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EP0690894A1 - PAINTS CONTAINING n-ALKYL-N-AZOLS AS PRESERVATIVES - Google Patents

PAINTS CONTAINING n-ALKYL-N-AZOLS AS PRESERVATIVES

Info

Publication number
EP0690894A1
EP0690894A1 EP94911882A EP94911882A EP0690894A1 EP 0690894 A1 EP0690894 A1 EP 0690894A1 EP 94911882 A EP94911882 A EP 94911882A EP 94911882 A EP94911882 A EP 94911882A EP 0690894 A1 EP0690894 A1 EP 0690894A1
Authority
EP
European Patent Office
Prior art keywords
methyl
alkyl
phenyl
paints
group
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.)
Ceased
Application number
EP94911882A
Other languages
German (de)
French (fr)
Inventor
Lutz Heuer
Martin Kugler
Heinrich Schrage
Wilfried Paulus
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 EP0690894A1 publication Critical patent/EP0690894A1/en
Ceased legal-status Critical Current

Links

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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C09D5/025—Preservatives, e.g. antimicrobial agents

Definitions

  • the application relates to the use of n-alkyl-N-azoles in the paint or in paints.
  • a prerequisite for the use of the compounds for protecting paints against growth or destruction by microorganisms such as fungi, yeasts, bacteria and algae is that the compounds are not only antimicrobially active, but also colorless and in the paint by interactions with the other components of the Paints or the paint or by environmental factors such as Light, temperature, weather are not destroyed or not, e.g. by forming complexes, discolouring.
  • the protective compounds do not evaporate or be washed out of the paint. It has now surprisingly been found that from the large number of known agents with fungicidal, algicidal or bactericidal properties, the n-alkyl-N-azoles have outstanding biological activities and, moreover, the targeted properties required for painting.
  • the application therefore relates to the use of at least one compound of the formula (I)
  • R represents an unbranched alkyl chain with preferably 7 to 12 carbon atoms, which is optionally interrupted by one or two sulfur or oxygen atoms,
  • W, X, Y, Z independently of one another represent nitrogen or the group CR 1 , at least two standing for the group CR 1 and in which
  • R 1 10 is hydrogen or straight or branched C -C j - represents alkyl
  • alkyl in the definition of R represents straight-chain alkyl, such as methyl, n-ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n- Decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl and n-pentadecyl.
  • alkyl is straight-chain or branched alkyl having 1 to 10, in particular 1 to 6, carbon atoms, such as methyl, ethyl, n-, i-, s-propyl, n-, i-, s-, t-butyl.
  • R is C 8 -C jj alkyl, which is optionally substituted by a sulfur and / or
  • Oxygen atom is interrupted
  • W represents the groups CH or C- (C r C 10 ) -alkyl
  • Z, X represents nitrogen or the group CH and
  • Y stands for the group CH.
  • R represents C 9 -C ⁇ - alkyl
  • W represents the groups CH or C- (C r C 3 ) - alkyl
  • Z represents nitrogen or the group CH.
  • the compounds are generally known or can be prepared by known methods (DE-A-2 706 838).
  • the active compounds which can be used according to the invention have a strong microbicidal action and can be used to protect paints against attack and destruction by undesired microorganisms.
  • painting is to be understood as a coating on a substrate made from paint materials.
  • the paint may have penetrated more or less into the surface. It can consist of one or more layers and can be produced by processes such as brushing, spraying, dipping, flooding or similar processes.
  • the compounds to be used according to the invention are incorporated in the paints or in precursors for the preparation of the paints by customary methods, e.g. by mixing the active ingredients with the other components.
  • the paints according to the invention therefore contain, in addition to the fungicidal active ingredient, customary paint components in e.g. liquid, pasty or powdery form such as
  • Colorants such as pigments or dyes, preferably pigments.
  • examples include titanium dioxide, zinc oxide and iron oxide.
  • Binders such as, for example, oxidatively drying alkyd resins, vinyl polymers and vinyl copolymers, acrylic polymers and acrylic copolymers, plastic powders, novolaks, amino resins, polyester resins, epoxy resins, silicone resins, isocyanate resins, vinyl polymers and vinyl copolymers, acrylic polymers and other acrylic copolymers are preferred, and other acrylic copolymers usable binders.
  • the paints may also contain the following additives Fillers such as heavy spar, calcite, dolomite and talc,
  • Solvents such as alcohols, ketones, esters, glycol ethers and aliphatic and aromatic hydrocarbons,
  • thickening and thixotropic agents dispersing and wetting agents, drying agents, skin-preventing agents, leveling agents, anti-foaming agents, corrosion inhibitors, UV absorbers, fragrances, antistatic agents, antifreeze agents.
  • paints or precursors for the production of paints may preferably be mentioned as paints or precursors for the production of paints:
  • Glues and adhesives based on the well-known animal, vegetable or synthetic raw materials.
  • Plastic dispersions such as latex dispersions or dispersions based on other polymers.
  • Starch solutions, dispersions or slurries or other starch-based products such as Pressure thickener.
  • Slurries of other raw materials such as color pigments (e.g. iron oxide pigments,
  • Concrete additives for example based on molasses or lignin sulfonates.
  • Bitumen emulsions. preliminary and intermediate products of the chemical industry, e.g. in the
  • Bacteria, fungi, yeasts, algae and slime organisms may be mentioned as microorganisms which can degrade or change the coatings.
  • the active substances which can be used according to the invention preferably act against fungi, in particular molds, discoloring and destructive fungi (Basidiomycetes) and against mucus 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 Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds to be used according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules.
  • the application concentrations of the active compounds to be used 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 one The amount used 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 effectiveness and the spectrum of activity of the active ingredients which can be used according to the invention or of 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 ingredients are used to enlarge the spectrum of activity or to achieve special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
  • Triazoles such as:
  • Succinate dehydrogenase inhibitors such as:
  • Naphthalene derivatives such as terbinafine, naftifine, butene fame, 3-chloro-7- (2-aza-2,7,7-trimethyl-oct-3-en-5-in);
  • Sulfenamides such as dichlofluanid, tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
  • Benzimidazoles such as Carbendazim, Benomyl, Furathiocarb, Fuberidazole, Thiophonat-methyl, Thiabendazole or their salts;
  • Morpholine derivatives such as tridemorph, fenpropimorph, falimorph, dimethomorph, dodemorph, aldimorph, fenpropidine and their arylsulfonic acid salts, e.g. p-
  • Benzothiazoles such as 2-mercaptobenzothiazole;
  • Benzamides such as 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide;
  • Boron compounds such as boric acid, boric acid ester, borax; Formaldehyde and formaldehyde-releasing compounds such as benzyl alcohol mono- (poly) hemiformal, oxazolidines, hexa-hydro-S-triazines, N-methylolchloroacetamide, paraformaldehyde, nitropyrin, oxolinic acid, tecloftalam;
  • Phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol and their alkali and alkaline earth metal salts;
  • Microbicides with activated halogen group such as chloroacetamide, bronopol, bronidox, tectamers such as 2-bromo-2-nitro-1,3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 2,2-dibromo-3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane, ⁇ -bromo- ⁇ -nitrostyrene; Pyridines such as l-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, 1-hy droxy-4-methy l-6- (2,4,4-trimethylpentyl) -2 (1 H) pyridine;
  • activated halogen group such as chloroacetamide, bronopol, bronidox, tect
  • 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,
  • Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;
  • Zeolites containing Ag, Zn or Cu alone or included in polymeric active substances Zeolites containing Ag, Zn or Cu alone or included in polymeric active substances.
  • Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, -l (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxy-pyrazole, chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, diazinon, dichlorvos, dimethoate , Ethoate, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophas, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulfprofos, Triazophos and Trichlorphone;
  • Carbamates such as aldicarb, bendiocarb, ⁇ -2- (l-methylpropyl) phenylmethyl carbamate, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb, methomyl, oxamyl, pirimicarb, promecarb, propoxur and thiodicarb;
  • Organosilicon compounds preferably dimethyl (phenyl) silylmethyl-3-phenoxybenzyl ether such as dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether or (Dimethylphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as dimethyl- (9-ethoxyphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether or [(phenyl) -3- (3-phenoxyphenyl) -propyl] (di
  • Moiluscicide fentin acetates, metaldehydes, methiocarb.
  • Niclosamide thiodicarb, trimethacarb.
  • Herbicides acetochlor, acifluorfen, aclonifen, acrolein, alachlor, alloxydim, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam atrazine, aziptrotryne, benazolin, benfluralin, benfuresate, bensulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron borax, dichlorprop, dichlorprop-P, diclofop, diethatyl, difenoxuron, difenzoquat, diflufen
  • chloromethoxyfen chloramben, chlorbromuron, chlorobutam, chlorofurenol, chloridazon, chlorimuron, chlornitrofen, chloroacetic acid, achloropicrin, chlorotoluron, chloroxuron, chlorprepham, clorosulfuron, chlorthal, chlorthinomidone, cinethonidomid, cinethonidomidomid, cinethonidomidomidomethomidomidone, cinethonomethane, chlorthinomidone, cinethonomethane, chlorthinomidone, cinchloromethane, chlorthinomidone, cinchloromethanone , dinoseb acetate, dinoterb, diphenamid, dipropetryn, diquat, dithiopyr, diduron, DNOC, PPX-A 788, DPX-E96361, DSMA, eglinazine, endothal,
  • 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 in an amount of 0.1 to 99.9%, in particular 1 to 75%, particularly preferably 5 to 50%, the rest being filled 100% by one or more of the above-mentioned mixing partners.
  • microbicidal agents or concentrates used to protect the industrial materials 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.
  • algicides such as diuron, molluscicides, active substances known as "sea animals", which relate to e.g. Place ship floor paints.
  • 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 activity.
  • An agar which is produced using malt extract is mixed with active substances according to the invention in concentrations of 0.1 mg / 1 to
  • 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.
  • the substance to be tested for its fungicidal activity is incorporated in the desired concentration in the (dispersion) color using a dissolver.
  • the paint is then spread on both sides on a suitable surface.
  • test specimens are leached with running water (24 h; 20 ° C) before the test for mold resistance.
  • test specimens prepared in this way are placed on an agar culture medium. Test specimens and culture medium are contaminated with fungal spores. After 1 to 3 weeks of storage at 29 ⁇ 1 ° C and 80-90% rel. Humidity is sampled. The paint is permanently mold-resistant if the test specimen remains free of fungi or if at most a slight edge infestation can be seen.
  • Fungus spores of the following nine molds which are known as paint destroyers or are frequently encountered on paints, are used for contamination:

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

Abstract

n-Alkyl-N-azols are used to protect paints.

