EP1569920A2 - Cyclopenta c]isoxazol-3-amine als materialschutzmittel - Google Patents

Cyclopenta c]isoxazol-3-amine als materialschutzmittel

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Publication number
EP1569920A2
EP1569920A2 EP03780032A EP03780032A EP1569920A2 EP 1569920 A2 EP1569920 A2 EP 1569920A2 EP 03780032 A EP03780032 A EP 03780032A EP 03780032 A EP03780032 A EP 03780032A EP 1569920 A2 EP1569920 A2 EP 1569920A2
Authority
EP
European Patent Office
Prior art keywords
compounds
cyano
nitro
alkyl
alkynyl
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Withdrawn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
EP03780032A
Other languages
German (de)
English (en)
French (fr)
Inventor
Rainer Bruns
Günther EBERZ
Wolfgang Kreiss
Oliver Kretschik
Martin Kugler
Hermann Uhr
Erasmus Vogl
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 EP1569920A2 publication Critical patent/EP1569920A2/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics

Definitions

  • the present invention relates to new cyclopenta [c] isoxazol-3-amines, processes for their preparation, their use for controlling unwanted microorganisms and new mixtures of cyclopenta [c] isoxazol-3-amines with other active substances.
  • New cyclopenta [c] isoxazol-3-amines have been found which surprisingly have an excellent bactericidal action.
  • the new cyclopenta [c] isoxazol-3-amines individually or in a mixture with one another, are suitable on account of their antibacterial and antifungal activity for combating microorganisms in and on technical materials.
  • the present invention relates to cyclopenta [c] isoxazol-3-amines of the general formula (I)
  • R 1 and R 2 independently of one another represent hydrogen, halogen, cyano, nitro or, in each case, optionally substituted alkyl, alkenyl, alkynyl, aryl, heterocyclicl, -COR 5 , -CONR 6 , -CSNR 7 or -SO 2 R 8 .
  • R 5 to R 8 each independently represent optionally substituted alkyl, alkenyl, alkynyl, aryl and heterocyclyl,
  • R 3 and R 4 independently of one another represent hydrogen, or each optionally substituted alkyl, alkenyl, alkynyl, aryl and heterocyclyl,
  • Heteroatoms such as in alkoxy, haloalkoxy, haloalkylthio or alkylthio. as well as in composite terms such as alkyl- or dialkylamino, each straight-chain or branched, unsubstituted or substituted one or more times, identically or differently.
  • alkyl radicals can in each case be the same or different.
  • Aryl stands for aromatic mono- or polycyclic unsubstituted or mono- or polysubstituted or differently substituted hydrocarbon inge, such as Example 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 stands for
  • Heterocyclyl stands for saturated and unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member has a heteroatom, i.e. is an atom other than carbon, which are unsubstituted or substituted one or more times, with the same or different substitution. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If appropriate, the ring-shaped compounds form a polycyclic ring system together with further carbocyclic or heterocyclic, fused or bridged rings. 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.
  • R 1 and R 2 independently of one another represent hydrogen, halogen, cyano, nitro or in each case optionally substituted Ci-Cg-alkyl, C 2 -Cg-alkenyl, C2-C 8 -alkynyl, phenyl or heterocyclyl, or a radical -COR 5 , -CONR 6 , -CSNR 7 or -SO 2 R 8 ,
  • R 5 to R 8 independently of one another represent hydrogen, halogen, cyano, nitro or, in each case, optionally substituted Cj-Cg-alkyl, C2-Cg-alkenyl, C2-Cg-alkynyl, phenyl or heterocyclyl, and
  • R 3 and R 4 independently of one another represent hydrogen, halogen, cyano, nitro or in each case optionally substituted Ci-Cg-alkyl, C2 ⁇ Cg-alkenyl, C2-C - alkynyl, phenyl or heterocyclyl.
