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WO1997018713A1 - Combinaison de matieres actives microbicides a base d'eau exemptes de solvants et d'emulsifiants - Google Patents

Combinaison de matieres actives microbicides a base d'eau exemptes de solvants et d'emulsifiants Download PDF

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Publication number
WO1997018713A1
WO1997018713A1 PCT/EP1996/004919 EP9604919W WO9718713A1 WO 1997018713 A1 WO1997018713 A1 WO 1997018713A1 EP 9604919 W EP9604919 W EP 9604919W WO 9718713 A1 WO9718713 A1 WO 9718713A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
active ingredient
triazole
carbon atoms
ethyl
Prior art date
Application number
PCT/EP1996/004919
Other languages
German (de)
English (en)
Inventor
Hans-Ulrich Buschhaus
Otto Exner
Martin Kugler
Yukihiro Nagano
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU75694/96A priority Critical patent/AU7569496A/en
Priority to KR1019980703264A priority patent/KR19990067289A/ko
Priority to EP96938169A priority patent/EP0863709A1/fr
Priority to PL96326609A priority patent/PL326609A1/xx
Priority to JP51934297A priority patent/JP4135979B2/ja
Priority to BR9611746-0A priority patent/BR9611746A/pt
Publication of WO1997018713A1 publication Critical patent/WO1997018713A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • 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 invention relates to new, in particular aqueous and optionally organic solvent-free and emulsifier-free, microbicidal active substance combinations of known azole fungicides, quaternary ammonium fungicides and an insecticide from the class of the nitromethylenes
  • imidazole and triazole fungicides such as, for example, the ⁇ - [2- (4-chlorophenyl) -e ⁇ yl] - ⁇ - (l, l-dimethylethyl) -lH-l, 2,4-triazole- l-ethanol (tebuconazole), the
  • the azole finigides such as the tebuconazole mentioned, have efficacy gaps in some germs relevant to the material, such as Trichoderma spec
  • the agonists and antagonists of the nicotinergic acetylcholine receptors are compounds which are known from the following publications
  • R represents hydrogen, optionally substituted radicals acyl, alkyl, aryl,
  • A represents a monofunctional group from the series hydrogen, acyl, alkyl, aryl or represents a bifunctional group which is linked to the radical Z, E represents an electron-withdrawing residue,
  • Atom can be linked to the radical Z
  • R represents hydrogen and also optionally substituted radicals from the
  • CpC ⁇ -alkyl in particular C ] -C 4 -alkyl, in particular methyl, ethyl, i-propyl, see- or t-butyl, which in turn may be substituted, may be mentioned as alkyl
  • Phenyl, naphthyl, especially phenyl, may be mentioned as aryl
  • Phenylmethyl and phenethyl may be mentioned as aralkyl
  • Alkyl with preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methyl, ethyl, n- and i-propyl and n-, i- and t-butyl; Alkoxy with preferably 1 to 4, in particular 1 or 2, carbon atoms, such as methoxy. Ethoxy.
  • A stands for hydrogen and optionally substituted radicals from the series acyl, alkyl, aryl, which preferably have the meanings given above, A furthermore stands for a bifunctional group.
  • Substituted alkylene with 1 to 4, in particular 1 to 2, carbon atoms may be mentioned, where the substituents listed above are mentioned as substituents.
  • a and Z together with the atoms to which they are attached, can form a saturated or unsaturated heterocyclic ring.
  • the hetero- Cyclic ring can contain a further 1 or 2 identical or different hetero atoms and / or hetero groups.
  • the heteroatoms are preferably oxygen, sulfur or nitrogen and the hetero groups are N-alkyl, alkyl of the N-alkyl group preferably containing 1 to 4, in particular 1 or 2, carbon atoms.
  • the heterocyclic ring contains 5 to 7, preferably 5 or 6 ring members.
  • Examples of the heterocyclic ring are pyrrolidine, piperidine, piperazine, hexamethyleneimine, morpholine and N-methylpiperazine
  • E stands for an electron-withdrawing radical, in particular NO 2 , CN,
  • Haloalkylcarbonyl such as 1,5-halogen-C r C 4 -carbonyl, in particular COCF 2 may be mentioned.
  • Z stands for optionally substituted radicals alkyl, -OR, -SR- -NRR, where R and the substituents preferably have the meaning given above.
  • the heterocyclic ring can contain a further 1 or 2 identical or different heteroatoms and / or hetero groups.
  • the hetero atoms are preferably oxygen, sulfur or nitrogen and the hetero groups are N-alkyl, the alkyl or N-alkyl group preferably containing 1 to 4, preferably 1 or 2, carbon atoms. Alkyl, methyl, ethyl, n- and i-propyl and n-, i- and t-butyl may be mentioned.
  • the heterocyclic ring contains 5 to 7, preferably 5 or 6 ring members.
  • heterocyclic ring examples include pyrrolidine, piperidine, piperazine, hexamethyleneimine, morpholine and N-methylpiperazine.
  • the agonists and antagonists of the nicotinergic acetylcholine receptors are particularly preferably compounds of the formula (II) R for
  • n 1 or 2
  • Subst is one of the substituents listed above, especially halogen, especially chlorine and A, Z, X and E have the meaning given above
  • Very particularly preferred agonists and antagonists of the nicotinergic acetylcholine receptors are compounds of the following formulas
  • Quaternary ammonium salts have long been known as broadly active microbicides and find e.g. Use in disinfection and textile preservation.
  • Property profile can be negatively influenced, or they can be deactivated. Furthermore, it is known that quaternary ammonium salts are easily deactivated by the presence of protein and dirt.
  • Water-insoluble solvents are incompatible with aqueous products such as leather liquors, emulsion paints, cooling and process water, disinfectants.
  • water-soluble solvents would be suitable as solubilizers in aqueous systems. But if they get into wastewater, they can see problems. In addition, solvents can interfere with the products to be protected.
  • Another way of imparting solvents for the production of water-based active ingredient formulations is to use emulsifiers. In the case of highly water-insoluble compounds such as azoles, this usually becomes large
  • Emulsifier narrowly required, which should be avoided for ecological reasons.
  • the effectiveness of microbicidal active substances can likewise be severely impaired by the use of emulsifiers.
  • the replaceability for certain systems can also be limited.
