EP0575341A1 - Amides d'acide carboxylique isoxazolique et isothiazolique-5 - Google Patents

Amides d'acide carboxylique isoxazolique et isothiazolique-5

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Publication number
EP0575341A1
EP0575341A1 EP92902976A EP92902976A EP0575341A1 EP 0575341 A1 EP0575341 A1 EP 0575341A1 EP 92902976 A EP92902976 A EP 92902976A EP 92902976 A EP92902976 A EP 92902976A EP 0575341 A1 EP0575341 A1 EP 0575341A1
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EP
European Patent Office
Prior art keywords
alkyl
alkoxy
halogen
group
substituted
Prior art date
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EP92902976A
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German (de)
English (en)
Inventor
Volker Maywald
Peter Muenster
Hartmann Koenig
Gerhard Hamprecht
Thomas Kuekenhoehner
Wolfgang Rohr
Helmut Walter
Karl-Otto Westphalen
Matthias Gerber
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen

Definitions

  • the present invention relates to carboxamides of the formula I.
  • C 1 -C 6 alkyl which can carry one to five halogen atoms and / or one or two of the following radicals: C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, cyano or phenyl, the up to can be substituted three times by halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, cyano or nitro; a C 3 -C 8 cycloalkyl substituted C 1 -C 6 alkyl group; C 3 -C 8 cycloalkyl or C 3 -C 6 cycloalkenyl, which can be substituted one to three times by C 1 -C 4 alkyl or halogen; a C 2 -C 6 alkenyl group, the double bond of which may be epoxidized, or a C 2 -C 6 alkyny
  • R 5 is also a 5- to 6-membered saturated or aromatic heterocyclic radical having one or two heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, where two oxygen and / or sulfur atoms cannot be directly adjacent and where the heterocycles contain one or carry two of the following substituents: halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy or C 1 -C 3 alkoxycarbonyl; a 5- to 6-membered saturated or aromatic heterocyclic radical with three heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, where two oxygen and / or sulfur atoms cannot be directly adjacent and where the heterocycles can also carry one or two of the following substituents: Halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy or C 1 -C 3 alkoxycarbonyl;
  • R 13 is hydrogen or C 1 -C 6 alkyl and R 14 C 1 -C 6 alkyl which is substituted by C 1 -C 4 alkanoyl or benzoyl which may be substituted by halogen or C 1 -C 3 alkyl, mean; a radical -WZ, where W is a C 2 -C 4 -alkylene chain, an ethoxyethylene chain, a but-2-enylene or a but-2-inylene chain and Z is a part of the molecule bonded to W in the ⁇ position, which is the same part of the molecule which is linked to W in the ⁇ -position of W; R 6
  • C 1 -C 6 alkyl which can carry one to three of the following substituents: hydroxy, halogen, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio or di- (C 1 -C 4 ) alkylamino; C 3 -C 8 cycloalkyl, which can be substituted one to three times by halogen, C 1 -C 4 alkyl and partially or completely halogenated C 1 -C 4 alkyl;
  • R 5 is not a C 3 -C 8 haloalkynyl radical means if R 1 for optionally substituted C 2 -C 6 alkenyl, the double bond of which may be epoxidized, optionally substituted C 3 -C 6 cycloalkenyl, optionally substituted C 2 -C 6 alkynyl or one substituted by C 3 - C 8 cycloalkyl substituted C 1 -C 6 alkyl group; as well as the environmentally compatible salts of the compound I.
  • the invention relates to herbicidal compositions which comprise the compounds I as active substances and processes for the preparation of the compounds I.
  • Herbicidally active isoxazole- and isothiazole-5-carboxamides or their derivatives are known from DE-A 38 12225. Despite the inherently good herbicidal activity of the known products, the object was to provide compounds with improved properties, in particular with regard to crop selectivity or environmental behavior .
  • the carboxamides of the formula I according to the invention can be prepared in various ways, preferably by the following processes: A process for the synthesis of the isoxazole according to the invention.
  • the isoxazole or isothiazole-4,5-dicarboxylic acid ester dialkyl esters II required for this process are either known from the literature, can be prepared in ways known from the literature, or are available, for example, in the following ways: a) A very widely applicable process for the synthesis of variously substituted isoxazole-4,5-dicarboxylic acid dialkyl esters of the formula II in which R 1 is, for example, hydrogen, optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, phenyl or
