WO2007031198A1 - Utilisation de triclosan pour la protection du bois - Google Patents

Utilisation de triclosan pour la protection du bois Download PDF

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Publication number
WO2007031198A1
WO2007031198A1 PCT/EP2006/008510 EP2006008510W WO2007031198A1 WO 2007031198 A1 WO2007031198 A1 WO 2007031198A1 EP 2006008510 W EP2006008510 W EP 2006008510W WO 2007031198 A1 WO2007031198 A1 WO 2007031198A1
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WIPO (PCT)
Prior art keywords
wood
triclosan
optionally
mixture according
destruction
Prior art date
Application number
PCT/EP2006/008510
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German (de)
English (en)
Inventor
Rainer Bruns
Martin Kugler
Thomas Jaetsch
Original Assignee
Lanxess Deutschland Gmbh
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Filing date
Publication date
Application filed by Lanxess Deutschland Gmbh filed Critical Lanxess Deutschland Gmbh
Priority to EP06791752A priority Critical patent/EP1926368A1/fr
Publication of WO2007031198A1 publication Critical patent/WO2007031198A1/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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
    • 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 the use of triclosan for the protection of wood and wood-based materials against attack and / or destruction " by soft rot fungi, as well as new fungicidal " agents and new, synergistic mixtures based on the active ingredient triclosan, and their use for the protection of industrial materials from infestation , Damage and / or destruction by microorganisms.
  • the skilled person distinguishes between a structural destruction of the wood by Basidiomyceten and - if the wood is exposed to a high humidity or earth contact environment - by soft rot fungi, and a visual impairment of the wood by wood-discoloring fungi.
  • Tar oils Active ingredients for the protection of wood against the destruction by fungi have been known for a long time, for example, tar oils were used to protect the wood. Tar oils are characterized by good permeability and high leaching resistance, but have significant disadvantages due to their persistence, their odor and their toxicologically unfavorable properties, so that their use in wood preservation today is very limited.
  • active ingredients based on chromium, copper and arsenic salts have been used for permanent wood preservation, but these are subject to substitution pressure due to their toxicological and in particular ecotoxicological disadvantages.
  • triazole fungicides such as tebuconazole or propiconazole, may be mentioned by way of example.
  • wood preservatives for this hazard class still inorganic wood preservatives such as boron compounds, silicofluorides, chromium and fluorine-containing salts, chromium- and copper-containing salts with and without arsenic, chromium and copper-containing salts with and without boron compounds and betaine preparations based on polymeric betain in Combination with boron and copper salts, and highly water-soluble quaternary ammonium compounds used.
  • fungicides against Basidiomycete infestation today include triazole fungicides such as e.g. Tebuconazole, propiconazole or cyproconazole used. Furthermore, the fungicides IPBC, Cabendazim, Folpet as well as Dichlofluanid and Tolylfluanid are used for protection against wood-discolouring fungi. However, both the triazoles and the mentioned fungicides with activity against fungal trees in the test against soft rot fungi according to ENV 807 completely fail or have only an insufficient effect.
  • Triclosan belongs to the class of diphenyl ethers and is already used as a chemical disinfectant and preservative. Triclosan is used, among other things, as an additive in sports and functional textiles, shoes and carpets to prevent unpleasant odors. Further fields of application are the use of triclosan in toothpastes, cleaners, household sponges or plastic dishes as well as in cosmetics, shampoos, soaps, deodorants or lotions. In hospitals and medical practices, triclosan-containing solutions are used for disinfection.
  • Triclosan is characterized by a low acute toxicity, the LD50 value against rats (oral administration) is e.g. at 3700 - 4500 mg / kg. Triclosan is as a pure substance only moderately irritating, also there are no signs of sensitization or photosensitizing potential. Triclosan is an inhibitor of bacterial fatty acid biosynthesis. Triclosan is not used in wood preservation. This may be due to the fact that triclosan is degraded by wood-destroying basidiomycetes (see Hundt et al., Applied and Environmental Microbiology, September 2000, page 4157-4160, Vol. 66, No. 9).
  • triclosan has an excellent action against soft rot fungi.
