • 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-hydroxymethyltetrahydrofuran 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 generally defines the compounds to be used as starting materials for process variant (a).
  • Formula IV generally defines the diols to be used as starting materials for process variant (b).
  • the formulas Va, Vb and Vc generally define the dihydrofuran derivatives to be used as starting materials for process variant (c).
  • Formula VI generally defines the furan derivatives to be used as starting materials for process variant (d).
  • the alcoholates of the formulas VIII, VIIIb, VIIIc and VIII are known or can be prepared by known methods. They are obtained, for example, by reacting the corresponding 2-hydroxymethyldihydrofuran 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 likewise known or can be prepared by known methods (cf., inter alia, H. Kröper in Houben-Weyl, 'Methods of Organic Chemistry', Volume 6/3, pp. 519ff [1965] and those therein literature cited).
  • 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. Generally 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 expediently started from a 2-hydroxymethyl-tetrahydrofuran derivative, the latter converted into the alkali metal alcoholate of the formula 11 in a suitable inert solvent using alkali metal hydride or amide, and the latter immediately without isolation reacted with a compound of the formula III and thus obtained the compounds of the formula according to the invention 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 one Two-phase system, such as aqueous sodium or potassium hydroxide solution / toluene or methylene chloride, carried out with the addition of a phase transfer catalyst, such as ammonium or phosphonium compounds.
  • a phase transfer catalyst such as 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 the water is then 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). Generally one works 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 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. In this case, it can occur that certain isomers have a greater activity than others, so that it may be expedient to prepare or isolate the more active components. All the 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 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.
  • the active compounds according to the invention can be used, for example, in the following plants: dicotyledon weeds of the genera: mustard (Sinapsis), cress (Lepidium), bedstraw (Galium), starwort (Stellaria), chamomile (Matricaria), dog chamomile (Anthemis), button herb (Galinsoga ), Goose foot (Chenopodium), nettle (Urtica), ragwort (Senecio), foxtail (Amaranthus), purslane (Portulaca), Norway burdock (Xanthium), winch (Convolvulus), morning glory (Ipomoea), knotweed (Polygonum), sesbanie (Sesbania ), Ambrosia (Ambrosia), Thistle (Cirsium), Thistle (Carduus), Goose Thistle (Sonchus), Nightshade (Solanum), Marsh Cress (Rorippa), Rotala, Ciderweed (Li
  • Monocot crops of the genera Rice (Orzya), 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 trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control 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 prepared in a known manner, for example 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. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • 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, for example, also be used as auxiliary solvents.
  • liquid 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, for example petroleum fractions, 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;
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as dichlorodifluoromethane or trichlorofluoromethane; as solid carriers: natural
  • 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 formulations or tank mixes 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 the plants emerge. 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.
  • 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.
  • the mixture is then heated under reflux for 30 minutes, cooled to 50 ° C. and 32 g (0.2 mol) of 2-chlorobenzyl chloride are then added dropwise to the sodium salt thus obtained.
  • the mixture is then heated under reflux for a further 3 hours, 20 ml of methanol are added to destroy excess sodium hydride and the mixture is concentrated by distilling off the solvent in vacuo.

Landscapes

  • 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)

Claims (5)

