EP0705160A1 - Fungizide wirkstoffkombinationen - Google Patents

Fungizide wirkstoffkombinationen

Info

Publication number
EP0705160A1
EP0705160A1 EP94920437A EP94920437A EP0705160A1 EP 0705160 A1 EP0705160 A1 EP 0705160A1 EP 94920437 A EP94920437 A EP 94920437A EP 94920437 A EP94920437 A EP 94920437A EP 0705160 A1 EP0705160 A1 EP 0705160A1
Authority
EP
European Patent Office
Prior art keywords
wood
weight
solvent
agent
methyl
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Withdrawn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
EP94920437A
Other languages
German (de)
English (en)
French (fr)
Inventor
Lutz Heuer
Martin Kugler
Hans-Ulrich Buschhaus
Heinrich Schrage
Franz Kunisch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19934320495 external-priority patent/DE4320495A1/de
Priority claimed from DE19944406819 external-priority patent/DE4406819A1/de
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0705160A1 publication Critical patent/EP0705160A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/343—Heterocyclic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/38—Aromatic compounds
    • B27K3/40—Aromatic compounds halogenated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/50—Mixtures of different organic impregnating agents

Definitions

  • the present application relates to new combinations of active ingredients which consist of the known a-butyl-a- (2,4-dichlorophenyl) -1H-1, 2,4-triazole-1-ethanol (hexaconazole) and / or 5- [ (4-Chlorophenyl) methyl] -2,2-dimethyl-l- (lH-l, 2,4-triazol-l-yl-methyl) cyclopentanol (metconazole) on the one hand and other known active substances on the other hand exist and are very good are suitable for protecting technical materials.
  • the blends are used in plant and material protection.
  • wood preservatives are subject to requirements that go beyond the pure fungicidal effectiveness.
  • the aim and object of the present invention was therefore to find a wood preservative which is highly effective against wood-staining and wood-destroying fungi and against wood-damaging insects, in particular against wood-destroying longhorn beetles (Cerambycidae, Lyctidae, Bostrychidae and Anobiidae) including termites and has a good long-term effect , the effectiveness of the fungicide not being impaired by the insecticide or returns.
  • the wood preservative should have a good penetration capacity in the wood and in the wood materials.
  • At least one additional azole fungicide is additionally added to this mixture.
  • the application therefore relates to a wood preservative containing a-butyl-a- (2,4-dichlo ⁇ henyl) -lH-l, 2,4-triazole-l -ethanol and at least one synergistically complementary insecticide.
  • a wood preservative containing hexaconazoles and at least one synergistically complementary insecticide and at least one further azole fungicide is preferred.
  • the wood preservatives contain 0.01 to 25% by weight of hexaconazoles and 0.00001 to 10% by weight of insecticides and optionally 0.1 to 99.9% by weight of azole fungicide.
  • the wood preservatives generally contain more than 40% of a mixture of solvents and / or diluents and / or organic chemical binders or fixatives, processing agents, dyes, pigments, dyes or pigments.
  • Preferred azoles as mixing partners are:
  • Azaconazoles l- ⁇ [2- (2,4-dichlorophenyl) -1, 3-dioxolan-2-yl] methyl ⁇ l-H-1,2,4-triazoles
  • Cyproconazole 2- (4-chlorophenyl) -3-cyclopropyl-1 - (1H-1, 2,4-triazol-1-yl) butan-2-ol
  • Particularly preferred mixtures contain as azoles in addition to hexaconazoles, tebuconazoles, propiconazoles, cycproconazoles and / or 2- (1-chloro-cyclopropyl) -1- (2-chlorophenyl) -3-1H- (1,2,4-triazole- l-yl) -propan-2-ol, preferably in a weight ratio to hexaconazole of 1: 9 to 9: 1.
  • fungicidal mixing partners are also particularly preferred:
  • insecticides are used as synergistic insecticidal mixing partners:
  • Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl. al (4-Chlo ⁇ henyl) -4- (O-ethyl, S-propyl) phosphoryloxy-pyrazole, Chlo ⁇ yrifos, Coumaphos, Demeton, Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoate, Ethoate.
  • Ethoprophos Etrimfos, Fenitrothion, Fenthion, Heptenophos, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofosm Prothiofos, Sulfprofos, Triazophos and Trichloiphon; 5 carbamates such as aldicarb, bendiocarb, a-2- (l-methylpropyl) phenylmethyl carbamate, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb, methomyl, oxamyl, pirimicarb, promecarb, propoxur and thiodicarb;
  • Organosilicon compounds preferably dimethyl (phenyl) silyl-methyl-3-! o phenoybenzyl ether such as dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether or
  • (Dimethylphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as, for example, dimethyl- (9-ethoxyphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether or [(phenyl) - 15 3- (3-phenoxyphenyl) -propyl] (dimethyl) -silanes such as (4-ethoxyphenyl) - [3- (4-fluoro-3-phenoxyphenyl-propyl] dimethyl-silane, sila fluofin