  • Heterocyclyl mean that an appropriately substituted aldoxime of the formula VI is reacted with dialkyl acetylenedicarboxylate VII in the presence of hypohalite. In this reaction, the aldoxime VI becomes the corresponding one through the hypohalite
  • Nitrile oxide oxidized.
  • the nitrile oxide is a reactive 1,3-dipole, which is trapped in a cycloaddition with the dipolarophile dialkyl acetylenedicarboxylate VII present in the reaction medium.
  • hypohalite can be added to the reaction mixture in a stoichiometric amount, but it is generally metered into the reaction mixture in a slightly excess amount, up to a two-fold excess. For process engineering reasons, it may be advantageous to reduce the conversion by using substoichiometric amounts of hypohalite - about 50 to 90 mol% of hypohalite per mol
  • hypohalites are generally used as hypohalites.
  • aqueous solutions of hypochlorous or bromonic acid can be used, but alkali metal or alkaline earth metal hypochlorites or hypobromites, for example, are preferred
  • Sodium hypochlorite, potassium hypochlorite, calcium hypochlorite, magnesium hypochlorite, strontium hypochlorite, barium hypochlorite or the corresponding hypobromites are used.
  • Sodium, potassium and calcium hypochlorite are particularly preferably used in the form of their commercially available aqueous solutions.
  • Suitable solvents for the process are, for example, alcohols, such as methanol, ethanol, propanol or isopropanol, ketones such as acetone or methyl ethyl ketone, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, hydrocarbons such as pentane,
  • Hexane, cyclohexane, petroleum ether, white oils or ligroin, halogenated aliphatic hydrocarbons such as
  • Toluene xylenes or chlorobenzenes, esters such as ethyl acetate and dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane, etc.
  • the temperature at which the reaction is carried out can be varied within a wide range. As a rule, the reaction takes place at temperatures of (-15 ° C) and lower, and the top is the
  • the temperature range is only limited by the boiling point of the solvent used, since the reaction is advantageously carried out at atmospheric pressure. Is preferably carried out at temperatures in the range of 0 to 40 ° C.
  • the reaction can also be carried out under elevated pressure, in particular under autogenously generated pressure, but the reaction at atmospheric pressure is preferred.
  • aldoximes VI required for this process are either known or can be prepared by processes known per se (e.g. Houben-Weyl, methods of organic
  • aldoximes VI can of course be used both in the form of their E or Z isomers and as mixtures thereof
  • acetylenedicarboxylic acid diesters are commercially available or can be prepared by methods known per se (for example Organic Syntheses Coll. Vol 4, page 329).
  • the procedure is expediently such that the 3-hydroxymethyl-isoxazole-4,5-dicarboxylic acid dialkyl ester is initially introduced in an inert solvent and an inorganic acid chloride is added dropwise.
  • the inorganic acid chloride itself can also serve as a solvent.
  • the reaction is generally carried out at from 20 ° C. to the boiling point of the solvent used.
  • Halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-oichloroethane and chlorobenzene, aromatic hydrocarbons such as benzene, toluene and xylene and ethers such as tetrahydrofuran and dioxane are suitable as solvents.
  • Halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-oichloroethane and chlorobenzene
  • aromatic hydrocarbons such as benzene, toluene and xylene and ethers such as tetrahydrofuran and dioxane are suitable as solvents.
  • solvents such as dichloromethane, chloroform, 1,2-oichloroethane and chlorobenzene
  • aromatic hydrocarbons such as benzene, toluene and xylene and ethers
  • tetrahydrofuran and dioxane are suitable as solvents.
  • 5-dicarboxylic acid dialkyl esters for example C 1 -C 3 alkoxyalkyl, C 1 -C 3 haloalkoxyalkyl or cyanoalkyl-substituted isoxazole-4, 5-dicarboxylic acid dialkyl esters are obtainable by adding the halide in known way replaced by appropriate nucleophilic residues.
  • the addition of a catalyst such as dimethylformamide or 4-dimethylaminopyridine can be advantageous.