Description

ANSTRICHMITTEL ENTHALTEND N-ALKYL-N-AZOLE ALS KONSERVIERUNGS-MITTEL.PAINT CONTAINING N-ALKYL-N-AZOLE AS A PRESERVATIVE.
Verwendung von n-Alkyl-N-azolen im Materialschutz.Use of n-alkyl-N-azoles in material protection.
Die Anmeldung betrifft die Verwendung von n-Alkyl-N-azolen im Anstrich bzw. in Anstrichmitteln.The application relates to the use of n-alkyl-N-azoles in the paint or in paints.
Geradkettige n-Alkyl-N-azole sind bekannt. Desweiteren ist bekannt, daß diese Ver¬ bindungen im Material schütz zur Desinfektion (DE-A-2 442 706) oder in Form ihrer Kupfer salze oder in Gemischen zum Schutz von Holz eingesetzt werden (DE-A- 3 520 394; DE-A- 3 613 232; DE-A-3 613 253; EP-A-277 556).Straight-chain n-alkyl-N-azoles are known. Furthermore, it is known that these compounds are used in a protective material for disinfection (DE-A-2 442 706) or in the form of their copper salts or in mixtures for protecting wood (DE-A-3 520 394; DE-A - 3,613,232; DE-A-3,613,253; EP-A-277,556).
Noch nicht bekannt ist, daß diese Verbindungen auch im Anstrich bzw. in An¬ strichmitteln verwendet werden können.It is not yet known that these compounds can also be used in paints or paints.
Voraussetzung für die Verwendung der Verbindungen zum Schutz von Anstrichen gegen Bewuchs oder Zerstörung durch Mikroorganismen wie Pilze, Hefen, Bakterien und Algen ist, daß die Verbindungen nicht nur antimikrobiell wirksam, sondern auch farblos sind und im Anstrich durch Wechselwirkungen mit den anderen Kompo¬ nenten der Anstrichmittel bzw. des Anstrichs oder durch Umwelteinflüsse wie z.B. Licht, Temperatur, Bewitterung nicht zerstört werden oder nicht, z.B. durch Bildung von Komplexen, verfärbend wirken.A prerequisite for the use of the compounds for protecting paints against growth or destruction by microorganisms such as fungi, yeasts, bacteria and algae is that the compounds are not only antimicrobially active, but also colorless and in the paint by interactions with the other components of the Paints or the paint or by environmental factors such as Light, temperature, weather are not destroyed or not, e.g. by forming complexes, discolouring.
Desweiteren ist für den Schutz von Anstrichen Voraussetzung, daß die schützenden Verbindungen nicht aus dem Anstrich ausdampfen oder ausgewaschen werden. Es wurde nun überraschenderweise gefunden, daß aus der Vielzahl bekannter Mittel mit fungiziden, algiziden oder bakteriziden Eigenschaften die n-Alkyl-N-azole her¬ vorragende biologische Aktivitäten und darüber hinaus die für den Anstrich gefor¬ derten gezielten Eigenschaften besitzen.Furthermore, it is a prerequisite for the protection of paints that the protective compounds do not evaporate or be washed out of the paint. It has now surprisingly been found that from the large number of known agents with fungicidal, algicidal or bactericidal properties, the n-alkyl-N-azoles have outstanding biological activities and, moreover, the targeted properties required for painting.
Gegenstand der Anmeldung ist daher die Verwendung mindestens einer Verbindung der Formel (I)The application therefore relates to the use of at least one compound of the formula (I)
in welcherin which
R für eine unverzweigte Alkylkette mit vorzugsweise 7 bis 12 Kohlenstoff- atomen steht, die gegebenenfalls durch ein oder zwei Schwefel- oder Sauer¬ stoffatome unterbrochen ist,R represents an unbranched alkyl chain with preferably 7 to 12 carbon atoms, which is optionally interrupted by one or two sulfur or oxygen atoms,
W,X,Y,Z unabhängig voneinander für Stickstoff oder die Gruppe CR1 stehen, wobei mindestens zwei für die Gruppe CR1 stehen und worinW, X, Y, Z independently of one another represent nitrogen or the group CR 1 , at least two standing for the group CR 1 and in which
R1 für Wasserstoff oder geradkettiges oder verzweigtes Cj-C10- Alkyl steht,R 1 10 is hydrogen or straight or branched C -C j - represents alkyl,
zum Schutz von Anstrichen, sowie Anstrichmittel, die mindestens eine dieser Verbin¬ dungen enthalten.for the protection of paints and paints which contain at least one of these compounds.
Alkyl steht im folgenden in der Definition von R für geradkettiges Alkyl, wie Methyl, n-Ethyl, n-Propyl, n-Butyl, n-Pentyl, n-Hexyl, n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl, n-Dodecyl, n-Tridecyl, n-Tetradecyl und n-Pentadecyl. Alkyl steht ansonsten für geradkettiges oder verzweigtes Alkyl mit 1 bis 10, ins¬ besondere 1 bis 6 Kohlenstoffatomen wie Methyl, Ethyl, n-, i-, s-Propyl, n-, i-, s-, t- Butyl.In the following, alkyl in the definition of R represents straight-chain alkyl, such as methyl, n-ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n- Decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl and n-pentadecyl. Otherwise alkyl is straight-chain or branched alkyl having 1 to 10, in particular 1 to 6, carbon atoms, such as methyl, ethyl, n-, i-, s-propyl, n-, i-, s-, t-butyl.
Bevorzugt sind Verbindungen der Formel (I), in welcherCompounds of the formula (I) in which
R für C8-Cj j -Alkyl, welches gegebenenfalls durch ein Schwefel- und/oderR is C 8 -C jj alkyl, which is optionally substituted by a sulfur and / or
Sauerstoff atom unterbrochen ist,Oxygen atom is interrupted
W für die Gruppen CH oder C-(CrC10)-Alkyl steht,W represents the groups CH or C- (C r C 10 ) -alkyl,
Z,X für Stickstoff oder die Gruppe CH steht undZ, X represents nitrogen or the group CH and
Y für die Gruppe CH stehen.Y stands for the group CH.
Besonders bevorzugt sind Verbindungen der Formel (I), in welcherCompounds of the formula (I) in which
R für C9-Cπ -Alkyl steht,R represents C 9 -C π- alkyl,
W für die Gruppen CH oder C-(CrC3)- Alkyl steht,W represents the groups CH or C- (C r C 3 ) - alkyl,
X für Stickstoff,X for nitrogen,
Y für die Gruppe CH,Y for the group CH,
Z für Stickstoff oder die Gruppe CH steht.Z represents nitrogen or the group CH.
Die Verbindungen sind allgemein bekannt oder nach bekannten Methoden herstellbar (DE-A-2 706 838). Die erfindungsgemäß verwendbaren Wirkstoffe weisen eine starke mikrobizide Wir¬ kung auf und können zum Schutz von Anstrichen gegen Befall und Zerstörung durch unerwünschte Mikroorganismen eingesetzt werden.The compounds are generally known or can be prepared by known methods (DE-A-2 706 838). The active compounds which can be used according to the invention have a strong microbicidal action and can be used to protect paints against attack and destruction by undesired microorganisms.
Unter Anstrich ist im vorliegenden Zusammenhang eine aus Anstrichstoffen herge- stellte Beschichtung auf einem Untergrund zu verstehen. Der Anstrich kann mehr oder weniger in den Untergrund eingedrungen sein. Er kann aus einer oder mehreren Schichten bestehen und durch Verfahren wie Streichen, Spritzen, Tauchen, Fluten oder ähnliche Verfahren hergestellt werden.In the present context, painting is to be understood as a coating on a substrate made from paint materials. The paint may have penetrated more or less into the surface. It can consist of one or more layers and can be produced by processes such as brushing, spraying, dipping, flooding or similar processes.
Die erfindungsgemäß zu verwendenden Verbindungen werden in die Anstrichmittel oder in Vorprodukte zur Herstellung der Anstrichmittel nach üblichen Methoden, z.B. durch Vermischen der Wirkstoffe mit den anderen Komponenten, eingearbeitet.The compounds to be used according to the invention are incorporated in the paints or in precursors for the preparation of the paints by customary methods, e.g. by mixing the active ingredients with the other components.
Die erfindungsgemäßen Anstrichmittel enthalten daher neben dem fungiziden Wirk¬ stoff allgemein übliche Anstrichkomponenten in z.B. flüssiger, pastöser oder pul- verförmiger Form wie z.B.The paints according to the invention therefore contain, in addition to the fungicidal active ingredient, customary paint components in e.g. liquid, pasty or powdery form such as
- Farbmittel, wie Pigmente oder Farbstoffe, bevorzugt Pigmente. Beispielsweise genannt sei Titandioxid, Zinkoxid und Eisenoxid.- Colorants, such as pigments or dyes, preferably pigments. Examples include titanium dioxide, zinc oxide and iron oxide.
Bindemittel, wie beispielsweise oxidativ trocknende Alkydharze, Vinylpoly- merisate und Vinylcopolymerisate, Acrylpolymerisate und Acrylcopolymeri- sate, Kunststoffpulver, Novolacke, Aminoharze, Polyesterharze, Epoxidharze, Silikonharze, Isocyanatharze, bevorzugt sind Vinylpolymerisate und Vinyl¬ copolymerisate, Acrylpolymerisate und Acrylcopolymerisate und andere in wasserverdünnbaren Anstrichstoffen verwendbare Bindemittel.Binders, such as, for example, oxidatively drying alkyd resins, vinyl polymers and vinyl copolymers, acrylic polymers and acrylic copolymers, plastic powders, novolaks, amino resins, polyester resins, epoxy resins, silicone resins, isocyanate resins, vinyl polymers and vinyl copolymers, acrylic polymers and other acrylic copolymers are preferred, and other acrylic copolymers usable binders.