  • Pyrethroids such as AUethrin, Alphamethrin, Bioresmethrin, Byfenthrin, Cycloprothrin, Cyfluthrin, Decamethrin, Cyhalothrin, Cypermethrin, Deltamethrin, Alpha-cyano-20 3-phenyl-2-methylbenzyl-2,2-dimethyl-3- (2-chloro-2- trifluoromethylvin yl) cyclopropanecarboxylate, fenpropathrin, fenfluthrin, fenvalerate, hucythrinate, flumethrin, fluvalinate, permethrin, resmethrin and tralomethrin;
  • Nitroimines and nitromethylenes such as l - [(6-chloro-3-pyridinyl) methyl] -4,5-dihydro-
  • Particularly preferred insecticides are:
  • Chlo ⁇ yrifos Phoxim, Silafluofen, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, Hexaflumuron, Lindane.
  • the synergistic effect of the mixtures is observed in mixing ratios from 99: 1 to 1:99, preferably from 3: 1 to 1: 3, very particularly preferably in a ratio of 1: 1.
  • the mixtures according to the invention produced in this way are effective not only against fungi but also against material-destroying insects.
  • the insecticides are generally present in a dosage of 0.00001% to 10%, preferably 0.0001% to 5%, particularly preferably 0.001% to 1%. To achieve further increased effects against wood-destroying fungi, the following fungicides can also be added.
  • Succinate dehydrogenase inhibitors such as:
  • Fenfuram Furcarbanil, Cyclafluramid, Furmecyclox, Seedvax, Metsulfovax, Pyrocarbolid, Oxycarboxin, Shirlan, Mebenil (Mepronil), Benodanil, Hutolanil (Moncut)
  • Sulfenamides such as dichlorfluanid, tolylfluanid, Folpet, Huorfolpet; Captan, Capto-fol,
  • Benzimidazoles such as carbendazim, benomyl, furathiocarb, fuberidazole, thiophonate methyl, thiabendazole or their salts;
  • Thiocyanates such as thiocyanatomethylthiobenzothiazole, methylene bisthiocyanate;
  • quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethldodecyclammonium chloride, didecyldimethylammonium chloride,
  • Mo ⁇ holinderivate such as Tridemo ⁇ h, Fenpropimo ⁇ h, Falimo ⁇ h, Dimethomo ⁇ h, Dodemo ⁇ h; Aldimo ⁇ h, fenpropidin and their arylsulfonic acid salts, e.g. p-toluenesulfonic acid and p-dodecylphenyl sulfonic acid,
  • Iodine derivatives such as diiodomethyl-p-tolyl sulfone, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formal, 3-bromo-2,3-diiodo-2-propenylethyl carbamate, 2,3,3-triiodallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 6-iodo-3-oxo-hex-5-in-ol-butyl carbamate, 6-iodo-3-oxo-hex-5-in-ol-phenyl carbamate, 3-iodo-2-propynyl-n-hexyl carbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenyl carbamate;
  • Phenol derivatives such as tribromophenol, tetrachlo ⁇ henol, 3-methyl-4-chl ⁇ henyl, dichlorophen, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol;
  • Bromine derivatives such as 2-bromo-2-niuO-l, 3-propanediol
  • Isothiazolinones such as N-methylisothiazolin-3-one, 5-chloro-N-methyl-isothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, N-octyl-isothiazolin-3-one; Benzisothiazolinones, 4,5-trimethylene-isothiazolinones;
  • Pyridines or pyrimidines such as l-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanil, mepanipyrim, dipyrithione;
  • Metal soaps such as tin, copper, zinc naphthenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;
  • Oxides such as tributyltin oxide, CU2O, CuO, ZnO;
  • Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates, tetramethylthiuram disulfide;
  • Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile, 2,3,5,6-tetrafluoroterephthalodinitrile;
  • Benzothiazoles such as 2-mercaptobenzothiazole
  • Benzamides such as 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide (XRD-563);
  • Boron compounds such as boric acid, boric acid ester, borax;
  • Formaldehyde and formaldehyde releasing compounds such as benzyl alcohol mono-
  • these combinations of active substances have a particularly high, microbicidal, in particular fungicidal activity, combined with a broad spectrum of activity against microorganisms and insects relevant in material protection; they are particularly effective against mold, wood-staining and wood-destroying fungi and insects.
  • microbicidal in particular fungicidal activity
  • fungicidal activity combined with a broad spectrum of activity against microorganisms and insects relevant in material protection; they are particularly effective against mold, wood-staining and wood-destroying fungi and insects.
  • the following groups of microorganisms may be mentioned by way of example, but without limitation:
  • Dactylium such as Dactylium fuerarioides Penicillium such as Penicillium brevicaule or Penicillium variabile
  • Trichoderma such as Trichoderma viride or Trichoderma lignorum
  • A3 Zygomycetes: j Mucor like Mucor spinorus
  • Gloeophyllum such as Gloeophyllum abietinum or
  • Lentinus such as Lentinus or cyathiformes
  • Lentinus edodes like Lentinus lepideus or
  • Paxillus such as Paxillus panuoides Pleurotus like Pleurotus ostreatus
