WO2003001913A1 - Thiazine und thiazole als materialschutzmittel - Google Patents
Thiazine und thiazole als materialschutzmittel Download PDFInfo
- Publication number
- WO2003001913A1 WO2003001913A1 PCT/EP2002/006489 EP0206489W WO03001913A1 WO 2003001913 A1 WO2003001913 A1 WO 2003001913A1 EP 0206489 W EP0206489 W EP 0206489W WO 03001913 A1 WO03001913 A1 WO 03001913A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dihydro
- cas
- sulfanyl
- thiazine
- thiazole
- Prior art date
Links
- 0 CCCC(*)N=C=S Chemical compound CCCC(*)N=C=S 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
Definitions
- the present invention relates to new thiazines and new thiazoles, processes for their preparation, new mixtures of thiazines and / or thiazoles with others
- the present invention relates to the use of new and known compounds of the general formula (I)
- R 1 represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl,
- R 2 represents hydrogen, alkoxycarbonyl or alkylcarbonyl
- n 1 or 2
- alkyl radicals mentioned are each straight-chain or branched, unsubstituted or substituted and contain 1 to 12 carbon atoms, in particular 1 to 8 carbon atoms.
- Preferred alkyl radicals are methyl, ethyl, propyl, butyl and octyl.
- the alkenyl and alkynyl radicals mentioned are each straight-chain or branched, unsubstituted or substituted and contain 2 to 6 C atoms, in particular 2 to 4 C atoms. Propenyl and butynyl are preferred.
- Cycloalkyl generally represents an unsubstituted or substituted cycloalkyl radical having 3 to 8 C atoms, in particular 3 to 6 C atoms. Cyclopropyl and cyclopentyl are preferred.
- the ATkoxy radicals mentioned in the meaning of alkoxycarbonyl are in each case straight-chain or branched, unsubstituted or substituted and contain 1 to 6 C atoms, in particular 1 to 3 C atoms. Methoxy and ethoxy are preferred.
- Aryl generally represents a substituted or unsubstituted 6- to 10-membered aromatic radical, in particular phenyl.
- Halogen generally represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine and bromine.
- Heterocyclyl generally represents a saturated, 1- or polyunsaturated or aromatic 5- to 7-membered ring, in particular a 5- or 6-membered ring, with one or more, identical or different heteroatoms, in particular with 1 to 4 heteroatoms and preferably with 1 to 3 heteroatoms from the series N, O and S, preferably N and S, to which, if appropriate, another ca bocyclic ring, in particular a 6-membered carbocyclic ring, preferably a 6-membered aromatic ring, is condensed.
- radicals are each optionally substituted 1 to more times, identically or differently, in particular 1 to 3 times, preferably 1 or 2 times, the following being suitable in each case: halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, Hydroxy, nitro, nitrile, amino, dialkylamino, carbonyl,
- R 1 stands for hydrogen or for C ⁇ -C ⁇ alkyl, which is optionally substituted one or more times, identically or differently, by Ci-Cg-alkoxy; Ci-Cg-alkoxycarbonyl; each phenyl or phenylcarbonyl optionally substituted by halogen and / or Ci- -alkoxy; C 1 -C 6 alkylcarbonyl; C3-Cg-cycloalkylcarbonyl optionally substituted by halogen; 5- or 6-membered heterocyclylcarbonyl with 1 to 3
- R 2 represents hydrogen, C 1 -C alkoxycarbonyl or C 1 -C 6 alkylcarbonyl
- R 1 represents hydrogen or C j -Cg-alkyl, which is optionally substituted, by -C-C 3 alkoxy; C 1 -C 3 alkoxycarbonyl; each phenyl or phenylcarbonyl optionally substituted by chlorine and / or methoxy;
- R 2 represents hydrogen, C1-C3-alkoxycarbonyl or C1-C3-alkylcarbonyl
- n 1 or 2.