  • the acid halide can be isolated in the customary manner, for example by distilling off the excess of inorganic acid chloride and the organic solvent.
  • PPA propanephosphonic anhydride
  • DCC dicyclohexylcarbodiimide
  • the starting materials are advantageously reacted in an approximately stoichiometric amount, preferably in the presence of an inert solvent such as tetrahydrofuran, dichloromethane, toluene or ethyl acetate.
  • Suitable solvents are ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene or aromatics such as benzene, toluene and xylene.
  • ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane
  • halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene or aromatics such as benzene, toluene and xylene.
  • the reaction temperature can be between -10 and 50 ° C, preferably 0 and 30 ° C.
  • Tertiary amines such as pyridine, N, N-dimethylaniline or triethylamine are preferably used as the auxiliary base.
  • the amines Vb required for processes 3 and 4 are known or can be prepared by known processes.
  • HO-CH 2 -CH N-OCH 3
  • HO-CH 2 -C (CH 3 ) N-OCH 3
  • HO-CH 2 -CH N-OCH 2 -C 6 H 5 ,
  • HO-CH 2 -C (CH 3 ) N-OC 2 H 5
  • HO-CH 2 -C (CH 3 ) N-OCH 2 -C 6 H 5
  • the reaction is generally complete after 4 to 20 hours and can be worked up as usual by adding water and extracting the product with an organic solvent.
  • the reaction temperature can vary between 0 and 100 ° C, preferably 20 to 60 ° C. Dimethyl sulfoxide is particularly suitable as a solvent.
  • the bases used are carbonates and alcoholates of the alkali or alkaline earth metals, in particular potassium carbonate and potassium tert-butoxide.
  • R 2 is COOR 5 , where R 5 is a salt-forming cation such as, for example, alkali metal, alkaline earth metal, ammonium, are reacted with a substituted isoxazole or isothiazole-4-carboxylic acid I with one equivalent of the salt-binding agent Receive cations. If it is an inorganic cation such as sodium, potassium or calcium, it is expedient to dissolve or suspend the acid I in water or a lower alcohol and add an equivalent of the salt-forming cation.
  • the salt-forming cation can, for example, in the form of its
  • Hydroxide, carbonate or bicarbonate preferably in the form of its hydroxide
  • the reaction is generally complete after a few minutes and can be worked up as usual, for example by precipitation and suction or by concentrating the solution.
  • an organic solvent such as, for example, diethyl ether, tetrahydrofuran or dioxane, and the mixture is treated with an equivalent of ammonia, an amine or a tetraalkylammonium hydroxide.
  • amines that can be used, the following should be mentioned: methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, Decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octodecylamine, methylethylamine, methyl isopropylamine, methylhexylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, dimylheptylamine
  • tetraalkylammonium hydroxides e.g. Tetramethyl, tetraethyl or trimethylbenzylammonium hydroxide can be used.
  • the ammonium salt or organic ammonium salt precipitates out of the solution and can be isolated by customary methods. Alternatively, the salt can also be obtained by concentrating the solvent.
  • C 1 -C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,
  • C 3 -C 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, in particular cyclopropyl, cyclopentyl and cyclohexyl or C 3 -C 6 cycloalkenyl, in particular cyclopenten-1-yl, cyclopenten-2-yl, cyclohexene 1-yl and cyclohexen-2-yl, one to three times by C 1 -C 4 alkyl as mentioned above, in particular methyl, ethyl and 1-methylethyl or
  • C 1 -C 6 alkyl preferably C 1 -C 4 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1,1-dimethylethyl, which carries one of the following radicals: C 5 -C 6 cycloalkaniminoxy such as Cyclopentaniminoxy and Cyclohexaniminoxy, a 5- to 6-membered saturated or aromatic heterocyclic radical with one to three heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen (except unsubstituted thienyl, furyl, tetrahydrofuryl and pyridyl), two oxygen and / or sulfur atoms not can be directly adjacent, in particular tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyran-2-yl, tetrahydr
  • heterocycles have one more or can carry two of the following substituents: halogen such as fluorine, chlorine, bromine and iodine, in particular fluorine and chlorine, C 1 -C 3 -alkyl in particular methyl, ethyl, propyl and 1-methylethyl, C 1 -C 3 -alkoxy in particular methoxy , Ethoxy, 1-methylethoxy, or C 1 -C 3 alkoxycarbonyl, in particular methoxycarbonyl and eth
