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WO2001046163A2 - 3-nitro-dihydro-isoxazole et -oxazine - Google Patents

3-nitro-dihydro-isoxazole et -oxazine Download PDF

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Publication number
WO2001046163A2
WO2001046163A2 PCT/EP2000/012640 EP0012640W WO0146163A2 WO 2001046163 A2 WO2001046163 A2 WO 2001046163A2 EP 0012640 W EP0012640 W EP 0012640W WO 0146163 A2 WO0146163 A2 WO 0146163A2
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WIPO (PCT)
Prior art keywords
nitro
dihydro
isoxazole
methyl
phenyl
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.)
Ceased
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PCT/EP2000/012640
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German (de)
English (en)
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WO2001046163A3 (fr
Inventor
Franz Kunisch
Hermann Uhr
Oliver Kretschik
Martin Kugler
Peter Wachtler
Hannes Oesen
Jochen KRAHNSTÖVER
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Bayer AG
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Bayer AG
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Priority to AU30105/01A priority Critical patent/AU3010501A/en
Publication of WO2001046163A2 publication Critical patent/WO2001046163A2/fr
Publication of WO2001046163A3 publication Critical patent/WO2001046163A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/02—1,2-Oxazines; Hydrogenated 1,2-oxazines

Definitions

  • the invention relates to the use of partially known 3-nitro-4,5-dihydro-isoxazoles and 3-nitro-5,6-dihydro-4H-1,2-oxazines as biocides for the protection of
  • W represents CR 1 R 2 -CR 3 R 4 or CR 5 R 6 -CR 7 R 8 -CR9R10,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently of one another represent
  • R n , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 can independently stand for
  • Hydrogen in each case optionally substituted alkyl, alkenyl, alkynyl or optionally substituted aryl,
  • microbicides are very suitable as microbicides for protecting plants and materials.
  • W has the meaning given above and X represents halogen or another leaving group such as mesylate or tosylate,
  • the compounds of the formula (I) have a strong biological activity, in particular a strong microbicidal action, and can be used particularly advantageously for controlling undesired microorganisms, for example in crop protection and in material protection.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, halogen, cyano, nitro, or each straight-chain or branched dC 8 - Alkyl, C 2 -C 8 alkenyl, C -C 8 alkynyl, which are optionally substituted one or more times, identically or differently, by halogen, nitro, cyano, phenyl, CrC ⁇ -alkoxy, dC ⁇ -haloalkoxy with 1 to 9 identical or different halogen atoms, CrC ⁇ -alkylthio, Ci-C 6 -haloalkylthio with 1 to 9 identical or different halogen atoms, CrC ⁇ -acyl, - -acyloxy, dC ö -alkoxy-carbonyl or amino, which is optionally identical or differently substituted by CrCö -Alkyl or
  • phenyl which is optionally mono- or polysubstituted by halogen, cyano, nitro, d-Cs-alkyl, d-d-haloalkyl having 1 to 6 identical or different halogen atoms, d-d-alkoxy, Q-
  • C 5 haloalkoxy having 1 to 6 identical or different halogen atoms, d-Cs-alkylthio, d-Cs-haloalkylthio with 1 to 6 identical or different halogen atoms, amino, dC 6 -alkylamino with straight-chain or branched d-C ⁇ -alkyl radical or di-d-Cs-alkylamino with the same or different, straight-chain or branched alkyl residues,
  • R ⁇ , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 can independently stand for
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro or each straight-chain 5 or branched d-C ⁇ -alkyl, C 2 -C 6 alkenyl, C 2 -C6 alkynyl, which are optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, phenyl, dC 4 -alkoxy , dC - haloalkoxy with 1 to 7 identical or different fluorine, chlorine or bromine atoms, dC 4 alkylthio, C 1 -C 4 haloalkylthio with 1 to 7 identical 10 or different fluorine, chlorine or bromine atoms, Ci-dj -Acyl, C1-C 4 -
  • phenyl which is optionally mono- to tetrasubstituted tuiert substitutable 15 by fluorine, chlorine, bromine, cyano, nitro, C ⁇ _-C 4 - alkyl, dC same 4 -Halo- genalkyl having 1 to 4 or different fluorine, Chlorine or bromine atoms, dC 4 alkoxy, dC 4 haloalkoxy with 1 to 4 identical or different fluorine, chlorine or bromine atoms, C 1 -C alkylthio, dC - haloalkylthio with 1 to 4 identical or different fluorine, chlorine - or 0 bromine atoms, amino, mono-C 1 -C 4 -alkylamino with straight-chain or branched alkyl radical, di-dd-alkylamino with identical or different, straight-chain or branched alkyl radicals,
