[go: up one dir, main page]

EP0975611A1 - 3-alcoxy-isothiazoles - Google Patents

3-alcoxy-isothiazoles

Info

Publication number
EP0975611A1
EP0975611A1 EP98916926A EP98916926A EP0975611A1 EP 0975611 A1 EP0975611 A1 EP 0975611A1 EP 98916926 A EP98916926 A EP 98916926A EP 98916926 A EP98916926 A EP 98916926A EP 0975611 A1 EP0975611 A1 EP 0975611A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
atoms
chain
straight
chlorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98916926A
Other languages
German (de)
English (en)
Inventor
Hermann Uhr
Martin Kugler
Peter Wachtler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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 AG filed Critical Bayer AG
Publication of EP0975611A1 publication Critical patent/EP0975611A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • A01N43/80—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 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof

Definitions

  • the invention relates to new 3-alkoxyisothiazoles, their use as microbicides and processes for their preparation.
  • R 1 represents optionally substituted alkyl, alkenyl or alkynyl,
  • R 2 represents optionally substituted alkyl, alkenyl, alkynyl or phenyl and
  • R 3 represents hydrogen or halogen.
  • R 1 stands for straight-chain and branched alkyl with 1 is 10 carbon atoms, straight-chain or branched alkenyl with 2 to 10 carbon atoms or straight-chain or branched alkynyl with 2 to 10 carbon atoms, which are each optionally substituted one or more times by the same or different substituents by halogen, alkoxy with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms and 1 to 9 identical or different halogen atoms, alkylthio with 1 to 6 carbon atoms, haloalkylthio with 1 to 6 carbon atoms and 1 to 9 identical or different halogen atoms, acyl with 1 to 6 carbon atoms, Acyloxy with 1 to 6 carbon atoms, (alkoxy) carbonyl with 1 to 6 carbon atoms, amino which is optionally substituted identically or differently by alkyl or aryl, optionally substituted phenoxy, aryl, pyridyl or
  • R 2 represents straight-chain and branched alkyl having 1 is 10 carbon atoms, straight-chain or branched alkenyl having 2 to 10 carbon atoms or straight-chain or branched alkynyl having 2 to 10 carbon atoms, which are each optionally substituted one or more times by the same or different substituents by halogen, alkoxy with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms and 1 to 9 identical or different halogen atoms, alkylthio with 1 to 6 carbon atoms, haloalkylthio with 1 to 6 carbon atoms and 1 to 9 identical or different halogen atoms, acyl with 1 to 6 carbon atoms, Acyloxy having 1 to 6 carbon atoms, (alkoxy) carbonyl having 1 to 6 carbon atoms, amino, which is optionally substituted identically or differently by alkyl or aryl, optionally substituted phenoxy, aryl, pyridyl or
  • halogen alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 8 carbon atoms and 1 to 8 identical or different halogen atoms,
  • R 3 represents halogen or hydrogen.
  • R 1 represents straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched alkenyl having 2 to 8 carbon atoms or straight-chain or branched alkynyl having 2 to 8 carbon atoms, which are in each case optionally substituted one to four times by identical or different substituents by fluorine, chlorine , Alkoxy with 1 to 5 carbon atoms,
  • Amino which is optionally substituted identically or differently by alkyl having 1 to 4 carbon atoms and / or phenyl, optionally substituted phenoxy, aryl, pyridyl or pyridyloxy, nitro or cyano, or for
  • phenyl which is optionally mono- to tetrasubstituted by fluorine, chlorine, alkyl having 1 to 8 carbon atoms, haloalkyl having 1 to 6 carbon atoms and 1 to 6 fluorine and / or chlorine atoms, alkoxy having 1 to 8 carbon atoms, haloalkoxy 1 to 6 carbon atoms and 1 to 6 fluorine and / or chlorine atoms, alkylthio with 1 to 8
  • R 3 represents chlorine, bromine or hydrogen.
  • R 1 is preferably methyl, ethyl, n- and i-propyl, n-, s-, i- and t-butyl, allyl and propargyl, which are each optionally substituted and are substituted by fluorine and / or chlorine, methoxy or methylthio, in particular R 1 represents methyl, ethyl or n-propyl.
  • R 3 preferably represents chlorine and in particular hydrogen.
  • R 2 preferably represents methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, which are each optionally substituted by methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethylcarbonyl, cyano or phenyl .
  • R 2 furthermore preferably represents phenyl. Phenyl in the meanings given above is optionally mono- or disubstituted by methyl, ethyl, fluorine, chlorine, methoxy, ethoxy or trifluoromethyl.
  • radical definitions specified for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, regardless of the combination specified in each case.
  • R 1 and R 3 have the meaning given above and
  • R 4 can independently have the same meaning as R 1 , but is preferably identical to R 1 , optionally reacted in the presence of catalysts,