  • the present invention thus relates to the use of triclosan (5-chloro-2- (2,4-dichlorophenoxy) phenol) for the protection of wood, wood-based materials and wood-plastic composites from infestation and / or destruction by soft rot fungi.
  • the use according to the invention substantially and decisively enriches the state of the art because ecotoxicologically hazardous heavy metal-containing wood preservatives protect wood with permanent soil contact or in environments with high humidity, i. For example, in hazard class 4, can be substituted. As a result, the environmental impact of heavy metals is significantly reduced.
  • Triclosan shows a broad activity against soft rot fungi such as. contrary to ENV 807 (Test method for the determination of the limit of activity against soft rot and others erdbe passende microorganisms, German version of 2001) described fungi such as Chaetomium globosum, Glenospora graphii, Humicola gisea, Petriella setifera, Trichurus spiralis and Lecythophora mutabilis and against Trichoderma viride, Stachybotrys cartarum, Chephaporium sp. and Acremonium sp ..
  • triclosan against soft rot can optionally be extended by adding at least one further microbicidal compound to increase the spectrum of action or to achieve special effects.
  • the activity spectrum can be supplemented by the addition of further fungicides and / or termiticides.
  • triazole fungicides examples include: azaconazoles, azocyclotin, bitertanol, bromuconazoles; Cyproconazole, diclobutrazole, difenoconazole, dinuconazole, epoxyconazole, etconazole, fenbuconazole, fenchlorazole, fenethanil, fluquinconazole, flusilazole, flutriafol, furconazole, hexaconazole, imibenconazole, ipconazole, izofos, myclobutanil, metconazole, paclobutrazole, penconazole, propiconazole, (+ / -) - cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol, 2- (1-tert-butyl) -1 - (2- chloroph
  • triclosan in combination with one or more of the following fungicidal components is preferred: chlorothalonil, captan, dichlofluanid, tolylfluanid, carbenzimine, thiabendazole, fenpropimorph, bethoxazine, folpet, fluorolipet, thiocyanato-methylthiobenzothiazole, 3-iodo 2-propynyl-n-butylcarbamate, zinc pyrithione, copper pyrithione, dichloroctylisothiazolinone, n-octylsisothiazolinone, N- (3-aminopropyl) -N-dodecylpropane-1,3-diamine and also boric acid compounds such as boric acid, boric acid ester, borax.
  • boric acid compounds such as boric acid, boric acid ester, borax.
  • triclosan in combination with one or more of the following fungicidal components: clorthalonill, dichlofluanid, tolylfluanid, bethoxazine, 3-iodo-2-propynyl-butylcarbamate, dichloroctylisothiazolinone, n-octylsisothiazolinone, folpet, zinc and copper pyrithione ,
  • triclosan in a mixture with one or more of the following termiticidal components:
  • triclosan in combinations with one or more of the following termiticidal components:
  • triclosan in combinations with one or more of the following termiticides:
  • triclosan if appropriate in combination with one or more of the above-mentioned mixing partners, can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and very fine encapsulations in polymeric substances.
  • Another object of this invention are agents containing triclosan for the protection of wood and wood-based materials and wood plastic composites before infestation and or destruction by soft rot fungi.
  • compositions of the invention comprise triclosan and at least one diluent or solvent, optionally further auxiliaries and additives and optionally at least one further microbicidal component, preferably from the series of the above-mentioned fungicides and termiticides.
  • the formulations can be prepared in a known manner, for example by mixing the active substance triclosan and optionally further active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants - greed and / or foaming agents.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants - greed and / or foaming agents.
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or Cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • liquefied gaseous extenders or carriers are meant liquids which are at normal temperature and are under normal pressure gaseous, for example, aerosol propellants, such as halogenated hydrocarbons and
  • Suitable solid carriers are: e.g. ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
  • Suitable solid carriers for granules are: e.g. Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • Suitable emulsifiers and / or foam-formers are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylarylpolyglycolether, alkyl sulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • Suitable dispersants are: e.g. Lignin-sulphite liquors and methylcellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • compositions according to the invention generally contain between 0.005 and 95% by weight of triclosan, preferably between 0.1 and 50% by weight of triclosan, and optionally between 0.005 and 50% by weight of said microbicidal components, preferably between 0.1 and 30% by weight.