- R 1 represents hydrogen or methyl, which is optionally substituted, by ethoxy, efhoxycarbonyl, phenylcarbonyl, methoxyphenylcarbonyl, chlorophenylcarbonyl, pyrrolylcarbonyl, thienylcarbonyl, chlorocyclopropylcarbonyl, thiazolylthio, thiazinylthio; or for ethyl, propyl, butyl, octyl, cyclopentyl, benzyl, chlorobenzyl, phenyl, chlorophenyl, mefhoxyphenyl, methylphenyl, nitrophenyl, dichlorophenyl, trichlorophenyl, fluorophenyl, difluorophenyl, trifluoromethoxyphenyl, trifluoromethylphenyl, dienylylylphenyl, thienylylphenyl, thienylylphenyl
- Trifluoromethylthiazolyl dimethylaminophenyl, phenoxy, phenyl, dimethylphenyl, dimethoxyphenyl, ethylphenyl, propylphenyl, butylphenyl, cyclopropylphenyl, chloromethylphenyl, dichloromethylphenyl, chloromethoxyphenyl, methoxymethylphenyl, methylpropene, ally -Sulfanyl-thiazolyl) -butin, (2-sulfanylthiazinyl) -butine,
- R 2 represents hydrogen or methoxycarbonyl
- n 1 or 2.
- the new compounds of formula (I) can be prepared by using mercaptans of formula (II) or their salts
- R 1 has the meaning given above
- R 2 and n have the meaning given above, and
- X represents halogen or a leaving group
- R 1 has the meaning given above
- R 2 and n have the meaning given above, and
- X represents halogen or a leaving group
- R 1 has the meaning described above, diazotized with a diazotizing agent and with compounds of the general formula (VI) or their salts
- R 1 has the meaning given above, and
- X represents halogen or a leaving group
- the salts can be prepared and reacted in situ or used in bulk.
- the alkali and alkaline earth metal salts preferably the alkali metal salts and particularly preferably the sodium and potassium salts, can be used as salts.
- the salts are prepared using common chemical methods.
- the compounds of the general formula (III) or (IV) can optionally be generated in situ and reacted directly or used as pure substance.
- Possible diluents added are both water and all customary inert organic solvents. These preferably include hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene, methylene chloride or chloroform, ketones such as acetone or
- Butanone ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether, dimethoxyethane or dioxane, nitriles such as acetonitrile, ide such as N, N-dimethylformamide or N-methylpyvolidone, sulfoxides such as dimethyl sulfoxide, sulfones such as sulfolane, and esters such as ethyl acetate or methyl acetate.
- ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether, dimethoxyethane or dioxane
- nitriles such as acetonitrile
- ide such as N, N-dimethylformamide or N-methylpyvolidone
- sulfoxides such as dimethyl sulfoxide
- sulfones such as sulf
- reaction temperatures can be varied over a wide temperature range in the manufacturing process. Generally one works between -30 ° C and + 150 ° C, preferably between -10 ° C and + 110 ° C.
- Both organic and inorganic bases can be used as acid scavengers. Carbonates, hydroxides, phosphates and. Come as inorganic bases
- the carbonates and hydrides of the alkali and alkaline earth metals are preferably used. Potassium carbonate, sodium carbonate and cesium carbonate, and sodium and potassium hydride are particularly preferred.
- Primary, secondary and tertiary amines can be used as organic bases. Tertiary amines such as trimethylamine, triethylamine, tributylamine, DBU, DBN and pyridine or N, N-dimethylaniline are preferred.
- the diazotizations can be carried out in the presence of an alkali metal nitrite or an alkyl nitrite.
- All customary alkali metal nitrites can be used as the alkali metal nitrite; sodium or potassium nitrite is preferably used.
- All customary alkyl nitrites preferably having 1 to 10 carbon atoms, in particular methyl nitrite, ethyl nitrite, n-propyl nitrite, i-propyl nitrite and iso-amyl nitrite, can be used as the alkyl nitrite.