Daneben enthalten die Anstriche gegebenenfalls folgende Zusatzstoffe Füllstoffe, wie beispielsweise Schwerspat, Calcit, Dolomit und Talk,The paints may also contain the following additives Fillers such as heavy spar, calcite, dolomite and talc,
Lösemittel, wie beispielsweise Alkohole, Ketone, Ester, Glykolether und ali- phatische sowie aromatische Kohlenwasserstoffe,Solvents, such as alcohols, ketones, esters, glycol ethers and aliphatic and aromatic hydrocarbons,
sowie Verdickungs- und Thixotropiermittel, Dispergier- und Netzmittel, Tro- ckenstoffe, Hautverhütungsmittel, Verlaufmittel, Antischaummittel, Korro- sionsinhibitoren, UV- Absorber, Duftstoffe, Antistatika, Frostschutzmittel.as well as thickening and thixotropic agents, dispersing and wetting agents, drying agents, skin-preventing agents, leveling agents, anti-foaming agents, corrosion inhibitors, UV absorbers, fragrances, antistatic agents, antifreeze agents.
Als Anstrichmittel bzw. Vorprodukte zur Herstellung von Anstrichmitteln seien vor¬ zugsweise folgende genannt:The following may preferably be mentioned as paints or precursors for the production of paints:
Leime und Klebstoffe auf Basis der bekannten tierischen, pflanzlichen oder synthetischen Rohstoffe.Glues and adhesives based on the well-known animal, vegetable or synthetic raw materials.
Kunststoffdispersionen wie Latexdispersionen oder Dispersionen auf Basis anderer Polymere.Plastic dispersions such as latex dispersions or dispersions based on other polymers.
Stärkelösungen, -dispersionen oder -slurries oder andere auf Basis von Stärke hergestellte Produkte wie z.B. Druckverdicker. - Slurries anderer Rohstoffe wie Farbpigmente (z.B. Eisenoxidpigmente,Starch solutions, dispersions or slurries or other starch-based products such as Pressure thickener. - Slurries of other raw materials such as color pigments (e.g. iron oxide pigments,
Rußpigmente, Titandioxidpigmente) oder Slurries von Füllstoffen wie Kaolin oder Calciumcarbonat.Carbon black pigments, titanium dioxide pigments) or slurries of fillers such as kaolin or calcium carbonate.
Betonadditive beispielsweise auf Basis von Melasse oder Ligninsulfonaten.Concrete additives, for example based on molasses or lignin sulfonates.
Bitumenemulsionen. - Vor- und Zwischenprodukte der chemischen Industrie, z.B. bei derBitumen emulsions. - preliminary and intermediate products of the chemical industry, e.g. in the
Färb Stoffproduktion und -lagerung.Dye fabric production and storage.
Tinten oder Tuschen.Inks or inks.
Dispersionsfarben für die Anstrichindustrie.Dispersion paints for the painting industry.
Schichten und Appreturen. Als Mikroorganismen, die einen Abbau oder eine Veränderung der Anstriche be¬ wirken können, seien beispielsweise Bakterien, Pilze, Hefen, Algen und Schleim¬ organismen genannt. Vorzugsweise wirken die erfindungsgemäß verwendbaren Wirk¬ stoffe gegen Pilze, insbesondere Schimmelpilze, verfärbende und zerstörende Pilze (Basidiomyceten) sowie gegen Schleimorganismen und Algen.Coats and finishes. Bacteria, fungi, yeasts, algae and slime organisms may be mentioned as microorganisms which can degrade or change the coatings. The active substances which can be used according to the invention preferably act against fungi, in particular molds, discoloring and destructive fungi (Basidiomycetes) and against mucus organisms and algae.
Es seien beispielsweise Mikroorganismen der folgenden Gattungen genannt:For example, microorganisms of the following genera may be mentioned:
Alternaria, wie Alternaria tenuis,Alternaria, such as Alternaria tenuis,
Aspergillus, wie Aspergillus niger,Aspergillus, such as Aspergillus niger,
Chaetomium, wie Chaetomium globosum, Coniophora, wie Coniophora puetana,Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana,
Lentinus, wie Lentinus tigrinus,Lentinus, such as Lentinus tigrinus,
Penicillium, wie Penicillium glaucum,Penicillium, such as Penicillium glaucum,
Polyporus, wie Polyporus versicolor,Polyporus, such as Polyporus versicolor,
Aureobasidium, wie Aureobasidium pullulans, Sclerophoma, wie Sclerophoma pityophila,Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila,
Trichoderma, wie Trichoderma viride,Trichoderma, like Trichoderma viride,
Escherichia, wie Escherichia coli,Escherichia, such as Escherichia coli,
Pseudomonas, wie Pseudomonas aeruginosa,Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, wie Staphylococcus aureus.Staphylococcus, such as Staphylococcus aureus.
Je nach Anwendungsgebiet können die erfindungsgemäß zu verwendenden Wirk¬ stoffe in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate.Depending on the field of application, the active compounds to be used according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules.
Die Anwendungskonzentrationen der erfindungsgemäß zu verwendenden Wirkstoffe richten sich nach der Art und dem Vorkommen der zu bekämpfenden Mikroorganis- men sowie nach der Zusammensetzung des zu schützenden Materials. Die optimale Einsatzmenge kann durch Testreihen ermittelt werden. Im allgemeinen liegen die Anwendungskonzentrationen im Bereich von 0,001 bis 5 Gew -%, vorzugsweise von 0,05 bis 1,0 Gew.-%, bezogen auf das zu schützende Material.The application concentrations of the active compounds to be used 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 one The amount used can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
Die Wirksamkeit und das Wirkungsspektrum der erfindungsgemäß verwendbaren Wirkstoffe bzw. der daraus herstellbaren Mittel, Vorprodukte oder ganz allgemein Formulierungen kann erhöht werden, wenn gegebenenfalls weitere antimikrobiell wirksame Verbindungen, Fungizide, Bakterizide, Herbizide, Insektizide oder andere Wirkstoffe zur Vergrößerung des Wirkungsspektrums oder Erzielung besonderer Effekte wie z.B. des zusätzlichen Schutzes vor Insekten zugesetzt werden. Diese Mischungen können ein breiteres Wirkungsspektrum besitzen als die erfin¬ dungsgemäßen Verbindungen.The effectiveness and the spectrum of activity of the active ingredients which can be used according to the invention or of 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 ingredients are used to enlarge the spectrum of activity or to achieve special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
In vielen Fällen erhält man dabei synergistische Effekte, d.h. die Wirksamkeit der Mischung ist größer als die Wirksamkeit der Einzelkomponenten. Besonders günstige Mischungspartner sind z.B. die folgenden Verbindungen:In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components. Particularly favorable mix partners are e.g. the following connections:
Triazole wie:Triazoles such as:
Amitrole, Azocyclotin, BAS 480F, Bitertanol, Difenoconazole, Fenbuconazole, Fenchlorazole, Fenethanil, Fluquinconazole, Flusilazole, Flutriafol, Imibenconazole, Isozofos, Myclobutanil, Metconazole, Epoxyconazole, Paclobutrazol, Penconazole, Propioconazole, (±)-cis-l-(4-chlorphenyl)-2-(lH-l,2,4-tri__zol-l-yl)-cycloheptanol, Tetraconazole, Triadimefon, Triadimenol, Triapenthenol, Triflumizole, Triticonazole, Uniconazole sowie deren Metallsalze und Säureaddukte. Imidazole wie:Amitrole, azocyclotine, BAS 480F, bitertanol, difenoconazole, fenbuconazole, fenchlorazole, fenethanil, fluquinconazole, flusilazole, flutriafol, imibenconazole, isozofos, myclobutanil, metconazole, epoxyconazole, paclobutrazole (4-) -conazazole-l, -conconazole-l, -cononazole-l, -conconazole-l, -conconazole-l, -conconazole-l, chlorphenyl) -2- (lH-l, 2,4-tri__zol-l-yl) -cycloheptanol, tetraconazole, triadimphone, triadimenol, triapenthenol, triflumizole, triticonazole, uniconazole and their metal salts and acid adducts. Imidazoles such as:
Imazalil, Pefurazoate, Prochlora__, Triflumizole, 2-(l-tert-Butyl)-l-(2-chlorphenyl)-3-Imazalil, Pefurazoate, Prochlora__, Triflumizole, 2- (l-tert-Butyl) -l- (2-chlorophenyl) -3-
(l,2,4-triazol-l-yl)-propan-2-ol, Thiazolcarboxanilide wie 2',6'-Dibromo-2-methyl-4- trifluoromethoxy^'-trifluoromethyl- 1 ,3-thiazole-5-carboxanilide, 1 -Imidazolyl- 1 -(41- chlorophenoxy)-3,3-dimethylbutan-2-on sowie deren Metallsalze und Säureaddukte.(l, 2,4-triazol-l-yl) propan-2-ol, thiazolecarboxanilides such as 2 ', 6'-dibromo-2-methyl-4-trifluoromethoxy ^' - trifluoromethyl-1, 3-thiazole-5- carboxanilide, 1 -imidazolyl-1 - (4 1 - chlorophenoxy) -3,3-dimethylbutan-2-one and their metal salts and acid adducts.
Methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate, methyl(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacryla- te, methyl©-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, memyl(E)-2-[2-[6-(2,6-difluorophenoxy)pyrimicl_n-4-yloxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate, methyl^)- 2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylatemethyl(E)- 2-[2-[3-(phenyl-sulfonyloxy)phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3- (4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl>Q )-2-[2-phenoxyphenyl]- 3-methoxyacrylatemethyl(E)-2-[2-(3,5-dimethylbenzoyl)pyrrol-l-yl]-3-methoxyacry- late,methyl(E)-2-[2-(3-methoxyphenoxy)phenyl]-.3-methoxyacrylate,methyl(E)-2-[2- (2-phenylethen-l-yl)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dichlorophen- oxy)pyridin-3-yl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(l,l,2,2-tetrafluoroethoxy)- phenoxy)phenyl)-3-methoxyacrylate, methyl(E)-2-(2-[3-(alpha-hydroxybenzyl)phen- oxy]phenyl)-3 -methoxyacrylate, methyl(E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3 - methoxyacrylate, methyl(Ε)-2-[2-(3-n-propyloxyphenoxy)phenyl]3-methoxyacrylate, methyl (E)-2- [2-(3 -i sopropyloxy phenoxy )phenyl] -3 -methoxy acr 1 ate, methyl (E)-2- [2- [3-(2-fluorophenoxy)pehnoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(3-ethoxy- phenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(4-tert.-butylpyridin-2-yloxy)phe- nyl]-3 -methoxyacrylate, methyl(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-meth- oxyacrylatemethyl(E)-2-[2-(3-methylpyridin-2-yloxymethyl)phenyl]-3-methoxyacry- latemethyl(E)-2-[2-[6-(2-methylphenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacry- late, methyl(E)-2-[2-(5-bromopyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, me- thyl(E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxy- acιylatej(E),(E)methyl-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]- 3-methoxyacrylate(E)-me_hyl-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]- phenyl}-3-methoxyacrylate, (E),(E)methyl-2-{2-(3-methoxyphenyl)methyloximinome- thyl]phenyl}-3-methoxyacrylate(E)methyl-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yl- oxy]phenyl}3-methoxyacrylate(E),(E)methyl-2-{2-[6-phenylpyrimidin-4-yl)-methyl- oximinomethyl]phenyl}-3-methoxyacrylate, {E),(E)methyl-2-{2-[(4-chlorophenyl)-me- thyloximinomethyl]phenyl}-3-methoxyacrylate, (E)methyl-2-{2-[6-(2-n-propylphen- oxy)- 1,3,5 -triazin-4-yloxy ]phenyl } -3 -methoxyacrylate, (E),(E)methyl-2- {2-[(3 -ni tro- phenyl)methyloximinomethyl]phenyl } -3 -methoxyacrylate;Methyl (E) -2- [2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl] 3-methoxyacrylates, methyl (E) -2- [2- [6- (2-thioamidophenoxy) pyrimidine- 4-yloxy] phenyl] -3-methoxyacrylate, methyl © -2- [2- [6- (2-fluorophenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, memyl (E) -2- [ 2- [6- (2,6-difluorophenoxy) pyrimicl_n-4-yloxy] phenyl] -3-methoxyacrylates, methyl (E) -2- [2- [3- (pyrimidin-2-yloxy) phenoxy] phenyl] - 3-methoxyacrylate, methyl ^) - 2- [2- [3- (5-methylpyrimidin-2-yloxy) phenoxy] phenyl] -3-methoxyacrylate methyl (E) - 2- [2- [3- (phenylsulfonyloxy ) phenoxy] phenyl] -3-methoxyacrylate, methyl (E) -2- [2- [3- (4-nitrophenoxy) phenoxy] phenyl] -3-methoxyacrylate, methyl> Q) -2- [2-phenoxyphenyl] - 3-methoxyacrylatemethyl (E) -2- [2- (3,5-dimethylbenzoyl) pyrrol-l-yl] -3-methoxyacrylate, methyl (E) -2- [2- (3-methoxyphenoxy) phenyl] - .3-methoxyacrylates, methyl (E) -2- [2- (2-phenylethen-l-yl) phenyl] -3-methoxyacrylates, methyl (E) -2- [2- (3,5-dichlorophenoxy) ) pyridin-3-yl] -3-methoxyacrylates, methyl (E) -2- (2- (3- (l, l, 2,2-tetrafluoroethoxy) phenoxy) phenyl) -3-me thoxyacrylates, methyl (E) -2- (2- [3- (alpha-hydroxybenzyl) phenoxy] phenyl) -3-methoxyacrylates, methyl (E) -2- (2- (4-phenoxypyridin-2-yloxy) phenyl) -3 - methoxyacrylate, methyl (Ε) -2- [2- (3-n-propyloxyphenoxy) phenyl] 3-methoxyacrylate, methyl (E) -2- [2- (3-isopropyloxy phenoxy) phenyl] - 3-methoxy acr 1 ate, methyl (E) -2- [2- [3- (2-fluorophenoxy) phenoxy] phenyl] -3-methoxyacrylate, methyl (E) -2- [2- (3-ethoxy-phenoxy ) phenyl] -3-methoxyacrylate, methyl (E) -2- [2- (4-tert-butylpyridin-2-yloxy) phenyl] -3-methoxyacrylate, methyl (E) -2- [2- [ 3- (3-cyanophenoxy) phenoxy] phenyl] -3-methoxyacrylate methyl (E) -2- [2- (3-methylpyridin-2-yloxymethyl) phenyl] -3-methoxyacrylic latemethyl (E) -2- [ 2- [6- (2-methylphenoxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacrylate, methyl (E) -2- [2- (5-bromopyridin-2-yloxymethyl) phenyl] -3-methoxyacrylate , methyl (E) -2- [2- (3- (3-iodopyridin-2-yloxy) phenoxy) phenyl] -3-methoxyacrylates, methyl (E) -2- [2- [6- (2-chloropyridin-3-yloxy) pyrimidin-4-yloxy] phenyl] -3-methoxyacylatej (E), (E) methyl-2- [2- (5,6-dimethylpyrazin-2-ylmethyloximinomethyl) phenyl] - 3-methoxyacrylate (E) -me_hyl-2- {2- [6- (6-methylpyridin-2-yloxy) pyrimidin-4-yloxy] - phenyl} - 3-methoxyacrylate, (E), (E) methyl-2- {2- (3-methoxyphenyl) methyloximinomethyl] phenyl} -3-methoxyacrylate (E) methyl-2- {2- (6- (2-azidophenoxy ) -pyrimidin-4-yl-oxy] phenyl} 3-methoxyacrylate (E), (E) methyl-2- {2- [6-phenylpyrimidin-4-yl) methyl-oximinomethyl] phenyl} -3-methoxyacrylate, {E), (E) methyl-2- {2 - [(4-chlorophenyl) methyloximinomethyl] phenyl} -3-methoxyacrylate, (E) methyl-2- {2- [6- (2-n- propylphenoxy) - 1,3,5 -triazin-4-yloxy] phenyl} -3-methoxyacrylate, (E), (E) methyl-2- {2 - [(3-ni-phenyl) methyloximinomethyl] phenyl } -3-methoxyacrylates;
Succinat-Dehydrogenase Inhibitoren wie:Succinate dehydrogenase inhibitors such as:
Fenfuram, Furcarbanil, Cyclafluramid, Furmecyclox, Seedvax, Metsulfovax, Pyro- carbolid, Oxycarboxin, Shirlan, Mebenil (Mepronil), Benodanil, Flutolanil (Moncut);Fenfuram, furcarbanil, cyclafluramide, furmecyclox, seedvax, metsulfovax, pyrocarbolide, oxycarboxin, shirlan, mebenil (mepronil), benodanil, flutolanil (moncut);
Naphthalin-Derivate wie Terbinafine, Naftifine, Butenafme, 3-Chloro-7-(2-aza-2,7,7- trimethyl-oct-3 -en-5-in);Naphthalene derivatives such as terbinafine, naftifine, butene fame, 3-chloro-7- (2-aza-2,7,7-trimethyl-oct-3-en-5-in);
Sulfenamide wie Dichlofluanid, Tolylfluanid, Folpet, Fluorfolpet; Captan, Captofol;Sulfenamides such as dichlofluanid, tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
Benzimidazole wie Carbendazim, Benomyl, Furathiocarb, Fuberidazole, Thiophonat- methyl, Thiabendazole oder deren Salze;Benzimidazoles such as Carbendazim, Benomyl, Furathiocarb, Fuberidazole, Thiophonat-methyl, Thiabendazole or their salts;
Morpholinderivate wie Tridemorph, Fenpropimorph, Falimorph, Dimethomorph, Dodemorph, Aldimorph, Fenpropidin und ihre arylsulfonsauren Salze, wie z.B. p-Morpholine derivatives such as tridemorph, fenpropimorph, falimorph, dimethomorph, dodemorph, aldimorph, fenpropidine and their arylsulfonic acid salts, e.g. p-
Toluolsulfonsäure und p-Dodecylphenyl-sulfonsäure;Toluenesulfonic acid and p-dodecylphenyl sulfonic acid;
Dithiocarbamate, Cufraneb, Ferbam, Mancopper, Mancozeb, Maneb, Metam,Dithiocarbamate, Cufraneb, Ferbam, Mancopper, Mancozeb, Maneb, Metam,
Metiram, Thiram Zeneb, Ziram;Metiram, Thiram Zeneb, Ziram;
Benzthiazole wie 2-Mercaptobenzothiazol; Benzamide wie 2,6-Dichloro-N-(4-trifluoromethylbenzyl)-benzamide;Benzothiazoles such as 2-mercaptobenzothiazole; Benzamides such as 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide;
Borverbindungen wie Borsäure, Borsäureester, Borax; Formaldehyd und Formaldehydabspaltende Verbindungen wie Benzylalkoholmono- (poly)-hemiformal, Oxazolidine, Hexa-hydro-S-triazine, N-Methylolchloracetamid, Paraformaldehyd, Nitropyrin, Oxolinsäure, Tecloftalam;Boron compounds such as boric acid, boric acid ester, borax; Formaldehyde and formaldehyde-releasing compounds such as benzyl alcohol mono- (poly) hemiformal, oxazolidines, hexa-hydro-S-triazines, N-methylolchloroacetamide, paraformaldehyde, nitropyrin, oxolinic acid, tecloftalam;
Tris-N-(cyclohexyldi-_zeniumdioxy)-aluminium,N-(Cyclo-hexyldiazeniumdioxy)-tri- butylzinn bzw. K-Salze, Bis-N-(cyclohexyldiazeniumdioxy)-kupfer;Tris-N- (cyclohexyldi-_zeniumdioxy) aluminum, N- (cyclo-hexyldiazeniumdioxy) -tributyltin or K salts, bis-N- (cyclohexyldiazeniumdioxy) copper;
N-Methylisothiazolin-3-on,5-Chlor-N-methylisothiazolin-3-on,4,5-Dichloro-N-octyl- isothiazolin-3-on, N-Octyl-isothiazolin-3-on, 4,5-Trimethylen-isothiazolinone, 4,5- Benzisothiazolinone, N-Methylolchloracetamid; Aldehyde wie Zimtaldehyd, Formaldehyd, Glutardialdehyd, ß-Bromzimtaldehyd; Thiocyanate wie Thiocyanatomethylthiobenzothiazol, Methylenbisthiocyanat, usw; quartäre Ammoniumverbindungen wie Benzyldimethyltetradecylammoniumchlorid, Benzyldimethyldodecylammoniumchlorid, Didecyldimethylammoniumchlorid; Iodderivate wie Diiodmethyl-p-tolylsulfon, 3-Iod-2-propinyl-alkohol, 4-Chlorphenyl- 3-iodprop__rgylformal, 3-Brom-2,3-diiod-2-propenylethylcarbamat, 2,3,3-Triiodallyl- alkohol, 3-Brom-2,3-diiod-2-propenylalkohol, 3-Iod-2-propinyl-n-butylcarbamat, 3- Iod-2-propinyl-n-hexylcarbamat, 3-Iod-2-propinyl-cyclohexylcarbamat, 3-Iod-2-pro- pinyl-phenylcarbamat;N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octyl-isothiazolin-3-one, N-octyl-isothiazolin-3-one, 4,5- Trimethylene-isothiazolinone, 4,5-benzisothiazolinone, N-methylolchloroacetamide; Aldehydes such as cinnamaldehyde, formaldehyde, glutardialdehyde, β-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-iodopropyl methyl 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;
