Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/16—Antifouling paints; Underwater paints
• • 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
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/16—Antifouling paints; Underwater paints
  • C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
  • C09D5/1612—Non-macromolecular compounds
  • C09D5/1625—Non-macromolecular compounds organic

Definitions

• the present invention relates to a method and means for protecting against the growth of objects, in particular hulls, screens, nets,
• BCD's Benzothiophene-2-carboxamide-S, S-dioxide (BCD's), a process for their preparation and their fungicidal activity are known (DE-A-41 15 184). Above all, their effectiveness against fungi and harmful plants is described
• BCDs are suitable for protecting technical materials against microbial change or destruction.
• EP 593 135 discloses their use for the finishing of mold-resistant emulsion paints.
• BCDs not only detect the types of mold that usually grow on paints, but also have an excellent antifouling effect.
• the application therefore relates to the use of benzothiophene-2-carboxamide-S, S-dioxides to protect objects from fouling.
• the compounds used as antifouling active ingredients in this invention are represented by the formula (I)
• R 1 stands for optionally substituted alkyl, for alkenyl or alkynyl, for each optionally substituted cycloalkyl or cycloalkylalkyl, or for each optionally substituted aralkyl, aralkenyl, aralkynyl or aryl,
• R represents hydrogen or optionally substituted alkyl or
• R 1 and R 2 together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle
• R 3 , R 4 , R 5 and R 6 each independently represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio
• R 1 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, n- or i-heptyl, n- or l-octyl, n- or i-nonyl, n- or i-decyl, n- or l-dodecyl, n- or i-octadecyl, for allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n- or i-butynyl, n- or i-pentynyl, n- or i-hexinyl, chloromethyl, bromomethyl,
• R and R together with the nitrogen atom to which they are attached, for a heterocycle of the formula which is optionally mono-, di- or trisubstituted by methyl and / or ethyl
• R 3 , R 4 , R 5 and R 6 independently of one another each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,
• R 1 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, n- or i-heptyl, n- or i-octyl, n- or i-nonyl, n- or i-decyl, n- or i-dodecyl, n- or i-octadecyl, for allyl, n- or i-
• Ethoxyethyl, ethoxypropyl in addition for cyclopropyl, cyclopropylmethyl, cyclopropylethyl substituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, dichloromethyl or trifluoromethyl, in each case optionally in the cycloalkyl part one to four times, identically or differently, Cyclopropylpropyl, cyclopentyl, cyclopentylmethyl,
• Cyclopentylethyl, cyclopentylpropyl, cyclohexyl, cyclohexylmethyl, cyclohexylethyl or cyclohexylpropyl also stands for phenylalkyl, phenylalkenyl, phenylalkynyl, phenyl or naphthyl which is monosubstituted or trisubstituted in the aryl part, optionally substituted in the aryl part, in each case optionally with up to 6 carbon atoms in straight-chain or branched chain or alkenyl or alkynyl part, where aryl substituents are in each case: fluorine, chlorine, bromine, hydroxy, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy
• R 2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, hydroxymethyl, hydroxyethyl, hydroxypropyl , Chloromethyl, bromomethyl, chloroethyl, bromethyl, chloropropyl,
• R 1 and R 2 together with the nitrogen atom to which they are attached represent a heterocycle of the formula which is optionally mono-, di- or trisubstituted by methyl and / or ethyl
• R 3 , R 4 , R 5 and R 6 independently of one another each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,
• R 1 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, n- or i-heptyl, n- or i-octyl, n- or i-nonyl, n- or i-decyl, n- or i-dodecyl, n- or i-octadecyl, for allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n- or i-butynyl, n- or i-pentynyl, n- or i-hexinyl, chloromethyl, bromomethyl, chloroethyl, bromethyl, chloroprop
