WO1995012315A1 - Stabilisation de composes de l'iode au moyen de supports inorganiques pour la protection des materiaux - Google Patents

Stabilisation de composes de l'iode au moyen de supports inorganiques pour la protection des materiaux Download PDF

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Publication number
WO1995012315A1
WO1995012315A1 PCT/EP1994/003465 EP9403465W WO9512315A1 WO 1995012315 A1 WO1995012315 A1 WO 1995012315A1 EP 9403465 W EP9403465 W EP 9403465W WO 9512315 A1 WO9512315 A1 WO 9512315A1
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WO
WIPO (PCT)
Prior art keywords
carrier
active ingredient
methyl
carbamate
phenyl
Prior art date
Application number
PCT/EP1994/003465
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German (de)
English (en)
Inventor
Lutz Heuer
Michael Schwamborn
Lothar Puppe
Heinrich Schrage
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 AU79391/94A priority Critical patent/AU7939194A/en
Priority to EP94930204A priority patent/EP0726710A1/fr
Priority to JP7512271A priority patent/JPH09504527A/ja
Publication of WO1995012315A1 publication Critical patent/WO1995012315A1/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
    • 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
    • A01N25/22—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 ingredients stabilising the active ingredients
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the application relates to iodine compounds of the formulas (I) to (XV) which are stabilized and / or fixed in the material to be protected by inorganic carrier materials against the action of light, heat or against washing out by water.
  • Iodine-containing microbicides and their use in protecting materials are known (US 3,923,870, US 4,865,892, DE 3,216,895, EP 490,566).
  • JP 5 117 105 proposed to include the compounds in cyclodextrins. These organic molecules are themselves only thermally stable to a limited extent, and due to their high molecular weight, the proportion of active ingredient in the formulation is low. In addition, these complex / inclusion compounds with cyclodextrins and the above-mentioned active substances are more water-soluble than the active substances themselves, which leads to leaching out of materials which are in contact with water and thus to a loss of activity. It has now been found that these disadvantages do not occur when the iodine compounds are applied to zeolites or similar inorganic support materials.
  • the application therefore relates to iodine compounds applied to inorganic carrier materials and their use for protecting industrial materials.
  • Suitable carrier materials are preferably: nat. and synthetic zeolites, layered silicates, clays, precipitated silicas, kieselguhrs, silicas, aerosils, bentonites, kaolins, activated carbons, natural and synthetic clay minerals, TiO 2 , ZnO, calcium carbonate, dolomites, pumice stones, attapulgites, sepiolites, ball clays, clays , including alumophosphates, silicoaluminophosphates, metal aluminophosphates and crystalline silicas with pore structure.
  • zeolites or molecular sieves which come under the following formula, have proven to be particularly suitable carrier materials:
  • M is an exchangeable cation
  • E 1 represents a trivalent element
  • E 2 represents a tetravalent element, E 1 and E 2 representing the anionic skeleton,
  • n / m is the ratio of the elements E 1 and E 2 and can assume values from 1 to 3,000, preferably 1 to 2,000,
  • the zeolites preferably have pore sizes of at least 4 ⁇ , in particular pore sizes in the range from 4 to 8 ⁇ , preferably in the range from 5 to 8 ⁇ .
  • the basic structure of zeolites consists of a network of SiO 4 and AlO 4 tetrahedra, whereby the individual tetrahedra are linked with each other by oxygen bridges via their corners and form a spatial network that is evenly interspersed with channels and cavities.
  • the aluminum as a representative of the element E 1 can be partially replaced by other trivalent or also divalent elements such as B, Ga, In, r ' e, Cr, V, As, Sb or Be, Cu or Co.
  • the silicon as a representative of the element E can be replaced by other tetravalent elements such as Ge. Interchangeable cations are stored to compensate for the negative charge of the lattice caused by the trivalent elements.
  • the individual zeolite structures also differ in the arrangement and size of the channels and cavities. Zeolites always contain q H 2 O as a sorbed water phase, which can be removed reversibly without the structure losing its structure. A detailed description of the zeolites can be found, for example, in the monograph "Introduction to Zeolite Science and Practice” Ed. H. van Bekkum, zH Flanigen, JC Jansen in the series Studies in Surface Science and Catalysis Vol. 58, Elsevier, Amsterdam, Oxford, New York - Tokyo, 1991.
  • aluminophosphates such as A1PO-5, A1PO-11, A1PO-8, A1PO-17 and silicoaluminophosphates such as SAPO-5, SAPO-11, SAPO-34, SAPO 17 and others.
  • layered silicates such as magadiite or SKS-6 can also be used as carriers.