  • C 1 -C 6 -alkyl in particular C 1 -C 4 -alkyl such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl and 1, 1-dimethylethyl,
  • R 5 furthermore:
  • C 3 -C 8 haloalkynyl in particular C 3 -C 4 haloalkynyl, such as l-methyl-3-iodo-prop-2-ynyl and preferably 3-iodoprop-2-ynyl;
  • a radical- N CR 8 R 9 , where R 8 is C 1 -C 3 alkoxy, in particular methoxy, ethoxy and 1-methylethoxy, C 1 -C 4 haloalkyl, in particular
  • C 1 -C 4 alkyl in particular methyl, ethyl and 1-methylethyl; a radical NR 13 R 14 , where R 13 is hydrogen or C 1 -C 6 -alkyl as mentioned above, in particular methyl, ethyl, 1-methylethyl and 1,1-dimethylethyl and R 14 C 1 -C 6 -alkyl as mentioned above , in particular methyl, ethyl, 1-methylethyl and 1,1-dimethylethyl, which by C 1 -C 4 alkanoyl, in particular Formyi, acetyl and
  • Propionyl or benzoyl which can be substituted by halogen, in particular fluorine and chlorine or C 1 -C 3 -alkyl, in particular methyl; a rest -WZ with w
  • Hydrogen C 1 -C 6 alkyl, in particular methyl, ethyl, 1-methylethyl and 1,1-dimethylethyl or C 3 -C 8 cycloalkyl, in particular cyclopropyl and cyclopentyl;
  • C 1 -C 6 alkyl preferably C 1 -C 4 alkyl such as methyl, ethyl, 1-methylethyl and 1,1-dimethylethyl, which can carry one to three of the following substituents: hydroxy, halogen, C 1 -C 4 -alkoxy such as methoxy and 1,1-dimethylethoxy, C 1 -C 4 -alkylthio such as methylthio and 1,1-dimethylethylthio or di- (C 1 -C 4 ) -alkylamino, preferably di- (C 1 -C 2 ) alkylamino such as dimethylamino and diethylamino;
  • C 3 -C 8 cycloalkyl preferably C 3 -C 6 cycloalkyl such as cyclopropyl, cyclopentyl and cyclohexyl, one to three times by halogen such as fluorine, chlorine and bromine, C 1 -C 4 alkyl such as methyl and 1.1 -Dimethylethyl or partially or completely halogenated C 1 -C 4 alkyl such as fluoromethyl, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl and 2-chloro-1,1,2-trifluoroethyl may be substituted; R 4
  • halogen such as fluorine, chlorine and bromine
  • C 1 -C 4 alkyl such as methyl and 1.1 -Dimethylethyl or partially or completely halogenated C 1 -C 4 alkyl
  • C 1 -C 4 alkoxy such as methoxy, ethoxy, 1-methylethoxy, 1,1-dimethylethoxy; branched or unbranched C 1 -C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 1, 1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl,
  • C 3 -C 8 cycloalkyl preferably C 3 -C 6 cycloalkyl, in particular cyclopropyl, cyclopentyl and cyclohexyl, which can each carry one to three of the following radicals: halogen such as fluorine, chlorine and Bromine, nitro, cyano, C 1 -C 6 alkyl, preferably C 1 -C 4 alkyl such as methyl, ethyl and 1, 1-dimethylethyl, partially or completely halogenated C 1 -C 6 alkyl, preferably C 1 -C 4- haloalkyl such as fluoromethyl, trichloromethyl, 2-chloro-1,1,2-trifluoroethyl and pentafluoroethyl, C 1 -C 4 alkoxy such as methoxy 1,1-dimethylethoxy or partially or completely halogenated C 1 -C 4 alkoxy such as fluoromethoxy , Trichlorometh
  • Di (C 1 -C 4 ) alkylamino preferably di (C 1 -C 2 ) alkylamino such as
  • Dimethylamino and diethylamino Dimethylamino and diethylamino; a 5- to 6-membered saturated or aromatic heterocyclic radical containing one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-tetrahydropyranyl, 3 Tetrahydropyranyl, 4-tetrahydropyranyl, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl,
  • Phenyl which can carry one to four of the following groups: C 1 -C 4 -alkyl as mentioned above, in particular methyl, ethyl and 1-methylethyl; partially or fully halogenated C 1 -C 4 -alkyl as mentioned above, in particular trifluoromethyl and chlorodifluoromethyl; C 1 -C 4 alkoxy as mentioned above, in particular methoxy and ethoxy; partially or fully halogenated C 1 -C 4 alkoxy as mentioned above, in particular trifluoromethoxy, trichloromethoxy and pentafluoroethoxy; C 1 -C 4 alkylthio as mentioned above, in particular methylthio and ethylthio; partially or fully halogenated C 1 -C 4 -alkylthio as mentioned above, in particular difluoromethylthio, trifluoromethylthio and pentafluoroethylthio, halogen as mentioned above, in particular fluor
  • C 2 -C 4 alkanoyl such as trifluoroethanoyl, trichloroethanoyl, pentafluoropropanoyl, in particular trifluoroethanoyl or C 1 -C 4 alkoxycarbonyl such as methoxycarbonyl and ethoxycarbonyl;
