EP1697329A1 - Carboxamides optiquement actifs et leur utilisation pour lutter contre des micro-organismes indesirables - Google Patents

Carboxamides optiquement actifs et leur utilisation pour lutter contre des micro-organismes indesirables

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Publication number
EP1697329A1
EP1697329A1 EP04803543A EP04803543A EP1697329A1 EP 1697329 A1 EP1697329 A1 EP 1697329A1 EP 04803543 A EP04803543 A EP 04803543A EP 04803543 A EP04803543 A EP 04803543A EP 1697329 A1 EP1697329 A1 EP 1697329A1
Authority
EP
European Patent Office
Prior art keywords
formula
optically active
methyl
trifluoromethyl
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04803543A
Other languages
German (de)
English (en)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Heiko Rieck
Benoit Hartmann
Jörg Nico GREUL
Ulrike Wachendorff-Neumann
Peter Dahmen
Karl-Heinz Kuck
Anne Suty-Heinze
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 CropScience AG
Original Assignee
Bayer CropScience 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
Priority claimed from DE102004005317A external-priority patent/DE102004005317A1/de
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1697329A1 publication Critical patent/EP1697329A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/16—Halogen atoms or nitro radicals
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Definitions

  • the present invention relates to new optically active carboxamides, several processes for their preparation and their use for controlling unwanted microorganisms.
  • R represents hydrogen, fluorine, chlorine, methyl, ethyl or trifluoromethyl
  • R 1 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl
  • a for the rest of the formula (AI) (AI) is in which R 2 represents methyl, trifluoromethyl or difluoromethyl, R 3 represents hydrogen, fluorine or chlorine, or A represents the rest of the formula (A2)
  • R 4 represents trifluoromethyl, chlorine, bromine or iodine, or
  • (A3) stands in which R 5 represents methyl, trifluoromethyl or difluoromethyl.
  • the compounds of formula (I) have the S configuration [S atom labeled C in formula (I)].
  • optically active carboxamides of the formula (I) are obtained by a) carboxylic acid derivatives of the formula (H) O ⁇ . ⁇ - -x, 'W in which A has the meanings given above and X 1 for Halogen or hydroxy, with an amine of the formula (Hl)
  • R, M and A have the meanings given above, or mixtures of both compounds in the presence of an optically active catalyst or a catalyst with optically active ligand.
  • the new optically active carboxamides of the formula (I) have very good microbicidal properties and can be used to combat unwanted microorganisms both in crop protection and in material protection.
  • the new optically active carboxamides of the formula (I) are notable in particular for their improved action or lower application rate and thus lower environmental impact and reduced toxicity.
  • optically active carboxamides according to the invention are generally defined by the formula (I).
  • Preferred radical definitions of the formulas above and below are given in Given below. These definitions apply equally to the end products of the formula (I) and to all intermediates.
  • R preferably represents hydrogen, methyl or ethyl.
  • R particularly preferably represents hydrogen or methyl.
  • M preferably stands for M-1.
  • M also preferably represents M-2.
  • M also preferably stands for M-3.
  • M also preferably represents M-4.
  • M particularly preferably represents Ml, where R 1 represents hydrogen.
  • M is also particularly preferably M-2, where R 1 is hydrogen.
  • R 1 preferably represents hydrogen.
  • R 1 also preferably represents fluorine, fluorine being particularly preferably in the 4-, 5- or 6-position, very particularly preferably in the 4- or 6-position, in particular in the 4-position of the anilide residue [cf. formula (I) above].
  • A preferably represents the radical A 1.
  • A also preferably represents the radical A2.
  • A also preferably stands for the rest A3.
  • R 2 preferably represents methyl or trifluoromethyl.
  • R 3 preferably represents hydrogen or fluorine.
  • R 4 preferably represents trifluoromethyl or iodine.
  • R 5 preferably represents trifluoromethyl.
  • Preferred, particularly preferred or very particularly preferred are compounds of the formula (T) which each carry the substituents mentioned under preferred, particularly preferred or very particularly preferred.
  • Formula (H) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out process (a) according to the invention.
  • A has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for A in connection with the description of the compounds of the formula (I) according to the invention.