  • zeolites Preferred among the zeolites are the easily accessible zeolite structures such as zeolite A and faujasite with the types zeolite X and zeolite Y and the following formulas:
  • Type X Na 86 [(AlO 2 ) 86 (SiO 2 ) 106 ] 264 H 2 O
  • the various ion-exchanged forms can also be used as carriers.
  • Preferred iodine compounds are compounds of the formulas (I) to (NU)
  • R represents phenyl, naphthyl, heterocyclyl or cyclohexyl optionally substituted by Cl, Me, Et, mono- to pentasubstituted, or
  • R represents the groups -CH 2 CH 2 -O-CO-NHR or -CO-NHR, where R represents linear, cyclic or branched preferably C 2 -C 6 alkyl, or has the meaning of R, or
  • R stands for the group -CO-NR'R ", in which R 'and R" are identical or different and stand for hydrogen or have the meanings given for R, or together form a heterocycle
  • n stands for the number zero or one.
  • the compounds of the formulas (I) to (VI) have a good microbicidal action against material-relevant microorganisms.
  • the carriers can be loaded with the iodine compounds in different ways, adapted to the respective carrier material. A description of such techniques can be found in DE 1 219 008.
  • molecular sieves or zeolites can be loaded by first removing water from the molecular sieve by heating, which can be done, for example, by heating at 400 to 450 ° C. for several hours, and then bringing it into contact with the active substance.
  • the loading can take place in any manner, for example by passing it into the vapor form brought active ingredient by the Zecüth or by immersing the zeolite in the liquid or melted active ingredient or a solution of the active ingredient in a non-polar volatile solvent with subsequent evaporation of the solvent.
  • the amount of the active ingredient to be applied can be varied within wide limits. It depends on the active ingredient used and the conditions under which the carrier / active ingredient mixture is to be used.
  • the carrier is loaded with amounts of 0.1 to about 40% by weight, preferably 0.5 to 30% by weight, in particular 1 to 20% by weight, of active compound, based on the carrier.
  • the maximum loading is preferably selected in order to achieve a high active ingredient concentration per mass of carrier.
  • the carrier A active substance combinations have a particularly high, microbicidal, in particular fungicidal activity, combined with a broad spectrum of activity against microorganisms relevant to material protection; they are particularly effective against mold, wood-staining and wood-destroying fungi.
  • the groups of microorganisms listed below may be mentioned as examples - but without limitation.
  • the carrier / active substance combinations according to the invention can be used practically to combat unwanted microorganisms.
  • the carrier / active substance combinations according to the invention are suitable for protecting industrial materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials made by Active substances according to the invention are to be protected against microbial change or destruction, adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms.
  • parts of production systems for example cooling water circuits, which may be impaired by the multiplication of microorganisms, may also be mentioned.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, coolants, lubricants and heat transfer liquids, particularly preferably paints.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the carrier / active ingredient combination which can be used according to the invention preferably acts against fungi, in particular molds, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucus organisms and algae.
  • microorganisms of the following genera may be mentioned:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium such as Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the carrier / active substance combinations according to the invention can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, for example by mixing the components with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents Means. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents Means.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents Means.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or Glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water;
  • Liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; the following are suitable as solid carriers: e.g.
  • rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates; solid carriers for granules are possible: e.g.
  • emulsifiers and / or foaming agents are suitable: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acids ureester, polyoxyethylene fatty alcohol ether, for example alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and Protein hydrolyzates; Possible dispersants are: lignin sulfite leaching and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, 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 can be used.