- Copper, copper salts, palladium or palladium salts can be used as the catalyst. Copper chips, copper
- the process according to the invention is generally carried out at atmospheric pressure. But it is also possible with reduced or increased pressures, namely in
- esters of sulfonic acids in particular mesylates, tosylates or triflates, can be used as leaving groups.
- the new and known compounds of the formula (I) have a strong microbicidal action and can be used to combat unwanted microorganisms, such as fungi and bacteria, in the protection of materials.
- the substances according to the invention can be used to protect technical 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.
- the technical materials are adhesives, glues, paper and cardboard, textiles, leather, wood, wood materials, paints and plastic articles, cooling lubricants and other materials that can be attacked or decomposed by microorganisms.
- technical materials within the scope of the present invention also include parts of production plants, for example cooling water circuits, which can be impaired by the multiplication of microorganisms.
- Technical materials which are preferably to be protected are adhesives, glues, papers and cartons, leather, wood, plastics, paints, cooling lubricants and heat transfer liquid chains.
- the compounds (I) to be used according to the invention are particularly suitable for protecting wood, plastics, paints and cooling lubricants against attack by microorganisms.
- Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
- the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime 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 Penicilliun 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 ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
- formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents , 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, ie emulsifiers and / or dispersants and / or foam-generating agents .
- surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents
- organic solvents can, for example, also be used as auxiliary solvents.
- aromatics such as xylene, toluene or alkylnaphthalenes
- chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methyl Lene chloride
- 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 cyclohexanone
- strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
- Liquids are meant which are gaseous at normal temperature and pressure, e.g. Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
- Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
- Possible solid carriers are: e.g. natural rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates. The following are suitable as solid carriers for granules: e.g.
- emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
- Possible dispersants are: e.g. Lignin sulfite ablaze 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,
- 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.
- the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
- fungicides bactericides
- acaricides nematicides or insecticides
- synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
- Imidazoles such as:
- Clotrimazole Bifonazole, Climbazole, Econazole, Fenapamil, Imazalil, Isoconazole, Ketoconazole, Lombazole, Miconazole, Pefurazoate, Prochloraz, Triflumizole, Thiazolcar l-Imidazolyl-l- (4'-chloropethyloxy) -3 on and their metal salts and acid adducts;
- Triazoles such as:
- Succinate dehydrogenase inhibitors such as: benodanil, carboxime, carboxime sulfoxide, cyclafluramide, fenfuram, flutanil,
- Furcarbanil Furmecyclox, Mebenil, Mepronil, Methfuroxam, Metsulfovax, Pyrocarbolide, Oxycarboxin, Shirlan, Seedvax;
- Naphthalene derivatives such as: terbinafone, naftifine, butenafine, 3-chloro-7- (2-aza-2,7,7-trimethyl-oct-3-en-5-in);
- Dichlorfluanide tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
- Benzimidazoles such as:
- Morpholine derivatives such as:
- Benzthiazoles such as:
- Benzothiophene dioxides such as:
- Benzamides such as: 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide, tecloftalam; Boron compounds such as:
- Formaldehyde and formaldehyde-releasing compounds such as: benzyl alcohol mono- ( ⁇ oly) hemiformal, n-butanol hemiformal, Dazomet, ethylene glycol hemiformal, hexa-hydro-S-triazine, hexamethylenetetramine, N-hydroxymethyl-N'-methylthiourea, N -Methylolchloroacetamide, oxazolidines, paraformaldehyde, tauroline, tetrahydro-l, 3-oxazine, N- (2-hydroxypropyl) amine-methanol;
- Isothiazolinones such as:
- Aldehydes such as:
- Cinnamaldehyde formaldehyde, glutardialdehyde, ⁇ -bromocinnamaldehyde
- Benzalkonium chloride benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, didecyldimethylammoniumchloride, dioctyldimethylammonium chloride, N-hexadecyltrimethylammonium chloride, 1-hexadadylchloride, 1-hexadadylchloride, 1-hexadadylchloride, 1-hexadadylchloride,
- Iodine derivatives such as:
- Phenols such as: tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, 2-benzyl-4-chlorophenol, 5-chloro-2- (2,4- dichlorophenoxy) -phenol, hexachlorophene, p-hydroxybenzoic acid ester, o-phenylphenol, m-phenylphenol, p-phenylphenol and their alkali and alkaline earth metal salts;
- Microbicides with activated halogen group such as:
- Pyridines such as: l-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, l-hydroxy-4-methyl-6 - (2,4,4-trimethylpentyl) -2 (1H) pyridine;
- N-methyl-benzeneacetamide alpha- (methoxyimino) -N-methyl-2- [[[[[1 - [3 - (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] -benzeneacetamide, trifloxystrobin, alpha- ( methoxymethylene) -2 - [[[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] -benzeneaceticacid methyl ester,
- alpha .- (methoxy-imino) -benzeneaceticacid-methyl ester alpha- (methoxyimino) -N-methyl-2- (4-methyl-5-phenyl-2,7-dioxa- 3,6-diazaocta-3,5-dien-1-yl) -benzeneacetamide, alpha- (methoxymethylene) -2- (4-methyl-5- ⁇ henyl-2,7-dioxa-3,6-diazaocta-3, 5-diene-1-yl) -benzeneaceticacid methyl ester, alpha- (methoxyimino) -N-methyl-2 - [[[[1- [3- (trifluoromethyl) phenyl] ethoxy] imino] methyl] -benzeneacetamide,
- Metal soaps such as: tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;
- Metal salts such as:
- Tributyltin oxide CU2O, CuO, ZnO;
- Dithiocarbamates such as: Cufraneb, Ferban, potassium N-hydroxymethyl-N'-methyldithiocarbamate, Na- or K-dimethyldithiocarbamate, Macozeb, Maneb, Metam, Metiram, Thiram, Zineb, Ziram;
- Nitriles such as:
- fungicides and bactericides such as: 5-hydroxy-2 (5H) furanon; 4,5-benzdithiazolinone, 4,5-trimethylene dithiazolinone, N-
- Fenamiphos Fenazaquin, Fenbutatinoxid, Fenflufhrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fensulfothion,
- Halofenocid HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnon,
- Imidacloprid Imiprothrin, Indoxycarb, Iodfenfos, Iprinomectin, Iprobefos, Isazophos, Isoamidophos, Isofenphos, Isoprocarb, Isoprothiolane, Isoxathion, Ivermectin, Lama-cyhalothrin, Lufenuron,
- Methamidophos methidathione, methiocarb, methomyl, metalcarb, milbemectin, monocrotophos, moxiectin,
- Molluscicides fentin acetates, metaldehydes, mefhiocarb, niclosamide;
- Fluazifop Fluazifop-P, Fuenachlor, Fluchloralin, Flufenacet, Flumeturon, Fluorocglycofen, Fluoronitrofen, Flupropanate, Flurenol, Fluridone, Flurochloridone, Fluroxypyr, Fomesafen, Fosamine, Flamprop-isopropyl, Flamprop-isopropyllorum, Flamprop-isopropylloro Flurtamone, Flumioxzim, Flupyrsul- furon-methyl, Glyphosate, glufosinate-ammonium
- Tmazethapyr Ioxynil, Isopropalin, Imazosulfuron, Imazomox, Isoxaflutole, Imazapic,
- MCPA MCPA-thioethyl
- MCPB Mecoprop, Mecoprop-P, Mefenacet, Mefluidide, Metam, Metamitron, Metazachlor, Methabenzthiazuron, Methazole, Methoroptryne, Methyldymron, Methylisothiocyanate, Metobromuron, Metoxuron, Metriburonon, Metriburonon, Metriburonon , Metolachlor, metosulam,
- Pretilachlor primisulfuron, prodiamine, prometryn, propachlor, propanil, propaquizafob, propazine, propham, propisochlor, pyriminobac-methyl, pelargonic acid, pyrithiobac,
- the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
- Application takes place in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc.
- the agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%.
- the application concentrations of the active compounds according to the invention depend on the type and the 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, based on the material to be protected.