  • microbicidal agents or concentrates used to protect the technical materials contain the active ingredient triclosan or the combination of triclosan with another microbicidal active ingredient in a concentration of 0.005 and 95 wt .-%, in particular 0.1 to 50 weight percent.
  • the use concentrations of the active substance triclosan to be used according to the invention or the active substance combination of triclosan with at least one further microbicidal active ingredient depends on the nature and occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimum amount used can be determined by test series. In general, the use concentrations of triclosan or the combination of triclosan with at least one other microbicidal active ingredient in the Range of 0.001 to 5 weight percent, preferably from 0.01 to 1.5 weight percent, based on the material to be protected.
  • compositions according to the invention exhibit good stability and advantageously have a broad spectrum of activity.
  • triclosan has excellent activity against soft rot fungi, but is resistant to wood-destroying basidiomycetes, e.g. Gloeophyllum trabeum, Coniophora souna, Poria placenta, Lentinus tigrinus, Coriolus versicolor and Stereum sanguinolentum are insufficiently effective and can be degraded by them.
  • basidiomycetes e.g. Gloeophyllum trabeum, Coniophora souna, Poria placenta, Lentinus tigrinus, Coriolus versicolor and Stereum sanguinolentum are insufficiently effective and can be degraded by them.
  • compositions comprising a synergistically effective amount of triclosan and at least one triazole fungicide, fungicidal compositions based on these mixtures and the use of these mixtures and agents for the protection of industrial materials, in particular wood and wood-based materials, from infestation, damage and / or Destruction by microorganisms.
  • the triazole fungicides to be used according to the invention are preferably azaconazoles, azocyclotin, bitertanol, bromuconazoles; Cyproconazole, diclobutrazoles, difenoconazole, diniconazole, epoxyconazole, etconazole, fenbuconazole, fenchlorazole, fenethanil, fluquinocynazole, flusilazole, flutriafol, furconazole, hexaconazole, imibenconazole, ipconazole, izofos, myclobutanil, metconazole, paclobutrazole, penconazole, propiconazole, (+/- ) -cis-1- (4-chlorophenyl) -2- (1H-l, 2,4-triazol-1-yl) cycloheptanol, 2- (1-tert-butyl) -1- (2-chlor
  • mixtures of triclosan with at least one triazole fungicide from the series propiconazoles, tebuconazoles, cyproconazoles, hexaconazoles and triadimefon, which are distinguished by pronounced synergism against wood-destroying basidiomycetes.
  • the mixtures according to the invention generally contain triclosan and at least one triazole fungicide in a weight ratio of from 1:99 to 99: 1, preferably from 1:10 to 10: 1.
  • the mixtures according to the invention may contain further active ingredients from the series of fungicidal and / or termiticides for increasing the activity and / or achieving particular effects.
  • the mixtures according to the invention preferably contain one or more of the following fungicidal components: clorthalonil, carbendazim, thiabendazole, dichloroctylisothiazolinone, n-octylisothazolinone, folpet, dichlofluanid, tolylfluanid, bethoxazine, 3-iodo-2-propynyl-butylcarbamate, zinc or Copper pyrithione, bifenthrin, chlorfenapyr, clothianidin, cyfluthrin, cypermethrin, deltamethrin, etofenprox, imidacloprid, permethrin, thiacloprid, thiamethoxam.
  • Captan carbendazim, fenpropimorph, bethoxazine, fluoro-folpet, thiocyanato-methylthiobenzothiazole, dichloroctylisothiazolinone, n-octylsisothiazolinone, N- (3-aminopropyl) -N-dodecylpropane-l, 3-diamine and boric acid compounds such as boric acid, boric acid ester, borax.
  • boric acid compounds such as boric acid, boric acid ester, borax.
  • the mixtures according to the invention particularly preferably comprise one or more of the following fungicidal components: clorthalonill, dichlofluanid, tolylfluanid, bethoxazine, 3-iodo-2-propynyl-butylcarbamate, dichloroctylisothiazolinone, n-octylsisothiazolinone, folpet, zinc pyrithione and copper pyrithione.
  • fungicidal components clorthalonill, dichlofluanid, tolylfluanid, bethoxazine, 3-iodo-2-propynyl-butylcarbamate, dichloroctylisothiazolinone, n-octylsisothiazolinone, folpet, zinc pyrithione and copper pyrithione.
  • the mixtures according to the invention generally contain 0.01-85% by weight of triclosan, 0.01-85% by weight of one or more triazole fungicides, optionally 0.01-80% by weight of at least one further microbicidal active ingredient from the series of fungicides, insecticides and termiticides.
  • the mixtures according to the invention are outstandingly suitable for the protection of industrial materials, in particular wood and wood-based materials, against infestation, damage and or destruction by microorganisms.
