WO1999048886A1 - Aminooxyalcancarboxamides substitues - Google Patents

Aminooxyalcancarboxamides substitues Download PDF

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Publication number
WO1999048886A1
WO1999048886A1 PCT/EP1999/001688 EP9901688W WO9948886A1 WO 1999048886 A1 WO1999048886 A1 WO 1999048886A1 EP 9901688 W EP9901688 W EP 9901688W WO 9948886 A1 WO9948886 A1 WO 9948886A1
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WO
WIPO (PCT)
Prior art keywords
cyano
optionally substituted
substituted
optionally
alkyl
Prior art date
Application number
PCT/EP1999/001688
Other languages
German (de)
English (en)
Inventor
Roland Andree
Markus Dollinger
Mark Wilhelm Drewes
Ingo Wetcholowsky
Randy Allen Myers
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU28368/99A priority Critical patent/AU2836899A/en
Publication of WO1999048886A1 publication Critical patent/WO1999048886A1/fr

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Classifications

    • 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
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen 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
    • A01N43/24—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 two or more hetero atoms
    • A01N43/26—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 two or more hetero atoms five-membered rings
    • A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • 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
    • A01N43/24—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 two or more hetero atoms
    • A01N43/32—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 two or more hetero atoms six-membered rings
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring

Definitions

  • the invention relates to new substituted aminooxyalkane carboxamides, a process for their preparation and their use as herbicides.
  • A represents optionally substituted alkanediyl
  • Rl represents hydrogen or optionally substituted alkyl
  • R.2 represents hydrogen or optionally substituted alkyl
  • R.3 represents hydrogen, hydroxy, amino, or optionally substituted alkyl, alkoxy, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and - 2 -
  • R ⁇ for hydrogen or for optionally substituted alkyl, alkoxy, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or together with R ⁇ for optionally substituted and / or optionally by a heteroatom from the O series (Oxygen), S (sulfur), N (nitrogen) at the beginning - or end - or interrupted alkanediyl in the carbon chain.
  • O series Oxygen
  • S sulfur
  • N nitrogen
  • the compounds of the general formula (I) according to the invention optionally contain asymmetrically substituted carbon atoms and can then be present in various enantiomeric (R- and S-configured forms) or diastereomeric forms.
  • the invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures of these stereoisomeric compounds.
  • hydrocarbon chains such as alkyl - also in connection with heteroatoms, such as in alkoxy - are each straight-chain or branched.
  • the invention preferably relates to compounds of the formula (I) in which
  • A represents alkanediyl with 1 to 4 carbon atoms optionally substituted by halogen, - 3 -
  • R 1 represents hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C1-C4-alkoxy,
  • R2 represents hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C1-C4alkoxy,
  • R ⁇ for hydrogen, hydroxy, amino, for each optionally substituted by hydroxy, cyano, halogen or C] -C4-alkoxy alkyl, alkoxy or alkylamino each having 1 to 6 carbon atoms, for each optionally substituted by cyano or halogen with alkenyl or alkynyl each having 2 to 6 carbon atoms, each for cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C1-C4alkyl
  • R4 for hydrogen, each for alkyl, alkoxy or alkylamino optionally substituted by hydroxy, cyano, halogen 'or C 1 -C 4 -alkoxy, each with
  • Carbon chain interrupted alkanediyl having 2 to 6 carbon atoms having 2 to 6 carbon atoms.
  • the invention relates in particular to compounds of the formula (I) in which
  • A represents methylene (-CH 2 -) or dimethylene (-CH 2 CH 2 -) optionally substituted by fluorine and / or chlorine,
  • R 1 represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, - 5 -
  • R ⁇ represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R ⁇ for hydrogen, hydroxy, amino, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, which are each optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy , Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for each optionally propenyl, butenyl, propynyl or butynyl substituted by cyano, fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,
  • R4 for hydrogen, for methyl, ethyl, n- or i-propyl, "n-, i-, s- or t-butyl, methoxy, ethoxy, n, each optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy or ethoxy - or i-propoxy, n-, i-, s- or t-
  • a very particularly preferred group are the compounds of formula (I) in which
  • Trifluorodimethylene (-CF 2 CHF-) or tetrafluorodimethylene (-CF CF 2 -), - 7 -
  • Rl stands for hydrogen
  • R ⁇ represents methyl, ethyl, n- or i-propyl
  • R ⁇ stands for hydrogen
  • R4 represents phenyl or benzyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or morpholinyl.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • the new substituted aminooxyalkane carboxamides of the general formula (I) are notable for strong and selective herbicidal activity.
  • the compounds of formula (I) also show insecticidal activity.
  • R2, R- 3 and R4 have the meaning given above,
  • Formula (I) carbonyl compounds to be used as starting materials are generally defined by formula (II).
  • a and R preferably have 1 or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for A and R 1 .
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. J. Org. Chem. 37 (1972), 673).
  • aminooxyalkane carboxamides to be used further as starting materials in the process according to the invention are generally defined by the formula (III).
  • R 2 , R 3 and R 4 preferably or in particular have those
  • the starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. J. Org. Chem. 32 (1967), 2417-2425; loc. Cit. 33 (1968), 2963- 2966; DE-A-3615473; EP-A-427445; EP-A-427549; US-A-5002605; US-A-5314865; manufacturing examples).
  • a diluent inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, 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-
  • ethylene glycol monomethyl ether 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 the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent 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: - 11 -
  • the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops for example forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants. genes, on ornamental and sports turf and pastures and for selective weed control in annual crops. - 12 -
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active compounds 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.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as
  • Chlorobenzenes chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol 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.
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. 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.
  • 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 silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: eg broken and fractionated natural rocks such as calcite, marble, - 13 -
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl
  • 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.
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin,
  • Benzofenap Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramethoxyfen Chloridazon, Chlor imuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlorotoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl),
  • Clomazone Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (- methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2, 4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufen- zopyr, 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.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. 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.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • Seeds of the test plants are sown in normal soil, after about 24 hours the soil is sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Solvent 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compounds according to Preparation Examples 1, 3 and 7 show with good tolerance to crop plants, such as e.g.

