WO1994012033A1 - Utilisation de derives du triazolylalkyle-dioxolane comme microbicides dans la protection des materiaux - Google Patents

Utilisation de derives du triazolylalkyle-dioxolane comme microbicides dans la protection des materiaux Download PDF

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Publication number
WO1994012033A1
WO1994012033A1 PCT/EP1993/003233 EP9303233W WO9412033A1 WO 1994012033 A1 WO1994012033 A1 WO 1994012033A1 EP 9303233 W EP9303233 W EP 9303233W WO 9412033 A1 WO9412033 A1 WO 9412033A1
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carbon atoms
alkyl
optionally substituted
branched
straight
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PCT/EP1993/003233
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German (de)
English (en)
Inventor
Hans-Ludwig Elbe
Eckart Kranz
Wilfried Paulus
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Bayer Aktiengesellschaft
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Priority to AU56252/94A priority Critical patent/AU5625294A/en
Publication of WO1994012033A1 publication Critical patent/WO1994012033A1/fr

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

Definitions

  • the present invention relates to the use of known triazolylalkyl dioxolane derivatives as microbicides for protecting industrial materials.
  • optionally substituted alkyl optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted aryloxyalkyl, optionally substituted arylthioalkyl, optionally substituted arylsulfinylalkyl, optionally substituted arylsulfonylalkyl, optionally substituted Les aralkyloxyalkyl, optionally substituted
  • the substances of the formula (I) which can be used according to the invention have two or more asymmetrically substituted ones
  • the substances which can be used according to the invention are more suitable for combating undesirable microorganisms in material protection than 1- (4-chlorophenoxy) -3,3-dimethyl-1- ( 1,2,4-triazol-1-yl) butane 2-ol, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -butan-2-one, 1- (2,4-dichlorophenyl) - 4,4-dimethyl-2- (1,2,4-t.riazol-1-yl) pentan-3-ol and 1- (4-chlorophenoxy) -3,3-dimethyl-2- (1,2 , 4-triazol-1-yl-methyl) -butan-2-ol, which are constitutionally similar,
  • the substances which can be used according to the invention also outperform dithiocarbamates, such as, for example, tetramethylthiuram disulfide, in their antimicrobial action. It is particularly advantageous that no discoloration occurs even if traces of heavy metal salts are present.
  • Formula (I) provides a general definition of the triazolylalkyl dioxolane derivatives which can be used according to the invention.
  • alkyl is hereinafter in individual and in alkyl-containing radicals, e.g.
  • straight-chain or branched alkyl having 1 to 12, preferably 1 to 8, in particular 1 to 7 and especially 3 to 7 carbon atoms,
  • alkenyl and alkynyl is, for example, straight-chain or branched alkenyl or alkynyl having 2 to 12, preferably 2 to 8, in particular 2 to 7 and especially 3 to 7 carbon atoms.
  • Cycloalkyl generally contains 3 to 7, preferably 3 to 6 carbon atoms in the cycloalkyl part.
  • Aryl generally contains 6 to 10 carbon atoms in the aryl part, phenyl, ⁇ -naphthyl or ⁇ -naphthyl radicals being mentioned as examples.
  • radicals can be substituted, for example, by one or more, identical or different substituents from the following groups:
  • Halogen atoms such as fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8, preferably 1 to 6 and in particular 1 to 4 carbon atoms in the alkyl part, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl each having 1 to 4 carbon atoms in the individual alkyl parts, unsubstituted or singly or multiply, identically or differently, halogen-substitute
  • R preferably represents straight-chain or branched alkyl having 1 to 12 carbon atoms, straight-chain or branched alkenyl having 2 to 12 carbons Substance atoms, straight-chain or branched alkynyl with 2 to 12 carbon atoms, alkoxyalkyl with 1 to 8 carbon atoms in the alkoxy part and 1 to 8 carbon atoms in the alkyl part, alkylthioalkyl with 1 to 8 carbon atoms in the alkylthio part and 1 to 8 carbon atoms in the alkyl part, alkylsulfinylalkyl with 1 to 8 Carbon atoms in the alkylsulfinyl part and 1 to 8 carbon atoms in the alkyl part, alkylsulfonylalkyl with 1 to 8 carbon atoms in the alkylsulfonyl part 1 and 1 to 8 carbon atoms in the alkyl part, alkoximinoalkyl with 1 to 8 carbon atoms in the
  • R 1 preferably represents cycloalkyl having 3 to 7 carbon atoms, it being possible for each of these cycloalkyl radicals to be mono- or polysubstituted, identical or different, by halogen and / or alkyl having 1 to 4 carbon atoms,
  • R 1 preferably represents cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl part and 1 to 8 carbon atoms in the alkyl part, it being possible for each of these radicals in the cycloalkyl part to be mono- or polysubstituted, identical or different, by halogen and / or alkyl having 1 to 4 carbon atoms,
  • R 1 preferably represents aryl having 6 to 10 carbon atoms, arylalkyl having 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in the alkyl part, aryloxyalkyl having 6 to 10 carbons Substance atoms in the aryl part and 1 to 8 carbon atoms in the alkyl part, arylthioalkyl with 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in the alkyl part, arylsulfinylalkyl with 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in the alkyl part, arylsulfonylalkyl with 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in the alkyl part, aralkyloxyalkyl with 6 to 10 carbon atoms in the aryl part and 1 to 8 carbon atoms in each alkyl part, aralkylthi