  • X 1 preferably represents chlorine, bromine or hydroxy, particularly preferably chlorine.
  • the carboxylic acid derivatives of the formula (H) are known (cf. WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313).
  • Formula (IH) provides a general definition of the amines which are further required as starting materials for carrying out process (a) according to the invention.
  • R and M have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or very particularly preferred for these radicals were specified.
  • M 1 represents Ml can be prepared, for example, by d) in a first step an aniline derivative of the formula (VI)
  • the hydrogenation of compounds of the formula (VIH) can, if appropriate, also take place in the presence of an optically active catalyst or in the presence of a catalyst and an optically active ligand and thus provide optically active compounds of the formula (Hl-a).
  • optically active acids can also be fractionally crystallized in the presence of optically active acids with salt formation, after which enantiomerically pure or enriched compounds of the formula (HI-a) are released.
  • All optically active acids are generally suitable as acids for the formation of diastereomeric salts. Examples include: (IS) - (+) - camphor-10-sulfonic acid, (1R) - (-) - camphor-10-sulfonic acid, S, S - (-) - tartaric acid, R, R - (+) - Tartaric acid, R-lactic acid, S-lactic acid or optically active amino acids, preferably naturally occurring optically active amino acids.
  • Formula (VI) provides a general definition of the aniline derivatives required as starting materials for carrying out process (d) according to the invention.
  • R 1 has preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or very particularly for these radicals were given preferably.
  • Formula (VH) provides a general definition of the alkenes still required as starting materials for carrying out process (d) according to the invention.
  • R preferably, particularly preferably or very particularly preferably those meanings which have already been given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention ,
  • Alkenes of the formula (VH) are known or can be obtained by known methods.
  • the formula (VuT) generally defines the alkenanilines which have passed through as intermediates when carrying out process (d) according to the invention.
  • R and R 1 have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or very particularly for these radicals were given preferably.
  • Alkenanilines of the formula (VEIT) are known and / or can be obtained by known processes.
  • M 2 stands for M-2, M-3 or M-4, can be prepared, for example, by e) racemic amines of the formula (Hl-b-rac)
  • racemic amines of the formula (Hl-b-rac) are known and / or can be obtained by known processes (cf. e.g. WO 02/38542, EP-A 1 036793 and EP-A 0 737 682).
  • the formula (I-rac) provides a general definition of the racemic compounds required as starting materials when carrying out process (b) according to the invention.
  • R, M and A are preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or very particularly preferred for these radicals were called.
  • the racemic compounds of the formula (I-rac) used in carrying out process (b) according to the invention are known and can be prepared by known processes (cf., for example, WO 03/010149, WO 02/38542 and DE-A 10229 595).
  • Racemic compounds of the formula (I-rac) can be obtained, for example, by comparing carboxylic acid derivatives of the formula (H) with racemic compounds of the formulas (IH-a-rac) or (Hl-b-rac) in analogy to that implementing method (a) according to the invention.
  • the method (b) according to the invention is carried out by preparative chromatography methods, preferably by the high performance liquid chromatography (HPLC) method.
  • HPLC high performance liquid chromatography
  • a chiral stationary silica gel phase is used.
  • Chiracel OD ® has proven to be particularly suitable for the separation of the compounds of the formula (I-rac) into the two enantiomers. This separation material is commercially available. However, other stationary phases can also be used as the chromatography material.
  • optically active acids are generally suitable for the formation of diastereomeric salts.
  • examples include: (IS) - (+) - camphor-10-sulfonic acid, (IR) - (-) - camphor-10-sulfonic acid, S, S - (-) - tartaric acid, R, R - (+) - Tartaric acid, R-lactic acid, S-lactic acid or optically active amino acids, preferably naturally occurring optically active amino acids.
  • process (c) can be illustrated by the following formula:
  • Formula (IV) and (V) provide a general definition of the compounds required as starting materials when carrying out process (c) according to the invention.
  • R, M and A have preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred or very particularly preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention were.
  • Compounds of the formula (TV) and (V) (or mixtures of these compounds) are obtained by f) carboxylic acid derivatives of the formula H) in which A has the meanings given above and X 1 represents halogen or hydroxy, either with an alkenaniline of the formula (VTfl)
  • Formula (TX) provides a general definition of the alkenanilines which are alternatively required as starting materials for carrying out process (f) according to the invention.