  • Naphthyl which can be substituted one to three times by C 1 -C 4 -alkyl as mentioned above, in particular methyl and ethyl, or halogen such as fluorine and chlorine; R 3 and R 4 together form a C 4 -C 7 methylene chain, which can be interrupted by oxygen, sulfur or N-methyl
  • the compounds I or the herbicidal compositions comprising them can be sprayed, atomized, for example in the form of directly sprayable solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules. Dusting, scattering or pouring can be used.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the compounds I are generally suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions.
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, as well as coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated
  • Naphthalenes or their derivatives methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or strongly polar solvents, such as N, N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water.
  • Aqueous use forms can be made from emulsion concentrates,
  • Dispersions, pastes, wettable powders or water-dispersible granules can be prepared by adding water.
  • emulsions, pastes or oil dispersions the substrates as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of active substance, wetting agent, adhesive, dispersant or emulsifier and possibly solvent or oil can also be prepared which are suitable for dilution with water.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin-,
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and herbal products, such as
  • Cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers contain between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight, of active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the compounds I according to the invention can be formulated, for example, as follows:
  • 1.001 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient. V. 20 parts by weight of active ingredient No. 1.001 are with
  • the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient are 0.001 to 1, preferably 0.01 to 0.5 kg / ha of active substance (as), depending on the control target, the season, the target plants and the growth stage.
  • the compounds according to the invention or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants, for example the following crops are suitable: Botanical name German name
  • Gossypium hirsutum Gossypium arboreum, cotton
  • Nicotiana tabacum N. rustica
  • the isoxazole- and isothiazole-5-carboxamides I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • mixing partners are diazines, 4H-3, 1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3- dione derivatives,
  • the 5-tert-butylaminocarbonyl-3-methyl-isoxazole-4-carboxylic acid-3-iodopropargylester was also prepared in an analogous manner (Example No. 1,010). Yield 65%; M.p. 55-60 ° C. 1,4-bis (5-tert-butylaminocarbonyl-3-isopropyl-4-carbonyloxyisoxazole) butane
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the pots were lightly sprinkled to promote germination and growth, and then covered with clear plastic covers until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.
  • test plants were treated with the active ingredients suspended or emulsified in water only at a height of 3 to 15 cm, depending on the growth habit.
  • the application rate for post-emergence treatment was 1 or
  • the plants were kept at 10-25 ° C and 20-35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to the individual treatments was evaluated.
  • Veronica spp. Honorary prize types With 1.0 or 0.5 kg / ha a.S. used in the post-emergence process, with example 1,001 broad-leaved unwanted plants can be combated very well while being compatible with the example culture maize.
  • the compound 1.008 shows at application rates of 1 or 0.5 kg / ha a.S. very good effect against undesired plants, e.g. Chenopodium album, Polygonum persicaria and Veronica spp. with good tolerance in the example cultures Triticum aestivum (winter wheat) and maize.
  • compound 1.012 When used appropriately, compound 1.012 is very selective against the peanut culture and effectively combats undesired broad-leaved plants such as Amaranthus retroflexus, Chenopodium album and Solanum nigrum.
  • the example compound No. 1.003 is very effective at the application rates mentioned against Amaranthus retroflexus, Solanum nigrum and Veronica spp. with compatibility at the same time in the maize crop.

