EP1937449A1 - Utilisation de diclosan pour la protection du bois - Google Patents

Utilisation de diclosan pour la protection du bois

Info

Publication number
EP1937449A1
EP1937449A1 EP06791753A EP06791753A EP1937449A1 EP 1937449 A1 EP1937449 A1 EP 1937449A1 EP 06791753 A EP06791753 A EP 06791753A EP 06791753 A EP06791753 A EP 06791753A EP 1937449 A1 EP1937449 A1 EP 1937449A1
Authority
EP
European Patent Office
Prior art keywords
wood
diclosan
optionally
mixture according
destruction
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Withdrawn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
EP06791753A
Other languages
German (de)
English (en)
Inventor
Rainer Bruns
Martin Kugler
Thomas Jaetsch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lanxess Deutschland GmbH
Original Assignee
Lanxess Deutschland GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH
Publication of EP1937449A1 publication Critical patent/EP1937449A1/fr
Withdrawn legal-status Critical Current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
    • 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 diclosan 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 diclosan, and their use diclosan diclosan for the protection of industrial materials against 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.
  • Diclosan belongs to the class of diphenyl ethers and is currently in the market introduction phase for applications in plastics, cosmetics and disinfectants.
  • diclosan has an excellent action against soft rot fungi.
  • the present invention thus relates to the use of diclosan (4,4'-dichloro-2-hydroxy-diphenyl ether) 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.
  • Diclosan shows a broad activity against soft rot fungi such as. against fungi such as Chaetomium globosum, Glenospora graphii, Humicola gisea, Petrieula setifera, Trichurus spiralis and Lecythophora mutabilis as described in ENV 807 (Test method for the determination of the limit of activity against soft rot and other soil-dwelling micro-organisms, German version of 2001) and Trichoderma viride , Stachybotrys cartarum, Chephalosporium sp. and Acremonium sp ..
  • diclosan 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, bitertanol, bromuconazoles; Cyproconazole, diclobutrazole, difenoconazole, diniconazole, epoxyconazole, etconazole, fenbuconazole, fenchlorazole, fluquinconazole, flusilazole, flutriafol, furconazole, hexaconazole, imibenconazole, ipconazole, myclobutanil, metconazole, paclobutrazole, penconazole, propiconazole, (+/-) - cis-1 (4-chlorophenyl) -2- (1H-l, 2,4-triazol-1-yl) cycloheptanol, 2- (1-tert-butyl) -1- (2-
  • diclosan in combination with one or more of the following fungicidal components: benzalkonium chloride, chlorothalonil, dichlofluanid, tolylfluanid, carbendazim, thiabendazole, fenpropimorph, bethoxazine, folpet, fluorfolpet, thiocyanato-methylthiobenzothiazole, 3-iodo-2-propynyl n-butylcarbamate, zinc pyrithione, copper pyrithione, dichloroctylisothiazolinone, n-octylsisothiazolinone, N- (3-aminopropyl) -N-dodecylpropane-1,3-diamine.
  • diclosan in combination with one or more of the following fungicidal components: benzalkonium chloride, clorthalonill, dichlofluanid, tolylfluanid, bethoxazine, 3-iodo-2-propynyl-butylcarbamate,
  • diclosan in combinations with one or more of the following termiticidal components:
  • diclosan in combinations with one or more of the following termiticides:
  • diclosan optionally 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 ultrafine encapsulations in polymeric substances.
  • Another object of this invention are agents containing diclosan for the protection of wood and wood-based materials and wood plastic composites before infestation and or destruction by moderately rot fungi.
  • inventive compositions contain diclosan and at least one Verdunnungs- 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 diclosan and optionally further active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or or dispersants and / or foam-forming 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, for example 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 also water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol
  • ketones such as acetone, Methyl ethyl ketone, methyl isobutyl ketone or cycl
  • liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example 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.
  • solid carriers for granules are: for example, broken 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, corncobs and tobacco stalks.
  • Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • Suitable dispersants are: for example, 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 of the invention generally contain between 0.005 and 95 wt .-% diclosan, preferably between 0.1 and 50 wt .-% diclosan, and optionally between 0.005 and 50 wt .-% 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 diclosan or the combination of diclosan 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 diclosan to be used according to the invention or the active substance combination of diclosan with at least one further microbicidal active ingredient depends on the type 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 diclosan or the combination of diclosan 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.
  • Further objects of the present invention are therefore mixtures comprising a synergistically effective amount of diclosan 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, especially 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, bitertanol, bromuconazoles; Cyproconazole, diclobutrazole, difenoconazole, diniconazole, epoxyconazole, etconazole, fenbuconazole, fenchlorazole, fluquinconazole, flulazole, flutriafol, furconazole, hexaconazole, imibenconazole, ipconazole, myclobutanil, metconazole, paclobutrazole, penconazole, propiconazole, (+/-) cis -1- (4-chlorophenyl) -2- (1H-l, 2,4-triazole-1-yl) cycloheptanol, 2- (1-tert-butyl) -1- (2-chlorophenyl) 3 - (1, 2,4-triazol-1-yl) -
  • mixtures of diclosan with at least one triazole fungicide from the series propiconazoles, tebuconazoles, cyproconazoles, hexaconazoles and triadimefon which are distinguished by a pronounced synergism against wood-destroying basidiomycetes.
  • the mixtures according to the invention generally contain diclosan 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: benzalkonium chloride, chlorothalonil, dichlofluanid, tolylfluanid, carbendazim, thiabendazole, fenpropimorph, bethoxazine, folpet, fluorolipet, thiocyanatomethylthiobenzothiazole, 3-iodo-2-propynyl-n-butylcarbamate, zinc Pyrite ion, copper pyrithione, dichloroctylisothiazolinone, n-octylsisothiazolinone, N- (3-arninopropyl) -N-dodecylpropane-1,3-diamine.
  • benzalkonium chloride chlorothalonil
  • dichlofluanid dichlofluanid
  • tolylfluanid carbendazim
  • thiabendazole fenprop
  • the mixtures according to the invention particularly preferably contain one or more of the following fungicidal components: benzalkonium chloride, dichlofluanid, tolylfluanid, bethoxazine, 3-iodo-2-propynyl-butylcarbamate, dichloroctylisothiazolinone, n-octylsisothiazolinone, zinc and copper pyrithione.
  • the mixtures according to the invention generally contain 0.01-85% by weight of diclosan, 0.01-85% by weight of one or more triazole fungicides, optionally 0.01-80% by weight of at least one further microbicidal active substance 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 ingredients diclosan and one or more triazole fungicides and optionally other 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 is protected against attack and / or destruction by soft rot fungi wood and wood materials and wood plastic composites containing diclosan or an agent based on diclosan.
  • wood, wood materials and wood plastic composites which can be protected by the active substance mixtures according to the invention or these agents, is to be understood by way of example: timber, wooden beams, railway sleepers, bridge parts, boat jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wood paneling, 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 carpentry, as well as wood-plastic composites.
  • MDF medium density fibreboard
  • OSB Oriented Strand Board
  • LDL Laminated Veneer Lumber
  • wood products commonly used in house building or carpentry as well as wood-plastic composites.
  • 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 substance diclosan 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 done in a conventional manner by the wood, the wood material or the wood-plastic composite with the active ingredient Diclosan, optionally in Combined with one or more microbicidal agents, or treated with an agent prepared therefrom in the form of a formulation or application form, for example by spraying, brushing, immersion and large-scale impregnation, eg vacuum, double vacuum or pressure method and by addition to the glue or masterbatch, as well as 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 diclosan 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, means Vacuum, double vacuum, pressure or dipping method is impregnated.
  • agar prepared using malt extract was added with diclosan at 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 0 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.
  • 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 diclosan and tebuconazole
  • Table 3 MIC values and synergistic index of diclosan and cyproconazole (test fungus Glenospora graphii)
  • Table 4 MIC values and synergistic index of diclosan and propiconazole (test fungus Sclerophoma pityophila)