  • the object of the invention was therefore to provide new, preferably water-based, low-solvent and emulsifier-free microbicidal active ingredient formulations based on azole fungicides and insecticides from the class of the nitromethylenes which can be easily diluted with water and at the same time provide storage-stable use solutions.
  • the compounds in which the compounds have asymmetric carbon atoms also include the isomers and isomer mixtures of the most varied compositions;
  • insecticide from the class of the nitromethylenes, preferably of the formulas (Ila) to (Hh), in particular the compound (Ih),
  • R 1 , R 2 , R 3 , R 4 are the same or different and each is unsubstituted or substituted, straight-chain or branched, saturated or unsaturated
  • X for an anion which requires solubility in water e.g. halide, sulfate,
  • Alkyl sulfonate or optionally substituted aryl sulfonate stable aqueous solutions or emulsions can be produced which have a particularly high microbicidal and insecticidal activity.
  • Preferred quaternary ammonium compounds are ammonium salts such as
  • DDAC Didecyldimethylammonium chloride
  • a combination of tebuconazole and / or propiconazole and imidacloprid and didecyldimethylammonium chloride is very particularly preferred.
  • the weight ratios of the active substances in the active substance combinations can be varied within relatively large ranges. They are generally dependent on the area of application and on the active ingredients used in each case. However, these weight ratios can easily be determined in test series by simply mixing the components.
  • the weight ratio of quaternary ammonium fungicide to azole fungicide to the insecticide is preferably 400: 20: 1 to 50: 10: 1.
  • the active ingredients are used individually or as a combination of active ingredients, e.g. in the form of powders, granules, pastes or concentrated solutions, suspensions or emulsions by simple mixing in water and are then in the form of an aqueous suspension, solution or emulsion.
  • aqueous solutions or emulsions preferably contain more than 20% by weight, in particular more than 40% by weight, of water and can be diluted with water to the application concentration as desired. It goes without saying / 18713 PC ⁇ 7EP96 / 04919
  • microbicidal compositions contain the active ingredient combination in a concentration of 0.001 to 95% by weight, in particular 0.01 to 60% by weight and, if appropriate, 0.001 to 30% by weight, in particular 0.1 to 20% by weight. %, very particularly 0.05 to 10% by weight of a suitable further fungicide, insecticide or another active substance.
  • the active substance combinations or agents according to the invention have a strong
  • microorganisms Action against microorganisms. They are used in the material to protect technical materials: they are particularly effective against mold, wood-staining and wood-destroying fungi and bacteria, and against yeasts, algae and slime organisms.
  • the following types of microorganisms may be mentioned by way of example, but without limitation:
  • Alternaria such as Alternaria tenuis, Aspergillus such as Aspergillus niger and Aspergillus terreus, Aureobasidium such as Aureobasidium pullulans, Chaetomium such as Chatomatium globosum, Cladosporium like Cladosporium herbarum, Coniophora like Coniophora souna, Gliocladium like Liocentinilominusces, such as Liocentinigrincesinces Penicillium such as Penicillium brevicaule, Penicillium glaueum and Penicillium pinophilum, Polyporus such as Polyporus versicolor, Sclerophoma such as Sclerophoma pityophila, Streptoverticillium such as Streptoverticillium reticulum, Trichoderma such as Trichoderma viride and Trichyophyton;
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas areuginosa
  • Staphylococcus such as Staphylococcus aureus
  • Candida like Candida aibicans.
  • the active compound combinations according to the invention are particularly suitable for protecting technical materials, in particular wood, even from infestation by wood-destroying insects, such as, for example 1.
  • wood-destroying insects such as, for example 1.
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucilugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • the active ingredient combinations according to the invention can generally be incorporated into all wood preservatives or formulations, 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 as well as other processing aids or as an additive to any other wood preservation formulations.
  • Easily or moderately volatile organic chemical solvents are preferably used as organic chemical solvents.
  • the readily or moderately volatile organic chemical solvents can be partially replaced by organic, non-volatile, oily or oil-like solvents, with the proviso that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture
  • aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups such as alcohols, glycol ethers, esters or the like, are used
  • the known organic-chemical binders are the water-dilutable synthetic resins and / or synthetic resins 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, for example 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 the basis of a natural and / or synthetic resin used
  • binders consisting of or containing an acrylate resin, a vinyl resin, for example 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,
  • 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, dyes, pigments, water-repellents, odor control agents known per se Gentien and inhibitors or corrosion protection agents and the like are used
  • At least one acrylate resin or modified acrylate resin and / or a drying alkyl resin is preferably contained in the agent or in the concentrate as the organic chemical binder
  • the binder mentioned can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation). 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 or glycerol, glycerol - Kolether, glycerol ester and p-toluenesulfonic acid ester
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone, ethyl enbenzophenone, amines such as alkanolamines such as monoethanolamine or ammonia
  • technical materials are non-living materials which have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention adhesives, glues, paper and cardboard, textiles, leather, wood, Coating agents and plastic articles, cooling lubricants and other materials that can be attacked or decomposed by microorganisms are also within the scope of the materials to be protected
  • Parts of production plants for example cooling water circuits, which can be impaired by the multiplication of microorganisms.