1. Dérivés du tétrahydrofuranne de formule I
Figure imgb0034
dans laquelle
R1 à R6, identiques ou différents, représentent l'hydrogène, un groupe alkyle en C1―C6 à chaîne droite ou ramifiée, haiogénoaikyie en C1―C2 contenant jusqu'à 3 atomes d'halogènes identiques ou différents, alcoxyalkyle contenant 1 ou 2 atomes de carbone dans chacune des parties alkyle, ou encore phényle ou benzyloxyalkyle contenant 1 ou 2 atomes de carbone dans la partie alkyle, ces deux derniers groupes pouvant le cas échéant être substitués par des halogènes, des groupes alkyle en C1―C2, alcoxy en C1―C2 ou halogénoalkyle en C1―C2 contenant jusqu'à 3 atomes d'halogènes identiques ou différents,
R5 et R6 forment également ensemble un noyau carbocyclique saturé contenant ou total 3 à 6 atomes de carbone,
R7 représente l'hydrogène, un groupe alkyle en C1―C6 à chaîne droite ou ramifiée, cycloalkyle en C3―C6, alcényle en C2―C4, alcynyle en C2―C4, alcoxyalkyle contenant 1 ou 2 atomes de carbone dans chacune des parties alkyle, ou encore phényle ou benzyloxyalkyle contenant 1 ou 2 atomes de carbone dans la partie alkyle, ces deux derniers groupes étant substitués par des halogènes, des groupes alkyle en C1―C2, alcoxy en C1―C2 ou halogénoalkyle en C1―C2 contenant jusqu'à 3 atomes d'halogènes identiques ou différents,
R8 et R9 identiques ou différents, représentent l'hydrogène, un groupe alkyle en C1―C6 à chaîne droite ou ramifiée, alcényle en C2―C4, alcynyle en C2―C4, cycloalkyle en C3― C6, alcoxy en en C1―C4 ou bien phényle, benzyle ou benzyloxy, ces trois derniers groupes pouvant le cas échéant être substitués par des halogènes, des groupes alkyle en C1―C2, alcoxy en C,-C2 ou halogénoalkyle en C1―C2 contenant jusqu'à 3 atomes d'halogènes identiques ou différents,
R10 représente l'hydrogène, un groupe alkyle en C1―C6 à chaîne droite ou ramifiée, alcényle en C2―C4, alcynyle en C2―C4, halogénoalkyle en C1―C2 contenant jusqu'à 3 atomes d'halogène identiques ou différents, ou encore phényle éventuellement substitué par des halogènes, des groupes alkyle en C1―C2, alcoxy en C1―C2 ou halogénoalkyle en C1―C2 contenant jusqu'à 3 atomes d'halogènes identiques ou différents, et
Y représente un groupe aryle éventuellement substitué en C1―C10, qui peut porter un ou plusieurs substituants identiques ou différents parmi les suivants: les halogènes, fluor, chlore ou brome; les groupes alkyle et alcoxy contenant chacun 1 à 4 atomes de carbone; les groupes halogénoalkyle, halogénoalcoxy et halogénoalkylthio contenant chacun jusqu'à 4 atomes de carbone et jusqu'à 5 atomes d'halogènes; un groupe phényle éventuellement substitué par des halogènes, des groupes alkyle et alcoxy contenant chacun 1 ou 2 atomes de carbone ou halogénoalkyle contenant jusqu'à 2 atomes de carbone et jusqu'à 3 atomes d'halogènes identiques ou différents, phénoxy ou phénoxycarbonyle; un groupe alcoxycarbonyle contenant 1 à 4 atomes de carbone dans la partie alkyle; le groupe méthylène-dioxy ou le reste tri-, tétra- ou penta-méthylène; étant spécifié que, lorsque Y représente un groupe phényle, celui-ci doit être substitué si R1 à R10 représentent l'hydrogène.
2. Procédé de préparation des dérivés du tétrahydrofuranne de formule I, caractérisé en ce que:
(a) on fait réagir des alcoolates de dérivés du 2-hydroxyméthyl-tétrahydrofuranne de formule
Figure imgb0035
dans laquelle
R' à R9 ont les significations indiquées ci-dessus, et
M représente un métal alcalin ou alcalino-terreux, avec un composé de formule
Figure imgb0036
dans laquelle
R10 et Y ont les significations indiquées ci-dessus, et
Z représente un halogène, le reste mésylate ou tosylate, de manière connue en soi, éventuellement en présence d'un diluant, ou bien
(b) on chauffe des diols de formule
Figure imgb0037
dans laquelle
R1 à R10 et Y ont les significations indiquées ci-dessus,

de manière connue en soi, en présence d'un catalyseur acide et éventuellement en présence d'un diluant; ou bien
(c) on obtient les composés de formule I dans laquelle ou bien R1 et R7, ou bien R1 et R4 ou bien R4 et R5 représentent l'hydrogène, en hydrogénant des dérivés du dihydrofuranne répondant aux formules
Figure imgb0038
Figure imgb0039
et/ou
Figure imgb0040
dans lesquelles
R1 à R10 et Y ont les significations indiquées ci-dessus,

de manière connue en soi, en présence d'un catalyseur et le cas échéant en présence d'un diluant, ou bien
(d) on obtient les composés de formule l dans laquelle R1, R4, R5 et R7 représentent l'hydrogène, en hydrogénant des dérivés du furanne de formule
Figure imgb0041
dans laquelle
R2, R3, R6, R8, R9, R10 et Y ont les significations indiquées ci-dessus,

de manière connue en soi, en présence d'un catalyseur et le cas échéant en présence d'un diluant.
3. Produit herbicide caractérisé en ce qu'il contient des dérivés du tétrahydrofuranne selon la revendication 1.
4. Utilisation des dérivés du tétrahydrofuranne selon la revendication 1, pour combattre la croissance des végétaux indésirables.
5. Procédé de préparation de produits herbicides caractérisé en ce que l'on mélange des dérivés du tétrahydrofuranne selon la revendication 1, avec des diluants et/ou des produits tensioactifs..
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 EP0000002A1 (fr) 1978-12-20
EP0000002B1 true EP0000002B1 (fr) 1981-08-26