  • R 1 and R 3 have the meanings given above and X is chlorine or
  • Bromine stands, optionally in the presence of acid-binding agents.
  • reaction temperatures can be varied within a substantial range. Generally one works between 0 ° C and 200 ° C, preferably between 20 ° C and 150 ° C. If appropriate, the reactions can be carried out in the presence of diluents. All solvents which do not react with the starting materials are suitable as diluents.
  • hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene, chloroform, methylene chloride, ethers such as methyl tert-butyl ether, nitriles such as acetonitrile, ketones such as acetone, and DMSO or DMF.
  • chlorinated hydrocarbons such as chlorobenzene, chloroform, methylene chloride
  • ethers such as methyl tert-butyl ether
  • nitriles such as acetonitrile
  • ketones such as acetone
  • DMSO or DMF DMSO or DMF
  • Acids or Lewis acids are generally used.
  • Inorganic acids such as Hcl, H2SO4, H3PO4, organic acids such as formic acid, acetic acid, p-toluenesulfonic acid or Lewis acids such as A1C1 3 , ZnCl 2 , TiCl 4 are preferably used.
  • reaction temperatures can be varied within a substantial range. Generally one works between -20 ° C and + 150 ° C, preferably between -10 ° C and + 80 ° C.
  • the reactions can be carried out in the presence of diluents.
  • diluents All solvents which cannot react with the starting materials are suitable as diluents.
  • Hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene, chloroform, methylene chloride, ethers such as e.g. Methyl tert-butyl ether, nitriles such as acetonitrile, ketones such as acetone, and DMSO or DMF.
  • acid-binding agents all customary acid-binding agents can be used here.
  • acid-binding agents include tertiary amines such as triethylamine and pyridine; Alkali hydroxides such as sodium and potassium hydroxide and alkali carbonates and hydrogen carbonates such as potassium carbonate and sodium hydrogen carbonate.
  • the hydroxyisothiazoles of the formula (II) are known and can be prepared according to literature regulations (for example Crow et al., J. Org. Chem. 30, 2660 (1965)).
  • the compounds of the formula (III) are known or can be prepared by methods known from the literature (for example W. Kantlehner et al., Just. Leisip Ann. Chemie 1974, 690).
  • the compounds of the formula (IV) are likewise known or can be prepared according to literature instructions (for example McLeod, JK, Tetrahedron. 23, 2095 (1967); Pihlaja, Kalevi et al., Acta Chem. Scand. Ser. B. 40, 196 (1986)).
  • the active compounds of the formula (I) have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active compounds of the formula (I) 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 which are to be protected from 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 are attacked or decomposed by microorganisms can be.
  • adhesives glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which are attacked or decomposed by microorganisms can be.
  • Materials are also parts of production systems, such as cooling water circuits, that can be affected by the proliferation of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids.
  • 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 or agents according to the invention preferably act against fungi, in particular mold, and against
  • 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 active compounds of the formula (I) can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and very fine encapsulations in polymeric substances.
  • formulations or agents 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, that is to say 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, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • 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, Chlorethylene, 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, as well as water;
  • Liquefied gaseous extenders or carriers mean 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;
  • Solid carrier materials are suitable: for example natural rock powder
  • 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, for example iron oxide, titanium oxide, ferocyanine blue and organic dyes such as alizarin, azo and metal phthalocya
  • inorganic pigments for example iron oxide, titanium oxide, ferocyanine blue and organic dyes such as alizarin, azo and metal phthalocya
  • organic dyes such as alizarin, azo and metal phthalocya
  • salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the effectiveness and the spectrum of activity of the active compounds of the formula (I) 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 compounds to enlarge the spectrum of action 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.
  • Triazoles such as:
  • Imidazoles such as:
  • Clotrimazole Bifonazole, Climbazole, Econazole, Fenapamil, Imazalil, Isoconazole, Ketoconazole, Lombazole, Miconazole, Pefurazoate, Prochloraz, Triflumizoles, thiazole car l-imidazolyl-l- (4'-chlorophenoxy) -3,3-dimethylbutan-2-one and their metal salts and acid adducts;