  • the mixtures according to the invention can be prepared by a generally known process by mixing a synergistically effective amount of the active substances triclosan and one or more triazole fungicides and optionally further active compounds from the series of fungicides, insecticides and termiticides and optionally adjuvants and additives in a suitable apparatus, ground, granulated, emulsified or dispersed.
  • Another object of this invention are protected against attack and / or destruction by soft rot fungi wood and wood-based materials and wood-plastic composites containing triclosan or an agent based on triclosan.
  • Wood, wood-based materials and wood-plastic composites which can be protected by the active substance mixtures according to the invention or agents contained in them, are exemplary understand: timber, wooden beams, railway sleepers, bridge parts, boat bridges, wooden vehicles,
  • Crates pallets, containers, telephone poles, wood cladding, wooden windows and doors, plywood, medium density fibreboard (MDF), chipboard, Oriented Strand Board (OSB), waferboard, laminated veneer lumber (LVL) or wood products commonly used in house building or in the joinery and wood plastic composites.
  • MDF medium density fibreboard
  • OSB Oriented Strand Board
  • LTL laminated veneer lumber
  • Another object of the invention is a method for the protection of wood, wood-based materials and wood-plastic composites against the infestation by soft rot fungi.
  • the active ingredient triclosan can be used as such, in the form of formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, pastes, soluble powders.
  • the application is usually carried out by treating the wood, the wood-based material or the wood-plastic composite with the active substance triclosan, optionally in combination with one or more microbicidal agents, or with an agent prepared therefrom in the form of a formulation or form of application, e.g. by spray, brush, dip and large scale impregnation methods, e.g. Vacuum, double vacuum or pressure method as well as by addition to the glue or masterbatch as well as via the compounder or mixer.
  • spray, brush, dip and large scale impregnation methods e.g. Vacuum, double vacuum or pressure method as well as by addition to the glue or masterbatch as well as via the compounder or mixer.
  • Particularly effective wood protection is provided by large scale impregnation methods, e.g. Achieved vacuum, double vacuum or printing process.
  • a method for the protection of wood is particularly preferred wherein the wood with an effective amount of triclosan and at least one diluent or solvent, optionally further auxiliaries and additives and optionally one or more microbicidal agents, preferably from the series of termiticides and fungicides Vacuum, double vacuum, pressure or dipping method is impregnated.
  • agar prepared using malt extract was added with triclosan in concentrations of 1 mg / l to 500 mg / l. After solidification of the agar, contamination was carried out with pure cultures of the soft rot fungi listed in Table 1. After 2 weeks of incubation at 26 ° C, the MIC was determined. MIC is the lowest concentration of active substance in which no fouling by soft rot fungi occurs., It is given in Table 1.
  • triclosan (A), tebuconazole (B) and mixtures (AB) of the two active substances mentioned were tested against the wood destroying basidiomycete Lentinus tigrinus.
  • Mycelium pieces were punched out of a colony of the wood destructor and incubated on a malt extract-peptone containing nutrient agar at 26 ° C.
  • radial hyphae growth was compared with and without addition of active ingredient.
  • the minimum inhibitory concentration (MIC) was given as the lowest active ingredient concentration in succession, which completely suppresses radial growth.
  • Qa concentration of substance A, which represents the MIC
  • Qb concentration of substance B, which represents the MIC
  • QB concentration of substance B in the concentration of A / B that inhibits microbial growth
  • SI> 1 means antagonism
  • SI ⁇ 1 means synergism
  • Table 2 MIC values and synergistic index of triclosan and tebuconazole (test fungus Lentinus tigrinus)
  • Table 3 MIC values and synergistic index of triclosan and cyproconazole (test fungus Gloephyllum trabeum)
  • Example 2 As described in Example 1, various concentrations of triclosan (A), propiconazole (B) and mixtures (AB) of the two active substances mentioned were tested against the moder rot causative agent Trichurus spiralis. According to the KuIl et al. (FCKuli, PC Eismann, HDSylvestrowicz, RL Mayer, Applied Microbiology 9, 538-541, 1961), the synergism was determined analogously to Example 2.
  • Table 3 MIC values and synergistic index of triclosan and propiconazole (test fungus Trichurus spiralis9

