EP1569894A2 - 2-oxyamino-1-cyclopenten-1-nitrile als materialschutzmittel - Google Patents

2-oxyamino-1-cyclopenten-1-nitrile als materialschutzmittel

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Publication number
EP1569894A2
EP1569894A2 EP03789076A EP03789076A EP1569894A2 EP 1569894 A2 EP1569894 A2 EP 1569894A2 EP 03789076 A EP03789076 A EP 03789076A EP 03789076 A EP03789076 A EP 03789076A EP 1569894 A2 EP1569894 A2 EP 1569894A2
Authority
EP
European Patent Office
Prior art keywords
compounds
formula
alkyl
cyano
nitro
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Withdrawn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
EP03789076A
Other languages
German (de)
English (en)
French (fr)
Inventor
Rainer Bruns
Oliver Kretschik
Martin Kugler
Peter Wachtler
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.)
Lanxess Deutschland GmbH
Original Assignee
Lanxess Deutschland GmbH
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 Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH
Publication of EP1569894A2 publication Critical patent/EP1569894A2/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed 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
    • 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
    • A01N37/34—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

Definitions

  • the present invention relates to new 2-oxyamino-1-cyclopentene-1-nitriles, processes for their preparation, their use in combating undesirable
  • the present invention relates to 2-oxyamino-1-cyclopentene-1-nitriles of the general formula (I)
  • R and R independently of one another represent hydrogen, halogen, cyano, nitro or in each case optionally substituted alkyl, alkenyl, alkynyl, aryl, heterocyclic or -COR 3 ,
  • R 3 represents in each case optionally substituted alkyl, alkenyl, alkynyl, aryl or heterocyclyl,
  • Hydrophosphonates or hydrosulfates are Hydrophosphonates or hydrosulfates.
  • the saturated and unsaturated hydrocarbon radicals such as alkyl, alkenyl or alkynyl
  • heteroatoms such as in alkoxy, haloalkoxy, haloalkylthio or alkylthio
  • composite terms such as alkyl- or dialkylamino or branched, unsubstituted or substituted one or more times, identically or differently.
  • alkyl radicals can in each case be the same or different.
  • Aryl generally stands for aromatic mono- or polycyclic unsubstituted or mono- or polysubstituted or substituted hydrocarbon rings, such as phenyl, naphthyl, anthranyl, phenanthranyl, preferably phenyl or
  • Naphthyl especially phenyl.
  • haloalkyl, haloalkoxy and haloalkylthio may each contain the same or different halogen atoms.
  • Halogen generally represents fluorine, chlorine, bromine, especially fluorine or chlorine.
  • Heterocyclyl generally stands for saturated and unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member is a hetero atom, ie an atom other than carbon, which are unsubstituted or substituted one or more times, identically or differently. If the ring contains several heteroatoms, these can be the same or different.
  • Heteroatoms are preferably oxygen,
  • the ring-shaped compounds together with further carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system.
  • a polycyclic ring system can be linked via the heterocyclic ring or via a fused-on carbocyclic ring.
  • Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.
  • Preferred heterocyclyl radicals are pyridyl, pyrimidyl, thienyl, furyl and pyrryl.
  • Rl and R ⁇ independently of one another represent hydrogen, halogen, cyano, nitro or in each case optionally substituted Ci-Cg-alkyl, C2-Cg-alkenyl, C2-Cg-alkynyl, phenyl or heterocyclyl, or represent a radical -COR ⁇ ,
  • R3 stands for hydrogen, halogen, cyano, nitro or for optionally substituted Ci-Cg-alkyl, C2-Cg-alkenyl, C2-Cg-alkynyl, phenyl or heterocyclyl.