  • microbicidal agents or concentrates used to protect the industrial materials contain the carrier / active ingredient combination in a concentration of 0.01 to 99% by weight, in particular 0.1 to 60% by weight.
  • the application concentrations of the carrier / active substance combinations to be used according to the invention depend on the type and occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
  • the optimal amount can be determined by test series.
  • the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, of the active ingredient, based on the material to be protected.
  • the carrier / active substance combinations are particularly preferably used in paints or antifouling agents or films.
  • painting is to be understood as meaning a coating made of paints on a substrate.
  • the paint may have penetrated more or less into the surface. It can consist of one or more layers and can be produced by processes such as brushing, spraying, dipping, flooding or similar processes.
  • the carrier / active ingredient combinations to be used according to the invention are incorporated into the paints or into precursors for producing the paints by customary methods, for example by mixing the carrier / active ingredient combinations with the other components.
  • the paints according to the invention therefore contain, in addition to at least one carrier / active ingredient combination, generally customary paint components in e.g. liquid, pasty or powdery form such as
  • Colorants such as pigments or dyes, preferably pigments.
  • examples include titanium dioxide, zinc oxide and iron oxide.
  • Binders such as, for example, oxidatively drying alkyd resins, vinyl polymers and vinyl copolymers, acrylic polymers and acrylic copolymers, plastic powder, novolacs, amino resins, polyester resins, epoxy resins, silicone resins, isocyanate resins, vinyl polymers and vinyl copolymers, acrylic polymers and acrylic copolymers are preferred other binders which can be used in water-dilutable paints.
  • the paints may contain the following additives
  • Fillers such as, for example, heavy spar, calcite, dolomite and talc (possibly partially substituted by the inorganic carrier used).
  • Solvents such as, for example, alcohols, ketones, esters, glycol ethers and aliphatic and aromatic hydrocarbons, as well as thickening and thixotropic agents, dispersing and wetting agents, drying agents, skin inhibitors, leveling agents, anti-foaming agents, corrosion inhibitors, UV absorbers, fragrances, antistatic agents and antifreezes.
  • paints or precursors for the production of paints Glues and adhesives based on the well-known animal, vegetable or synthetic raw materials.
  • Plastic dispersions such as latex dispersions or dispersions based on other polymers.
  • Starch products such as Pressure thickener.
  • Carbon black pigments, titanium dioxide pigments) or slurries of fillers such as
  • Kaolin or calcium carbonate are examples of materials that are used in the trade. - coats and finishes.
  • the carrier / active substance combinations according to the invention e.g. not only equip aqueous paints with fungicide and algicide (film protection), but also preserve them reliably and permanently during storage in tanks or containers.
  • the effectiveness and the spectrum of activity of the carrier / active substance combinations according to the invention or the agents, precursors or very generally formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active substances are used to enlarge the spectrum of activity or Achieving special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
  • Particularly favorable mixture partners are, for example, one or more of the following compounds: N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, N-octyl-isothiazolin-3-one, 4,5-trimethylene isothiazolinone, 4,5-benzisothiazolinone, benzyl alcohol mono (poly) hemiformal, N-methylolchloroacetamide;
  • Aldehydes such as cinnamaldehyde, formaldehyde, glutardialdehyde, bromcinnamaldehyde;
  • Thiocyanates such as thiocyanatomethylthiobenzothiazole, methylene bisthiocyanate;
  • quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, didecyldimethaylammonium chloride;
  • Phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol;
  • Bromine derivatives such as 2-bromo-2-nitro-1,3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 2,2-dibromo-3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane , -Bromo-nitrostyrene;
  • Pyridines such as l-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione;
  • Metal soaps such as tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;
  • Oxides such as tributyltin oxide, Cu 2 O, CuO, ZnO;
  • Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates, tetramethylthiuram disulfide, potassium N-methyldithiocarbamate;
  • Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;
  • Quinolines such as 8-hydroxyquinoline and their Cu salts; Mucochloric acid, 5-hydroxy-2 (5H) furanone;
  • Preferred mixing partners are also:
  • Succinate dehydrogenase inhibitors such as: Fenfuram, furcarbanil, cyclafluramide, furmecyclox, seedvax, metsulfovax, pyrocarbolide, oxycarboxin, shirlan, mebenil (mepronil), benodanil, flutolanil (moncut);
