WO1998039969A1 - Agents algicides - Google Patents

Agents algicides Download PDF

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Publication number
WO1998039969A1
WO1998039969A1 PCT/EP1998/001093 EP9801093W WO9839969A1 WO 1998039969 A1 WO1998039969 A1 WO 1998039969A1 EP 9801093 W EP9801093 W EP 9801093W WO 9839969 A1 WO9839969 A1 WO 9839969A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
fluridones
paints
algae
chlorella
Prior art date
Application number
PCT/EP1998/001093
Other languages
German (de)
English (en)
Inventor
Hermann Uhr
Martin Kugler
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU67256/98A priority Critical patent/AU6725698A/en
Publication of WO1998039969A1 publication Critical patent/WO1998039969A1/fr

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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
    • C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
    • C09D5/1612—Non-macromolecular compounds
    • C09D5/1625—Non-macromolecular compounds organic
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the present application relates to new applications of the known active ingredient Fluridone, and also mixtures with other known active ingredients, for combating the algae growth of paints, antifouling paints and other technical materials
  • fluridone can be used as a herbicide for combating undesirable growth of surface waters with aquatic plants and algae (see also DE-OS 2 537 753, US-PA 4,235,619). In order to be able to act in these media, a certain level of water solubility is necessary It is also known that fluridones show a certain leaching behavior in soil (see also Zandvoort, Neth J Agric. Sei 37, 257 (1989))
  • fluridones can also be used to combat the algae growth of paints, antifouling paints and other technical materials, and that the active ingredient is not washed out of this medium despite its water solubility and its known leaching behavior in soil
  • the compound according to the invention also acts against lichens. In combination with fungicides, this often shows a synergistic increase in the potency In addition, it was found that the effect of fluridones can be improved significantly, in some cases even synergistically, if other herbicides, algicides and / or material protection agents are added as a mixing partner
  • the algae to be controlled are prokaryotic algae
  • Examples - but not restrictive - are from the order Chroococcales species of the genera Synechococcus, Chroococcus, Gloeocapsa, Aphanocapsa,
  • Aphanothece, Microcystis and Me ⁇ smopedia from the orders Chamaesiphonales and Pleurocapsales species of the genera Chamaesiphon and Dermatocarpa, from the order Oscillato ⁇ ales species of the genera Phormidium, Schizoth ⁇ x, Spiru na, Plectonix and Lyngbyoc Npa, from the order Nypotosta, Gostolotulaa, Gostolotulaa, Gostolotulaa, Gost, Nostra, Gostlotulaa, from the order Nyp, Scytonema, Anabaenopsis, Caloth ⁇ x and Aulosira, from the
  • Stigonematatles called species of the genera Stigonema, Fischerella, Hapalosiphon and Mastigocladus
  • the compound according to the invention also shows good activity against eukaryotic representatives from the departments Heterocontophyta, Rhodophyta, Chlorophyta, Euglenophyta, Cryptophyta, Dinophyta and Haptophyta.
  • Examples - but without being restrictive - are from the class Xanthophyceae of the genera T ⁇ bonema and Vauche from the class Chrysophyceae species of the genera Chrysocapsa, Rhizochrysis, Cfhrysosphaera, Phaeothammon and Thallochrysis, from the class Phaeophyceae (brown algae) species of the genera Ectocarpus, Pylaiella,
  • the media and technical materials to be treated with algicide are preferably wood preservative paints and glazes, plastic coatings, latices,
  • Dispersion paints are understood to mean aqueous, alkaline paints based on polymer dispersions which serve as binders
  • emulsion paints related to polymer dispersions include, for example, polyacrylates, styrene acrylates, polyvinyl acetate, polyvinyl propionate and polymers
  • Fluridone can be incorporated into the above-mentioned emulsion paints or in their starting products either directly, or in the form of formulations or mixtures
  • Antifouling paints generally consist of the components described in Ungerer, Chem Ind 37 (1985), 730-732 and Williams, Antifouling Marin Coatings 1973, Park
  • Examples of recognized binders in antifouling paints are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, especially in an aqueous system,
  • the antifouling agents also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Furthermore, the antifouling agents can contain materials such as rosin.
  • the antifouling agents can also contain plasticizers, the theological Fluridones can be incorporated into the above-mentioned antifouling paints or into their starting products either directly or as a formulation / mixture. Fluridones can also be incorporated into self-polishing antifouling systems, such as, for example, in the combinations mentioned below
  • the fluridone 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 fluridone with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or Foaming agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or Foaming agents
  • Water as an extender for example, organic solvents can also be used as auxiliary solvents.
  • Essentially suitable liquid solvents are aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as Cyclohexane or paraffins, eg petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulfoxide, and water, with liquefied gaseous extenders or Carriers are liquids that are gaseous at normal temperature and pressure, e.g.
  • aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide
  • solid carriers include natural rock powders such as kaoli ne, clays, talc, chalk, quartz, attapulgite, Montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminum oxide and silicates, as solid carrier materials for granules, e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules organic material like sawdust,