  • Kalotermes flavicollis The amount of the agents or concentrates used depends on the type and the occurrence of the insects, microorganisms, the number of germs and on the medium. The optimum amount used can be determined in each case by test series. In general, however, it is sufficient to use 0.001 to 20% by weight, preferably 0.05 to 10% by weight, of the active compound mixture, based on the material to be protected.
  • the active ingredient mixture can be used as such, in the form of concentrates or generally customary formulations, such as solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with solvents or diluents, emulsifiers, dispersants and / or binders or fixatives, water repellants, optionally siccatives and UV stabilizers and optionally dyes and pigments and other processing aids.
  • organic-chemical solvent or solvent mixture and / or an oily or oily or slightly volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and / or water and at least one emulsifier and / or wetting agent or consists thereof.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a hammock point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents
  • Mineral oils with a boiling range of 170 to 220 ° C, test gasoline with a boiling range of 170 to 220 ° C, spindle oil with a boiling range range from 250 to 350 ° C, petroleum or aromatics with a boiling range from 160 to 280 ° C, te ⁇ entin oil and the like.
  • organic low-volatility oily or oily solvents with an evaporation number above 35 and a vapor point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture is also a Evaporation number above 35 and a Hammddling above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • the organic-chemical binders used are the water-dilutable synthetic resins known per se and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, eg polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin are used.
  • binders consisting of or containing an acrylate resin, a vinyl resin, eg polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention
  • binder mentioned can be replaced by a fixative (mixture) or a plasticizer (mixture).
  • fixative mixture
  • plasticizer mixture
  • additives are intended to volatilize the active ingredients and crystallize or precipitate! prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate glycerol glycerol ether or higher , Glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • stearates such as butyl stearate
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and ethylene benzophenone.
  • Wood that can be protected by the active substance mixture according to the invention or agents containing it is to be understood as examples: construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors, 10 Plywood, chipboard, carpentry or wood products that are generally used in house construction or joinery.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • microbicidal agents or concentrates used to protect wood and wood-based materials contain the active substance combination in a concentration of 0.01 to 95% by weight, in particular 0.01 to 60% by weight.
  • Preferred agents preferably contain 0.2 to 3% by weight, in particular 0.5 to 2% by weight, of hexaconazole in a mixture with the further azole, 0.005 to 1% by weight, preferably 0.01 up to 0.5% by weight of the insecticide and at least one organic chemical solvent or solvent mixture and / or one oily or oil-like non-volatile organic chemical
  • Particularly preferred (ready to use) means comprise 2 to 30 wt .-%, in ⁇ preferably 5 to 22 wt .-%, calculated as solid, of a synthetic resin binder, preferably an alkyd resin and / or a drying vegetable oil as well min ⁇ least one organically -chemical solvent or solvent mixture and / or an oily or oily low volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and emulsifier
  • ⁇ RS ⁇ RZBLATT (RULE 26) 5 and / or wetting agents and optionally desiccants, dyes, color pigments, anti-settling agents and / or UV stabilizers as a residual component.
  • Concentrates for preserving wood and wood-based materials preferably contain 0.2 to 25% by weight, preferably 3 to 8% by weight, of hexaconazole in mi
  • mean concentrations are the other azoles from 0 to 50 wt .-%, preferably from 0.5 to 25 wt .-% employed (based on 100 wt .-%) hexaconazole included.
  • the agents according to the invention advantageously make it possible to replace the previously available microbicidal agents with more effective ones. They show good stability and advantageously have a broad spectrum of activity.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP94920437A 1993-06-21 1994-06-08 Fungizide wirkstoffkombinationen Withdrawn EP0705160A1 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE4320495 1993-06-21
DE19934320495 DE4320495A1 (de) 1993-06-21 1993-06-21 Fungizide Wirkstoffkombinationen
DE4406819 1994-03-02
DE19944406819 DE4406819A1 (de) 1994-03-02 1994-03-02 Fungizide Wirkstoffkombination
PCT/EP1994/001868 WO1995000303A1 (de) 1993-06-21 1994-06-08 Fungizide wirkstoffkombinationen