  • R 1 and R 2 independently of one another are hydrogen, halogen, cyano, nitro, or for C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl, which in each case optionally one or more times, the same or different, is substituted by halogen, nitro, cyano, phenyl, -CC 6 alkoxy, Ci-Cö-haloalkoxy with 1 to 9 same or different halogen atoms, d-Cö-alkylthio, C ⁇ -C 6 -haloalkylthio with 1 to 9 identical or different halogen atoms, Ci-Ce acyl, d-C ⁇ -acyloxy, dC 6 -alkoxy-carbonyl or amino, C ⁇ -C 6 alkylamino, di-d-C ⁇ -alkylamino, phenylamino or diphenylamino;
  • phenyl which is optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, Ci-Cs-alkyl, C ⁇ - d-haloalkyl having 1 to 6 identical or different halogen atoms, Ci-C 5 alkoxy , d-Cs-haloalkoxy with 1 to 6 identical or different halogen atoms, Ci-Cs-alkylthio, Ci-Cs-haloalkylthio with 1 to 6 identical or different halogen atoms, amino, Ci-C ⁇ -alkylamino di- dC ö -alkylamino, Phenylamino or diphenylamino;
  • heterocyclyl which is optionally mono- or polysubstituted, identical or different, substituted by halogen, cyano, nitro, C 1 -C 5 -alkyl,
  • Ct-d-haloalkyl with 1 to 6 identical or different halogen atoms Ci-Cs-alkoxy, dC 5 -haloalkoxy with 1 to 6 identical or different halogen atoms, d-Cs-alkylthio, d-Cs-haloalkylthio with 1 to 6 identical or different halogen atoms, amino, Ci-Cö-alkylamino or di-Ci-Cö-alkylarnino;
  • heterocyclyl which is optionally monosubstituted or polysubstituted by identical or different, substituted by halogen, cyano, nitro, C1-C 5 - same or alkyl, Ci-d-haloalkyl having 1 to 6 different halogen atoms, dd alkoxy, Ci- Cs-haloalkoxy with 1 to 6 identical or different halogen atoms, Ci-Cs-alkylthio, dd-haloalkylthio with 1 to 6 identical or different halogen atoms, amino, Ci-C ö alkylamino or
  • Di-dC ⁇ -alkylamino is.
  • R 1 and R 2 independently of one another for hydrogen, fluorine, chlorine, bromine, cyano,
  • dC ö -alkenyl, CrC ö -alkynyl which is in each case optionally mono- to tetrasubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, nitro, cyano, phenyl, C ⁇ -C -A ⁇ koxy , dC - haloalkoxy with 1 to 7 identical or different fluorine, chlorine or bromine atoms, dC 4 -alkylthio, -C-C 4 -haloalkylthio with 1 to 7 identical or different fluorine, chlorine or bromine atoms, C j -C 4 acyl, C j -C 4 - are alkylamino, phenylamino or diphenylamino - C 4 acyloxy, C 1 -C 4 -alkoxy-carbonyl, amino, C 1 -C 4 alkylamino, di
  • phenyl which is optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, -CC - Alkyl, C ⁇ -C 4 haloalkyl having 1 to 4 identical or different fluorine, chlorine or bromine atoms, dC alkoxy, C 1 -C 4 -haloalkoxy having 1 to 4 identical or different fluorine, chlorine or bromine atoms, dC - Alkylthio, dC -haloalkylthio with 1 to 4 identical or different fluorine, chlorine or bromine atoms, amino, dC 4 -alkylamino or di-dC - alkylamino;
  • heterocyclyl which is optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, dC 4 -haloalkyl with 1 to 4 identical or different fluorine,
  • Chlorine or bromine atoms dC alkoxy, C 1 -C 4 haloalkoxy with 1 to 4 identical or different fluorine, chlorine or bromine atoms, C 1 -C 4 alkylthio, dC 4 haloalkylthio with 1 to 4 identical or different fluorine , Chlorine or bromine atoms, amino, C 1 -C -alkylamino or di-dC - alkylamino;
  • phenyl which is optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, d-C -
  • heterocyclyl which is optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, d-C-alkyl, Ct-C 4 -haloalkyl with 1 to 4 identical or different fluorine, chlorine - Or bromine atoms, -CC alkoxy, dC -haloalkoxy with 1 to 4 identical or different fluorine, chlorine or bromine atoms, -C-alkylthio, -C-C 4 -haloalkylthio with 1 to 4 identical or different fluorine, Chlorine or bromine atoms, amino, dC 4 - alkylamino or Di-C ⁇ -C - alkylamino.