Phenol derivate wie Tribromphenol, Tetrachlorphenol, 3-Methyl-4-chlorphenol, 3,5- Dimethyl-4-chlorphenol, Phenoxyethanol, Dichlorphen, o-Phenylphenol, m-Phenyl- phenol, p-Phenylphenol, 2-Benzyl-4-chlorphenol und deren Alkali- und Erdalkali¬ metallsalze;Phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol and their alkali and alkaline earth metal salts;
Mikrobizide mit aktivierter Halogengruppe wie Chloracetamid, Bronopol, Bronidox, Tectamer wie 2-Brom-2-nitro-l,3-propandiol, 2-Brom-4'-hydroxy-acetophenon, 2,2- Dibrom-3-nitril-propionamid, 1 ,2-Dibrom-2,4-dicyanobutan, ß-Brom-ß-nitrostyrol; Pyridine wie l-Hydroxy-2-pyridinthion (und ihre Na-, Fe-, Mn-, Zn-Salze), Tetrachlor-4-methylsulfonylpyridin, Pyrimethanol, Mepanipyrim, Dipyrithion, 1- Hy droxy-4-methy l-6-(2,4,4-trimethylpentyl)-2( 1 H)-py ridin;Microbicides with activated halogen group such as chloroacetamide, bronopol, bronidox, tectamers such as 2-bromo-2-nitro-1,3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 2,2-dibromo-3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane, β-bromo-β-nitrostyrene; Pyridines such as l-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, 1-hy droxy-4-methy l-6- (2,4,4-trimethylpentyl) -2 (1 H) pyridine;
Metallseifen wie Zinn-, Kupfer-, Zinknaphtenat, -octoat, 2-ethylhexanoat, -oleat, -phosphat, -benzoat; Metallsalze wie Kupferhydroxycarbonat, Natriumdichromat, Kaliumdichromat,Metal soaps such as tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate; Metal salts such as copper hydroxycarbonate, sodium dichromate, potassium dichromate,
Kaliumchromat, Kupfersulfat, Kupferchlorid, Kupferborat, Zinkfluorosilikat, Kupfer- fluorosilikat;Potassium chromate, copper sulfate, copper chloride, copper borate, zinc fluorosilicate, copper fluorosilicate;
Oxide wie Tributylzinnoxid, Cu2O, CuO, ZnO; Dialkyldithiocarbamate wie Na- und Zn-Salze von Dialkyldithiocarbamaten,Oxides such as tributyltin oxide, Cu 2 O, CuO, ZnO; Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates,
Tetramethylthiuramdisulfid, Kalium-N-methyl-dithiocarbamat;Tetramethylthiuram disulfide, potassium N-methyldithiocarbamate;
Nitrilewie2,4,5,6-Tetrachlorisophthalodinitril,Dinatrium-cyano-dithioimidocarbamat;Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;
Chinoline wie 8-Hydroxychinolin und deren Cu-Salze;Quinolines such as 8-hydroxyquinoline and their Cu salts;
Mucochlorsäure, 5-Hydroxy-2(5H)-furanon; 4,5-Dichlorodithiazolinon, 4,5-Benzdithiazolinon, 4,5-Trimethylendithiazolinon, 4,5-Mucochloric acid, 5-hydroxy-2 (5H) furanone; 4,5-dichlorodithiazolinone, 4,5-benzdithiazolinone, 4,5-trimethylene dithiazolinone, 4,5-
Dichlor-(3H)-l,2-dithiol-3-on, 3,5-Dimethyl-tetr__hydro-l,3,5-thiadiazin-2-thion,Dichloro- (3H) -l, 2-dithiol-3-one, 3,5-dimethyl-tetr__hydro-l, 3,5-thiadiazin-2-thione,
N-(2-p-Chlorbenzoylethyl)-hexaminiumchloridKalium-N-hydroxymethyl-N'-methyl- dithiocarbamat,N- (2-p-chlorobenzoylethyl) hexaminium chloride potassium N-hydroxymethyl-N'-methyldithiocarbamate,
2-Oxo-2-(4-hydroxy-phenyl)acethydroximsäure-chlorid, Phenyl-(2-chlor-cyan-vinyl)sulfon,2-oxo-2- (4-hydroxy-phenyl) acethydroximic acid chloride, phenyl- (2-chloro-cyano-vinyl) sulfone,
Phenyl-(l,2-dichlor-2-cyan-vinyl)sulfon;Phenyl- (1,2-dichloro-2-cyano-vinyl) sulfone;
Ag, Zn oder Cu-haltige Zeolithe allein oder eingeschlossen in polymere Wirkstoffe.Zeolites containing Ag, Zn or Cu alone or included in polymeric active substances.
Ganz besonders bevorzugt sind Mischungen mitMixtures with are very particularly preferred
Azaconazole, Bromuconazole, Cyproconazole, Dichlobutrazol, Diniconazole, Hexa- conazole, Metaconazole, Penconazole, Propiconazole, Tebuconazole, Methyl-(E)- methoximino[α-(o-tolyloxy)-o-tolyl)]acetate, Methyl-(E)-2-{2-[6-(2-cyanphenoxy)-py- rimidin-4-yl-oxy]phenyl}-3-methoxyacrylat, Methfuroxam, Carboxin, Fenpiclonil, 4- (2,2-Difluoro-l,3-benzodioxol-4-yl)-lH-pyrrol-3-carbonitril, Butenafine, Imazalil, N- Methyl-isothiazolin-3-on, 5-Chlor-N-methylisothiazolin-3-on, N-Octylisothiazolin-3- on, Benzisothiazolinone, N-(2-Hydroxypropyl)-amino-methanol, Benzylalkohol- (hemi)-formal, Glutaraldehyd, Omadine, Dimethyldicarbonat, und/oder 3-Iodo-2-pro- pinyl-n-butylcarbamate. Desweiteren werden auch gut wirksame Mischungen mit den folgenden Wirkstoffen hergestellt:Azaconazole, bromuconazole, cyproconazole, dichlobutrazole, diniconazole, hexaconazole, metaconazole, penconazole, propiconazole, tebuconazole, methyl- (E) - methoximino [α- (o-tolyloxy) -o-tolyl)] acetate, methyl- (E) -2- {2- [6- (2-cyanophenoxy) -py-rimidin-4-yl-oxy] phenyl} -3-methoxyacrylate, methfuroxam, carboxin, fenpiclonil, 4- (2,2-difluoro-1,3 -benzodioxol-4-yl) -lH-pyrrole-3-carbonitrile, butenafine, imazalil, N-methyl-isothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, N-octylisothiazolin-3-one, Benzisothiazolinone, N- (2-hydroxypropyl) amino-methanol, benzyl alcohol (hemi) formal, glutaraldehyde, omadine, dimethyl dicarbonate, and / or 3-iodo-2-propynyl-n-butyl carbamate. Furthermore, well-effective mixtures with the following active ingredients are also produced:
Fungizide:Fungicides:
Acypetacs, 2-Aminobutane, Ampropylfos, Anilazine, Benalaxyl, Bupirimate, Chinomethionat, Chloroneb, Chlozolinate, Cymoxanil, Dazomet, Diclomezine, Dichloram, Diethofencarb, Dimethirimol, Diocab, Dithianon, Dodine, Drazoxolon, Edifenphos, Ethirimol, Etridiazole, Fenarimol, Fenitropan, Fentin acetate, Fentin Hydroxide, Ferimzone, Fluazinam, Fluromide, Flusulfamide, Flutriafol, Fosetyl, Fthalide, Furalaxyl, Guazatine, Hymexazol, Iprobenfos, Iprodione, Isoprothiolane, Metalaxyl, Methasulf ocarb, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadiyl, Perfiur- azoate, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Procymidone, Propamocarb, Propineb, Pyrazophos, Pyrifenox, Pyroquilon, Quintozene, Tar Oils, Tecnazene, Thicyofen, Thiophanate-methyl, Tolclofos-methyl, Triazoxide, Trichlamide, Tricyclazole, Triforine, Vinclozolin.Acypetacs, 2-aminobutane, Ampropylfos, anilazine, benalaxyl, Bupirimate, chinomethionat, chloroneb, chlozolinate, cymoxanil, dazomet, Diclomezine, Dichloram, diethofencarb, dimethirimol, Diocab, dithianon, dodine, Drazoxolon, edifenphos, ethirimol, etridiazole, fenarimol, Fenitropan, Fentin acetate, Fentin Hydroxide, Ferimzone, Fluazinam, Fluromide, Flusulfamide, Flutriafol, Fosetyl, Fthalide, Furalaxyl, Guazatine, Hymexazol, Iprobefos, Iprodione, Isoprothiolane, Metalaxyl, Methasulfocarb, Nitrothal-isopropyl, Perfarurol, Nuarimol , Pencycuron, Phosdiphen, Pimaricin, Piperalin, Procymidone, Propamocarb, Propineb, Pyrazophos, Pyrifenox, Pyroquilon, Quintozene, Tar Oils, Tecnazene, Thicyofen, Thiophanate-methyl, Tolclofos-methyl, Triazoxide, Trichlamine, Tricyclinezoline, Tricycolinezole, Tricyclinezoline, Tricyclazine
Insektizide:Insecticides:
Phosphorsäureester wie Azinphos-ethyl, Azinphos-methyl, -l(4-Chlorphenyl)-4-(O- ethyl, S-propyl)phosphoryloxy-pyrazol, Chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoate, Ethoate, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophas, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulfprofos, Triazophos und Trichlorphon;Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, -l (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxy-pyrazole, chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, diazinon, dichlorvos, dimethoate , Ethoate, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophas, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulfprofos, Triazophos and Trichlorphone;
Carbamate wie Aldicarb, Bendiocarb, α-2-(l-Methylpropyl)-phenylmethylcarbamat, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl, Pirimicarb, Promecarb, Propoxur und Thiodicarb; Organosiliciumverbindungen,vorzugsweiseDimethyl(phenyl)silyl-methyl-3-phenoxy- benzylether wie Dimethyl-(4-ethoxyphenyl)-silylmethyl-3-phenoxybenzylether oder (Dimethylphenyl)-silyl-methyl-2-phenoxy-6-pyridylmethyletherwiez.B.Dimethyl-(9- ethoxy-phenyl)-silylmethyl-2-phenoxy-6-pyridylmethylether oder [(Phenyl)-3-(3- phenoxyphenyl)-propyl](dimethyl)-silane wie z.B. (4-Ethoxyphenyl)-[3-(4-fluoro-3- phenoxyphenyl-propyl]dimethyl-silan, Silafluofen; Pyrethroide wie Allethrin, Alphamethrin, Bioresmethrin, Byfenthrin, Cycloprothrin, Cyfiuthrin, Decamethrin, Cyhalothrin, Cypermethrin, Deltamethrin, Alpha-cyano-3- phenyl-2-methylbenzyl-2,2-dimethyl-3-(2-chlor-2-trifluor-methylvinyl)cyclopropan- carboxylat, Fenpropathrin, Fenfluthrin, Fenvalerate, Flucythrinate, Flumethrin, Fluvalinate, Permethrin, Resmethrin und Tralomethrin; Nitroimine und Nitromethylene wie 1 -[(6-Chlor-3-pyridinyl)-methyl]-4,5-dihydro-N- nitro-lH-imidazol-2-amin (Imidacloprid), N-[(6-Chlor-3-pyridyl)methyl-]N2-cyano- N'-methylacetamide (NI-25);Carbamates such as aldicarb, bendiocarb, α-2- (l-methylpropyl) phenylmethyl carbamate, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb, methomyl, oxamyl, pirimicarb, promecarb, propoxur and thiodicarb; Organosilicon compounds, preferably dimethyl (phenyl) silylmethyl-3-phenoxybenzyl ether such as dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether or (Dimethylphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as dimethyl- (9-ethoxyphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether or [(phenyl) -3- (3-phenoxyphenyl) -propyl] (dimethyl) -silanes such as (4-ethoxyphenyl) - [3- (4-fluoro-3-phenoxyphenyl-propyl] dimethyl-silane, silafluofen; pyrethroids such as allethrin, alphamethrin, bioresmethrin, byfenthrin, cycloprothrin, cyfiuthrin, Decamethrin, cyhalothrin, cypermethrin, deltamethrin, alpha-cyano-3-phenyl-2-methylbenzyl-2,2-dimethyl-3- (2-chloro-2-trifluoromethylvinyl) cyclopropane-carboxylate, fenpropathrin, fenfluthrin, fenvalerate, flucythrinate , Flumethrin, fluvalinate, permethrin, resmethrin and tralomethrin; nitroimines and nitromethylenes such as 1 - [(6-chloro-3-pyridinyl) methyl] -4,5-dihydro-N-nitro-1H-imidazole-2-amine (imidacloprid ), N - [(6-chloro-3-pyridyl) methyl-] N 2 -cyano-N'-methylacetamide (NI-25);