  • Pyridines and pyrimidines such as: ancymidol, buthiobate, fenarimol, nuarimol, triamirol;
  • Succinate dehydrogenase inhibitors such as:
  • Naphthalene derivatives such as:
  • Sulfenamides such as:
  • Dichlorfluanide tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
  • Benziniidazoles such as:
  • Morpholine derivatives such as:
  • Benzthiazoles such as:
  • Benzamides such as: 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide, tecloftalam;
  • Formaldehyde and formaldehyde releasing compounds such as:
  • Isothiazolinones such as:
  • Aldehydes such as:
  • Cinnamaldehyde formaldehyde, glutardialdehyde, ß-bromocinnamaldehyde
  • Thiocyanates such as: thiocyanatomethylthiobenzothiazole, methylene bisthiocyanate;
  • Benzalkonium chloride benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, didecyldimethylammonium chloride, dioctyldimethylammonium chloride,
  • Iodine derivatives such as:
  • Phenols 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-tr imethylpentyl) -2 (1 H) pyridine;
  • Metal salts such as:
  • Oxides such as: tributyltin oxide, CU2O, CuO, ZnO; Dithiocarbamates such as:
  • Cufraneb ferban, potassium-N-hydroxymethyl-N'-methyl-dithiobarbamate, Na- or K-dimethyldithiocarbamate, Macozeb, Maneb, Metam, Metiram, Thiram, Zineb, Ziram;
  • Nitriles such as:
  • Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials.
  • Bacillus thuringiensis Barthrin, 4-Bromo-2 (4-chlorophenyl) -l- (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, Bioresmethrin, Bioallethrin Bromophos A, Bromophos M, Bufencarb, Buprofezin, Butathiophos, Butocarboxin, Butoxycarboxim,
  • Eflusilanate Emamectin, Empenthrin, Endosulfan, EPN, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fensulfothion, Fenthion, Fenvalerate, Fipronil, Fluazuron, Flucycloxuron, Flxthroxinphonate, Floxethrinifurinate, Flucythrinolanate, Flucythrinone, Flucythrininate, Flucythrinone, Flucythrininate, Flucythrininate, Flucythrininate, Flucythrininate, Flucyth
  • HCH Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnon, Hydroprene, Imidacloprid, Iodfenfos, Iprobefos, Isazophos, Isoamidophos, Isofenphos, Isoprocarb, Isoprothiolane, Isoxathion, Ivermectin, Lama-cyhalothrinadhronuronuronurinuronurinuronurinuronurinuronurinuronurinuronurinuronurinuronuronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurinurluronurin
  • Parathion A Parathion M, Penfluron, Permethrin, 2- (4-phenoxyphenoxy) ethyl ethyl carbamate, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Prallethrin, Profenophos, Promecarb, Propaphos Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
  • Carbetamides chloromethoxyfen, chloramben, chlorbromuron, chlorflurenol, chloridazon, chlorimuron, chloronitrofen, chloroacetic acid, chlorotoluron, chloroxuron, chlorpropham, chlorosulfuron, chlororthhal, chlorothiamide,
  • Diflufenican Dimefuron, Dimepiperate, Dimethachlor, Dimethipin, Dinitramine, Dinoseb, Dinoseb Acetate, Dinoterb, Diphenamid, Dipropetryn, Diquat, Dithiopyr, Diduron, DNOC, DSMA, 2,4-D, Daimuron, Dalapon, Dazomet, 2,4-DB , Desmedipham, Desmetryn, Dicamba, Dichlobenil, Dimethamid, Dithiopyr, Dimethametryn,
  • Haloxy fop Hexazinone, Imazamethabenz, Isoproturon, Isoxaben, Isoxapyrifop, Imazapyr, Imazaquin,
  • MCPA MCPA-thioethyl
  • MCPB Mecoprop, Mecoprop-P, Mefenacet, Mefluidide, Metam, Metamitron, Metazachlor, Methabenzthiazuron, Methazole,
  • Methoroptryne methyldymron, methylisothiocyanate, metobromuron, metoxuron,
  • Pentanochlor Petroleum oils, Phenmedipham, Picloram, Piperophos, Pretilachlor, Primisulfuron, Prodiamine, Prometryn, Propachlor, Propanil, Propaquizafob,
  • Trietazine Trifluralin, Tycor, Thdiazimin, Thiazopyr, Triflusulfuron, Vernolate.
  • the weight ratios of the active ingredients in these active ingredient combinations can be varied within relatively large ranges.
  • the active compound combinations preferably contain the active compound at 0.1 to
  • microbicidal agents used to protect the technical materials or
  • Concentrates contain the active ingredient or combination of active ingredients in a concentration of 0.01 and 95% by weight, in particular 0.1 to 60% by weight.
  • the application concentrations of the active substances to be used or the active substance combinations 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.
  • the active substances or agents according to the invention advantageously make it possible to replace the microbicidal agents available to date with more effective ones. They show good stability and advantageously have a broad spectrum of action.
  • MIC minimum inhibitory concentrations
  • a defined candy agar 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, it is contaminated with pure cultures of the test organisms listed in Table 2. After 3 days of storage at 28 ° C and 60 to 70% relative humidity, the MIC is determined. MIC is the lowest concentration of active ingredient at which no growth occurs due to the type of microbe used, it is shown in Table 2 below.