  • R and R ! preferred, particularly preferred or very particularly preferred those meanings which are already in connection with the description of the compounds of the formula according to the invention
  • Alkenanilines of the formula (IX) are known and / or can be obtained by known processes.
  • Formula (X) provides a general definition of the carboxamides required as starting materials for carrying out process (g) according to the invention.
  • M and A have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or very particularly preferred for these radicals were specified.
  • Carboxamides of the formula (X) are known and / or can be obtained by known methods (cf. WO 03/010149).
  • Alkenes of the formula (XT) are known or can be obtained by known methods.
  • Suitable diluents for carrying out processes (a) and (f) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as e.g. Petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, e.g.
  • Chlorobenzene dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N- Dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
  • Ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethan
  • Processes (a) and (f) according to the invention are optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as e.g.
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicyclound
  • Processes (a) and (f) according to the invention are optionally carried out in the presence of a suitable condensing agent.
  • a suitable condensing agent All condensation agents that can normally be used for such amidation reactions are suitable as such.
  • Acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride may be mentioned as examples;
  • Anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfate fonylchlorid;
  • Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimid
  • Processes (a) and (f) according to the invention are optionally carried out in the presence of a catalyst.
  • a catalyst examples include 4-dimethylaminopyridine, 1-hydroxy-benzotriazole or dimethylformamide.
  • reaction temperatures can be varied within a substantial range when carrying out processes (a) and (f) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • Suitable eluents for carrying out process (b) according to the invention are all customary inert, organic solvents and mixtures of these, or else mixtures of these with water.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, can preferably be used; Dichloromethane, chloroform; Alcohols, such as methanol, ethanol, propanol; Nitriles such as acetonitrile; Esters such as methyl acetate or ethyl acetate.
  • aliphatic hydrocarbons such as hexane or heptane
  • alcohols such as methanol or propanol, very particularly preferably n-heptane and isopropanol or mixtures of these.
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between 10 ° C and 60 ° C, preferably between 10 ° C and 40 ° C, particularly preferably at room temperature.
  • n-hexane or cyclohexane and ethyl acetate are used as eluents, the composition of which must be adapted to the particular compound to be purified.
  • Suitable diluents for carrying out the first step of process (d) according to the invention and of process (g) according to the invention are all inert organic solvents. These preferably include nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide.
  • nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile
  • amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide.
  • the first step of process (d) according to the invention and process (g) according to the invention are optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as e.g.
  • DABCO diazabicyclooctane
  • DBU diazabicyclonones
  • DBU diazabic
  • the first step of process (d) according to the invention and process (g) according to the invention are carried out in the presence of one or more catalysts.
  • Palladium salts or complexes are particularly suitable for this.
  • Palladium chloride, palladium acetate, tetrakis (1riphenylphosphine) palladium or bis (triphenylphosphine) palladium dichloride are preferably used for this purpose.
  • a palladium complex can also be generated in the reaction mixture if a palladium salt and a complex ligand are added separately to the reaction.
  • Organophosphorus compounds are preferred as ligands.
  • Examples include: triphenylphosphine, tri-o-tolylphosphine, 2,2'-bis (diphenylphosphino) -l, r-binaphthyl, dicyclohexylphosphine biphenyl, 1,4-bis (diphenylphosphino) butane, bisdiphenylphosphinoferrocene, di (tert- butylphosphino) biphenyl, di (cyclo- hexylphosphino) biphenyl, 2-dicyclohexylphosphino-2 '-N, N-dimethylaminobiphenyl, tricyclohexylphosphine, tri-tert-butylphosphine.
  • ligands can also be dispensed with.
  • the first step of process (d) according to the invention and process (g) according to the invention are also optionally carried out in the presence of a further metal salt, such as copper salts, for example copper (I) iodide.
  • a further metal salt such as copper salts, for example copper (I) iodide.
  • reaction temperatures can be varied within a substantial range. In general, temperatures from 20 ° C to 180 ° C, preferably at temperatures from 50 ° C to 150 ° C.