Publications (1)

Publication Number Publication Date
EP0705160A1 true EP0705160A1 (de) 1996-04-10

Family

ID=25926961

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94920437A Withdrawn EP0705160A1 (de) 1993-06-21 1994-06-08 Fungizide wirkstoffkombinationen

Country Status (9)

Country Link
US (1) US5972971A (fi)
EP (1) EP0705160A1 (fi)
JP (1) JPH08509437A (fi)
AU (1) AU689480B2 (fi)
BR (1) BR9407120A (fi)
CA (1) CA2165560A1 (fi)
FI (1) FI956113A0 (fi)
NO (1) NO955107D0 (fi)
WO (1) WO1995000303A1 (fi)

Cited By (1)

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EP1609361A3 (de) * 1994-07-28 2010-01-06 Bayer CropScience Aktiengesellschaft Mittel zur Bekämpfung von Pflanzenschädlingen

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DE4233337A1 (de) * 1992-10-05 1994-04-07 Bayer Ag Mikrobizide Mittel
US5714507A (en) * 1994-07-01 1998-02-03 Janssen Pharmaceutica, N.V. Synergistic compositions containing metconazole and another triazole
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JP4599762B2 (ja) * 2001-05-01 2010-12-15 株式会社エス・ディー・エス バイオテック 木材の防汚方法
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AU689480B2 (en) 1998-04-02
FI956113A (fi) 1995-12-19
NO955107L (no) 1995-12-15
JPH08509437A (ja) 1996-10-08
US5972971A (en) 1999-10-26
CA2165560A1 (en) 1995-01-05
AU7123194A (en) 1995-01-17
BR9407120A (pt) 1996-09-03
WO1995000303A1 (de) 1995-01-05
FI956113A0 (fi) 1995-12-19
NO955107D0 (no) 1995-12-15

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