  • R 1 and R 2 independently of one another for hydrogen, or for C 1 -C 4 -alkyl, C 2 -C - alkenyl, dd-alkynyl, which are each optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine Nitro
  • phenyl which is optionally mono- to disubstituted, identical or different, substituted by fluorine, chlorine, bromine, cyano, nitro, dC 2 -alkyl, Cj-haloalkyl with 1 to 3 identical or different fluorine, or
  • Chlorine atoms amino, monomethylamino or dimethylamino
  • heterocyclyl which is optionally substituted once or twice, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 2 -alkyl, C 1 -haloalkyl having 1 to 3 identical or different fluorine or chlorine atoms, Amino, monomethylamino or dimethylamino; or represent -COR 3 , where
  • R 3 is hydrogen, or is dC 5 -alkyl, C 2 -C 5 -alkenyl, C 2 -C 5 -alkynyl, which is in each case optionally substituted once to three times, identically or differently, by fluorine, chlorine, bromine, nitro, Cyano, or phenyl;
  • phenyl which is optionally substituted once or twice, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 2 -alkyl, C 1 -haloalkyl with 1 to 3 identical or different fluorine, or
  • Chlorine atoms methoxy, amino, monomethylamino, or dimethylamino
  • Ci-haloalkyl having 1 to 3 identical or different fluorine or chlorine atoms, amino, monomethylamino, or dimethylamino.
  • R 1 and R 2 independently of one another represent hydrogen, Ci-Cs-alkyl, or benzyl, 4-methylbenzyl, 4-chlorobenzyl, 4-fluorobenzyl, 4-methoxybenzyl;
  • phenyl which is optionally substituted by fluorine, chlorine, alkyl, Ci-haloalkyl with 1 to 3 identical or different fluorine, or
  • Chlorine atoms are available
  • R 3 represents d-Cs-alkyl, which is optionally monosubstituted to trisubstituted by identical or different substituents by fluorine or chlorine; or represents phenyl, which is optionally substituted by fluorine, chlorine, methoxy, alkyl, d-haloalkyl having 1 to 3 identical or different fluorine or chlorine atoms;
  • Residues specified radical definitions are replaced independently of the combination specified, as desired with radical definitions of other combinations.
  • residual definitions from each preferred area can also be omitted.
  • R 1 and R 2 do not simultaneously represent -COR 3 ,
  • Possible diluents added are both water and all customary organic solvents. These preferably include alcohols such as ethanol or propanol, hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene, methylene chloride or chloroform, ketones such as acetone or butanone, ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether, dimethoxyethane or dioxane, Nitriles such as acetonitrile, amides such as NN-dimethylformamide, NN-dimethylacetamide or N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, sulfones such as sulfolane, and esters such as ethyl acetate or methyl acetate.
  • alcohols such as ethanol or propanol
  • hydrocarbons such
  • the solvents can be used individually or in any mixture with one another.
  • Weak organic bases such as, for example, tertiary amines, preferably triethylamine, diethylamine, dimethylpyridine and pyridine or mixtures thereof, are suitable as the base.
  • the reaction temperature can be varied within a wide temperature range in the manufacturing process. In general, one works between -30 ° C and + 150 ° C, preferably between 0 ° C and + 110 ° C.
  • R 1 and R 2 are the same and represent -COR 3 ,
  • Possible diluents added are both water and all customary organic solvents. These preferably include
  • Alcohols such as ethanol or propanol, hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene, methylene chloride or chloroform, ketones such as acetone or butanone, ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether, dimethoxyethane or dioxane, nitriles such as acetonitrile , Amides such as NN-dimethylformamide, NN-dimethylacetamide or N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, sulfones such as sulfolane, and esters such as ethyl acetate or methyl acetate.
  • the solvents can be used individually or in any mixture with one another.
  • Weak organic bases such as e.g. tertiary amines, preferably triethylamine, diethylamine, dimethylpyridine and pyridine or mixtures thereof.
  • the reaction temperature in the manufacturing process can be varied over a wide temperature range. Generally one works between -30 ° C and
  • + 150 ° C preferably between 0 ° C and + 110 ° C.