Abamectin, AC 303, 630, Acephate, Acrinathrin, Alanycarb, Aldoxycarb, Aldrin, Amitraz, Azamethiphos, Bacillus thuringiensis, Phosmet, Phosphamidon, Phosphine, Prallethrin, Propaphos, Propetamphos, Prothoate, Pyraclofos, Pyrethrins, Pyridaben, Pyridafenthion, Pyriproxyfen, Quinalphos, RH-7988, Rotenone, Sodium fluoride, Sodium hexafluorosilicate, Sulfotep, Sulfuryl fluoride, Tar Oils, Teflubenzuron, Tefluthrin, Temephos, Terbufos, Tetrachlorvinphos, Tetramethrin, O-2-tert.-Butyl- pyrimidin-5-yl-o-isopropyl-phosphorothiate, Thiocyclam, Thiofanox, Thiometon, Tralomethrin, Triflumuron, Trimethacarb, Vamidothion, VerticiUium Lacanii, XMC, Xylylcarb, Benfuracarb, Bensultap, Bifenthrin, Bioallethrin, MERbioallethrin (S)- cyclopentenyl isomer, Bromophos, Bromophos-ethyl, Buprofezin, Cadusafos, Calcium Polysulfide, Carbophenothion, Cartap, Chinomethionat, Chlordane, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloropicrin, Chlorpyrifos, Cyanophos, Beta-Cyfluthrin, Alpha-cypermethrin, Cyophenothrin, Cyromazine, Dazomet, DDT, Demeton-S-methylsulphon, Diafenthiuron, Dialifos, Dicrotophos, Diflubenzuron, Dinoseb, Deoxabenzofos, Diaxacarb, Disulfoton, DNOC, Empenthrin, Endosulfan, EPN, Esfenvalerate, Ethiofencarb, Ethion, Etofenprox, Fenobucarb, Fenoxycarb, Fensulfothion, Fipronil, Flucycloxuron, Flufenprox, Flufenoxuron, Fonofos, Formetanate, Formothion, Fosmethilan, Furathiocarb, Heptachlor, Hexaflumuron, Hydramethylnon, Hydrogen Cyanide, Hydroprene, IPSP, Isazofos, Isofenphos, Isoprothiolane, Isoxathion, Iodfenphos, Kadethrin, Lindane, Malathion, Mecarbam, Mephosfolan, Mercurous, chloride, Metam, Metarthizium, anisopliae, Methacrifos, Methami dophos, Methidathion, Methiocarb, Methoprene, Methoxychlor, Methyl isothiocyanate, Metholcarb, Mevinphos, Monocrotophos, Naled, Neodiprion sertifer NPV, Nicotine, Omethoate, Oxydemeton-methyl, Pentachlorophenol, Petroleum oils, Phenothrin, Phenthoate, Phorate;Abamectin, AC 303, 630, Acephate, Acrinathrin, Alanycarb, Aldoxycarb, Aldrin, Amitraz, Azamethiphos, Bacillus thuringiensis, Phosmet, Phosphamidon, Phosphine, Prallethrin, Propaphos, Propetamphos, Prothoate, Pyraclofos, Pyrethriproxyphid, Pyrethridafid, Pyrethridafid, Pyrethrinsafid, Pyrethrinsafid, Pyrethrinsafid, Pyrethrinsafid, Pyrethrinsafid, Pyrethrinsafid, Pyrethrinsafid, Pyrethrinsafid, Pyrethrinsafide, RH-7988, Rotenone, Sodium fluoride, Sodium hexafluorosilicate, Sulfotep, Sulfuryl fluoride, Tar Oils, Teflubenzuron, Tefluthrin, Temephos, Terbufos, Tetrachlorvinphos, Tetramethrin, O-2-tert.-Butyl-pyrimidin-5-yl-o-isopropyl -phosphorothiate, Thiocyclam, Thiofanox, Thiometon, Tralomethrin, Triflumuron, Trimethacarb, Vamidothion, VerticiUium Lacanii, XMC, Xylylcarb, Benfuracarb, Bensultap, Bifenthrin, Bioallethrin, MERbioomeretophin, Bromine-Bophentophos, Ethyl Biosulphophos, Ethyl Biosulphos, Ethyl Biosulphosphate Calcium polysulfide, carbophenothione, cartap, quinomethionate, chlordane, chlorfenvinphos, chlorfluazuron, chlormephos, chloropicrin, chlorpyrifos, cyanophos, beta-cyfluthrin, alpha-cypermethrin, cyopheno thrin, Cyromazine, Dazomet, DDT, Demeton-S-methylsulphone, Diafenthiuron, Dialifos, Dicrotophos, Diflubenzuron, Dinoseb, Deoxabenzofos, Diaxacarb, Disulfoton, DNOC, Empenthrin, Endosulfan, EPN, Esfenvalcarbx, Feni Fensulfothione, fipronil, flucycloxuron, flufenprox, flufenoxuron, Fonofos, Formetanate, Formothion, Fosmethilan, Furathiocarb, Heptachlor, Hexaflumuron, Hydramethylnon, Hydrogen Cyanide, Hydroprene, IPSP, Isazofos, Isofenphos, Isoprothiolane, Isoxathion, Iodfenphos, Kadethrin, Lindane, Metathamamusamos, Malathionphosphate, Chloride , anisopliae, Methacrifos, Methami dophos, Methidathion, Methiocarb, Methoprene, Methoxychlor, Methyl isothiocyanate, Metholcarb, Mevinphos, Monocrotophos, Naled, Neodiprion sertifer NPV, Nicotine, Omethoate, Oxydemeton-methyl, Petroleum Phophlorophenol; Phonachlorophenol;
Moiluscicide: Fentinacetate, Metaldehyde, Methiocarb. Niclosamide, Thiodicarb, Trimethacarb.Moiluscicide: fentin acetates, metaldehydes, methiocarb. Niclosamide, thiodicarb, trimethacarb.
Algicide:Algicide:
Coppersulfate, Dichlororphen, Endothal, Fentinacetate, Quinoclamine.Coppersulfate, dichlororphen, Endothal, Fentinacetate, Quinoclamine.
Herbicides: acetochlor, acifluorfen, aclonifen, acrolein, alachlor, alloxydim, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam atrazine, aziptrotryne, benazolin, benfluralin, benfuresate, bensulfuron, bensulfide, bentazone, benzofencap, benzthiazuron, bifenox, bilanafos, borax, dichlorprop, dichlorprop-P, diclofop, diethatyl, difenoxuron, difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethipin, dimethylarsinic acid, dinitramine, dinoseb, dinoseb, dinoseb acetate, dinoseb, bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, butamifos, fuenachlor, butralin, butylate, carbetamide, CGAHerbicides: acetochlor, acifluorfen, aclonifen, acrolein, alachlor, alloxydim, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam atrazine, aziptrotryne, benazolin, benfluralin, benfuresate, bensulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron borax, dichlorprop, dichlorprop-P, diclofop, diethatyl, difenoxuron, difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethipin, dimethylarsinic acid, dinitramine, dinoseb, dinoseb, dinoseb acetate, dinosebomobomilomomolomomom butachlor, butamifos, fuenachlor, butralin, butylates, carbetamides, CGA
184927, chlormethoxyfen, chloramben, chlorbromuron, chlorbutam, chlorfurenol, chloridazon, chlorimuron, chlornitrofen, chloroacetic acid, achloropicrin, chlorotoluron, chloroxuron, chlorprepham, chlorsulfuron, chlorthal, chlorthiamid, cinmethylin, cinofulsuron, clethodim, clomazone, clomeprop, clopyralid, cyanamide, cyanazine, dinoseb acetate, dinoterb, diphenamid, dipropetryn, diquat, dithiopyr, diduron, DNOC, PPX-A 788, DPX-E96361, DSMA, eglinazine, endothal, EPTC, esproca b, ethalfluralin, ethidimuron, ethofumesate, fenoxaprop, fenoxaprop-P, fenuron, flamprop, flamprop-M, flazasulfuron, fluazifop, fluazifop-P, fluchloralin, flumeturon, fluorocgycofen, fluoronitrofen, flupropanate, flurenol, fluridone, flurochloridone, fluoroxypyr, cycloate, cycloxydim, 2,4-D, daimuron, dalapon, dazomet, 2,4-DB, desmedipham, desmetryn, dicamba, dichlorbenil, isoproturon, isouron, isoxaben, isoxapyrifop, lactofen, lenacil, linuron, LS830556, MCPA, MCPA- thioethyl, MCPB, mecoprop, mecoprop-P, mefenacet, mefluidide, metam, metamitron, metazachlor, methabenzthiazuron, methazole, methoproptryne, methyldymron, methylisothiocyanate, metobromuron, fomosafen, fosamine, furyloxyfen, glufosinate, glyphosate, haloxyfop, hexazinone, imazamethabenz, imazapyr, imazaquin, imazethapyr, ioxynil, isopropalin, propyzamide, prosulfocab, pyrazolynate, pyrazolsulfuron, pyrazoxyfen, pyributicarb, pyridate, quinclorac, quinmerac, quinocloamine, quizalofop, quzizalofop-P, S-23121, sethoxydim, sifuron, simazine, simetryn, SMY 1500, sodium chlorate, sulfometuron, tar oils, TCA, metolachlor, metoxuron, metribzin, metsulfuron, molinate, monalide, monolinuron, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, norflurazon, orbencarb, oaryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, pentachlorophenol, pentaochlor, petroleum oils, phenmedipham, picloram, piperophos, pretilachlor, primisulfuron, prodiamine, proglinazine, propmeton, prometryn, propachlor, tebutam, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thiazafluoron, thifensulfuron, thiobencarb, thiocarbazil, tioclorim, tralkoxydim, tri-allate, triasulfuron, tribenzuron, triclopyr, tridiphane, trietazine, trifluralin, IBI-C4874 vernolate, propanil, propaquizafop, propazine, propham.184927, chloromethoxyfen, chloramben, chlorbromuron, chlorobutam, chlorofurenol, chloridazon, chlorimuron, chlornitrofen, chloroacetic