  • R 2 , R 3 , R 4 , R 5 and R 6 are independent of one another
  • R 1 particularly preferably represents straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms or
  • Alkyl part the substituents in the cycloalkyl part in each case being: fluorine, chlorine or bromine or straight-chain or branched alkyl having 1 to 4 carbon atoms; or for each unsubstituted or in the aryl part mono- to pentasubstituted, identical or differently substituted arylalkyl, aryloxyalkyl, arylthioalkyl, arylsulfinylalkyl, arylsulfonylalkyl, aralkyloxyalkyl, aralkylthioalkyl, aralkylsulfinylalkyl, aralkylsulfonylalkyl, aryl, each having 1 to 6 carbon atoms in the individual straight-chain parts, where aryl is in each case phenyl, ⁇ -naphthyl or ⁇ -naphthyl, the phenyl substituents in each case being suitable:
  • naphthyl substituents are in each case: fluorine, chlorine, bromine, cyano, methyl,
  • Ethyl, n- or i-propyl, R 2 , R 3 , R 4 , R 5 and R 6 are independent of one another
  • R 1 very particularly preferably represents straight-chain or branched alkyl having 1 to 7 carbon atoms, straight-chain or branched alkenyl having 2 to 7 carbon atoms, straight-chain or branched alkynyl having 2 to 7 carbon atoms, straight-chain or branched methoxyalkyl, chain or branched dimethoxyalkyl, straight-chain or branched trimethoxyalkyl, straight-chain or branched methylthioalkyl, straight-chain or branched dimethylthioalkyl, straight-chain or branched trimethylthioalkyl, straight-chain or branched methylsulfinylalkyl, straight-chain or branched methylsulfonylalkyl, straight-chain or branched hydroxyl or 3-chain hydroxyl-alkyl or straight-chain or branched methoximinoal
  • X represents oxygen, sulfur, sulfinyl, sulfonyl or one of the groups -CH 2 -; -O-CH 2 -;
  • m each represents a number 0 or 1 and n each represents a number 0, 1 or 2, the following being suitable as phenyl substituents: fluorine, chlorine, bromine , Cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, propane 1,3- diyl, butane-1,4-diyl, pentane 1,5-diyl, dimethylpropane-1,3-diyl, tetramethylpropane-1,3-diyl
  • naphthyl substituents in question are in each case: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, R 2 , R 3 , R 4 , R 5 and R 6 are independent of one another
  • R 1 in particular represents straight-chain or branched alkyl having 3 to 7 carbon atoms, straight-chain or branched alkenyl having 3 to 7 carbon atoms or straight-chain or branched alkynyl having 3 to 7 carbon atoms; or for one to three times by fluorine,
  • Ar in each case for unsubstituted or mono- to triple, identical or different by fluorine, chlorine, bromine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, difluoromethyl, Difluoromethoxy, difluoromethylthio, phenyl or phenoxy substituted phenyl or represents unsubstituted or substituted by fluorine, chlorine or methyl, ⁇ -naphthyl or ⁇ -naphthyl,
  • X for oxygen, sulfur or for one of the groups -CH 2 -, -O-CH 2 -, -S-CH 2 -, -O-CH 2 -CH 2 - or
  • R 2 , R 3 , R 4 , R 5 and R 6 are in particular hydrogen.
  • Preferred compounds which can be used according to the invention are also addition products of acids and those triazolylalkyldioxolane derivatives of the formula (I) in which the substituents R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings which are already preferred for these substituents.
  • the acids which can be added preferably include hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono-, bi- and trifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, B, acetic acid, Maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, sulfonic acids, such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid as well as saccharin or thiosaccharin.
  • hydrohalic acids such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono-, bi- and trifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, B,
  • preferred compounds which can be used according to the invention are addition products from salts of metals of the II. To IV. Main and I, and II, and IV, to VIII, subgroup and those triazolylalkyl-dioxolane derivatives of the formula (I) in which the Substituents R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings which have preferably already been mentioned for these substituents.
  • Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred.
  • Anions of these salts are those which are derived from acids which lead to environmentally compatible addition products.
  • Particularly preferred such acids in this context are the hydrogen halide acids, such as, for example, the hydrochloric acid and the hydrobromic acid, nitric acid and
  • triazolylaIkyl-dioxolane derivatives of the formula (I) which can be used in accordance with the invention and their acid addition salts and metal salt complexes are known (cf. DE-OS 3 827 134). They can be prepared by using oxiranyl-dioxolanes of the formula
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the meaning given above, with 1,2,4-triazole of the formula
  • Inert organic solvents are suitable as diluents for carrying out the above process.
  • Aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl, are preferably usable.
  • ketones such as acetone or butanone
  • nitriles such as acetonitrile or propionitrile