Landscapes

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

Abstract

L'invention concerne de nouveaux 3-alcoxy-isothiazoles, leur utilisation comme microbicides et des procédés permettant de les préparer.
EP98916926A 1997-03-25 1998-03-12 3-alcoxy-isothiazoles Withdrawn EP0975611A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19712409 1997-03-25
DE19712409A DE19712409A1 (de) 1997-03-25 1997-03-25 3-Alkoxyisothiazole
PCT/EP1998/001434 WO1998042689A1 (fr) 1997-03-25 1998-03-12 3-alcoxy-isothiazoles

Publications (1)

Publication Number Publication Date
EP0975611A1 true EP0975611A1 (fr) 2000-02-02

Family

ID=7824506

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98916926A Withdrawn EP0975611A1 (fr) 1997-03-25 1998-03-12 3-alcoxy-isothiazoles

Country Status (6)

Country Link
EP (1) EP0975611A1 (fr)
JP (1) JP2001518105A (fr)
AU (1) AU7034298A (fr)
CA (1) CA2284821A1 (fr)
DE (1) DE19712409A1 (fr)
WO (1) WO1998042689A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000041524A2 (fr) 1999-01-11 2000-07-20 President And Fellows Of Harvard College Amplification isotherme d'adn

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957808A (en) * 1969-09-03 1976-05-18 Rohm And Haas Company 3-alkoxyisothiazoles
CA941828A (en) * 1969-09-03 1974-02-12 Sheldon N. Lewis 3-hydroxyisothiazoles
US3706757A (en) * 1970-07-22 1972-12-19 Rohm & Haas Certain organotin derivatives of 3-hydroxyisothiazole
US5384326A (en) * 1991-11-12 1995-01-24 Rohm And Haas Company Girondalones
US5508417A (en) * 1994-02-23 1996-04-16 Rohm And Haas Company Broad-spectrum isothiazole antimicrobial agents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9842689A1 *

Also Published As

Publication number Publication date
WO1998042689A1 (fr) 1998-10-01
AU7034298A (en) 1998-10-20
CA2284821A1 (fr) 1998-10-01
DE19712409A1 (de) 1998-10-01
JP2001518105A (ja) 2001-10-09

Similar Documents

Publication Publication Date Title
EP1395117B2 (fr) Utilisation de derives de triazolopyrimidine en tant que microbicides pour la protection de materiel
US20020151570A1 (en) Thiosulfonic acid S-esters as agents for protecting material
US6075019A (en) Arylthio-dithiazindioxides and their use as pesticides
EP0982995B1 (fr) Algicides
EP1773125B1 (fr) 5-iode tetrazole
US7084137B2 (en) Thiazines and thiazoles as agents for protecting materials
AU735796B2 (en) Pyridylthio-dithiazole dioxide derivatives and their use as pesticides
EP1527054A1 (fr) Thiazines substituees utilisees comme agents protecteurs de materiaux
WO1998042689A1 (fr) 3-alcoxy-isothiazoles
US6638958B2 (en) 3-nitroisoxazoles and their use in the protection of materials
DE10256187A1 (de) 2-Oxyamino-1-cyclopenten-1-nitrile als Materialschutzmittel
WO1998039969A1 (fr) Agents algicides
EP1569920A2 (fr) Cyclopenta c]isoxazol-3-amines utilisees comme agents de protection de materiaux
MXPA99010762A (en) Pyridylthio-dithiazole derivatives adn their use as pest control agents
MXPA99006254A (es) Ariltio-ditiazindioxidos y su empleo como agentespesticidas

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19991025

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB IT LI NL

17Q First examination report despatched

Effective date: 20001026

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Withdrawal date: 20010202