• R 2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, hydroxymethyl, hydroxyethyl, hydroxypropyl , Chloromethyl, bromomethyl, chloroethyl, bromethyl, chloropropyl,
• R 3, R 4, R 5 and R 6 independently of one another, o each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t Butyl, methoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio
• the benzothiophene-2-carboxamide-S, S-dioxide are accessible by the processes mentioned in EP 0 512 349
• the BCDs can be used as individual active ingredients or in combination with active ingredients normally used in the antifouling sector.
• These can preferably be heavy metals such as tin or Cu or heavy metal compounds such as bis (trialkyltin) sulfides, tri-n-butyltin laurate, tri-n -butyl- tin chloride, copper (I) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri- n-butylzinnfluorid, manganese ethylenebisdithiocarbamate, zinc dimethyldithiocarbamate
• Naphthalene derivatives such as
• Sulfenamides such as dichlofluanid, tolylfluanid, folpet, fluorfolpet, captan, captofol,
• Benzimidazoles such as carbendazim, benomyl, furathiocarb, Fube ⁇ dazole, thiophonate methyl, thiabendazole or their salts,
• Morpholine derivatives such as tndemorph, fenpropimorph, fahmorph, dimethomorph, dodemorph, aldimorph, fenpropidine and their arylsulfonic acid salts, such as, for example, p-toluenesulfonic acid and p-dodecylphenyl sulfonic acid,
• Benzamides such as 2,6-D ⁇ chloro-N- (4-t ⁇ fluoromethylbenzyl) -benzam ⁇ de, boron compounds such as boric acid, boric acid ester, borax,
• Formaldehyde and formaldehyde-releasing compounds such as benzyl alcohol mono- (poly) -hem ⁇ formal, oxazohdine, hexa-hydro-S-t ⁇ azine, N-methylolchloroacetamide, paraformadehyde, nitropy ⁇ n, oxyacid, tecloftalam,
• Aldehydes such as cinnamaldehyde, formaldehyde, glutardialdehyde, ⁇ -bromocinnamaldehyde; Thiocyanates such as thiocyanatomethylthiobenzothiazole, methylene bisthiocyanate, etc;
• quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, didecyldimethylammonium chloride;
• Iodine derivatives such as diiodomethyl p-tolyl sulfone, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formal, 3-bromo-2,3-diiodo-2-propenylethyl carbamate, 2,3,3-tri- iodallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynyl-n-butyl carbamate, 3-iodo-2-propynyl-n-butyl urea, 3-iodo-2-propynyl n-hexyl carbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenyl carbamate;
• Phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol and their alkali - and
• Alkaline earth metal salts Alkaline earth metal salts.
• Microbicides with activated halogen group such as chloroacetamide, N-methylolchloroacetamide, Bronopol, Bronidox, tectamers such as 2-bromo-2-nitro-l, 3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 2,2-dibromo 3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane, ⁇ -bromo- ⁇ -nitrostyrene;
• activated halogen group such as chloroacetamide, N-methylolchloroacetamide, Bronopol, Bronidox, tectamers such as 2-bromo-2-nitro-l, 3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 2,2-dibromo 3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane, ⁇ -bromo- ⁇ -nitros
• Pyridines such as 1-hydroxy-2-pyridinthione (and their Na, Fe, Cu, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione;
• Metal soaps such as tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;
• Metal salts such as copper hydroxycarbonate, sodium dichromate, potassium dichromate,
• Oxides such as tributyltin oxide, Cu 2 O, CuO, ZnO; Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates, tetramethylthiuram disulfide, potassium N-methyldithiocarbamate,
• Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate,
• Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, ⁇ -l (4-chloro-phenyl) -4- (O-ethyl, S-propyl) phosphoryloxy-pyrazole, chloro-pyrifos, Coumaphos, Demeton,
• Demeton-S-methyl Diazinon, Dichlorvos, Dimethoate, Ethoate, Ethoprophos, Et ⁇ mfos, Fenitrothion, Fenthion, Heptenophas, Parathion, Parathion-methyl, Phosalone, Phoxim, Pinmiphos-ethyl, Pi ⁇ miphos-methyl, Profenofos, Prothiofos ⁇ , Sulfpr T ⁇ chlo ⁇ hon,
• Carbamates such as aldicarb, bendiocarb, ⁇ -2- (l-methylpropyl) phenylmethyl carbamate,