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

Abstract

L'invention concerne de nouveaux aminooxyalcancarboxamides substitués de la formule générale (I) où A représente alcandiyle éventuellement substitué; R1 représente de l'hydrogène ou alkyle éventuellement substitué; R2 représente de l'hydrogène ou alkyle éventuellement substitué; R3 représente de l'oxygène, hydroxy, amino, ou bien alkyle, alcoxy, alkylamino, alcényle, alcinyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle éventuellement substitués, et R4 représente de l'oxygène ou bien alkyle, alcoxy, alkylamino, alcényle, alcinyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle, ou représente avec R3 alcandiyle éventuellement substitué et/ou éventuellement interrompu par un hétéroatome de la série O (oxygène), S (soufre), N (azote) au début, à la fin de la chaîne de carbone ou encoure dans la chaîne de carbone. L'invention concerne également leur procédé de production ou leur utilisation comme herbicide.
PCT/EP1999/001688 1998-03-25 1999-03-15 Aminooxyalcancarboxamides substitues WO1999048886A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU28368/99A AU2836899A (en) 1998-03-25 1999-03-15 Substituted aminooxyalkanecarboxamides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1998113047 DE19813047A1 (de) 1998-03-25 1998-03-25 Substituierte Aminooxyalkancarboxamide
DE19813047.3 1998-03-25

Publications (1)

Publication Number Publication Date
WO1999048886A1 true WO1999048886A1 (fr) 1999-09-30

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Application Number Title Priority Date Filing Date
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Country Link
AU (1) AU2836899A (fr)
DE (1) DE19813047A1 (fr)
WO (1) WO1999048886A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0012158A2 (fr) * 1978-09-01 1980-06-25 Ciba-Geigy Ag Dérivés d'oxime et leur utilisation dans la protection des cultures de plantes
US5002605A (en) * 1988-12-21 1991-03-26 Ici Americas Inc. Alkylidine aminooxyamide compounds useful in controlling undesirable vegetation
EP0427445A1 (fr) * 1989-11-09 1991-05-15 Ube Industries, Ltd. Dérivés amidés d'acides benzylidène-aminooxyalcane(thi)oiques, procédé pour leur préparation et herbicides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0012158A2 (fr) * 1978-09-01 1980-06-25 Ciba-Geigy Ag Dérivés d'oxime et leur utilisation dans la protection des cultures de plantes
US5002605A (en) * 1988-12-21 1991-03-26 Ici Americas Inc. Alkylidine aminooxyamide compounds useful in controlling undesirable vegetation
US5314865A (en) * 1988-12-21 1994-05-24 Ici Americas Inc. Certain alkylidine aminooxyamide compounds useful as herbicides
EP0427445A1 (fr) * 1989-11-09 1991-05-15 Ube Industries, Ltd. Dérivés amidés d'acides benzylidène-aminooxyalcane(thi)oiques, procédé pour leur préparation et herbicides

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DE19813047A1 (de) 1999-09-30
AU2836899A (en) 1999-10-18

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