  • Suitable diluents for carrying out process (c) according to the invention and the second step (hydrogenation) of process (d) according to the invention are all inert organic solvents. These preferably include aliphatic or alicyclic hydrocarbons, e.g.
  • Ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether,
  • the second step (hydrogenation) of process (d) according to the invention is carried out in the presence of a catalyst.
  • catalysts which are usually used for hydrogenations are suitable as such. Examples include: Raney nickel, palladium, ruthenium or platinum, optionally on a carrier material, such as e.g. Activated carbon.
  • the hydrogenation in the second step of process (d) according to the invention can also be carried out in the presence of triethylsilane instead of in the presence of hydrogen in combination with a catalyst.
  • reaction temperatures can be varied within a substantial range when carrying out process (c) according to the invention and the second step of process (d) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 100 ° C.
  • Process (c) according to the invention and the second step of process (d) according to the invention are carried out under a hydrogen pressure between 0.5 and 200 bar, preferably between 2 and 50 bar, particularly preferably between 3 and 10 bar.
  • Suitable eluents for carrying out the third step of process (d) according to the invention or of process (e) according to the invention are all customary inert, organic solvents and mixtures of these or, if appropriate, mixtures with water.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, can preferably be used; Dichloromethane, chloroform; Alcohols, such as methanol, ethanol, propanol; Nitriles such as acetonitrile; Esters such as methyl acetate or ethyl acetate.
  • aliphatic hydrocarbons such as hexane or heptane
  • alcohols such as methanol or propanol, very particularly preferably n-heptane and isopropanol or mixtures of these.
  • reaction temperatures can be varied over a wide range when carrying out the third step of process (d) or process (e) according to the invention.
  • temperatures between 10 ° C and 60 ° C, preferably between 10 ° C and 40 ° C, particularly preferably at room temperature.
  • an approximately 1% strength solution of the racemic compound (IH-a-rac) or (Hl-b-rac) is generally used for the chromatographic separation is used.
  • concentrations it is also possible to use other concentrations.
  • the processing takes place according to usual Methods. In general, the procedure is such that the eluate is largely concentrated, solid constituents are filtered off and dried after washing with n-heptane. If necessary, the residue is chromatographically freed of any impurities still present. Mixtures of n-hexane or cyclohexane and ethyl acetate are used as eluents, the composition of which must be adapted to the particular compound to be purified.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species e.g. Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species e.g. Pseudomonas syringae pv. Lachrymans;
  • Erwinia species e.g. Erwinia amylovora
  • Pythium species e.g. Pythium ultimum
  • Phytophthora species e.g. Phytophthora infestans
  • Pseudoperonospora species e.g. Pseudoperonospora humuli or
  • Plasmopara species e.g. Plasmopara viticola
  • Bremia species e.g. Bremia lactucae
  • Peronospora species e.g. Peronospora pisi or P. brassicae;
  • Erysiphe species e.g. Erysiphe graminis
  • Sphaerotheca species e.g. Sphaerotheca fuliginea
  • Podosphaera species e.g. Podosphaera leucotricha
  • Venturia species such as Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species e.g. Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species e.g. Uromyces appendiculatus
  • Puccinia species e.g. Puccinia recondita
  • Sclerotinia species e.g. Sclerotinia sclerotiorum
  • Tilletia species such as Tilletia caries
  • Ustilago species e.g. Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as e.g. Pellicularia sasakii; Pyricularia species, e.g. Pyricularia oryzae;
  • Fusarium species e.g. Fusarium culmorum
  • Botrytis species e.g. Botrytis cinerea
  • Septoria species e.g. Septoria nodorum
  • Leptosphaeria species e.g. Leptosphaeria nodorum
  • Cercospora species e.g. Cercospora canescens
  • Alternaria species e.g. Alternaria brassicae
  • Pseudocercosporella species e.g. Pseudocercosporella herpotrichoides
  • Rhizoctonia species e.g. Rhizoctonia solani.
  • the active compounds according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can thus be used to protect plants against attack by the pests mentioned within a certain period of time after the treatment.
  • the period of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.
  • the good plant tolerance of the active ingredients in the fight against plant diseases necessary concentrations allow a treatment of above-ground parts of plants, of plant and seed, and the soil.