  • R 1 and R 2 independently of one another for hydrogen, halogen, cyano, nitro, or for CrCs-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, -C ö alkoxy, Ci-C ⁇ -haloalkoxy having 1 to 9 identical or different halogen atoms, -Ce-alkylthio, C I -C ⁇ -
  • Ci-Cs-alkyl C 1 -C 5 - haloalkyl having 1 to 6 identical or different halogen atoms
  • Ci-Cs- alkoxy C ⁇ -C 5 -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
  • heterocyclyl which is optionally mono- or polysubstituted by halogen or cyano, nitro, -Cs-alkyl, Ci-Cs-haloalkyl with 1 to 6 identical or different halogen atoms,
  • CrCs alkoxy Ci-Cs haloalkoxy with 1 to 6 identical or different Halogen atoms, C 1 -C 5 -alkylthio, d-Cs-haloalkylfio with 1 to 6 identical or different halogen atoms, amino, -C ö -alkylamino, di-CrCs-alkylamino,
  • R 5 to R 8 independently of one another for hydrogen, halogen, cyano, nitro, or for Ci-C ⁇ -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, which in each case optionally one or more times, the same or are substituted differently, by halogen, nitro, cyano, phenyl, C ⁇ -C 6 -alkoxy, C Coe-halogenoalkoxy having 1 to 9 identical or different halogen atoms, Ci-C ö alkylthio, C ⁇ -C 6 - halogenoalkylthio having 1 to 9 identical or various halogen atoms, Ci-C ⁇ -acyl, -C-C 6 -acyloxy, dC ⁇ -alkoxy-carbonyl, amino, C j -C ß -alkylamino, di-Ci-Cg-alkylamino, phenylamino or diphenylamino;
  • phenyl which is optionally mono- or polysubstituted, identical or different, by halogen, cyano, nitro, Ci-Cs-alkyl, d-Cs-haloalkyl with 1 to 6 identical or different halogen atoms, C 1 -C 5 -
  • halogen or cyano which is optionally mono- or polysubstituted by halogen or cyano, nitro, Ci-Cs-alkyl, d-Cs-haloalkyl with 1 to 6 identical or different halogen atoms, -C-C 5 alkoxy, Ci Cs-haloalkoxy with 1 to 6 identical or different halogen atoms, -CC 5 alkylthio, Ci-Cs-haloalkylthio with 1 to 6 the same or different halogen atoms, amino, C 1 -C 6 -alkylamino or di-C 1 -C 5 -alkylamino;
  • R 3 and R 4 independently of one another for hydrogen, halogen, cyano, nitro, or for dC 8 -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 substituted by halogen, nitro, cyano, phenyl, C ⁇ -C 6 -alkoxy, C ö -haloalkoxy having 1 to 9 identical or different halogen atoms, Ci-C ö alkylthio, C ⁇ -C 6 -
  • Ci-Cs-alkyl C 1 -C 5 -haloalkyl having 1 to 6 identical or different halogen atoms, C 1 -C 5 -alkoxy , Ci-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 or Di-C ⁇ -C 5 - alkylamino stand;
  • R 1 and R 2 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro or C ⁇ -C 6 - alkyl, C 2 -C 6 - alkenyl or C 2 -C 6 - alkynyl, which in each case optionally mono- are substituted four times, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, phenyl, C 1 -C 4 -alkoxy, C 1 -C 4 - haloalkoxy with 1 to 7 identical or different fluorine, chlorine or bromine atoms, C ⁇ -C 4 -Alkylthio, -C-C 4 -haloalkylthio with 1 to 7 identical or different fluorine, chlorine or bromine atoms, C, 1-C ⁇ , t-Acy J l, 'C 1 -C 4 - acyloxy, C . -C 4 -alkoxy-carbonyl, amino, -
  • phenyl which is optionally monosubstituted to tetrasubstituted, identically or differently by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 - alkyl, C ⁇ -C 4 haloalkyl having 1 to 4 identical or different fluorine,
  • Chlorine or bromine atoms C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy with 1 to 4 identical or different fluorine, chlorine or bromine atoms, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio with 1 to 4 identical or different Fluorine, chlorine or bromine atoms, amino, C 1 -C 4 alkylamino or di-C 1 -C 4 alkylamino;
  • heterocyclyl which is optionally monosubstituted to tetrasubstituted by identical or substituted by fluorine, chlorine, bromine, cyano, nitro, C ⁇ -C 4 - same alkyl, C ⁇ -C 4 -halogenoalkyl having 1 to 4 or different fluorine, chlorine or bromine atoms, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy with 1 to 4 identical or different fluorine, chlorine or bromine atoms, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio with 1 to 4 identical or different Fluorine, chlorine or bromine atoms, A-mino, -C-C 4 alkylamino or di-C ⁇ -C 4 - alkylamino,