  • 5,6-Dmydro-4H-cyclopenta [c] isoxazol-3-amine can be prepared by reacting 2-amino-1-cyclopentene-1-carbonitrile with hydroxylamine hydrochloride and then reacting it with sodium hydroxide solution.
  • the compounds of the general formula (I) 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.
  • the present invention furthermore relates to the use of the compounds of the formula (I) according to the invention as microbicides for protecting industrial materials.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as 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, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms , Parts of production plants, for example, are also part of the materials to be protected
  • Cooling water circuits 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 fluids.
  • 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 (Basiidiomycetes) and against mucus organisms and bacteria.
  • microorganisms of the following genus are mentioned:
  • 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 compounds (I) according to the invention can be used individually or in any mixture with one another to protect industrial materials. Furthermore, the compounds according to the invention or their mixtures can be in
  • formulations can be prepared in a known manner, e.g. by mixing the individual active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water can also include organic solvents can be used as auxiliary solvents.
  • organic solvents can 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, and the like 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
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as
  • Halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide Possible solid carriers are: e.g. natural rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • the following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Possible emulsifiers and / or foaming agents are: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters,
  • Polyoxyethylene fatty alcohol ethers e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin sulfite 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 also 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, for example 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% by weight of active compound or mixture of materials, preferably between 2 and 75% by weight.
  • the present invention furthermore relates to microbicidal compositions based on the compounds according to the invention, comprising at least one solvent or
  • Diluents and, if applicable, processing aids and, if appropriate, further antimicrobial substances are included in Diluents and, if applicable, processing aids and, if appropriate, further antimicrobial substances.
  • the effectiveness and the spectrum of activity of the active compounds of the formulas (I) or the agents, precursors or very generally formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active compounds are used to enlarge the spectrum of action or Achieving special effects such as added protection against insects.
  • These mixtures can have a broader W 1 mg spectrum than the compounds according to the invention.
  • Triazoles such as:
  • Imidazoles such as:
  • Succinate dehydrogenase inhibitors such as: benodanil, carboxime, carboxime sulfoxide, cyclafluramide, fenfuram, flutanil,
  • Furcarbanil Furmecyclox, Mebenil, Mepronil, Meth tartroxam, Metsulfovax, Nicobifen, Pyrocarbolid, Oxycarboxin, Shirlan, Seedvax;
  • Naphthalene derivatives such as: terbinafine, naftifine, butenafine, 3-chloro-7- (2-aza-2,7,7-trimefhyl-oct-3-en-5-in);
  • Sulfenamides such as:
  • Dichlorfluanide tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
  • Benzimidazoles such as:
  • Benzthiazoles such as:
  • Benzothiophene dioxides such as: benzo [b] thiophene-S, S-dioxide-carboxylic acid cyclohexylamide;
  • Formaldehyde and formaldehyde releasing compounds such as:
  • Isothiazolinones such as:
  • Cinnamaldehyde formaldehyde, glutaraldehyde, ß-bromocinnamaldehyde, o-phthalaldehyde;
  • Benzalkonium chloride benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, didecyldimethylammonium chloride, dioctyldimethylammomum chloride, N-hexadecyltrimethylammonium chloride, 1-hexadecylpisidiumchloride (imidyl) pyridium chloride;
  • Iodine derivatives such as:
  • Phenols such as:
  • Microbicides with activated halogen group such as: Bronopol, Bronidox, 2-bromo-2-nitro-l, 3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 1-bromo-3-chloro-4,4,5 , 5-tetiamethyl-2-imidazoldinone, ß-bromo-ß-nitrostyrene, Chloroacetamide, chloramine T, l, 3-dibromo-4,4,5,5-tetrametyl-2-imidazoldinone, di-chloroamine T, 3,4-dichloro- (3H) -l, 2-dithiol-3-one, 2,2-dibromo-3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane, halanes, halazones, mucochloric acid, phenyl- (2-chloro-cyanovinyl) sulfone, phen
  • Pyridines such as: l-hydroxy-2-pyridinthione (and their Cu, Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, l-hydroxy-4-methyl 6- (2,4,4-trimethylpentyl) -2 (lH) -pyridine;
  • Azoxystrobin dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, 2,4-dihydro-5-methoxy-2-methyl-4- [2 - [[[[l- [3- (trifluoromethyl ) phenyl] ethylidene] amino] oxy] - methyl] phenyl] -3H-1, 2,4-triazol-3-one (CAS No. 185336-79-2);
  • Salts of the metals tin, copper and zinc with higher fatty, resin, naphthenic and phosphoric acids such as e.g. Tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;
  • Metal salts such as:
  • Salts of the metals tin, copper, zinc, as well as chromates and dichromates such as Copper hydroxycarbonate, sodium dichromate, potassium dichromate, potassium chromate, copper sulfate, copper chloride, copper borate, zinc fluorosilicate, copper fluorosilicate;
  • Oxides of the metals tin, copper and zinc such as tributyltin oxide, Cu2 ⁇ , CuO, ZnO; Oxidizing agents such as:
  • Dithiocarbamates such as: Cufraneb, Ferban, potassium N-hydroxymethyl-N'-methyldithiobarbamate, Na- or K-dimethyldithiocarbamate, Macozeb, Maneb, Metam, Metiram, Thiram, Zineb, Ziram;
  • Nitriles such as:
  • fungicides and bactericides such as: Bethozaxin, 5-Hydroxy-2 (5H) -furanon; 4,5-benzdithiazolinone, 4,5-trimethylene di-thiazolinone, N- (2-p-chlorobenzoylethyl) hexaminium chloride, 2-oxo-2- (4-hydroxyphenyl) acethydroximic acid chloride, Tris-N- (cyclohexyldiazer ⁇ umdioxy) -aluminium, N- (cyclo-hexyldiazeniumdioxy) -tributyltin or K-salts, bis-N- (cyclohexyldiazeniumdioxy) -copper, iprovalicarb, fenhexamide, spiroxamine, Ca ⁇ ropamid, difluoromorin, quinoxyfen, Famoxadone acenzoliboromolorimoliborim
  • Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials.
  • Halofenocid HCH (CAS RN: 58-89-9), heptenophos, hexaflumuron, hexythiazox,
  • Methamidophos methidathione, methiocarb, methomyl, metalcarb, milbemectin,
  • Parathion A Parathion M, Penfluron, Permethrin, 2- (4-phenoxyphenoxy) ethyl ethyl carbamate, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim,
  • Pirimicarb, Pirimiphos M, Pirimiphos A Prallethrin, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyridophenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyridalyl, Pyrimidifenium, Pyridaben
  • sulprofos Tau fluvalinate, Taroils, Tebufenozide, Tebufenpyrad, Tebupirimphos, Tefluben- •on, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Tetramethrin, Tetramethacarb, Thiacloprid, Thiafenox, Thiamarboxi, Thiarboxi, Thioxoxiamoxi, Oxi Thuringiensine, tralomethrin, transfluthrin, triarathes, triazophos, triazamates, triazuron, trichlorfon,
  • Molluscicides fentin acetate, metaldehyde, methiocarb, niclosamide;
  • Imazamethabenz Isoproturon, Isoxaben, Isoxapyrifop, Imazapyr, Imazaquin, Imazethapyr, Ioxynil, Isopropalin, Imazosulfuron, Imazomox, Isoxaflutole, Imazapic, Ketospiradox,
  • MCPA MCPA-hydrazid
  • MCPA-fhioefhyl Mecoprop, Mecoprop-P, Mefenacet, Mefluidid, Mesosulfuron, Metam, Metamifop, Metamitron, Metazachlor, Methabenzthiazuron, Methazol, Methoroptryne, Metdobronomononium, Moxenonium, Moxenonium, Moxenonium, Moxenonium, Moxenon, Chromium Metsulfuron, Molinat, Monalid,
  • Pyributicarb pyridate, paraquat, pebulate, pendimethalin, pentachlorophenol, pentoxazone, pentanochlor, petroleum oils, phenmedipham, picloram, piperophos, pretilachlor, primisulfuron, prodiamine, profoxydim, prometryn, propachlor, propanafloro, propanafloro, propanil, propanil, propanil, propanil, propanil, propanil, propanil, propanil, propanil, propanil, propanil, propanil, propanil, propanil, propanob, Pelargonic acid, pyrithiobac, pyraflufen-ethyl,
  • the weight ratios of the active substances in these combinations of active substances can be varied within relatively large ranges.