  • amides such as dimethyl formamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide
  • esters such as ethyl acetate
  • sulfoxides such as dimethyl sulfoxide or alcohols
  • Methanol, ethanol, propanol, butanol, methoxyethanol or ethoxyethanol Methanol, ethanol, propanol, butanol, methoxyethanol or ethoxyethanol.
  • the above process is preferably carried out in the presence of a suitable acid binder.
  • a suitable acid binder All commonly used inorganic and organic bases are suitable as such.
  • a conventional radical generator such as, for example, ⁇ , ⁇ '-azodiisobutyronitrile (AIBN)
  • reaction temperatures can be varied within a substantial range when carrying out the above process. In general, temperatures between 0 ° C and 200 ° C, preferably at temperatures between 60 ° C and 150 ° C.
  • 1.0 to 5.0 moles, preferably 1.0 to 1.2 moles, of azole of the formula (III) and optionally 1.0 to 5 moles are generally employed per mole of oxiranyldioxolane of the formula (II) , 0 moles, preferably 1.0 to 2.0 moles of acid binder.
  • reaction products are worked up, worked up and isolated using generally customary methods (cf. also the preparation examples).
  • the acid addition salts of the compounds of the formula (I) can be obtained in a simple manner by customary salt formation methods, for example by dissolving a compound of the formula (I) in a suitable inert solvent and adding the acid, such as, for example, hydrochloric acid. are obtained and isolated in a known manner, for example by filtering off and, if appropriate, purified by washing with an inert organic solvent,
  • the metal salt complexes of compounds of formula (I) can be obtained in a simple manner by conventional methods, e.g. by dissolving the metal salt in alcohol, e.g. Ethanol and adding to the compound of formula (I).
  • alcohol e.g. Ethanol
  • the active substances which can be used according to the invention have a strong microbicidal action and can be used to protect 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 which are to be protected against microbial change or destruction by active substances according to the invention can be 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 such as cooling water circuits, called that can be affected by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood,
  • Bacteria, fungi, yeasts, algae and, for example, are microorganisms which can cause degradation or a change in the technical materials
  • Called slime organisms The active substances which can be used according to the invention preferably act against fungi, in particular mold, wood-staining and
  • microorganisms of the following genera may be mentioned:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium like 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 active compounds to be used according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules.
  • Liquid solvents for the active ingredients can be, for example, water, alcohols, such as lower aliphatic alcohols, preferably ethanol or isopropanol, or benzyl alcohol, ketones such as acetone or methyl ethyl ketone, liquid hydrocarbons such as gasoline fractions, halogenated hydrocarbons such as 1,2-dichloroethane.
  • alcohols such as lower aliphatic alcohols, preferably ethanol or isopropanol, or benzyl alcohol
  • ketones such as acetone or methyl ethyl ketone
  • liquid hydrocarbons such as gasoline fractions
  • halogenated hydrocarbons such as 1,2-dichloroethane.
  • Agents generally contain the active substances in an amount of 1 to 95% by weight, preferably 10 to 75
  • the application concentrations of the active ingredients to be used according to the invention depend on the type and the occurrence of the microorganisms to be controlled and according to the composition of the material to be protected, the optimal amount can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
  • the effectiveness and the spectrum of activity of the active compounds which can be used according to the invention or of the agents, concentrates or very generally formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active compounds are used to increase the spectrum of action or to achieve special effects such as added protection against insects.
  • These mixtures can have a broader spectrum of activity than the compounds according to the invention,
  • Sulfenamides such as dichlorofluoride (Euparen), tolylfluanid (methyleuparen), folpet, fluorfolpet;
  • Benzimidazoles such as Carbendazim (MBC), Benomyl, Fuberidazole, Thiabendazole or their salts; Thiocyanates such as thiocyanatomethylthiobenzothiazole
  • TCMTB methylene bisthiocyanate
  • MTT methylene bisthiocyanate
  • quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dodecyldimethylammonium chloride
  • Morpholine derivatives such as C 11 -C 14 -4-alkyl-2,6-dimethyl-morpholine homologue (tridemorph), ( ⁇ ) -cis-4- [3- (tert-butylphenyl) -2-methylpropyl] -2,6- dimethylmorpholine (fenpropimorph), falimorph;
  • Phenols such as o-phenylphenol, tribromophenol, tetrachlorophenol, pentachlorophenol, 3-methyl 1-4-chlorophenol, dichlorophen, chlorophen or their salts; Azoles such as triadimefon, triadimenol, bitertanol, tebuconazole, propiconazole, azaconazole, hexaconazole, prochloraz, cyproconazole, 1- (2-chlorophenyl) -2- (1-chlorocyclopropyl) -3- (1,2,4-triazol-1-yl ) -propan-2-ol and 1- (2-chlorophenyl) -2- (1,2,4-triazol-1-yl-methyl) -3,3-dimethyl-butan-2-ol,