  • R ⁇ , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 independently of one another represent 30 Hydrogen or for straight-chain or branched dC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, which are optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, Phenyl, phenoxy, dC -alkoxy, dC - haloalkoxy with 1 to 7 identical or different fluorine, chlorine or bromine atoms, C 1 -C -alkylthio, -C-C 4 -haloalkylthio with 1 to 7 identical or different fluorine, chlorine or bromine atoms, dC acyl, acyloxy 4 dC, dC alkoxy-carbon
  • phenyl which is optionally monosubstituted to tetrasubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, dC - haloalkyl with 1 to 4 identical or different fluorine, chlorine or bromine atoms, dC 4 -Alkoxy, dC 4 -haloalkoxy with 1 to 4 identical or different fluorine, chlorine or bromine atoms, C 1 -C 4 -alkylthio, C 1 -C -haloalkylthio with 1 to 4 identical or different fluorine, chlorine or bromine atoms , Amino, mono-dC 4 -alkylamino with straight-chain or branched C 1 -C 4 -alkyl radical, di- d- C 4 -alkylamino with identical or different, straight-chain or branched alkyl radicals.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently of one another represent
  • phenyl which is optionally monosubstituted to tetrasubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, trifluoromethoxy , Methylthio, ethylthio, n-propylthio, iso-propylthio, trifluoromethylthio, amino, methylamino, ethylamino, n-proylamino, iso-propylamino, dimemylamino, diethylamino, methylethylamino, di-n-propylamino,
  • R n , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 independently of one another stand for hydrogen, or for methyl, ethyl, n-propyl, isopropyl, n -Butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, AUyl, vinyl, propargyl, which are optionally monosubstituted to tetrasubstituted by fluorine, chlorine, bromine, nitro, cyano , Phenyl, phenoxy, methoxy, ethoxy, n-propoxy, iso-propoxy, butoxy, triflourmethoxy, methylthio, ethylthio, n-propylthio, iso-propylthio,
  • phenyl which is optionally monosubstituted to tetrasubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, trifluoromethylthio, amino, methylamino, ethylamino, n-proylamino, iso- Propylamino, dimethylamino, diethylamino, methylethylamino, di-n-propylamino or di-iso-propylamino.
  • radical definitions specified in the respective combinations or preferred and particularly preferred combinations of radicals, in particular for these radicals, are also replaced as desired by radical definitions of other combinations, regardless of the combination specified in each case. You can also
  • Residual definitions from each preferred area are omitted.
  • a preferred group of compounds of the formula (I) are those in which W represents CR 1 R 2 -CR 3 R 4 (formula TA)
  • R 1 represents hydrogen, halogen, OH, OCOR 12 , OCOOR 13 , OCSOR 13 , OCONR 1 R 15 or OSO 2 R 16 ,
  • R 12 , R 13 , R 14 , R 15 and R 16 have the meanings mentioned as being particularly preferred, in particular in which
  • R 12 represents Ci-alkyl, in particular methyl, ethyl, n-propyl, iso-propyl, n-butyl or t-butyl represents phenyl which is optionally substituted by halogen, in particular phenyl or chlorophenyl
  • Phenyl-Ci-Cö-alkyl, in particular benzyl stands for C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl, in particular for methoxy methyl, for phenoxy-C 1 -C 6 -alkyl, in particular for phenoxymethyl,
  • R 13 stands for Cj-Cg-alkyl, in particular for methyl, ethyl, n-propyl, isopropyl or n-butyl, for C 2 -C 6 -alkenyl, in particular for vinyl, for phenyl-Ci-Cö-alkyl represents, in particular benzyl, represents phenyl which is optionally substituted by halogen, in particular phenyl and chlorophenyl,
  • R 14 represents hydrogen
  • R 15 represents Cj-Cg-alkyl or phenyl, in particular n-butyl or phenyl and
  • R 16 represents C 1 -C 6 -alkyl, in particular methyl or phenyl, which is optionally substituted by C 1 -C 4 -alkyl, in particular methylphenyl,
  • R 2 represents hydrogen or methyl, in particular hydrogen
  • R 3 represents hydrogen or methyl, in particular hydrogen
  • R 4 represents hydrogen
  • R 1 has the meanings mentioned as being particularly preferred and R 2 , R 3 and R 4 represent hydrogen.
  • the compounds of the formula (TJ) are cyclized in the presence of an alkali metal nitrite or an alkyl nitrite.
  • alkali metal nitrites can be used as the alkali metal nitrite.