  • Preferred technical materials for the purposes of the invention are adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants, aqueous hydraulic fluids and cooling circuits
  • the active substance combinations, compositions or concentrates according to the invention are preferably used to protect wood and wood-based materials against microorganisms, for example against wood-destroying or wood-staining fungi, in particular in tropical wood preservation
  • Wood which can be protected by the active substance mixture according to the invention or agents containing it, is to be understood, for example, as construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors, plywood, chipboard , Carpentry or wood products that are generally used in house building or in carpentry
  • a particularly effective wood protection is achieved by large-scale impregnation processes, eg vacuum, double vacuum or printing processes
  • the amount of the active ingredient combinations used depends on the type and the occurrence of the microorganisms, the number of bacteria, the insects 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 mixtures, based on the material to be protected.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient combination in a concentration of 0.001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the new active ingredient combinations can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • Water is preferably used as the solvent or diluent, if appropriate in a mixture with one or more of the abovementioned solvents or diluents, emulsifiers and dispersants.
  • Sulfenamides such as dichlofluanid (Euparen), tolylfluanid (Methyleuparen), Folpet, Fluorfolpet; Benzimidazoles (optionally in the form of their salts) such as carbendazim
  • MLC Benomyl, Fuberidazole, Thiabendazole
  • Thiocyanates such as thiocyanatomethylthiobenzothiazole (TCMTB), methyl enbisthiocyanat (MBT)
  • Morpholine derivatives such as C j pC j ⁇ alkyl ⁇ ⁇ -dimethylmorpholine homologue (tridemorph), (+) - cis-4- [3- (tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (fenpropimorph) , Falimorph
  • Phenols such as o-phenylphenol, halogenated cresols, tribromophenol,
  • Tetrachlorophenol pentachlorophenol, 3-methyl-4-chlorophenol, dichlorophen; Iodine propargyl derivatives such as iodopropargyl butyl carbamate (IPBC), chlorophenyl formal, -phenyl carbamate, -hexyl carbamate, -cycl ohexyl carbamate, isothiazolinones such as N-methylisothiazolin-3-one, 5-chloro-N-methyl-isothiazolin-3-one, 4,5-dichloro-N-octyhsothiazol ⁇ n- 3-one, N-octyl ⁇ sothiazolin-3-one (octhilinones), pyridines such as l-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methyl-sulfonyl-py ⁇ din , Tetrachloro-4-
  • Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, l- (4-chlorophenyl) -4- (O-ethyl, S-propyl) -phosphoryloxypyrazole (TIA-230), Chlorpy ⁇ fos, Coumaphos, Demeton, Demeton-S-methyl , Diazinon, Dichlorvos, Dimethoate, Ethoprophos, Et ⁇ m- fos, Fenitrothion, Fention, Heptenophos, Parathion, Parathion-methyl, Phosalone, Phoxion, Pinmiphos-ethyl, Pi ⁇ miphos-methyl, Profenofos, Prothiofos, Sulprofos, T ⁇ azophon, and Trichlorophos, and Trichlorophos, and Trichlorophos
  • Carbamates such as aldicarb, bendiocarb, BPMC (2- (l-methylpropyl) phenylmethyl carbamate), butocarboxime, butoxy carboxime, carbaryl, carbofuran, carbosulfane,
  • Cloethocarb isoprocarb, methomyl, oxamyl, pimicarb, promecarb, propoxur and thiodicarb,
  • Pyrethroids such as Allethnn, Alphameth ⁇ n, Bioresmeth ⁇ n, Byfenthnn (FMC 54 800), Cycloprothrin, Cyfluthrin, Decameth ⁇ on, Cyhaloth ⁇ n, Cypermethnn, Deltameth ⁇ n, Alpha-cyano-3-phenyl-2-methylbenzyl-2,2-dimethyl chloro-2-t ⁇ - fluoromethylv ⁇ nyl) cyclopropane carboxylate, fenpropath ⁇ n, fenfluth ⁇ n, fenvalerate, flucyth ⁇ nate, flumethrin, fluvalinate, permethrin and resmeth ⁇ n, nitroimides such as l - [(6-chloro-3-py ⁇ d ⁇ nyl) methyl] -4,5-dehydro N-n ⁇ tro-lH- ⁇ m ⁇ dazol-2-an ⁇ n (Imida-clop ⁇ d)
  • Algicides, molluscicides, active substances against "sea animals" which, for example, settle on ship's floor paints come into consideration as other active substances
  • the combinations of active substances or agents according to the invention advantageously make it possible to replace the previously available biocidal agents with more effective and more environmentally compatible ones. They show good stability and advantageously have a broad spectrum of activity
  • test sample in water 50-, 75-, 100- and 200-fold dilutions of the test sample in water are in closed polyethylene bottles at 2 ° C and 40 ° C for 3
  • Crystals and precipitates are patterned and evaluated according to the following criteria
  • test sample 50-, 75-, 100- and 200-fold aqueous dilutions of the test sample are made
  • Test specimens measuring 2 cm x 2 cm x 12 cm are cut out of Cryptomeria sapwood, all surfaces except for one end face are sealed with epoxy resin from these test specimens
  • test specimens After each weighing, 10 test specimens are stored in a 1,000 ml beaker in such a way that floating is not possible. After storage for 2 hours under vacuum (60 mm Hg), the dilutions are introduced and the test specimens in at normal pressure for 22 hours kept immersed in the dilutions Then the test specimens are removed from the dilutions and weighed back to determine the amount taken up (kg / m 3 )
  • the treated test specimens are cut open at a distance of 2 cm and 8 cm from the unclosed front end for analysis of the active substances DDAC, tebuconazole and imidcloprid after they have been stored under a polyethylene film at 26 ° C. for 1 month. The following results have been achieved
  • test sample 50, 75, 100 and 200-fold aqueous dilutions of the test sample are prepared.
  • the controls used are 1.0%, 0.7%, 0.5% and 0.3% DDAC in water 2 1 described test samples, which are stored for 3 months at 2 ° C
  • Test specimens with the dimensions 2 cm x 2 cm x 10 cm are cut out of Cryptomeria sapwood each 5 of these test specimens are stored in a 1,000 ml beaker in such a way that floating is not possible After storage for 2 hours under vacuum (60 mm Hg) the dilutions are introduced and the test specimens are kept immersed in the dilutions for 2 hours at normal pressure. The test specimens are then removed from the dilutions and stored individually for 21 days under a polyethylene film The treated and untreated test specimens are alternately stored in wood-destroying soil at 26 ° C and 90% relative atmospheric humidity for 6 months, as described in standard ENV 807 parts 1 and 2. After 6 months, protection against wood-destroying fungi is assessed as follows