  • R 5 to R 8 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro or C ⁇ -C 6 - alkyl, C -C 6 - alkenyl or C 2 -C 6 - alkynyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents chlorine, bromine, nitro, cyano, phenyl, C ⁇ -C C 1 -C 4 by fluorine, 4 alkoxy, - halogenoalkoxy having 1 to 7 identical or different fluorine, chlorine or bromine atoms, C ⁇ -C 4 -Alkylthio, -C-C 4 -haloalkylthio with 1 to 7 identical or different fluorine, chlorine or bromine atoms, C.-C 4 -acyl, C -C -acyl, C -C -C -
  • phenyl which is optionally monosubstituted to tetrasubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl,
  • heterocyclyl which is optionally monosubstituted to tetrasubstituted by identical or substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 - alkyl, C ⁇ -C same 4 haloalkyl having 1 to 4 or different fluorine, chlorine - Or bromine atoms, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy with 1 to 4 identical or different fluorine, chlorine or bromine atoms, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio with 1 to 4 identical or different Fluorine, chlorine or bromine atoms, amino, C 1 -C 4 alkylamino or di-C 1 -C 4 alkylamino;
  • R 4 independently of one another for hydrogen, fluorine, chlorine, bromine, cyano, nitro or for -C-C 6 - alkyl, C 2 -C 6 - alkenyl or C 2 -C 6 - alkynyl, which in each case optionally up to four times, the same or is differently substituted by fluorine, chlorine, bromine, nitro, cyano, phenyl, -CC 4 alkoxy, C 1 -C 4 -
  • phenyl which is optionally monosubstituted to tetrasubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl with 1 to 4 identical or different fluorine, chlorine or bromine atoms, C ⁇ -C - alkoxy, C ⁇ -C 4 haloalkoxy having 1 to 4 identical or different fluorine, chlorine or bromine, C 1 -C 4 - alkylthio, C ⁇ -C4-haloalkylthio having 1 to 4 identical or different are, alkylamino - fluorine, chlorine or bromine atoms, amino, C ⁇ -C 4 alkylamino or D1-C 1 -C 4;
  • heterocyclyl which is optionally monosubstituted to tetrasubstituted by identical or substituted by fluorine, chlorine, bromine, cyano, nitro, C ⁇ -C 4 - same alkyl, C ⁇ -C 4 -halogenoalkyl having 1 to 4 or different fluorine, chlorine or bromine atoms, C ⁇ -C 4 -alkoxy, C 4 -haloalkoxy having 1 to 4 identical or different fluorine, chlorine or bromine atoms, C ⁇ -C 4 -
  • R 1 and R 2 independently of one another for hydrogen, or for C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl or C 2 -C 4 -alkynyl, which are each optionally monosubstituted to trisubstituted by fluorine or chlorine Bromine
  • phenyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 2 -alkyl, halomethyl with 1 to 3 identical or different fluorine, or
  • Chlorine atoms amino, monomethylamino or dimethylamino
  • heterocyclyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C - alkyl, Ci-haloalkyl with 1 to 3 identical or different fluorine or chlorine atoms, amino, monomethylamino , or dimethylamino,
  • R 5 to R 8 independently represent hydrogen, or C ⁇ -C 5 alkyl, C 2 -C 5 - alkenyl or C 2 -C 5 alkynyl, which are in each case optionally mono- to trisubstituted by identical or different substituents consisting of fluorine, Chlorine, bromine, nitro, cyano, or phenyl;
  • phenyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 2 -alkyl, halomethyl with 1 to 3 identical or different fluorine or chlorine atoms, methoxy, amino, Monomethylamino, or dimethylamino; or for heterocyclyl, which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 2 -alkyl, halomethyl with 1 to 3 identical or different fluorine or chlorine atoms, amino, monomethylamino, or dimethylamino;
  • R 3 and R 4 are independently hydrogen, or C ⁇ -C 5 alkyl, C 2 -C 5 - alkenyl or C -C 5 alkynyl, each of which is optionally mono- to trisubstituted by identical or different substituents consisting of fluorine, chlorine , Bromine, nitro, cyano or phenyl;
  • phenyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, nitro, methoxy,
  • C 1 -C 2 alkyl halomethyl with 1 to 3 identical or different fluorine or chlorine atoms, amino, monomethylamino or dimethylamino;
  • C 2 alkyl halomethyl with 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 or Ci-Cs-alkyl