- MIC minimum inhibitory concentrations
- a chemically defined nutrient agar is mixed with the active substances according to the invention in concentrations of 0.1 mg / ml to 5000 mg / ml. After the agar has solidified, it is contaminated with pure cultures of the test organisms listed in Table 2. After a 3-day incubation period at 28 ° C and 60 to 70% relative humidity, the MIC is determined. MIC is the lowest concentration of active substance at which no growth occurs due to the microbe species used, it is shown in Table 2.
- MIC minimal inhibitory concentrations
- the active substances according to the invention are each added to an agar which is produced using malt extract in concentrations of 0.1 mg / 1 to 5,000 mg / 1. After the agar solidifies, it is contaminated with pure cultures of the test organisms listed in Table 3. After a 2-week incubation period at 28 ° C and 60 to 70% relative humidity, the MIC is determined. MIC is the lowest concentration of active substance at which no growth occurs due to the type of microbe used; it is given in Table 3.
- the procedure for testing dispersion paints for mold resistance is as follows: The paint to be tested is coated on both sides on a suitable surface. In order to obtain practical results, some of the test specimens are 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).
- the samples prepared in this way are then placed on an agar culture medium and both the sample and the culture medium are contaminated with fungal spores. After 2-3 weeks of storage (29 ⁇ 1 ° C, 80-90% rel. Air humidity), a sample is taken.
- the paint is classified as permanently mold-resistant if the sample remains free of fungi or if at most a small edge infestation can be seen.
- Fungus spores of the following molds are used for the contamination
- Paint destroyers are known or are commonly found on paints:
- Coatings are resistant to mold in accordance with recipe A (even after leaching and exposure to the wind tunnel) if, for example, they contain 1.5% (based on solids) of compound 25.
- Recipe A exterior emulsion paint based on Acroal 290 D (styrene acrylate)
- Solids content 135.5 61.6%.
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR0210709-0A BR0210709A (pt) | 2001-06-26 | 2002-06-13 | Tiazinas e tiazóis como agentes de proteção de material |
EP02743186A EP1437940A1 (de) | 2001-06-26 | 2002-06-13 | Thiazine und thiazole als materialschutzmittel |
JP2003508168A JP2004530720A (ja) | 2001-06-26 | 2002-06-13 | 物質保護剤としてのチアジン類及びチアゾール類 |
NO20035652A NO20035652L (no) | 2001-06-26 | 2003-12-17 | Tiaziner og tiazoler som materialbeskyttelsesmidler |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10130706A DE10130706A1 (de) | 2001-06-26 | 2001-06-26 | Thiazine und Thiazole als Materialschutzmittel |
DE10130706.3 | 2001-06-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003001913A1 true WO2003001913A1 (de) | 2003-01-09 |
Family
ID=7689455
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/006489 WO2003001913A1 (de) | 2001-06-26 | 2002-06-13 | Thiazine und thiazole als materialschutzmittel |
Country Status (8)
Country | Link |
---|---|
US (2) | US20030129081A1 (de) |
EP (1) | EP1437940A1 (de) |
JP (1) | JP2004530720A (de) |
BR (1) | BR0210709A (de) |
DE (1) | DE10130706A1 (de) |
NO (1) | NO20035652L (de) |
PL (1) | PL367522A1 (de) |
WO (1) | WO2003001913A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004013113A1 (de) * | 2002-07-29 | 2004-02-12 | Lanxess Deutschland Gmbh | Substituierte thiazine als materialschutzmittel |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3936189B2 (ja) * | 1999-09-14 | 2007-06-27 | 塩野義製薬株式会社 | 2−イミノ−1,3−チアジン誘導体 |