  • Iodopropargyl derivatives such as iodopropargyl butyl carbamate (IPBC), chlorophenyl formal, phenyl carbamate, hexyl carbamate, cyclohexyl carbamate, iodopropargyloxyethyl phenyl carbamate;
  • IPBC iodopropargyl butyl carbamate
  • chlorophenyl formal phenyl carbamate
  • hexyl carbamate hexyl carbamate
  • cyclohexyl carbamate iodopropargyloxyethyl phenyl carbamate
  • Iodine derivatives such as diiodomethyl-p-arylsulfones, for example diiodomethyl-p-tolylsulfone; Bromine derivatives such as bromopol;
  • Isothiazolines such as N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, N-octylisothiazolin-3-one (octilinones);
  • Pyridines such as 1-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulphonylpyridine;
  • Metal soaps such as tin, copper, zinc naphthenate, octoate, -2-ethylhexanoate, oleate, phosphate, benzoate,
  • Oxides such as TBTO, Cu 2 O, CuO, ZnO;
  • Organic tin compounds such as tributyltin naphthenate and tributyltin oxide;
  • Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates, tetramethyltiuramide disulfide (TMTD);
  • Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile (chlorothalonil) etc.
  • Microbicides with activated halogen groups such as Cl-Ac, MCA, tectamer, bromopol, bromidox;
  • Benzothiazoles such as 2-mercaptobenzothiazoles; says Dazomet; Quinolines such as 8-hydroxyquinoline; Formaldehyde releasing compounds such as benzyl alcohol mono (poly) hemiformal, oxazolidines, hexahydro-s-triazine, N-methylol chloroacetamide;
  • phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, 1- (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxypyrazole (TIA-230), chlorpyrifos, Coumaphos, demetone , Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoate, Ethoprophos, Etrimfos, Feni trothion, Fention, Heptenophos, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Trofion Trichlorphone,
  • phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, 1- (4-chlorophenyl) -4- (O-ethyl, S-propyl)
  • Carbamates such as aldicarb, bendiocarb, BPMC (2- (1-methylpropyl) phenylmethyl carbamate), butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb, methomyl, oxamyl, pirimicarb, promecarb, alloxethrin, methinephinide, pyridhrinamethine, methoxide, thyridamine, such as methoxy carburate, pyridhrin, methoxy carburate, methoxy carburate, methoxy carburate, methoxy carburate, and methiodine carboxy , Bioresmethrin, byfenthrin (FMC 54 800), cycloprothrin, cyfluthrin, decamethrione, cyhalothrin, cypermethrin, delta
  • Nitroimines and nitroimides such as 1 - [(6-chloro-3-pyridinyl) - methyl] -4,5-dihydro-N-nitro-1H-imidazol-2-amine (imidacloprid),
  • Organosilicon compounds preferably dimethyl (phenyl) silylmethyl-3-phenoxy-benzyl ether such as e.g. Dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether or dimethyl (phenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as e.g. Dimethyl- (2-ethoxyphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether or (phenyl) [3- (3-phenoxyphenyl) propyl] (dimethyl) silanes such as e.g. (4-ethoxyphenyl) - [3 (4-fluoro-3-phenoxyphenyl) propyl] dimethylsilane.
  • dimethyl (phenyl) silylmethyl-3-phenoxy-benzyl ether such as e.g. Dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether or dimethyl (pheny
  • Algicides are considered as other active substances
  • Molluscicides active substances against "sea animals", which relate to e.g. Place ship floor paints.
  • MIC minimum inhibitory concentrations
  • An agar made from wort and peptone is mixed with active substances according to the invention in concentrations of 0.1 mg / 1 to 5000 mg / 1. After the agar has solidified, there is contamination with pure cultures of the test organisms listed in the table. After 2 weeks of storage at 28 ° C. and 60 to 70% rel., Air humidity is determined. MIC is the lowest concentration of active ingredient at which no growth occurs due to the type of microbe used.
  • Example 12 0 to 1.5% of the active ingredient according to Example 12 is homogeneously distributed in samples of the commercially available emulsion paint based on polyvinyl acetate, based on the total solids content.
  • samples are prepared which contain 0 to 5% tetramethylthiuram disulfide (TMTD, comparison substance E).
  • Coatings are made from the paint samples and tested for mold resistance using the described method. Test method:
  • the paint to be tested is coated on both sides on a suitable surface.
  • test specimens In order to obtain practical results, a part of the test specimens is leached with running water (24 h; 20 ° C) before the test for mold resistance; another part is treated with a warm fresh air flow (7 days; 40 ° C),
  • test specimens prepared in this way are placed on an agar medium, test specimens and medium are contaminated with fungal spores. After storage for 1 to 3 weeks at 29 ⁇ 1 ° C and 80 to 90% rel, humidity is checked. The paint is permanently mold-resistant if the test specimen remains free of fungi or if at most a slight edge infestation can be seen.
  • Molds are used that are known as paint destroyers or are commonly found on paints:
  • Coatings which contain 0.5% of active ingredient according to Example 12 are also extremely mold-resistant even after the loads mentioned above.
  • coatings containing TMTD are only mold-resistant if they contain 4% TMTD. However, such coatings are discolored yellow after exposure (leaching) with iron-containing water.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