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Forests & Forestry (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouvelles combinaisons de matières actives ou de nouveaux agents microbicides, éventuellement sans solvant et sans émulsifiant, constitués de fongicides connus de type azole, d'un insecticide de la classe des nitrométhylènes et de composés quaternaires d'ammonium. L'invention concerne également leur utilisation dans la protection des matériaux.
PCT/EP1996/004919 1995-11-22 1996-11-11 Combinaison de matieres actives microbicides a base d'eau exemptes de solvants et d'emulsifiants WO1997018713A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU75694/96A AU7569496A (en) 1995-11-22 1996-11-11 Water-based solvant-free and emulsifier-free microbicidal combination of active substances
KR1019980703264A KR19990067289A (ko) 1995-11-22 1996-11-11 용매 및 유화제가 없는 물-기재의 살미생물 활성 화합물 배합물
EP96938169A EP0863709A1 (fr) 1995-11-22 1996-11-11 Combinaison de matieres actives microbicides a base d'eau exemptes de solvants et d'emulsifiants
PL96326609A PL326609A1 (en) 1995-11-22 1996-11-11 Aqueous solvent- and emulsifier-fire mixture of microbicidal active substances
JP51934297A JP4135979B2 (ja) 1995-11-22 1996-11-11 水を基剤とする溶媒不含および乳化剤不含の殺微生物性の、活性物質の組み合わせ物
BR9611746-0A BR9611746A (pt) 1995-11-22 1996-11-11 Combinação de substância ativa microbicida á base de água, sem solvente e sem emulsificante