  • coconut shells, corn cobs and tobacco stalks are suitable as emulsifiers and / or foam-generating agents, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein Dispersants are suitable, for example, lignin sulfite liquor and methyl cellulose
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable Be Ole
  • Dyes such as inorganic pigments, for example 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.
  • Antifouling agents are added.
  • the mixtures have a broader spectrum of activity than fluridones alone
  • Triazoles such as:
  • Imidazoles such as:
  • Clotrimazole Bifonazole, Climbazole, Econazole, Fenapamil, Imazalil, Isoconazole, Ketoconazole, Lombazole, Miconazole, Pefurazoate, Prochloraz, Triflumizole, Thiazolcar, l-Imidazolyl-l- (4'-chlorophenoxyutan) as well as their metal salts and acid adducts;
  • Succinate dehydrogenase inhibitors such as:
  • Naphthalene derivatives such as:
  • Sulfenamides 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: boric acid, boric acid ester, borax;
  • Formaldehyde and formaldehyde releasing compounds such as:
  • Isothiazolinones such as:
  • Cinnamaldehyde formaldehyde, glutardialdehyde, ß-bromocinnamaldehyde
  • Benzalkonium chloride benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethylalkylammonium 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-triiodallyl alcohol , 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynyl-n-butyl carbamate, 3-iodo-2-propynyl-n-hexyl carbamate, 3-iodo-2-propynyl-cyclohexyl carbamate, 3 Iodine-2-propynylphenyl carbamate;
  • Phenols such as:
  • 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;
  • Metal salts such as:
  • Tributyltin oxide Cu2 ⁇ , CuO, ZnO;
  • Dithiocarbamates such as: Cufraneb, Ferban, potassium N-hydroxymethyl-N ' -methyl-dithiobarbamate, Na- or
  • Nitriles such as: 2,4,5, 6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;
  • Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials.
  • Insecticides / acaricides / nematicides such as:
  • Bacillus thuringiensis Barthrin, 4-Bromo-2 (4-chloro-phenyl) -l- (ethoxymethyl) -5- (tri- fluoromethyl) -lH-pyrrole-3-carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, Bioresmethrin, Bioailethrin, Bromophos A, Bromophos M, Bufencarb, Buprofezin, Butathiophos, Butocarboxin, Butoxycarboxim,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fensulfothion, Fenthion, Fenvalerate, Fipronil, Fluazuron, Flucycloxuron, Floxumhrateurin, Flucythrinin, Flucythrinin, Flucythrinin, Flucythrinin, Flucythrinin, Flucythrinin, Flucythrinin - mothion, fosmethilane fosthiazate, Fubfenprox, furathiocarb,
  • HCH Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnon, Hydroprene,
  • Imidacloprid Iodfenfos, Iprobefos, Isazophos, Isoamidophos, Isofenphos, Iso procarb, Isoprothiolane, Isoxathion, Ivermectin, Lama-cyhalothrin, Lufenuron,
  • 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, Pyridophenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
  • Molluscicides such as: fentin acetates, metaldehydes, methiocarb. Niclosamide;
  • Diflufenican Dimefuron, Dimepiperate, Dimethachlor, Dimethipin, Dinitramine, Dinoseb, Dinoseb Acetate, Dinoterb, Diphenamid, Dipropetryn, Diquat, Dith ⁇ opyr, Diduron, DNOC, DSMA, 2,4-D, Daimuron, Dalapon, Dazomet, 2,4 -DB, Desmedipham, Desmetryn, Dicamba, Dichlobenil, Dimethamid, Dithiopyr, Dimethametryn,
  • MCPA MCPA-thioethyl
  • MCPB Mecoprop, Mecoprop-P, Mefenacet, Mefluidide, Metam, Metamitron, Metazachlor, Methabenzthiazuron, Methazole, Methoroptryne, Methyldymron, Methyl isothiocyanate, Metobromuron, Metoxuron, Metri- uron, Metri- uron, Metri- uron, Metri- uron , Monalide, Monolinuron, MSMA, Metolachlor, Metosulam, Metobenzuron,
  • 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 0.1 to 99.9% of the fluridone, in particular 1 to 75%, particularly preferably 5 to 50%, the
  • the rest is filled 100% by one or more of the above mentioned mixing partners.
  • a concentrate that can be used to protect emulsion paints, antifouling paints and other technical materials against algae contains the fluridone or the
  • Active ingredient combination in a concentration of 0.01 to 95% by weight, in particular 0.1 to 60% by weight.
  • the application concentrations of the fluridone or the active ingredient combinations depend on the type and occurrence of the algae to be controlled and on the composition of the color 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 color to be protected.
  • fluridones 0.5% fluridones are incorporated into an exterior emulsion paint based on styrene acrylate. The paint containing fluridone is then spread on both sides of cardboard.
  • test specimen is contaminated by immersion in an algae suspension of Phormidium, Oscillatoria, Chlorella and Scenedesmus species and placed on petri dishes filled with Allen's agar and inoculated with the algae mentioned.
  • the fluridone-containing plate After 4 weeks of incubation at room temperature and 1 200-1 500 LUX, the fluridone-containing plate showed very good algae resistance, while an active ingredient-free control of test organisms is completely covered.
  • fluridones 0.5% fluridones are incorporated into an exterior emulsion paint based on styrene acrylate. Then the fluridone-containing paint is applied on both sides
  • test specimen is then observed for 24 h at 12 l / h flow rate and 20 ° C.
  • the sample is removed from the water, rinsed and dried for 24 hours.
  • test specimen is contaminated by immersion in an algae suspension of Phormidium, Oscillatoria, Chlorella and Scenedesmus species and placed on petri dishes filled with Allen's agar and inoculated with the algae mentioned. After 4 weeks of incubation at room temperature and 1 200-1 500 LUX, the fluridone-containing plate shows very good algae resistance, while an active ingredient-free control of test organisms was completely overgrown