acid, achloropicrin, chlorotoluron, chloroxuron, chlorprepham, clorosulfuron, chlorthal, chlorthinomidone, cinethonidomid, cinethonidomidomid, cinethonidomidomidomethomidomidone, cinethonomethane, chlorthinomidone, cinethonomethane, chlorthinomidone, cinchloromethane, chlorthinomidone, cinchloromethanone , dinoseb acetate, dinoterb, diphenamid, dipropetryn, diquat, dithiopyr, diduron, DNOC, PPX-A 788, DPX-E96361, DSMA, eglinazine, endothal, EPTC, esproca b, ethalfluralin, ethidimuron, ethofumesate, fenoxaprop, fenoxaprop-P, fenuron, flamprop, flamprop-M, flazasulfuron, fluazop-, fluazifop P, fluchloralin, flumeturon, fluorocgycofen, fluoronitrofen, flupropanate, flurenol, fluridone, flurochloridone, fluoroxypyr, cycloate, cycloxydim, 2,4-D, daimuron, dalapon, dazomet, 2,4-DB, desmedipham, desmetrynil, dicamba, dichlor isoproturon, isouron, isoxaben, isoxapyrifop, lactofen, lenacil, linuron, LS830556, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, mefenacet, mefluidide, metam, metamitron, metazachlor, methabenzthiazdronate, methylazole methylthiuron, methazethole, methyl, methabenzthiazuron, methyl metobromuron, fomosafen, fosamine, furyloxyfen, glufosinate, glyphosate, haloxyfop, hexazinone, imazamethabenz, imazapyr, imazaquin, imazethapyr, ioxynil, isopropalin, propyzamide, prosulfocab, pyrazolynate, pyrazolsulfclora, pyrutoxine, pyrutoxine, pyrutoxine, pyrutoxine, pyrutoxine, pyrutoxine, pyrutoxine, pyrutoxine, pyrutoxin c, quinmerac, quinocloamine, quizalofop, quzizalofop-P, S-23121, sethoxydim, sifuron, simazine, simetryn, SMY 1500, sodium chlorate, sulfometuron, tar oils, TCA, metolachlor, metoxuron, metribzin, metsulfuron, moninolinur, moninolinur, moninolinur , MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, norflurazon, orbencarb, oaryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, pentachlorophenol, pentaochlor, petroleum oils, phenmedulfineuron, phenmedipilone, phenmedipilone proglinazine, propmeton, prometryn, propachlor, tebutam, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thiazafluoron, thifensulfuron, thiobencarb, thiocarbazil, tioclorim, tralkoxydim, tri-allic, trisulfuron, triasulfuron, triasulfuron C4874 vernolate, propanil, propaquizafop, propazine, propham.
Die Gewichtsverhältnisse der Wirkstoffe in diesen Wirkstoffkombinationen können in relativ großen Bereichen variiert werden. Vorzugsweise erhalten die Wirkstoffkombinationen den Wirkstoff zu 0, 1 bis 99,9 %, insbesondere zu 1 bis 75 %, besonders bevorzugt 5 bis 50 %, wobei der Rest zu 100 % durch einen oder mehrere der obengenannten Mischungspartner ausgefüllt wird.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 in an amount of 0.1 to 99.9%, in particular 1 to 75%, particularly preferably 5 to 50%, the rest being filled 100% by one or more of the above-mentioned mixing partners.
Die zum Schutz der technischen Materialien verwendeten mikrobiziden Mittel oder Konzentrate enthalten den Wirkstoff bzw. die Wirkstoffkombination in einer Konzentration von 0,01 und 95 Gew.-%, insbesondere 0,1 bis 60 Gew.-%.The microbicidal agents or concentrates used to protect the industrial materials 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.
Als andere Wirkstoffe kommen auch in Betracht Algizide wie Diuron, Molluskizide, Wirkstoffe egen "sea animals", die sich auf z.B. Schiffsbodenanstrichen ansiedeln.Other active substances which may also be used are algicides such as diuron, molluscicides, active substances known as "sea animals", which relate to e.g. Place ship floor paints.
Die erfindungsgemäßen Wirkstoffe bzw. Mittel ermöglichen in vorteilhafter Weise, die bisher verfügbaren mikrobiziden Mittel durch effektivere zu ersetzen. Sie zeigen eine gute Stabilität und haben in vorteilhafter Weise ein breites Wirkungsspektrum.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 activity.
Die nachfolgenden Beispiele dienen zur Verdeutlichung der Erfindung. Die Erfindung ist nicht auf die Beispiele beschränkt. The following examples serve to illustrate the invention. The invention is not limited to the examples.
HersteHungsbeispieleMANUFACTURING EXAMPLES
Beispiel 1example 1
2 Mol 2-Ethylimidazol und 2,2 Mol n-Dodecylbromid werden 30 Minuten auf 130°C erhitzt und anschließend mit 3,2 Mol NaOH versetzt. Anschließend wird das Reaktionsgemisch noch 2 Stunden auf 150°C erhitzt. Der anorganische Rückstand wird abfiltriert und mit Benzol gewaschen. Die vereinigten Filtrate werden destilliert. Dabei gehen zwischen 118 und 122°C und 0,5 Torr 468 g l-Dodecyl-2-ethyl- imidazol über.2 mol of 2-ethylimidazole and 2.2 mol of n-dodecyl bromide are heated to 130 ° C. for 30 minutes and then 3.2 mol of NaOH are added. The reaction mixture is then heated to 150 ° C. for a further 2 hours. The inorganic residue is filtered off and washed with benzene. The combined filtrates are distilled. 468 g of l-dodecyl-2-ethylimidazole pass between 118 and 122 ° C. and 0.5 Torr.
In analoger Weise werden die in der nachfolgenden Tabelle aufgeführten Verbin¬ dungen hergestellt:The connections listed in the table below are produced in an analogous manner:
Typ A Typ B Typ C Ty D Type A Type B Type C Ty D
AnwendungsbeispielApplication example
A. Zum Nachweis der Wirksamkeit gegen Pilze werden die minimalen Hemm- Konzentrationen (MHK) von erfindungsgemäßen Mitteln bestimmt:A. To demonstrate the activity against fungi, the minimum inhibitory concentrations (MIC) of agents according to the invention are determined:
Ein Agar, der unter Verwendung von Malzextrakt hergestellt wird, wird mit erfindungsgemäßen Wirkstoffen in Konzentrationen von 0,1 mg/1 bisAn agar which is produced using malt extract is mixed with active substances according to the invention in concentrations of 0.1 mg / 1 to
5000 mg/1 versetzt. Nach Erstarren des Agars erfolgt Kontamination mit Reinkulturen der in der Tabelle 1 aufgeführten Testorganismen. Nach 2- wöchiger Lagerung bei 28°C und 60 bis 70 % relativer Luftfeuchtigkeit wird die MHK bestimmt. MHK ist die niedrigste Konzentration an Wirkstoff, bei der keinerlei Bewuchs durch die verwendete Mikrobenart erfolgt, sie ist in der nachstehenden Tabelle 2 angegeben. 5000 mg / 1 added. After the agar solidifies, it is contaminated with pure cultures of the test organisms listed in Table 1. After 2 weeks 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.
Tabelle 2 (Vergleich) MHK's bei der Einwirkung erfindungsgemäßer Verbindungen auf PilzeTable 2 (comparison) MICs when fungi act on compounds of the invention
B. Prüfung der Schimmelfestigkeit von AnstrichenB. Testing the mold resistance of paints
Die auf ihre fungizide Wirksamkeit zu prüfende Substanz wird in der ge¬ wünschten Konzentration in die (Dispersions)-Farbe mittels eines Dissolvers eingearbeitet. Anschließend wird die Farbe beidseitig auf eine geeignete Unterlage gestrichen.The substance to be tested for its fungicidal activity is incorporated in the desired concentration in the (dispersion) color using a dissolver. The paint is then spread on both sides on a suitable surface.
Um praxisnahe Ergebnisse zu erhalten wird ein Teil der Prüflinge vor dem Test auf Schimmelfestigkeit mit fließendem Wasser (24 h; 20°C) ausgelaugt.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.
Die so vorbereiteten Prüflinge werden auf einen Agar-Nährboden gelegt. Prüflinge und Nährboden werden mit Pilzsporen kontaminiert. Nach 1- bis 3- wöchiger Lagerung bei 29 ± 1°C und 80-90 % rel. Luftfeuchte wird abge¬ mustert. Der Anstrich ist dauerhaft schimmelfest, wenn der Prüfling pilzfrei bleibt oder höchstens einen geringen Randbefall erkennen läßt.The test specimens prepared in this way are placed on an agar culture medium. Test specimens and culture medium are contaminated with fungal spores. After 1 to 3 weeks of storage at 29 ± 1 ° C and 80-90% rel. Humidity is sampled. The paint is permanently mold-resistant if the test specimen remains free of fungi or if at most a slight edge infestation can be seen.
Zur Kontamination werden Pilzsporen folgender neun Schimmelpilze ver¬ wendet, die als Anstrichzerstörer bekannt sind oder häufig auf Anstrichen an- getroffen werden:Fungus spores of the following nine molds, which are known as paint destroyers or are frequently encountered on paints, are used for contamination:
1. Alternaria tenuis1. Alternaria tenuis
2. Aspergillus flavus2. Aspergillus flavus
3. Aspergillus niger3. Aspergillus niger
4. Aspergillus ustus 5. Cladosporium herbarum4. Aspergillus ustus 5. Cladosporium herbarum
6. Paecilomyces variotii6. Paecilomyces variotii
7. Penicillium citrinum7. Penicillium citrinum
8. Aureobasidium pullulans8. Aureobasidium pullulans
9. Stachybotrys atra Corda -.9. Stachybotrys atra Corda -.
Wirkstoffkonzentrationen, bei denen der Anstrichprüfling pilzfrei bleibt (Konzen¬ tration bezogen auf Feststoff gehalt der Dispersionfarbe)Active substance concentrations at which the paint sample remains free of fungi (concentration based on the solids content of the emulsion paint)