CN101137289B (zh) * | 2005-01-26 | 2012-09-05 | 梅瑞尔有限公司 | 杀虫的经取代的硫醚 |
JP5364936B2 (ja) | 2010-11-09 | 2013-12-11 | ダウ グローバル テクノロジーズ エルエルシー | フルメツラムまたはジクロスラムとジヨードメチル−p−トリルスルホンとの相乗的組み合わせ |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH535536A (de) * | 1965-06-18 | 1973-04-15 | Agripat Sa | Mikrobizides Mittel |
GB1379754A (en) * | 1971-03-30 | 1975-01-08 | Lilly Industries Ltd | Methods and compositions for treating plants susceptible to fungal attack |
DE2533604A1 (de) * | 1975-07-26 | 1977-02-10 | Bayer Ag | 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide |
JPS5241235A (en) * | 1976-07-15 | 1977-03-30 | Ajinomoto Co Inc | Fungicidal composition for agricultural and gardening use |
DE2721401A1 (de) * | 1976-05-12 | 1977-12-01 | Siegfried Ag | Thioaether, verfahren zu ihrer herstellung und deren verwendung |
GB1511390A (en) * | 1975-12-04 | 1978-05-17 | Pfizer Ltd | Imidazolylalkyl sulphide antifungal agents |
EP0005153A1 (de) * | 1978-03-11 | 1979-11-14 | BASF Aktiengesellschaft | 4-Nitro-2-trichlormethylphenyldisulfide, Verfahren zu ihrer Herstellung, den Wirkstoff enthaltende Mittel und Verwendung gegen Mikroorganismen |
GB2052481A (en) * | 1979-05-09 | 1981-01-28 | Hoechst Ag | 4-Substituted 5,6,7,8- tetrahydroquinolines, their preparation and use |
EP0040310A2 (de) * | 1980-04-12 | 1981-11-25 | Hoechst Aktiengesellschaft | Fungizide, heterocyclisch substituierte Thioglykolsäureanilide, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel |
DE3539476A1 (de) * | 1985-11-07 | 1987-05-14 | Hoechst Ag | Neue pyridylverbindungen sowie deren n-oxide, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz |
EP0299694A2 (de) * | 1987-07-11 | 1989-01-18 | AgrEvo UK Limited | Acrylsäure-Derivate als Fungizide |
EP0545103A1 (de) * | 1991-12-04 | 1993-06-09 | American Cyanamid Company | In 1-Stellung mit einer substituierten Thioalkylgruppe substituierte Pyrrole als Insektizide, Akarizide und Molluskizide |
WO1999052874A1 (fr) * | 1998-04-10 | 1999-10-21 | Ube Industries, Ltd. | Derives difluoroalcene, procede de production associe, et agent de lutte contre les ravageurs dans l'agriculture et l'horticulture |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3178425A (en) * | 1965-04-13 | Dihydro-l:j:x-thiazenes | ||
US3131183A (en) * | 1964-04-28 | Certificate of correction | ||
CH447207A (de) | 1965-06-18 | 1967-11-30 | Agripat Sa | Verfahren zur Herstellung von neuen 5-Sulfonyl-1,2-dithiol-3-onen und ihre Verwendung zur Bekämpfung von Pilzen und Bakterien |
US4584305A (en) | 1972-08-17 | 1986-04-22 | Janssen Pharmaceutica N.V. | Aiding the regression of neoplastic disease with 2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole |
JPS54145680A (en) * | 1978-05-04 | 1979-11-14 | Kuraray Co Ltd | 2-(substituted phenylthio)-4,5-dihydro-6h-1,3-thiazine |
JP3870515B2 (ja) * | 1997-11-07 | 2007-01-17 | 宇部興産株式会社 | 5,6−ジヒドロ−(4h)−1,3−チアジン誘導体、その製法及び農園芸用の有害生物防除剤 |
-
2001
- 2001-06-26 DE DE10130706A patent/DE10130706A1/de not_active Withdrawn
-
2002
- 2002-06-13 EP EP02743186A patent/EP1437940A1/de not_active Withdrawn
- 2002-06-13 JP JP2003508168A patent/JP2004530720A/ja not_active Withdrawn
- 2002-06-13 WO PCT/EP2002/006489 patent/WO2003001913A1/de not_active Application Discontinuation
- 2002-06-13 PL PL02367522A patent/PL367522A1/xx not_active Application Discontinuation
- 2002-06-13 BR BR0210709-0A patent/BR0210709A/pt not_active IP Right Cessation
- 2002-06-24 US US10/178,134 patent/US20030129081A1/en not_active Abandoned
-
2003