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)

Abstract

Le diclosan, ainsi que de nouveaux agents fongicides et de nouveaux mélanges synergiques à base de l'ingrédient actif diclosan 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.
EP06791753A 2005-09-13 2006-08-31 Utilisation de diclosan pour la protection du bois Withdrawn EP1937449A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510043427 DE102005043427A1 (de) 2005-09-13 2005-09-13 Verwendung von Diclosan für den Holzschutz
PCT/EP2006/008511 WO2007031199A1 (fr) 2005-09-13 2006-08-31 Utilisation de diclosan pour la protection du bois

Publications (1)

Publication Number Publication Date
EP1937449A1 true EP1937449A1 (fr) 2008-07-02

Family

ID=37635321

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06791753A Withdrawn EP1937449A1 (fr) 2005-09-13 2006-08-31 Utilisation de diclosan pour la protection du bois

Country Status (3)

Country Link
EP (1) EP1937449A1 (fr)
DE (1) DE102005043427A1 (fr)
WO (1) WO2007031199A1 (fr)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH432119A (de) * 1963-02-22 1967-03-15 Geigy Ag J R Verwendung von Halogen-o-hydroxy-diphenyläthern als antimikrobielle Mittel
EP0264488B1 (fr) * 1986-09-15 1991-07-03 DESOWAG Materialschutz GmbH Agent protecteur du bois
DE10248335A1 (de) * 2002-10-17 2004-05-06 Bayer Ag Fungizide Wirkstoffkombinationen
DE10256187A1 (de) * 2002-12-02 2004-06-09 Bayer Ag 2-Oxyamino-1-cyclopenten-1-nitrile als Materialschutzmittel
AU2003902552A0 (en) * 2003-05-21 2003-06-12 Novapharm Research (Australia) Pty Ltd Biofilm growth prevention

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007031199A1 *

Also Published As

Publication number Publication date
DE102005043427A1 (de) 2007-03-15
WO2007031199A1 (fr) 2007-03-22

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