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  • 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)

Abstract

Le triclosan, ainsi que de nouveaux agents fongicides et de nouveaux mélanges synergiques à base de l'ingrédient actif triclosan sont parfaitement adaptés pour la protection de matériaux techniques contre les infestations, les dommages et / ou la destruction dus à des micro-organismes, en particulier pour la protection du bois et des matériaux dérivés du bois contre les infestations et / ou la destruction par des champignons provoquant la pourriture molle.
PCT/EP2006/008510 2005-09-13 2006-08-31 Utilisation de triclosan pour la protection du bois WO2007031198A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP06791752A EP1926368A1 (fr) 2005-09-13 2006-08-31 Utilisation de triclosan pour la protection du bois

Applications Claiming Priority (2)

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DE200510043428 DE102005043428A1 (de) 2005-09-13 2005-09-13 Verwendung von Triclosan für den Holzschutz
DE102005043428.2 2005-09-13

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WO2007031198A1 true WO2007031198A1 (fr) 2007-03-22

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CN101579873A (zh) * 2008-05-09 2009-11-18 朗盛德国有限责任公司 生产基于木材的材料的方法
WO2016133479A1 (fr) * 2015-02-19 2016-08-25 Yeditepe Universitesi Formulation de revêtement pour la stérilisation de semences et de surfaces

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WO2016133479A1 (fr) * 2015-02-19 2016-08-25 Yeditepe Universitesi Formulation de revêtement pour la stérilisation de semences et de surfaces
US20170135339A1 (en) * 2015-02-19 2017-05-18 Yeditepe Universitesi Coating formulation for seed and surface sterilization
AU2016220556B2 (en) * 2015-02-19 2017-09-21 Yeditepe Universitesi Coating formulation for seed and surface sterilization
JP2017537872A (ja) * 2015-02-19 2017-12-21 イェディテペ・ウニヴェルシテシＹｅｄｉｔｅｐｅ Ｕｎｉｖｅｒｓｉｔｅｓｉ 種子および表面滅菌のためのコーティング製剤

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