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

Abstract

L'invention concerne de nouvelles applications du principe actif connu dénommé fluridone, ainsi que des mélanges comportant d'autres principes actifs connus, s'utilisant pour lutter contre la prolifération d'algues dans des peintures antisalissure et dans d'autres matériaux à usage technique.
PCT/EP1998/001093 1997-03-11 1998-02-26 Agents algicides WO1998039969A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU67256/98A AU6725698A (en) 1997-03-11 1998-02-26 Algicidal agents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19709876.2 1997-03-11
DE1997109876 DE19709876A1 (de) 1997-03-11 1997-03-11 Algizide Mittel

Publications (1)

Publication Number Publication Date
WO1998039969A1 true WO1998039969A1 (fr) 1998-09-17

Family

ID=7822899

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/001093 WO1998039969A1 (fr) 1997-03-11 1998-02-26 Agents algicides

Country Status (3)

Country Link
AU (1) AU6725698A (fr)
DE (1) DE19709876A1 (fr)
WO (1) WO1998039969A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000042845A1 (fr) * 1999-01-20 2000-07-27 Bayer Aktiengesellschaft Utilisation de substances naturelles pour empecher la lixiviation de principes actifs agrochimiques
WO2015031873A1 (fr) * 2013-08-30 2015-03-05 Rohm And Haas Company Combinaison synergique constituée d'un composé de lénacil et de flurochloridone pour une protection sous forme de films secs