  • Sodium or potassium nitrite is preferably used.
  • alkyl nitrites preferably having 1 to 10 carbon atoms, in particular methyl nitrite, ethyl nitrite, n-propyl nitrite, i-propyl nitrite and isoamyl nitrite, can be used as alkyl nitrite.
  • the alkali metal nitrite and the alkyl nitrite are generally in excess, based on the amount of the compound
  • Formula (II) used 1.2 to 4 molar equivalents of alkali metal nitrite and 2 to 7 molar equivalents of alkyl nitrite are preferably used.
  • Both water and organic solvents are suitable as diluents which may be added.
  • These preferably include hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene, methylene chloride or chloroform, ketones such as acetone, ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether and dioxane, nitriles such as acetonitrile, and DMSO, DMF and NMP.
  • hydrocarbons such as toluene, xylene or hexane
  • chlorinated hydrocarbons such as chlorobenzene
  • methylene chloride or chloroform ketones
  • ketones such as acetone
  • ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether and dioxane
  • nitriles such as
  • reaction temperatures can be varied over a wide temperature range in this process. Generally one works between - 30 ° C and + 150 ° C, preferably between -10 ° C and + 70 ° C. It is also possible not to isolate the compounds of the formula (U), but to prepare them in a preceding step as a crude mixture and to cyclize them directly to the compounds of the formula (I).
  • the compounds of the formula (11) are known or can be prepared according to known ones
  • Y represents halogen or another leaving group such as mesylate or tosylate
  • Sodium nitrite, potassium nitrite, calcium nitrite or silver nitrite is preferably used as the metal nitrite.
  • Possible diluents used are water and organic solvents. These preferably include hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene, methylene chloride or chloroform, ketones such as acetone, ethers such as tetrahydrofuran, diethyl ether,
  • Methyl tert-butyl ether and dioxane nitriles such as acetonitrile, and DMSO, DMF and NMP.
  • the reaction temperatures can be varied within a wide range in this process. Generally one works between -30 ° C and + 150 ° C, preferably between -10 ° C and + 70 ° C.
  • the compounds of the formula (I) can also be obtained by starting from compounds which obey the formula (I) and one or more of the substituents R 1 to R 10 by a chemical reaction, such as, for example, reduction, oxidation, Elimination, substitution, esterification, etherification, amidation, sulfonation changed.
  • R has the meaning given above with the exception of hydrogen and Z 1 represents halogen or another leaving group, preferably chlorine, bromine, iodine, mesylate or tosylate, or with compounds of the formula (V)
  • R has the meaning given above and Z represents halogen, preferably chlorine, bromine, fluorine,
  • R 19 and R 20 have the meaning given above and R 21 represents alkyl, in particular methyl, ethyl, propyl or isopropyl, optionally in the presence of a diluent and optionally in the presence of a base.
  • organic solvents can be used as diluents.
  • hydrocarbons such as toluene, xylene or hexane
  • chlorinated hydrocarbons such as chlorobenzene, methylene chloride or chloroform
  • ketones such as acetone
  • ethers such as tetrahydrofiiran, diethyl ether, methyl tert-butyl ether and dioxane
  • nitriles such as acetonitrile
  • DMSO DMF and NMP.
  • reaction temperatures can be varied over a wide temperature range in this process. Generally one works between -30 ° C and + 150 ° C, preferably between -10 ° C and + 70 ° C.
  • Fungicides can be used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans; Erwinia species, such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pelücularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Altemaria species such as, for example, Alternaria brassicae
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • the active compounds according to the invention are also suitable for increasing the crop yield.
  • 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 that are to be protected against microbial change or destruction by active ingredients according to the invention can
  • parts of production plants, 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, coolants 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 bacteria and fungi, in particular molds, wood-coloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera may be mentioned:
  • Altemaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium such as Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as PemciUium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds can be converted into the customary formulations, such as
  • 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, 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, organic solvents can, for example, 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.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid 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 their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methylsobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous triangular agents or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol
  • Propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, 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 and 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 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 Foamuherept generally contain between 0.1 and 95 percent by weight of active ingredient, 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 spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Fungicides Aldimo h, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole,
  • Iodocarb Ipconazol, Iprobefos (JSP), Iprodione, Irumamycin, Isoprothiolan,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfbcarb, methfuroxam, metiram, metomeclam, metsulfovax,
  • Nickel dimethyldithiocarbamate Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphene, pimaricin, piperalin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole,
  • Thicyofen Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,
  • Tolylfluanid Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triflumizol, Triforin, Triticonazol,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenoxuron
  • Mecarbam Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb,
  • Triazoles such as:
  • Azaconazole Azocyclotin, Bitertanol, Bromuconazole, Cyproconazole,
  • Imidazoles such as:
  • Succinate dehydrogenase inhibitors such as:
  • Naphthalene derivatives such as:
  • Sulfenamides such as: dichlorfluanid, tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
  • Benzimidazoles such as:
  • Benzthiazoles such as:
  • Benzothiophene dioxides such as: benzo [b] tbiophen-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; Thiocyanates such as:
  • quaternary ammonium compounds and guanidines such as: benzalkonium chloride, benzyldimethyltetiadecylarnmonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyl-d ⁇ ethyl-alkyl-ammonium chloride, dide-cyldimethylarnmonium chloride, dioctyl-methyl-ammonium-ammonium chloride, N-hexadecium chloride, 1-hexadecium chloride, 1-hexadecyl chloride, trimethyl .Iminoctadine-tris- (albesilate);
  • 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, l-bromo-3-chloro-4,4,5 , 5-tetramethyl-2-imidazoldinone, ß-bromo-ß-nitrostyrene, chloroacetamide, chloramine T, l, 3-dibromo-4,4,5,5-tetrametyl-2-imidazoldinone, dichloramine T, 3,4-dichloro - (3H) -l, 2-dithiol-3-one, 2,2-dibromo-3-nitrile-propionamide, l, 2-dibromo-2,4-dicyanobutane, halanes, halazones, mucochloric acid, phenyl- (2- chloro-cyan-vinyl) sulfone, phenyl
  • N-methylbenzeneacetamide alpha- (methoxyimino) -N-methyl-2 - [[[[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] -benzeneacetamide,
  • Trifloxystrobin alpha- (methoxymethylene) -2 - [[[[l- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] -benzeneaceticacid-methyl ester, 2 - [[[5-chloro-3- ( trifluoromethyl) -2-pyridinyl] oxy] methyl] -. alpha .- (methoxyimino) -N-methyl-benzeneacetamide,
  • Metal salts such as:
  • Tributyltin oxide CU2O, CuO, ZnO;
  • Cufraneb, ferban potassium N-hydroxymethyl-N'-methyldithiobarbamate, Na- or K-dimethyldithiocarbamate, Macozeb, Maneb, Metam, Metiram, Thiram, Zineb, Ziram;
  • Nitriles such as: 2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;
  • Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials.
  • Bacillus thuringiensis Barthrin, 4-Bromo-2 (4-chloro-phenyl) -l- (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, Bioresmethrin, Bioallesmethrin, Bio Bromophos A, Bromophos M, Bufencarb, Buprofezin, Butathiophos, Butocarboxin, Butoxycarboxim, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chinomethionate, Cloethocarb, Chlordane, Chlorethoxyfos, Chlorfenapyr, Chlorfenvin- phos, chlorfluazuron, chlormephos, N - [(6