  • R 5 represents C 1 -C 5 alkyl, which is optionally monosubstituted to trisubstituted by identical or different substituents by fluorine or chlorine,
  • R 6 represents phenyl, which is optionally mono- to disubstituted by fluorine, chlorine, methyl, halomethyl with 1 to 3 identical or different fluorine or chlorine atoms,
  • R 7 represents C 1 -C 5 alkyl, or phenyl, which is optionally substituted by fluorine, chlorine, methyl, halomethyl having 1 to 3 identical or different fluorine or chlorine atoms;
  • R 8 for C 1 -C 5 -alkyl which are optionally monosubstituted to trisubstituted, identically or differently, by fluorine or chlorine, or for phenyl, which is optionally substituted by fluorine, chlorine, methyl, methoxy, halomethyl with 1 to 3 of the same or different fluorine or chlorine atoms, or represents 2-furyl or 2-thienyl, which is in each case optionally substituted by methyl, fluorine or chlorine;
  • R 3 and R 4 independently of one another for hydrogen, or for Ci-Cs-alkyl, which are optionally monosubstituted to trisubstituted by identical or different substituents by fluorine or chlorine,
  • phenyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, methyl, methoxy, halomethyl with 1 to 3 identical or different fluorine or chlorine atoms, or for furyl, thienyl, pyridyl, which in each case are optionally monosubstituted or disubstituted or is differently substituted by fluorine, chlorine, methyl, halomethyl with 1 to 3 identical or different fluorine or chlorine atoms.
  • radical definitions given in detail for these radicals in the respective combinations or preferred and particularly preferred and particularly preferred combinations of radicals can be replaced by radical definitions of other combinations, irrespective of the combination specified in each case.
  • residual definitions from each preferred area can also be omitted.
  • R 1 and R 2 are hydrogen
  • diluents can be prepared by reacting hyckoxylamine or its salts with 2-amino-1-cyclopentene-1-carbonitrile, optionally in the presence of diluents and optionally in the presence of a catalytic or stoichiometric amount of base.
  • 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, N, N-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 as toluene, xylene or hexane
  • 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 independently of one another for hydrogen, halogen, cyano, roitro or for optionally substituted alkyl, alkenyl, alkynyl, aryl, heterocyclyl, -COR 5 , -CO ⁇ R 6 , -CSNR ? or -SO 2 R 8 ,
  • R 5 to R 8 each independently represent optionally substituted alkyl, alkenyl, alkynyl, aryl and heterocyclyl,
  • R 3 and R 4 independently of one another represent hydrogen, or each optionally substituted alkyl, alkenyl, alkynyl, aryl and heterocyclyl,
  • A stands for a residue -
  • R1 stands for
  • R 1 and R 2 are hydrogen
  • R 5 has the meaning given above
  • R 5 has the meaning given above and X represents Cl and Br
  • Both water and all customary organic solvents can be used as optional diluents. 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 N, N-dimethylformamide, N, N-dimethylacetamide or N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, sulfones such as sulfolane, and esters such as ethyl acetate or methyl acetate.
  • 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
  • R and R have the meaning given above if appropriate in the presence of diluents and if appropriate in the presence of a catalytic or stoichiometric amount of base.
  • 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.
  • hydrocarbons such as toluene, xylene or hexane
  • chlorinated hydrocarbons such as chlorobenzene,
  • 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.
  • the compounds of the general formulas (I) and (IT) according to the invention have a strong microbicidal action and can be used to control undesired microorganisms, such as fungi and bacteria, in crop protection and in
  • Material protection can be used.
  • 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 that 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, kitchen lubricants and other materials that attack or decompose from microorganisms can be.