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4082709A (en) * 1974-01-31 1978-04-04 The United States Of America As Represented By The Secretary Of The Navy Low leaching antifouling organometallic polyesters
US4235619A (en) * 1977-06-27 1980-11-25 Eli Lilly And Company Method of controlling aquatic weeds and algae
JPS59157005A (ja) * 1983-02-25 1984-09-06 Mitsui Toatsu Chem Inc 除草剤組成物
EP0127433A1 (fr) * 1983-05-27 1984-12-05 Eli Lilly And Company Combinaison aquatique
EP0438857A1 (fr) * 1990-01-22 1991-07-31 Troy Chemical Corporation Compositions biocides
US5173110A (en) * 1988-02-08 1992-12-22 Waitomo Industrial Investments Ltd. Antifouling composition
DE4411237A1 (de) * 1994-03-31 1995-10-05 Bayer Ag Stabilisierung von Wirkstoffen mit Hilfe anorganischer Tr{germaterialien im Materialschutz

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4082709A (en) * 1974-01-31 1978-04-04 The United States Of America As Represented By The Secretary Of The Navy Low leaching antifouling organometallic polyesters
US4235619A (en) * 1977-06-27 1980-11-25 Eli Lilly And Company Method of controlling aquatic weeds and algae
JPS59157005A (ja) * 1983-02-25 1984-09-06 Mitsui Toatsu Chem Inc 除草剤組成物
EP0127433A1 (fr) * 1983-05-27 1984-12-05 Eli Lilly And Company Combinaison aquatique
US5173110A (en) * 1988-02-08 1992-12-22 Waitomo Industrial Investments Ltd. Antifouling composition
EP0438857A1 (fr) * 1990-01-22 1991-07-31 Troy Chemical Corporation Compositions biocides
DE4411237A1 (de) * 1994-03-31 1995-10-05 Bayer Ag Stabilisierung von Wirkstoffen mit Hilfe anorganischer Tr{germaterialien im Materialschutz

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 105, no. 7, 18 August 1986, Columbus, Ohio, US; abstract no. 56281, SCHROEDER, JILL ET AL: "Persistence of fluridone in five Georgia soils" XP002071113 *
CHEMICAL ABSTRACTS, vol. 112, no. 3, 15 January 1990, Columbus, Ohio, US; abstract no. 17710, ZANDVOORT, R.: "Leaching of fluridone, hexazinone and simazine in sandy soils in the Netherlands" XP002071112 *
CHEMICAL ABSTRACTS, vol. 91, no. 1, 2 July 1979, Columbus, Ohio, US; abstract no. 1191, BANKS, P. A. ET AL: "Soil detection and mobility of fluridone" XP002071114 *
NETH. J. AGRIC. SCI. (1989), 37(3), 257-62 CODEN: NETMAW;ISSN: 0028-2928, 1989 *
PATENT ABSTRACTS OF JAPAN vol. 9, no. 1 (C - 259) 5 January 1985 (1985-01-05) *
WEED SCI. (1979), 27(3), 309-12 CODEN: WEESA6;ISSN: 0043-1745, 1979 *
WEED SCI. (1986), 34(4), 612-16 CODEN: WEESA6;ISSN: 0043-1745, 1986 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000042845A1 (fr) * 1999-01-20 2000-07-27 Bayer Aktiengesellschaft Utilisation de substances naturelles pour empecher la lixiviation de principes actifs agrochimiques
WO2015031873A1 (fr) * 2013-08-30 2015-03-05 Rohm And Haas Company Combinaison synergique constituée d'un composé de lénacil et de flurochloridone pour une protection sous forme de films secs
CN105472982A (zh) * 2013-08-30 2016-04-06 罗门哈斯公司 用于干膜保护的环草定化合物和氟咯草酮的协同组合
US9408389B2 (en) * 2013-08-30 2016-08-09 Dow Global Technologies Llc Synergistic combination of a lenacil compound and flurochloridone for dry film protection
RU2679249C2 (ru) * 2013-08-30 2019-02-06 Ром Энд Хаас Компани Синергетическая комбинация ленацила и флурохлоридона, предназначенная для защиты с помощью сухой пленки

Also Published As

Publication number Publication date
AU6725698A (en) 1998-09-29
DE19709876A1 (de) 1998-09-17

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