Des dérivés du triazolylalkyle-dioxolane de formule (I) dans laquelle R1 désigne un alkyle éventuellement substitué, un alcényle éventuellement substitué, un alcinyle éventuellement substitué, un cycloalkyle éventuellement substitué, un cycloalkylalkyle éventuellement substitué, un aryle éventuellement substitué, un aryalkyle éventuellement substitué, un aryloxyalkyle éventuellement substitué, un arylthioalkyle éventuellement substitué, un arylsulfinylalkyle éventuellment substitué, un arylsulfonylalkyle éventuellement substitué, un aralkyloxyalkyle éventuellement substitué, un aralkylthioalkyle éventuellement substitué, un aralkylsulfinylalkyle éventuellement substitué, ou un aralkylsulfonylalkyle éventuellement substitué, R?2, R3, R4, R5 et R6¿ désignent indépendamment l'hydrogène, un alkyle ou un cycloalkyle, ou R3 et R4 désignent ensemble un alcanediyle à double réticulation, ainsi que leurs sels d'acide d'addition et leurs complexes de sels métalliques, conviennent très bien pour la protection de matériaux techniques contre les attaques de micro-organismes nuisibles.
PCT/EP1993/003233 1992-12-01 1993-11-18 Utilisation de derives du triazolylalkyle-dioxolane comme microbicides dans la protection des materiaux WO1994012033A1 (fr)

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AU56252/94A AU5625294A (en) 1992-12-01 1993-11-18 Use of triazolylalkyldioxolane derivatives as microbicides to protect materials

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DEP4240307.3 1992-12-01
DE19924240307 DE4240307A1 (de) 1992-12-01 1992-12-01 Verwendung von Triazolylalkyl-dioxolan-Derivaten als Mikrobizide im Materialschutz

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EP0050738A1 (fr) * 1980-10-28 1982-05-05 BASF Aktiengesellschaft Agent de protection du bois
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EP0050738A1 (fr) * 1980-10-28 1982-05-05 BASF Aktiengesellschaft Agent de protection du bois
DE3827134A1 (de) * 1988-08-10 1990-03-15 Bayer Ag Substituierte triazolyl- bzw. imidazolyl-hydroxyalkyldioxolane, verfahren zu ihrer herstellung und ihre verwendung als mikrobizide, oxiranyldioxolane, dioxolanylketone, oxiranylketone und (alpha)-halogenketone als zwischenprodukte und verfahren zu deren herstellung

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DE4240307A1 (de) 1994-06-09

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