  • the active compounds according to the invention can be used with particularly good results in combating cereal diseases, such as e.g. against Puccinia species and diseases in wine, fruit and vegetable growing, e.g. against Botrytis, Venturia or Alternaria species.
  • cereal diseases such as e.g. against Puccinia species and diseases in wine, fruit and vegetable growing, e.g. against Botrytis, Venturia or Alternaria species.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are understood to mean non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paint and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
  • parts of production systems for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned, for example:
  • Alternaria such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV Cold and warm fog formulations.
  • These formulations 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, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally 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.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol
  • 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 those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Solid carrier materials come into question: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Solid carriers for granules are possible: e.g.
  • emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 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 in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • 2-Phenyl ⁇ henol 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos; binapacryl;
  • epoxiconazole ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; Fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph; fluoromides; Fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl
  • isoprothiolane Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone;
  • mepanipyrim mepronil; metalaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam;
  • metiram metiram
  • metominostrobin Metsulfovax
  • mildiomycin myclobutanil
  • myclozoline myclozoline
  • natamycin metiram
  • nicobifen Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefurazoate; penconazole; pencycuron;
  • phosdiphen phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz; Procymidones; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole;
  • pyraclostrobin Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; Sp oxamine; Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl;
  • Acetylcholinesterase (AChE) inhibitors 1.1 carbamates (for example alanycarb, aldicarb, aldoxycarb, Allyxycarb, aminocarb, azamethiphos, benzyl diocarb, Ben Positionacarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, carbaryl, carbofuran, carbosulfan, Chloethocarb, coumaphos, Cyanofenphos, Cyanophos , Dimetilan, Ethiofencarb, Fenobarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Tri ethacarbylCarb
  • Organophosphates e.g. acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-maphos-ethyl) , Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethi- on , Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion
  • Pyrethroids e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioemanomethrin, biopermethrin, bioresmethrin, chlova-porthrin, cis , Cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha, beta, theta, zeta), cyphenothrin, DDT, deltamethrin, empenetrin (lR-isomer), esfenproxerate , Fenfluthrin, Fenpropathrin, Fenpyrithrin,
  • Oxadiazines e.g. indoxacarb
  • Acetylcholine receptor agonist antagonists e.g. indoxacarb
  • Chloronicotinyls / neonicotinoids e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam
  • Fiprole e.g. Acetoprole, Ethiprole, Fipronil, Vaniliprole
  • Chloride channel activators e.g. Acetoprole, Ethiprole, Fipronil, Vaniliprole
  • Mectins e.g. abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, mitemectin, milbemycin
  • Diacylhydrazine e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide
  • Benzoyl ureas e.g. bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, tri-flumuron
  • Buprofezin e.g. bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, tri-flumuron
  • METI's e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad
  • Inhibitors of fat synthesis 16.1 tetronic acids (e.g. spirodiclofen, spiromesifen)
  • 16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg.-No .: 382608-10-8) and Carbonic acid, cis-3- ( 2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg.No .: 203313-25-1)] 17.
  • Carboxamides e.g. flonicamide
  • Octopaminergic agonists e.g. Amitraz
  • Bios, hormones or pheromones e.g. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhician spec, Paecilomyces spec, Thuringiensin, Verticillium spec.
  • Fumigants e.g. aluminum phosphide, methyl bromide, sulfuryl fluoride
  • Selective feeding inhibitors e.g. cryolite, flonicamide, pymetrozine
  • mite growth inhibitors e.g. clofentezine, etoxazole, hexythiazox
  • the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad spectrum of antifungal effects, in particular against dermatophytes and shoot fungi, mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillophytonophytonyspecytonyspecyspecific trichomes mentagrophytes, microsporon species such as microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillophytonophytonyspecytonyspecyspecific trichomes mentagrophytes
  • microsporon species such as microsporon canis and audouinii.
  • the list of these fungi is in no way
  • 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, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to prepare the active ingredient or the active ingredient itself Inject soil. It can also be the seed of the plants are treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 gha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • plants and their parts can be treated.
  • plant species and plant varieties and their parts occurring wildly or obtained by conventional biological breeding methods, such as crossing or protoplast fusion, are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or one Enhancing the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher Nutritional value of the crop products, higher shelf life and / or workability of the crop products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, Increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvest products, longer shelf life and / or Processability of the crop products Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or vire n and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed.