Family

ID=6010385

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 (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3982114A1 (fr) 2020-10-06 2022-04-13 Eitel, Veronika Support pour un objet à examiner
EP4063016A1 (fr) 2021-03-25 2022-09-28 Verein zur Förderung von Innovationen durch Forschung, Entwicklung und Technologietransfer e.V. (Verein INNOVENT e.V.) Buse d'atomiseur

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4289884A (en) * 1979-01-08 1981-09-15 Shell Oil Company Herbicidal tetrahydrofuran derivatives
US4400198A (en) * 1980-01-21 1983-08-23 Shell Oil Company Herbicidal tetrahydrofuran derivatives
CA1152510A (fr) * 1980-01-21 1983-08-23 Shell Canada Limited Alcools insatures et utilisation dans la preparation d'oxolanes
US4356023A (en) 1980-06-30 1982-10-26 Shell Oil Company Certain herbicidal tetrahydrofurans
DE3271239D1 (en) * 1981-05-01 1986-06-26 Shell Int Research Substituted tetrahydrofuran herbicides
US4670041A (en) * 1981-12-16 1987-06-02 E. I. Du Pont De Nemours And Company Oxabicycloalkane herbicides
US4493936A (en) * 1982-06-14 1985-01-15 Shell Oil Company 2-Cyano-tetrahydrofuran-5-methanols
US4439225A (en) * 1982-06-14 1984-03-27 Shell Oil Company Herbicidal cyano-tetrahydrofuranylmethyl ether and cyano-tetrahydropyranylmethyl ether derivatives
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
US4725302A (en) * 1984-11-27 1988-02-16 Ciba-Geigy Corporation Substituted phenylhydrazines and phenyloxadiazolinones and pesticidal usage thereof
JPS6234626A (ja) * 1985-08-06 1987-02-14 Kawasaki Steel Corp 電縫管の製造方法
DE3628287A1 (de) * 1986-08-20 1988-02-25 Erlau Ag Eisen Drahtwerk Reifenkette
IT1197873B (it) * 1986-10-15 1988-12-21 Erba Farmitalia Procedimento per la preparazione di azetidinoni
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
US7295509B2 (en) 2000-09-13 2007-11-13 Qualcomm, Incorporated Signaling method in an OFDM multiple access system
FR2873555B1 (fr) * 2004-07-28 2008-04-18 Compin Sa Siege pour vehicule de transport en commun
PT2254549E (pt) 2008-03-17 2014-01-30 Alcon Res Ltd Composições farmacêuticas aquosas que contêm complexos de borato-poliol
US10268277B2 (en) 2014-09-30 2019-04-23 Hewlett-Packard Development Company, L.P. Gesture based manipulation of three-dimensional images
WO2024108053A1 (fr) 2022-11-17 2024-05-23 Sanofi Conjugués anticorps-médicaments de ceacam5 et leurs méthodes d'utilisation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7712227A (nl) * 1976-11-08 1978-05-10 Inco Europ Ltd Werkwijze voor het opslaan van waterstof waarbij het later weer kan worden vrijgemaakt.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1370678A (fr) * 1962-06-29 1964-08-28 Shell Res Ltd Dérivés molluscicides de l'éther diméthylique
GB1591093A (en) * 1976-11-10 1981-06-17 Shell Int Research 2-benzyloxymethylfuran derivatives and their use as herbicides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7712227A (nl) * 1976-11-08 1978-05-10 Inco Europ Ltd Werkwijze voor het opslaan van waterstof waarbij het later weer kan worden vrijgemaakt.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3982114A1 (fr) 2020-10-06 2022-04-13 Eitel, Veronika Support pour un objet à examiner
EP4063016A1 (fr) 2021-03-25 2022-09-28 Verein zur Förderung von Innovationen durch Forschung, Entwicklung und Technologietransfer e.V. (Verein INNOVENT e.V.) Buse d'atomiseur