  • As part of the Protective materials are also parts of production systems, such as cooling water circuits, that can be affected by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids.
  • 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 such as 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, depending on their respective physical and / or chemical properties, the compounds according to the invention or their mixtures can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and very fine encapsulations in polymeric substances.
  • 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. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorefhylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions
  • alcohols such as butanol or glycol
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Carriers are meant liquids which are gaseous at normal temperature and pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • the following are suitable as solid carriers: 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.
  • Possible solid carriers for granules are: e.g.
  • Possible emulsifiers and / or foam-generating 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 dispersing agents are, for example, 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 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, 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% by weight of active compound or mixture of active compounds, 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 diluent and, if appropriate, processing aids and, if appropriate, further antimicrobially active substances.
  • the effectiveness and the spectrum of activity of the active compounds of the formulas (I) and (Tf) 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 Enlarging the spectrum of activity or achieving special effects such as additional protection against insects.
  • This Mixtures can have a broader spectrum of activity than the compounds according to the invention.
  • Triazoles such as:
  • Imidazoles such as: Clotrimazole, Bifonazole, Climbazole, Econazole, Fenapamil, Imazalil, Isoconazole,
  • Succinate dehydrogenase inhibitors such as:
  • Sulfenamides such as:
  • Dichlorfluanide tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
  • Benzimidazoles such as:
  • Morpholine derivatives 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: N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, 5-chloro-N-octylisothiazolinone, N-octyl -isothiazolin-3-one, 4,5-trimethylene-isothiazolinone, 4,5-benzisothiazolinone;
  • Aldehydes such as: cinnamaldehyde, formaldehyde, glutardialdehyde, ⁇ -bromocinnamaldehyde, o-phthalaldehyde;
  • Benzalkonium chloride berizyldimemyltetradecylammonium chloride, benzyldimefhyldodecylammonium chloride, dicorborbyldimethylalkylammonium chloride, didecyldimethylammonium chloride, dioctyldimethylammonium chloride, N-hexadecyltrimethylammoniumchloride, 1-hexadiumchloride, 1-hexadium chloride-1
  • Iodine derivatives such as:
  • Microbicides with activated halogen group such as:
  • Pyridines such as: l-hydroxy-2-pyridinthione (and their Cu, Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimefhanol, 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-memyl-4- [2 - [[[[[[[- (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 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, O12O, CuO,
  • Oxidizing agents such as:
  • Cufraneb, ferban potassium N-hydroxymethyl-N'-methyldithiobarbamate, Na- or K-dimethyldithiocarbamate, Macozeb, Maneb, Meta, Metiram, Thiram, Zineb, Ziram;
  • Nitriles such as:
  • Befhozaxin 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- (cyclohexyldiazenium dioxy) -aluminium, N- (cyclo-hexyldiazeniumdioxy) -tributyltin or K-salts, bis-N- (cyclohexyldiazeniumdioxy) -copper, iprovalicarb, fenhexamide, spiroxamine, Ca ⁇ ropamid, difluoromorin, quinoxyfen, Famoxadone acenzoliboromolorimoliborimoliborimoliboro S-methyl, furametpyr, thifluzamide
  • Aldoxycarb Aldrin, Allethrin, Alpha-cypermethrin, Amidoflumet, Amitraz, Avermectin, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
  • Bacillus thuringiensis Barthrin, 4-Bromo-2 (4-chloro-phenyl) -l- (ethoxymethyl) -5- (tri- fluoromethyl) -lH-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin, bifenthrin, Bioresmethrin, Bioallethrin, Bistrifluron, Bromophos A,
  • Imidacloprid Imiprothrin, Indoxycarb, Iodfenfos, Iprinomectin, Iprobefos, Isazophos, Isoamidophos, Isofenphos, Isoprocarb, Isoprothiolane, Isoxathion, Ivermectin, Kadedrin Lambda-Cyhalothrin, Lufenuron,
  • Molluscicides fentin acetate, metaldehyde, methiocarb, niclosamide;
  • MCPA MCPA-hydrazide, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, mefenacet, Mefiuidid, mesosulfuron, metam, Metamifop, metamitron, metazachlor, Memabenzthiazuron, Mefhazol, Methoroptryne, Methyldyrnron, cyanate Methylisothio-, metobromuron, metoxuron, metribuzin, Metsulfuron, Molinat, Monalid, Monolinuron, MSMA, Metolachlor, Metosulam, Metobenzuron, Naproanilide, Napropamid, Naptalam, Neburon, Nicosulfuron, Norflurazon, sodium chlorate,
  • Pentoxazone pentanochlor, petroleum oils, phenmedipham, picloram, piperophos,
  • Pelargonic acid pyrithiobac, pyraflufen-ethyl, quinmerac, quinocloamine, quizalofop, quizalofop-P, quinchlorac,
  • the weight ratios of the active substances in these combinations of active substances can be varied within relatively large ranges.