  • Naphthalene derivatives such as:
  • Sulfenamides such as dichlorfluanide, tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
  • Benzimidazoles such as carbendazim, benomyl, furathiocarb, fuberidazole, thiophonate methyl, thiabendazole or their salts;
  • Morpholine derivatives such as tridemorph, fenpropimorph, falimorph, dimethomorph, dodemorph; Aldimorph, fenpropidine and their arylsulfonic acid salts, e.g. p-toluenesulfonic acid and p-dodecylphenyl sulfonic acid;
  • Benzothiazoles such as 2-mercaptobenzothiazole
  • Benzamides such as 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide
  • Boron compounds such as boric acid, boric acid ester, borax;
  • Formaldehyde and formaldehyde-releasing compounds such as benzyl alcohol mono- (poly) -hemiformal, oxazolidines, hexa-hydro-S-triazines, N-methylolchloroacetamide, paraformadehyde, nitropyrin, oxolinic acid, tecloftalam;
  • the active compounds are present in the active compound combinations according to the invention in certain weight ratios, the synergistic effect is particularly evident.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within a relatively wide range.
  • Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, -l (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxy-pyrazole, chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, diazinon, dichlorvos, dimethoate , Ethoate, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophas, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulfprofos, Triazophos and Trichlorphone;
  • Carbamates such as aldicarb, bendiocarb, -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-phenoxybenzyl ether such as dimethyl- (4-ethoxyphenyl) -silylmethyl-3-phenoxybenzylether or
  • (Dimethylphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as e.g. Dimethyl- (9-ethoxy-phenyl) -silylmethyl-2-phenoxy-6-pyridylmethylether or [(phenyl) -3- (3-phenoxyphenyl) -propyl] (dimethyl) -silanes such as e.g. (4-ethoxyphenyl) - [3- (4-fluoro-3-phenoxyphenyl-propyl] dimethyl silane, silafluofen;
  • Pyrethroids such as ailethrin, alphamethrin, bioresmethrin, byfenthrin, cycloprothrin, cyfluthrin, decamethrin, cyhalothrin, cypermethrin, deltamethrin, alpha-cyano-3-phenyl-2-methylbenzyl-2,2-dimethyl-3- (2-chloro-2-trif -methylvinyl) cyclopropane carboxylate, fenpropathrin, fenfluthrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin and tralomethrin;
  • Nitroimines and nitromethylenes such as l - [(6-chloro-3-pyridinyl) methyl] -4,5-dihydro-N-nitro-lH-imidazol-2-amine (imidacloprid), N - [(6-chloro-3 -pyridyl) methyl-] N 2 - cyano-N ⁇ methylacetamide (NI-25); Abamectin, AC 303, 630, Acephate, Acrinathrin, Alanycarb, Aldoxycarb, Aldrin, Amitraz, Azamethiphos, Bacillus thuringiensis, Phosmet, Phosphamidon, Phosphine, Prallethrin, Propaphos, Propetamphos, Prothoate, Pyraclofos, Pyrethriproxyphid, Pyrethridafid, Pyrethridafid, Pyrethrinsafid, Pyrethrins
  • the weight ratios of the active ingredients or the carrier / active ingredient combination in these active ingredient combinations can be varied within relatively large ranges.
  • the active substance combinations preferably contain the carrier / active substance combination in an amount of 0.1 to 99.9%, in particular 1 to 75%, particularly preferably 5 to 50%, the rest being filled 100% by one or more of the above-mentioned mixing partners.
  • Carrier / active ingredient combinations with zeolites as the carrier material and with active ingredients such as iodopropyl carbamates such as iodopropargyl butyl carbamate, chlorophenyl formal, phenyl carbamate, hexyl carbamate, cyclohexyl carbamate, iodopropargyloxyethylenyl carbamate compounds and iodopropargyloxyamate carbamate compounds and binders thereof with iodopropargyloxyamate carbamate Diuron.
  • iodopropyl carbamates such as iodopropargyl butyl carbamate, chlorophenyl formal, phenyl carbamate, hexyl carbamate, cyclohexyl carbamate, iodopropargyloxyethylenyl carbamate compounds and iodopropargyloxyamate carbamate compounds and
  • iodine compounds bound to a carrier are: tetrachloroisophthalonitrile, benzisothiazolinones, n-octylisothiazolinones, 2,3,5 3 6-tetrachloro-4-methylsulfonylpyridine, 4,5-dichloro-2-n-octyl 4-isothiazolin-3-one and / or propi conazole.
  • Example 1 (not according to the invention, comparative example)
  • IPBC 3-iodo-2-propynyl-n-butyl carbamate
  • Example 2 (not according to the invention, comparative example)
  • IPBC IP-binding protein
  • IPBC IP-binding protein
  • Example 3 A sample of the white powder from Example 3 was irradiated as described in Example 1. No discoloration, even superficial, was observed after the same period. After 75 min. No discoloration was observed when irradiated with a high pressure mercury lamp.
  • Example 3 A sample of the white powder as from Example 3 was suspended in water as described in Example 2 and also irradiated. No discoloration was observed, neither of the solution nor of the crystals. After 15 minutes of exposure to a high pressure mercury lamp, no discoloration was observed.