  • the active compound combinations preferably contain the active compound of the general formula (I) in an amount of 0.1 to 99.9%, in particular 1 to 75%, particularly preferably 5 to 50%, the rest being 100% by one or more of the abovementioned
  • microbicidal agents or concentrates used to protect the industrial materials contain the active ingredient of the general formula (I) or the active ingredient combination of the active ingredient of the general formula (I) with one of the above-mentioned mixing partners in a concentration of 0.01 and 95% by weight , in particular 0.1 to 60 wt .-%.
  • the application concentrations of the active substances to be used or the active substance combinations depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
  • the optimal amount can be determined by test series.
  • the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
  • the active substances or agents according to the invention advantageously make it possible to replace the microbicidal agents available to date with more effective ones. They show good stability and advantageously have a broad spectrum of activity.
  • MIC minimum inhibitory concentrations
  • a defined Landy Agar was mixed with active substances according to the invention in concentrations of 0.1 mg / ml to 5000 mg / ml. After the agar had solidified, it was contaminated with pure cultures of the test organisms listed in Table 2. After 3 days of storage at 28 ° C and 60 to 70% relative humidity, the MIC was determined. The MIC is the lowest concentration of active ingredient at which no growth occurs due to the microbe species used, it is shown in the table below.
  • the minimum inhibitory concentrations (MIC) of agents according to the invention were determined to demonstrate the activity against fungi: Active ingredients according to the invention were added to an agar which was produced using malt extract in concentrations of 0.1 mg / 1 to 5000 mg / 1. After the agar had solidified, it was contaminated with pure cultures of the test organisms listed in Table 3. After 2 weeks of storage at 28 ° C and 60 to 70% relative humidity, the MIC was determined. The MIC is the lowest concentration of active ingredient at which no growth occurs due to the type of microbe used, it is shown in Table 3 below.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
EP03789076A 2002-12-02 2003-11-25 2-oxyamino-1-cyclopenten-1-nitrile als materialschutzmittel Withdrawn EP1569894A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10256187 2002-12-02
DE10256187A DE10256187A1 (de) 2002-12-02 2002-12-02 2-Oxyamino-1-cyclopenten-1-nitrile als Materialschutzmittel
PCT/EP2003/013198 WO2004050608A2 (de) 2002-12-02 2003-11-25 2-oxyamino-1-cyclopenten-1-nitrile als materialschutzmittel

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EP1569894A2 true EP1569894A2 (de) 2005-09-07

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EP (1) EP1569894A2 (enExample)
JP (1) JP2006508158A (enExample)
AU (1) AU2003293719A1 (enExample)
BR (1) BR0316949A (enExample)
DE (1) DE10256187A1 (enExample)
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DE102005043427A1 (de) * 2005-09-13 2007-03-15 Lanxess Deutschland Gmbh Verwendung von Diclosan für den Holzschutz
JP5389458B2 (ja) * 2009-01-29 2014-01-15 日本エンバイロケミカルズ株式会社 工業用抗菌組成物

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US3536760A (en) * 1964-09-23 1970-10-27 Union Carbide Corp Carbamoyloximes
US3400153A (en) * 1964-09-23 1968-09-03 Union Carbide Corp Nitroalkyl carbamoyloximes
US3483231A (en) * 1966-02-23 1969-12-09 Union Carbide Corp O-acetoacetyl oximes
AU668181B2 (en) * 1992-05-20 1996-04-26 Merck & Co., Inc. Ester derivatives of 4-aza-steroids

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BR0316949A (pt) 2005-10-18
NO20053110L (no) 2005-06-24
WO2004050608A2 (de) 2004-06-17
NO20053110D0 (no) 2005-06-24
US20060142384A1 (en) 2006-06-29
WO2004050608A3 (de) 2004-10-07
DE10256187A1 (de) 2004-06-09
AU2003293719A1 (en) 2004-06-23

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