- 2003-12-17 NO NO20035652A patent/NO20035652L/no not_active Application Discontinuation
-
2004
- 2004-04-29 US US10/835,224 patent/US7084137B2/en not_active Expired - Fee Related
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH535536A (de) * | 1965-06-18 | 1973-04-15 | Agripat Sa | Mikrobizides Mittel |
GB1379754A (en) * | 1971-03-30 | 1975-01-08 | Lilly Industries Ltd | Methods and compositions for treating plants susceptible to fungal attack |
DE2533604A1 (de) * | 1975-07-26 | 1977-02-10 | Bayer Ag | 2-substituierte 5-trifluormethyl1,3,4-thiadiazole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und insektizide |
GB1511390A (en) * | 1975-12-04 | 1978-05-17 | Pfizer Ltd | Imidazolylalkyl sulphide antifungal agents |
DE2721401A1 (de) * | 1976-05-12 | 1977-12-01 | Siegfried Ag | Thioaether, verfahren zu ihrer herstellung und deren verwendung |
JPS5241235A (en) * | 1976-07-15 | 1977-03-30 | Ajinomoto Co Inc | Fungicidal composition for agricultural and gardening use |
EP0005153A1 (de) * | 1978-03-11 | 1979-11-14 | BASF Aktiengesellschaft | 4-Nitro-2-trichlormethylphenyldisulfide, Verfahren zu ihrer Herstellung, den Wirkstoff enthaltende Mittel und Verwendung gegen Mikroorganismen |
GB2052481A (en) * | 1979-05-09 | 1981-01-28 | Hoechst Ag | 4-Substituted 5,6,7,8- tetrahydroquinolines, their preparation and use |
EP0040310A2 (de) * | 1980-04-12 | 1981-11-25 | Hoechst Aktiengesellschaft | Fungizide, heterocyclisch substituierte Thioglykolsäureanilide, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel |
DE3539476A1 (de) * | 1985-11-07 | 1987-05-14 | Hoechst Ag | Neue pyridylverbindungen sowie deren n-oxide, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz |
EP0299694A2 (de) * | 1987-07-11 | 1989-01-18 | AgrEvo UK Limited | Acrylsäure-Derivate als Fungizide |
EP0545103A1 (de) * | 1991-12-04 | 1993-06-09 | American Cyanamid Company | In 1-Stellung mit einer substituierten Thioalkylgruppe substituierte Pyrrole als Insektizide, Akarizide und Molluskizide |
WO1999052874A1 (fr) * | 1998-04-10 | 1999-10-21 | Ube Industries, Ltd. | Derives difluoroalcene, procede de production associe, et agent de lutte contre les ravageurs dans l'agriculture et l'horticulture |
Non-Patent Citations (15)
Title |
---|
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ABDEL-LATEEF ET AL.: "Systemic and chemotherapeutic fungicidal activity-chemical structure relation of some 4-methyl-5-thiazolecarboxylic acid derivatives", XP002210633, Database accession no. 1974:515750 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; COMBY ET AL: "Antibacterial, antiparasitic and antifungal sulfonamides derived from imidazole: estimation of antithyroid effects in the rat", XP002210627, Database accession no. 1994:153466 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HAN ET AL.: "Synthesis and fungicidal activity of substituted arylimonothiazolines", XP002210636, Database accession no. 2000:813766 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HIROSE ET AL: "Oxonaphthyridine- and oxoquinoline-3-carboxylic acid as microbicides", XP002210630, Database accession no. 1990:20980 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MUTHUSUBRAMANIAN ET AL: "Convenient synthesis of thiocyanomethylthio heteroaromatics as antifungal agents", XP002210625, Database accession no. 1998:395793 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; NIHON TOKUSHU NOYAKU SEIZO KK: "Benzisothiazole compounds", XP002210632, Database accession no. 1982:142839 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; RANI ET AL.: "Thiazoline analogs of epiderstatin, new inhibitors of cell cycle of tdFT-21 