  • the active substance combinations preferably contain 0.1 to 99.9%, in particular 1 to 75%, particularly preferably 5 to 50% of the active substance, the rest being filled 100% by one or more of the above-mentioned mixing partners.
  • the microbicidal agents or concentrates used to protect the technical materials contain the active ingredient or combination of active ingredients in a concentration of 0.01 and 95% by weight, in particular 0.1 to 60% by weight.
  • the application concentrations of the active ingredients to be used or the active ingredient 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. In general, the application concentrations are in the range from 0.001 to
  • 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.
  • 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 type of microbe used. The determined MIC values are given in Table 2 below.
  • MIC Concentrations (MIC) of active substances according to the invention determined: 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 5,000 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. The determined MIC values are given in Table 3 below.
  • the minimal inhibitory concentrations (MIC) of active substances according to the invention were determined in analogy to application example B.
  • the tested compounds show minimal inhibitory concentrations against fungi such as Fusarium solani, Geotrichum candidum and Rhodo ⁇ orula rubra: ⁇ 500 ppm: Table 4
  • the minimal inhibitory concentrations (MIC) of active substances according to the invention were determined in analogy to application example A.

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  • Agricultural Chemicals And Associated Chemicals (AREA)
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EP03780032A 2002-12-02 2003-11-22 Cyclopenta c]isoxazol-3-amine als materialschutzmittel Withdrawn EP1569920A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10256186 2002-12-02
DE10256186A DE10256186A1 (de) 2002-12-02 2002-12-02 Cyclopenta(c)isoxazol-3-amine als Materialschutzmittel
PCT/EP2003/013140 WO2004050644A2 (de) 2002-12-02 2003-11-22 Cyclopenta[c]isoxazol-3-amine als materialschutzmittel

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EP1569920A2 true EP1569920A2 (de) 2005-09-07

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BR (1) BR0316943A (enExample)
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DK3153506T3 (en) * 2015-10-07 2018-03-26 Sanko Tekstil Isletmeleri San Ve Tic As ISOXAZOLES, PROCEDURE FOR THEIR PREPARATION AND APPLICATIONS THEREOF

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JPS5973575A (ja) * 1982-10-05 1984-04-25 Shionogi & Co Ltd プロピニルアミノイソオキサゾ−ル誘導体
US5591761A (en) * 1993-05-20 1997-01-07 Texas Biotechnology Corporation Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
US5464853A (en) * 1993-05-20 1995-11-07 Immunopharmaceutics, Inc. N-(5-isoxazolyl)biphenylsulfonamides, N-(3-isoxazolyl)biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin
US5378715A (en) * 1992-02-24 1995-01-03 Bristol-Myers Squibb Co. Sulfonamide endothelin antagonists
TW224462B (enExample) * 1992-02-24 1994-06-01 Squibb & Sons Inc
DE10053160A1 (de) * 2000-10-26 2002-05-08 Bayer Ag 3-Nitroisoxazole und deren Verwendung im Materialschutz

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US20060142359A1 (en) 2006-06-29
BR0316943A (pt) 2005-10-18
NO20053117D0 (no) 2005-06-24
WO2004050644A2 (de) 2004-06-17
DE10256186A1 (de) 2004-06-09
WO2004050644A3 (de) 2004-07-29
JP2006515289A (ja) 2006-05-25
AU2003288149A1 (en) 2004-06-23
AU2003288149A8 (en) 2004-06-23

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