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fensulfothion, Fenthion, Fenvalerate, Fipronil, Fluazuron, Flucycloxuron, Flcyufenhrinuminate, Flcyufenhrinofinate, Flyufhrinofinate, Flucythrinofinone, Flucythrinofinate, Flyufhrinofinate, Flucythrinofinate, Flucythrinofinate, Flucythrinofinate, Flucythrinofinate, Flucythrinofinate, Flucythrinofinate, Flucythrinofinate, Flucythrinofinate, Flucythrinofinate, Flucyth
  • Isazophos Isoamidophos, Isofenphos, Isoprocarb, Isoprothiolane, Isoxathion, Ivermectin, Lama-cyhalothrin, Lufenuron, Kadedrin Lambda-Cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos
  • Methamidophos Methidathion, Methiocarb, Methomyl, Metalcarb, Milbemectin, Monocrotophos, Moxiectin, Naled, NC 184, NI 125, Nicotin, Nitenpyram, Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Penhrinon, Penfluron, Permoluron 4-phenoxyphenoxy) ethyl ethyl carbamate, phenthoat, phorate, phosalon, phosmet, phosphamidon, phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Prallethrin, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyre
  • Teflubenzuron tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Tetramethrin, Tetramethacarb, Thiacloprid, Thiafenox, Thiamethoxam, Thiapronil,
  • Thiodicarb Thiofanox, Thiazophos, Thiocyclam, Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Transfluthrin, Triarathen, Triazophos, Triazamate, Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Vamidetametl, XMC, XMC, XMC;
  • Herbicides and algicides acetochlor, acifluorfen, aclonifen, acrolein, alachlor, alloxydim, ametryn,
  • Carbetamides Carfentrazone-ethyl, Carfenstrole, Chlomethoxyfen, Chloramben, Chlorbromuron, Chlorflurenol, Chloridazon, Chlorimuron, Chlornitrofen, Chloroacetic acid, Chloransulam-methyl, Cinidon-ethyl, Chlorotoluron, Chloroxuron, Chlo ⁇ ropham, Chlortorphidluron, Chlorosulfuron .
  • Fluazifop Fluazifop, fluazifop-P, fuenachlor, fluchloralin, flufenacet flumeturon,
  • Haloxyfop Hexazinone, Imazamethabenz, Isoproturon, Isoxaben, Isoxapyrifop, Imazapyr, Imazaquin,
  • MCPA MCPA-thioethyl
  • MCPB Mecoprop, Mecoprop-P, Mefenacet, Mefluidide, Metam, Metamitron, Metazachlor, Methaberizthiazuron, Methazole, Methoroptryne,
  • 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 usual way, e.g. by pouring, spraying, spraying,
  • 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 g / ha.
  • 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.
  • the agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%.
  • the application concentrations of the active compounds according to the invention 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.
  • MIC minimum inhibitory concentrations
  • a defined Landy Agar is mixed with active substances according to the invention in concentrations of 0.1 mgml to 5000 mg / ml. After the agar has solidified, it is 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 is determined. MIC is the lowest concentration of active substance at which no growth occurs due to the type of microbe used, it is shown in the table below.
  • agar which is produced using malt extract is mixed with active substances according to the invention in concentrations of 0.1 mg / 1 to 5,000 mg / 1 added. After the agar solidifies, it is 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 is determined. 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)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne l'utilisation comme biocides d'isoxasoles et d'oxazines en partie connues.
PCT/EP2000/012640 1999-12-21 2000-12-13 3-nitro-dihydro-isoxazole et -oxazine Ceased WO2001046163A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU30105/01A AU3010501A (en) 1999-12-21 2000-12-13 3-nitro-dihydro-isoxazoles and -oxazines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999161602 DE19961602A1 (de) 1999-12-21 1999-12-21 3-Nitro-dihydro-isoxazole und -oxazine
DE19961602.7 1999-12-21

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WO2001046163A2 true WO2001046163A2 (fr) 2001-06-28
WO2001046163A3 WO2001046163A3 (fr) 2001-11-15

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002042282A1 (fr) * 2000-11-22 2002-05-30 Bayer Aktiengesellschaft Procede pour la production de nitro-dihydroisoxazoles

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3207761A (en) * 1963-03-01 1965-09-21 Abbott Lab 3-nitro-2-isoxazoline and its production

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002042282A1 (fr) * 2000-11-22 2002-05-30 Bayer Aktiengesellschaft Procede pour la production de nitro-dihydroisoxazoles

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AU3010501A (en) 2001-07-03
WO2001046163A3 (fr) 2001-11-15

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