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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Des amides d'acide carboxylique isoxazolique et isothiazolique-5 ont la formule (I), dans laquelle X désigne oxygène ou soufre, R1 désigne hydrogène, alkyle, cycloalkyle, cycloalcényle, alcényle (le cas échéant à la liaison double époxydée), alcinyle, alcoxyle éventuellement substitués, un résidu hétérocyclique ou phényle; r2 représente une fonction carboxylique dérivée; et R3, R4 ont la notation donnée dans la description. L'invention concerne également des herbicides contenant les composés (I).
EP92902976A 1991-03-14 1992-01-29 Amides d'acide carboxylique isoxazolique et isothiazolique-5 Withdrawn EP0575341A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4108183A DE4108183A1 (de) 1991-03-14 1991-03-14 Isoxazol- und isothiazol-5-carbonsaeureamide
DE4108183 1991-03-14

Publications (1)

Publication Number Publication Date
EP0575341A1 true EP0575341A1 (fr) 1993-12-29

Family

ID=6427224

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92902976A Withdrawn EP0575341A1 (fr) 1991-03-14 1992-01-29 Amides d'acide carboxylique isoxazolique et isothiazolique-5

Country Status (7)

Country Link
US (1) US5399544A (fr)
EP (1) EP0575341A1 (fr)
JP (1) JPH06505228A (fr)
CA (1) CA2105974A1 (fr)
DE (1) DE4108183A1 (fr)
WO (1) WO1992016514A1 (fr)
ZA (1) ZA921865B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4406209A1 (de) 1994-02-25 1995-08-31 Basf Ag Cyanoisoxazole
EP0761654B1 (fr) * 1995-08-24 2003-06-18 Basf Aktiengesellschaft Dérivés d'isoxazole- et d'isothiazole-5-carboxamide, leur préparation et leur utilisation comme herbicides
JP2000204085A (ja) * 1998-11-13 2000-07-25 Nippon Bayer Agrochem Co Ltd イソチアゾ―ルカルボン酸誘導体および病害防除剤
EP2576635B1 (fr) * 2010-05-25 2017-09-13 Stepan Company Compositions de revêtement filmogènes contenant des solvants de coalescence carboxamides et leurs procédés d'utilisation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3506814A1 (de) * 1985-02-27 1986-08-28 Basf Ag, 6700 Ludwigshafen 5-isoxazolcarbonsaeureamide, ihre herstellung und verwendung als fungizide
DE3812225A1 (de) * 1988-04-13 1989-10-26 Basf Ag Isoxazol(isothiazol)-5-carbonsaeureamide
US5205854A (en) * 1988-04-13 1993-04-27 Basf Aktiengesellschaft Isoxazole(isothiazole)-5-carboxamides
EP0418667B1 (fr) * 1989-09-22 1995-08-16 BASF Aktiengesellschaft Amides d'acides carboxyliques
US5201932A (en) * 1989-09-22 1993-04-13 Basf Aktiengesellschaft Carboxamides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9216514A1 *

Also Published As

Publication number Publication date
ZA921865B (en) 1993-09-13
WO1992016514A1 (fr) 1992-10-01
DE4108183A1 (de) 1992-09-17
CA2105974A1 (fr) 1992-09-15
JPH06505228A (ja) 1994-06-16
US5399544A (en) 1995-03-21

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