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19543477A DE19543477A1 (de) 1995-11-22 1995-11-22 Wasserbasierte, lösungsmittel- und emulgatorfreie mikrobizide Wirkstoffkombination
DE19543477.3 1995-11-22

Publications (1)

Publication Number Publication Date
WO1997018713A1 true WO1997018713A1 (fr) 1997-05-29

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PCT/EP1996/004919 WO1997018713A1 (fr) 1995-11-22 1996-11-11 Combinaison de matieres actives microbicides a base d'eau exemptes de solvants et d'emulsifiants

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JP (1) JP4135979B2 (fr)
KR (1) KR19990067289A (fr)
AU (1) AU7569496A (fr)
BR (1) BR9611746A (fr)
CA (1) CA2238033A1 (fr)
DE (1) DE19543477A1 (fr)
PL (1) PL326609A1 (fr)
WO (1) WO1997018713A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002503681A (ja) * 1998-02-23 2002-02-05 バイエル・アクチエンゲゼルシヤフト 皮膚適用のための殺寄生虫剤の水性調剤
JP2002517417A (ja) * 1998-06-10 2002-06-18 バイエル アクチェンゲゼルシャフト 植物有害生物の防除剤
DE102004007747B3 (de) * 2004-02-18 2004-12-23 Jöst, Peter Schleifbandträger und Schleifbandanordnung
CN1294812C (zh) * 1998-02-23 2007-01-17 拜尔公司 抗人体寄生虫和螨虫的含水制剂
WO2011161404A1 (fr) 2010-06-21 2011-12-29 Arch Timber Protection Limited Compositions de produit de préservation du bois utiles pour le traitement de champignons tolérants au cuivre
US9603358B2 (en) 2011-11-04 2017-03-28 Arch Timber Protection Limited Additives for use in wood preservation
US11312038B2 (en) 2014-05-02 2022-04-26 Arch Wood Protection, Inc. Wood preservative composition