Claims

Patentansprüche Claims
1. Verwendung von mindestens einer Verbindung der Formel (I)1. Use of at least one compound of the formula (I)
in welcherin which
R für eine unverzweigte Alkylkette mit vorzugsweise 7 bis 12 Kohlen¬ stoffatomen steht, die gegebenenfalls durch ein oder zwei Schwefel¬ oder Sauerstoffatome unterbrochen ist,R represents an unbranched alkyl chain with preferably 7 to 12 carbon atoms, which is optionally interrupted by one or two sulfur or oxygen atoms,
W,X, Y,Z unabhängig voneinander für Stickstoff oder die Gruppe CR1 stehen, wobei mindestens zwei für die Gruppe CR1 stehen und worinW, X, Y, Z independently of one another represent nitrogen or the group CR 1 , at least two standing for the group CR 1 and in which
R1 für Wasserstoff oder geradkettiges oder verzweigtes Cj-C10-R 1 is hydrogen or straight-chain or branched C j -C 10 -
Alkyl steht,Alkyl stands,
zum Schutz von Anstrichen.to protect paints.
2. Verwendung gemäß Anspruch 1, dadurch gekennzeichnet, daß in den Verbin¬ dungen der Formel (I)2. Use according to claim 1, characterized in that in the connections of the formula (I)
R für eine unverzweigte Alkylkette mit 7 bis 12 Kohlenstoffatomen steht, die gegebenenfalls durch ein oder zwei Schwefel- und/oder Sauerstoffatome unterbrochen ist. R represents an unbranched alkyl chain with 7 to 12 carbon atoms, which is optionally interrupted by one or two sulfur and / or oxygen atoms.
3. Verwendung gemäß Anspruch 1, dadurch gekennzeichnet, daß in den Verbin¬ dungen der Formel (I)3. Use according to claim 1, characterized in that in the connections of the formula (I)
R für C8-Cπ-Alkyl steht, welches gegebenenfalls durch ein Schwefel und/oder Sauerstoff atom unterbrochen ist,R represents C 8 -C π- alkyl, which is optionally interrupted by a sulfur and / or oxygen atom,
W für die Gruppe CH oder C(CrC10- Alkyl) steht,W represents the group CH or C (C r C 10 alkyl),
Z,X unabhängig voneinander für Stickstoff oder die Gruppe CH stehen undZ, X independently of one another represent nitrogen or the group CH and
Y für die Gruppe CH steht.Y stands for the group CH.
4. Verwendung gemäß Anspruch 1, dadurch gekennzeichnet, daß in den Verbin¬ dungen der Formel (I)4. Use according to claim 1, characterized in that in the connections of the formula (I)
R für C8-C^ -Alkyl steht,R is C 8 -C ^ alkyl,
W für die Gruppen CH oder C(CrC3- Alkyl) steht,W represents the groups CH or C (C r C 3 alkyl),
X für Stickstoff,X for nitrogen,
Y für die Gruppe CH,Y for the group CH,
Z für Stickstoff oder die Gruppe CH steht.Z represents nitrogen or the group CH.
5. Anstrichmittel enthaltend neben Anstrichmittelkomponenten mindestens eine5. Paints containing at least one in addition to paint components
Verbindung der Formel (I) nach Anspruch 1. A compound of formula (I) according to claim 1.
6. Dispersionsfarben enthaltend mindestens eine Verbindung der Formel (I) nach6. Emulsion paints containing at least one compound of the formula (I)
Anspruch 1. Claim 1.
EP94911882A 1993-03-25 1994-03-14 PAINTS CONTAINING n-ALKYL-N-AZOLS AS PRESERVATIVES Ceased EP0690894A1 (en)

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US5693631A (en) * 1995-05-30 1997-12-02 Buckman Laboratories International, Inc. Potentiation of the microbicide 2-(thiocyanomethylthio) benzothiazole using an N-alkyl heterocyclic compound
JP5398177B2 (en) * 2007-06-06 2014-01-29 エスケー化研株式会社 Bactericidal composition

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US4801362A (en) * 1987-12-11 1989-01-31 Buckman Laboratories International, Inc. Control of microorganisms in aqueous systems with 1-hydroxymethylpyrazoles
DE3804981A1 (en) * 1988-02-18 1989-08-31 Bayer Ag SUBSTITUTED TRIAZOLES
CA2056672A1 (en) * 1990-12-10 1992-06-11 Adam Chi-Tung Hsu Halopropargyl mercaptotriazole compounds, compositions, uses and processes of preparation
US5250194A (en) * 1991-02-13 1993-10-05 Buckman Laboratories International, Inc. N-dodecyl heterocyclic compounds useful as industrial microbicides and preservatives

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