• Butocarboxim Butoxy carb oxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl, Pi ⁇ micarb, Promecarb, Propoxur and Thiodicarb,
• Organosihciumharmen preferably dimethyl (phenyl) silyl methyl 3-phenoxybenzyl ether such as dimethyl (4-ethoxyphenyl) silylmethyl 3-phenox ⁇ - benzyl ether or
• (D ⁇ methylphenyl) -s ⁇ lyl-methyl-2-phenoxy-6-py ⁇ dylmethylether such as dimethyl- (9-ethoxy-phenyl) -s ⁇ lylmethyl-2-phenoxy-6-py ⁇ dylmethylether or [(phenyl) -3- (3-phenoxyphenyl) propyl] (dimethyl) silanes such as (4-ethoxyphenyl) - [3- (4-fluoro-3-phenoxyphenyl propyl] dimethyl silane, silafluofen,
• Methamidophos Methidathion, Methiocarb, Methoprene, Methoxychlor, Methyl isothiocyanate, Metholcarb, Mevinphos, Monocrotophos, Naled, Neodiprion sertifer NPV, Nicotine, Omethoate, Oxydemeton-methyl, Pentachlorophenol, Petroleum oils, Phenothror, Phatehoate;
• algicides such as diuron, dichlorophen, endothal, fentin acetate, quinoclamine, molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb
• fungicides such as dichlofluanid, tolylfluanid, iodopropargyl butylcarbamate, fluorfolpet and azoles such as tebuconazole or conventional antifouling suitable
• algicides such as diuron, dichlorophen, endothal, fentin acetate, quinoclamine, molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb
• fungicides such as dichlofluanid, tolylfluanid, iodopropargyl but
• the BCD's in their use in antifouling agents furthermore contain the usual constituents as e.g. in Ungerer, Chem. Ind. 37 (1985), 730-732 and Williams, Antifouling Marin Coatings 1973, Park Ridge: Noyes 1973.
• Antifouling agents therefore contain, in addition to the active substances mentioned or their combinations, in particular binders.
• Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene. Rubbers, butadiene / acrylonitrile rubbers, butadiene / styrene / acrylonitrile rubbers, drying oils, such as linseed oil, asphalt and epoxy compounds, resin esters or modified Hard resins in combination with tar or bitumen, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
• the antifouling agents may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Furthermore, the antifouling agents can contain materials, such as rosin, in order to enable controlled release of the active substances or the active substance combinations. The antifouling agents can also contain plasticizers, modifying agents which influence the theological properties and other conventional constituents.
• the compounds of the formula (I) or combinations mentioned at the outset can also be incorporated into self-polishing antifouling systems.
• the BCD's are preferably present in the antifouling agent in concentrations of 1 to 20% by weight.
• the means according to the invention advantageously make it possible to replace the previously available means with more effective ones. They show good stability and advantageously have a broad spectrum of activity.

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• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Wood Science & Technology (AREA)
• Engineering & Computer Science (AREA)
• Health & Medical Sciences (AREA)
• Plant Pathology (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Materials Engineering (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Detergent Compositions (AREA)

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• 1995
  • 1995-09-20 DE DE19534868A patent/DE19534868A1/de not_active Withdrawn
• 1996
  • 1996-09-09 KR KR1019980701970A patent/KR19990045729A/ko not_active Application Discontinuation
  • 1996-09-09 US US09/043,364 patent/US6217642B1/en not_active Expired - Fee Related
  • 1996-09-09 AU AU69883/96A patent/AU6988396A/en not_active Abandoned
  • 1996-09-09 EP EP96931051A patent/EP0851899A1/de not_active Withdrawn
  • 1996-09-09 CA CA002232455A patent/CA2232455A1/en not_active Abandoned
  • 1996-09-09 WO PCT/EP1996/003941 patent/WO1997011131A1/de not_active Application Discontinuation
  • 1996-09-09 JP JP9512355A patent/JPH11512447A/ja active Pending
• 1998
  • 1998-03-11 NO NO981070A patent/NO981070L/no not_active Application Discontinuation

Non-Patent Citations (1)

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