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020074899A (ko) * 2001-03-22 2002-10-04 김용국 살균·살충·소독제 조성물
KR20020074903A (ko) * 2001-03-22 2002-10-04 김용국 농약 조성물 및 그 용도
DE102005043139A1 (de) * 2005-09-10 2007-03-22 Lanxess Deutschland Gmbh Synergistische Mischungen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0533017A1 (fr) * 1991-09-19 1993-03-24 Bayer Ag Combinaison microbicide à base d'eau des agents actifs, qui ne contienent pas de solvant ni d'émulsifiant
EP0664081A2 (fr) * 1994-01-20 1995-07-26 Hoechst Schering AgrEvo GmbH Combinaisons synergiques des sels d'ammonium
WO1996003045A1 (fr) * 1994-07-28 1996-02-08 Bayer Aktiengesellschaft Pesticides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0533017A1 (fr) * 1991-09-19 1993-03-24 Bayer Ag Combinaison microbicide à base d'eau des agents actifs, qui ne contienent pas de solvant ni d'émulsifiant
EP0664081A2 (fr) * 1994-01-20 1995-07-26 Hoechst Schering AgrEvo GmbH Combinaisons synergiques des sels d'ammonium
WO1996003045A1 (fr) * 1994-07-28 1996-02-08 Bayer Aktiengesellschaft Pesticides

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002503681A (ja) * 1998-02-23 2002-02-05 バイエル・アクチエンゲゼルシヤフト 皮膚適用のための殺寄生虫剤の水性調剤
CN1294812C (zh) * 1998-02-23 2007-01-17 拜尔公司 抗人体寄生虫和螨虫的含水制剂
CN1328958C (zh) * 1998-02-23 2007-08-01 拜尔公司 施用于皮肤的含水杀寄生物制剂
JP2002517417A (ja) * 1998-06-10 2002-06-18 バイエル アクチェンゲゼルシャフト 植物有害生物の防除剤
DE102004007747B3 (de) * 2004-02-18 2004-12-23 Jöst, Peter Schleifbandträger und Schleifbandanordnung
AU2011268757B2 (en) * 2010-06-21 2014-07-10 Arch Timber Protection Limited Wood preservative compositions useful for treating copper-tolerant fungi
CN103079403A (zh) * 2010-06-21 2013-05-01 拱门木材保护有限公司 用于处理耐铜真菌的木材防腐剂组合物
US20130209823A1 (en) * 2010-06-21 2013-08-15 Arch Timber Protection Limited Wood preservative compositions useful for treating copper-tolerant fungi
WO2011161404A1 (fr) 2010-06-21 2011-12-29 Arch Timber Protection Limited Compositions de produit de préservation du bois utiles pour le traitement de champignons tolérants au cuivre
US9023483B2 (en) 2010-06-21 2015-05-05 Arch Timber Protection Limited Wood preservative compositions useful for treating copper-tolerant fungi
CN103079403B (zh) * 2010-06-21 2015-11-25 拱门木材保护有限公司 用于处理耐铜真菌的木材防腐剂组合物
EA023359B1 (ru) * 2010-06-21 2016-05-31 Арч Тимбер Протекшн Лимитед Композиции для защиты древесины, пригодные для обработки грибов, устойчивых к меди
AU2011268757C1 (en) * 2010-06-21 2016-11-10 Arch Timber Protection Limited Wood preservative compositions useful for treating copper-tolerant fungi
US9603358B2 (en) 2011-11-04 2017-03-28 Arch Timber Protection Limited Additives for use in wood preservation
US9961895B2 (en) 2011-11-04 2018-05-08 Arch Timber Protection Limited Additives for use in wood preservation
US11312038B2 (en) 2014-05-02 2022-04-26 Arch Wood Protection, Inc. Wood preservative composition

Also Published As

Publication number Publication date
KR19990067289A (ko) 1999-08-16
JP4135979B2 (ja) 2008-08-20
CA2238033A1 (fr) 1997-05-29
DE19543477A1 (de) 1997-05-28
AU7569496A (en) 1997-06-11
EP0863709A1 (fr) 1998-09-16
BR9611746A (pt) 2000-03-28
JP2000500475A (ja) 2000-01-18
PL326609A1 (en) 1998-10-12

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