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

Abstract

L'invention concerne des microbicides iodés connus, qui sont stabilisés au moyen de supports inorganiques contre l'action de la lumière, ainsi que l'utilisation de ces combinaisons d'un support et d'un produit actif pour la protection de matériaux techniques.
PCT/EP1994/003465 1993-11-03 1994-10-21 Stabilisation de composes de l'iode au moyen de supports inorganiques pour la protection des materiaux WO1995012315A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU79391/94A AU7939194A (en) 1993-11-03 1994-10-21 Stabilisation of iodine compounds using inorganic supporting materials for use in material protection
EP94930204A EP0726710A1 (fr) 1993-11-03 1994-10-21 Stabilisation de composes de l'iode au moyen de supports inorganiques pour la protection des materiaux
JP7512271A JPH09504527A (ja) 1993-11-03 1994-10-21 材料保護における使用のための無機担体材料を用いるヨウ素化合物の安定化

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19934337433 DE4337433A1 (de) 1993-11-03 1993-11-03 Stabilisierung von Iodverbindungen mit Hilfe anorganischer Trägermaterialien zur Verwendung im Materialschutz
DEP4337433.6 1993-11-03

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WO1995012315A1 true WO1995012315A1 (fr) 1995-05-11

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PCT/EP1994/003465 WO1995012315A1 (fr) 1993-11-03 1994-10-21 Stabilisation de composes de l'iode au moyen de supports inorganiques pour la protection des materiaux

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EP (1) EP0726710A1 (fr)
JP (1) JPH09504527A (fr)
AU (1) AU7939194A (fr)
CA (1) CA2175480A1 (fr)
DE (1) DE4337433A1 (fr)
WO (1) WO1995012315A1 (fr)

Cited By (2)

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WO2010142790A1 (fr) * 2009-06-12 2010-12-16 Lanxess Deutschland Gmbh Supports inorganiques contenant des composés hétérocycliques à 3 cycles
WO2011103969A3 (fr) * 2010-02-23 2011-10-27 Clariant S. A. Brazil Procédé de co-encapsulation de composés actifs sur le plan biocide dans des minéraux argileux fonctionnalisés par des composés azote

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19818115B4 (de) * 1998-04-23 2005-07-21 Kiesel Bauchemie Gmbh & Co. Kg Lösemittelarmer oder lösemittelfreier Verlegewerkstoff zum Verlegen von Bodenbelägen
EP2236033A1 (fr) * 2009-04-01 2010-10-06 LANXESS Deutschland GmbH Stabilisation de composés contenant de l'iode
EP2462805A1 (fr) * 2010-12-10 2012-06-13 LANXESS Deutschland GmbH Formulations comprenant des composés stabilisés contenant de l'iode
JP5529833B2 (ja) * 2010-12-22 2014-06-25 ダウ グローバル テクノロジーズ エルエルシー グリホサート化合物とｄｍｉｔｓとの相乗的組み合わせ
JP6109502B2 (ja) * 2012-07-13 2017-04-05 大阪ガスケミカル株式会社 抗生物活性粒子およびその製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4276211A (en) * 1980-03-10 1981-06-30 Troy Chemical Corporation Stabilization composition for coating composition
GB2074449A (en) * 1980-04-28 1981-11-04 Ici America Inc Fungicides containing iodo substituted alkylene urethanes
JPH02164803A (ja) * 1988-12-15 1990-06-25 Takeda Chem Ind Ltd 安定な殺菌組成物
DE9400236U1 (de) * 1994-01-08 1994-03-03 Milker, Roland, Dipl.-Chem. Dr.rer.nat., 56587 Straßenhaus Festes Desinfektionsmittel

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4276211A (en) * 1980-03-10 1981-06-30 Troy Chemical Corporation Stabilization composition for coating composition
GB2074449A (en) * 1980-04-28 1981-11-04 Ici America Inc Fungicides containing iodo substituted alkylene urethanes
JPH02164803A (ja) * 1988-12-15 1990-06-25 Takeda Chem Ind Ltd 安定な殺菌組成物
DE9400236U1 (de) * 1994-01-08 1994-03-03 Milker, Roland, Dipl.-Chem. Dr.rer.nat., 56587 Straßenhaus Festes Desinfektionsmittel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Week 9031, Derwent World Patents Index; AN 90-236123/31 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010142790A1 (fr) * 2009-06-12 2010-12-16 Lanxess Deutschland Gmbh Supports inorganiques contenant des composés hétérocycliques à 3 cycles
WO2010142795A3 (fr) * 2009-06-12 2012-04-26 Lanxess Deutschland Gmbh Supports inorganiques azotés
WO2011103969A3 (fr) * 2010-02-23 2011-10-27 Clariant S. A. Brazil Procédé de co-encapsulation de composés actifs sur le plan biocide dans des minéraux argileux fonctionnalisés par des composés azote
US9228121B2 (en) 2010-02-23 2016-01-05 Clariant S.A. Process for the co-encapsulation of biocidally active compounds in clay minerals functionalized by nitrogen compounds

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AU7939194A (en) 1995-05-23
DE4337433A1 (de) 1995-05-04
CA2175480A1 (fr) 1995-05-11
EP0726710A1 (fr) 1996-08-21
JPH09504527A (ja) 1997-05-06

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