cells", XP002210626, Database accession no. 1995:897719 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; REISDORFF ET AL.: "2-substituted 5-(trifluoromethyl)-1,3,4-thiadiazoles as antiparasitic agents", XP002210635, Database accession no. 1977:171462 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TERACHI ET AL: "Preparation of succinimides as agrochemical fungicides for Phytophtora and Puccinica control", XP002210629, Database accession no. 1990:510914 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TERNANSKI RJ ET AL: "Discovery and structure-activity relationship of a series of 1-catrba-1-dethiacephems exhibiting activity against methicillin-resistant Staphylococcus aureus", XP002210628, Database accession no. 1993:117001 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TSYMBAL ET AL.: "Anti-Ustilaginacea activity of some chemical compounds", XP002210634, Database accession no. 1968:451135 * |
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; YAMASHITA ET AL: "2-substituted thioazoline derivatives", XP002210631, Database accession no. 1986:168454 * |
DATABASE CHEMCATS [online] CHEMICAL ABSTRACT ONLINE; 21 January 2002 (2002-01-21), AMBITER: "Exploratory library 66839 (CAS 438481-76-6)", XP002211695, Database accession no. 2002:2834310 * |
DATABASE WPI Week 197719, Derwent World Patents Index; AN 1977-33719Y, XP002210637 * |
DATABASE WPI Week 199954, Derwent World Patents Index; AN 1999-633815, XP002210638 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004013113A1 (de) * | 2002-07-29 | 2004-02-12 | Lanxess Deutschland Gmbh | Substituierte thiazine als materialschutzmittel |
Also Published As
Publication number | Publication date |
---|---|
US7084137B2 (en) | 2006-08-01 |
NO20035652D0 (no) | 2003-12-17 |
BR0210709A (pt) | 2004-07-20 |
US20030129081A1 (en) | 2003-07-10 |
JP2004530720A (ja) | 2004-10-07 |
DE10130706A1 (de) | 2003-01-02 |
US20040204405A1 (en) | 2004-10-14 |
NO20035652L (no) | 2004-02-25 |
EP1437940A1 (de) | 2004-07-21 |
PL367522A1 (en) | 2005-02-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1395117B2 (de) | Verwendung von triazolopyrimidin-derivaten als mikrobizide im materialschutz | |
WO2002048100A2 (de) | Thiosulfonsäure-s-ester als materialschutzmittel | |
EP1773125B1 (de) | 5-iodtetrazole | |
EP0950055A1 (de) | Arylthio-dithiazindioxide und ihre verwendung als schädlingsbekämpfungsmittel | |
WO2003001913A1 (de) | Thiazine und thiazole als materialschutzmittel | |
EP1527054A1 (de) | Substituierte thiazine als materialschutzmittel | |
DE19721627A1 (de) | S-Pyridyl-dithiazoldioxide | |
WO2007025586A1 (de) | 1-cycloalkyl-5-iodtetrazole | |
US6638958B2 (en) | 3-nitroisoxazoles and their use in the protection of materials | |
DE10256187A1 (de) | 2-Oxyamino-1-cyclopenten-1-nitrile als Materialschutzmittel | |
WO1998042689A1 (de) | 3-alkoxyisothiazole | |
WO2004050644A2 (de) | Cyclopenta[c]isoxazol-3-amine als materialschutzmittel | |
DE19709876A1 (de) | Algizide Mittel | |
MXPA99010762A (en) | Pyridylthio-dithiazole derivatives adn their use as pest control agents |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG US UZ VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG UZ VN YU ZA ZM ZW GH GM KE LS MW |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2002743186 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2003508168 Country of ref document: JP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWP | Wipo information: published in national office |
Ref document number: 2002743186 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 2002743186 Country of ref document: EP |