  • plants The properties (“traits”) which are particularly emphasized are the plants' increased defense against insects, arachnids, nematodes and snails due to toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryIA (a) , CryIA (b), Cry ⁇ A (c), CryHA, CryHIA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter, "plants").
  • the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytotoxins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as traits.
  • Traits are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example” PAT "gene).
  • the genes imparting the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants.
  • Examples of “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YTJELD GARD® (eg corn , Cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g.
  • rapeseed rapeseed
  • HVH® tolerance to Imidazolinone
  • STS® tolerance to sulfonylureas such as maize
  • the herbicide-resistant plants include the varieties marketed under the name Clearf ⁇ eld® (eg maize).
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the solution is then chromatographed on the Chiralcel OD ® silica gel phase [manufacturer: Daicel (Japan), column dimension: 500 mm ⁇ 40 mm (ID), particle size: 20 ⁇ m, flow rate: 40 ml / min] with n-heptane / Isopropanol 9: 1 (v / v) as an eluent according to the principle of high performance liquid chromatography (HPLC). To separate the entire amount, 5 ml (corresponding to 40 mg of the racemate) are applied to the column every 30 minutes. The compounds are detected with a UV detector at a wavelength of 210 nm.
  • logP values specified in the tables and manufacturing examples above are determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. applications
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at approximately 21.degree. C. and a relative atmospheric humidity of approximately 90%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Botrytis test (bean) / protective
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

La présente invention concerne de nouveaux carboxamides optiquement actifs de formule (I) dans laquelle R, M et A possèdent la signification figurant dans le descriptif, plusieurs procédés de production de ces substances et leur utilisation pour lutter contre des micro-organismes indésirables, ainsi que des nouveaux produits intermédiaires et leur production.
EP04803543A 2003-12-18 2004-12-06 Carboxamides optiquement actifs et leur utilisation pour lutter contre des micro-organismes indesirables Withdrawn EP1697329A1 (fr)

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DE10359511 2003-12-18
DE102004004141 2004-01-28
DE102004005317A DE102004005317A1 (de) 2003-12-18 2004-02-04 Optisch aktive Carboxamide
PCT/EP2004/013834 WO2005058839A1 (fr) 2003-12-18 2004-12-06 Carboxamides optiquement actifs et leur utilisation pour lutter contre des micro-organismes indesirables

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DE102005022147A1 (de) * 2005-04-28 2006-11-02 Bayer Cropscience Ag Wirkstoffkombinationen
EP2027773A1 (fr) * 2007-08-24 2009-02-25 Bayer CropScience AG Utilisation de N-[2-(1,3-diméthylbutyl)phényl]-5-fluor-1,3-diméthyl-1H-pyrazole-4-carboxamide
EP2272346A1 (fr) * 2009-07-08 2011-01-12 LANXESS Deutschland GmbH Penthiopyrade pour la protection du bois
JP5706179B2 (ja) * 2010-08-20 2015-04-22 住友化学株式会社 有害節足動物防除組成物及び有害節足動物の防除方法
WO2012055673A1 (fr) 2010-10-25 2012-05-03 Lanxess Deutschland Gmbh Penflufène en tant qu'agent de protection du bois contre les basidiomycètes détruisant le bois
EP2443928A1 (fr) 2010-10-25 2012-04-25 LANXESS Deutschland GmbH Mélanges fongicides de penflufen
EP2443927A1 (fr) 2010-10-25 2012-04-25 LANXESS Deutschland GmbH Penflufen comme moyen de protection du bois contre les basidiomycètes détruisant le bois
LT2632267T (lt) 2010-10-25 2016-12-27 Lanxess Deutschland Gmbh Fungicidiniai penfufeno mišiniai
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US20070276022A1 (en) 2007-11-29
WO2005058839A1 (fr) 2005-06-30
KR20060126713A (ko) 2006-12-08
AR047148A1 (es) 2006-01-11
CA2549821A1 (fr) 2005-06-30
MXPA06006744A (es) 2006-08-18
AU2004299217A1 (en) 2005-06-30
JP2007516261A (ja) 2007-06-21

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