Also Published As

Publication number Publication date
EP0000002A1 (fr) 1978-12-20
DE2860975D1 (en) 1981-11-19
ZA783090B (en) 1979-06-27
JPS543057A (en) 1979-01-11
IT7823999A0 (it) 1978-05-30
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

Similar Documents

Publication Publication Date Title
EP0000002B1 (fr) Dérivés du tétrahydrofuranne, leurs procédés de préparation et leur utilisation comme herbicides
EP0423482B1 (fr) Dérivés de 5H-furan-2-one
CH633548A5 (de) Tetrahydrofuranaether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide.
EP0030676B1 (fr) Dérivés d'acide phénoxybenzoique, procédé pour leur préparation et leur utilisation comme herbicides et comme agents de régulation de la croissance des plantes
EP0000051B1 (fr) N-acylméthyl-chloroacétanilides, procédé pour leur préparation et leur utilisation comme herbicides.
EP0011179B1 (fr) N-phénylurées, procédé pour leur préparation, leur utilisation comme herbicides, ainsi que les intermédiaires et leur préparation
DE2538178A1 (de) Trifluormethylphenoxy-phenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DE2937645A1 (de) Tetrahydropyranether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
EP0002214B1 (fr) Ethers benzyliques de 1,2-diols cycliques, leurs méthodes de préparation et leur utilisation comme herbicides
EP0024017A2 (fr) N-pyrimidinylméthyl-halogénoacétanilides, procédé pour leur préparation et leur utilisation comme herbicides; intermédiaires et leur préparation
EP0010163A1 (fr) N-Diazolylalcoyl-chloroacétanilides, procédé pour leur préparation et leur utilisation comme herbicides
DE2703477A1 (de) Chlormethansulfonsaeureanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
EP0300307A2 (fr) Hétérocycles azotés N-arylés
EP0010715A1 (fr) N-alcoylene-halogenoacetanilides substitués par un groupe oxime, procédés pour leur préparation, herbicides les contenant, procédé pour la lutte contre les mauvaises herbes, procédé pour la préparation de ces herbicides
EP0008091A1 (fr) N-Pyrazolylméthyl-halogénoacétanilides substituées, procédé pour leur préparation ainsi que leur utilisation comme herbicides
EP0009693B1 (fr) N-(1,3-Thiazolyl)-alcoyl-chloroacétanilides, procédé pour leur préparation et leur utilisation comme herbicides
EP0351676A2 (fr) Benzothiazolones
DE2426651C3 (de) (-)-Antipode des 3-(p-Chlorphenyl)-2-chlorpropionsäuremethylesters, Verfahren zu dessen Herstellung sowie dessen Verwendung als Herbizid
EP0089538B1 (fr) Dérivés optiquement actifs de l'acide phénoxybenzoique, procédé de préparation et utilisation comme herbicides
EP0010166A1 (fr) N-(1,2-Azolyl)alcoyl chloroacétanilides, procédé pour leur préparation et leur application comme herbicides
DE3513488A1 (de) Herbizide mittel
DE2647460A1 (de) Heterocyclisch substituierte 4-amino-1,2,4-triazin-5-one, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2520815A1 (de) 4-trifluormethyl-4'-sulfonsaeureamid- diphenylaether, verfahren zu ihrer herstellung und ihre verwendung als herbizide
EP0094538A2 (fr) 4,6-Diamino-s-triazines contenant du fluor, procédé et intermédiaires pour leur préparation et leur utilisation comme herbicide
EP0247486A1 (fr) Dérivés d'oxabicyclo[2.2.1]heptène

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

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE CH DE FR GB NL SE

17P Request for examination filed
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH DE FR GB NL SE

Kind code of ref document: B1

Designated state(s): BE CH DE FR GB NL SE

REF Corresponds to:

Ref document number: 2860975

Country of ref document: DE

Date of ref document: 19811119

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: LU

Payment date: 19820331

Year of fee payment: 5

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19820601

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Effective date: 19820630

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19820630

Year of fee payment: 5

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19830101

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19830301

GBPC Gb: european patent ceased through non-payment of renewal fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19830331

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19830602

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19881117

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GR

Payment date: 19910827

Year of fee payment: 5

REG Reference to a national code

Ref country code: CH

Ref legal event code: AUVA

Free format text: DAS OBENGENANNTE PATENTGESUCH IST ZURUECKGEWIESEN WORDEN.

EUG Se: european patent has lapsed

Ref document number: 78100007.0

Effective date: 19850610

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

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

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT