US20140088041A1 - Fungicidal penflufen mixtures - Google Patents

Fungicidal penflufen mixtures Download PDF

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Publication number
US20140088041A1
US20140088041A1 US13/880,985 US201113880985A US2014088041A1 US 20140088041 A1 US20140088041 A1 US 20140088041A1 US 201113880985 A US201113880985 A US 201113880985A US 2014088041 A1 US2014088041 A1 US 2014088041A1
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Prior art keywords
penflufen
iodo
propynyl
compounds
wood
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US13/880,985
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English (en)
Inventor
Bernd Koop
Martin Kugler
Thomas Jaetsch
Johannes Kaulen
Tanja Gerharz
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Lanxess Deutschland GmbH
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Lanxess Deutschland GmbH
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Priority claimed from EP10188713A external-priority patent/EP2443928A1/de
Application filed by Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH
Assigned to LANXESS DEUTSCHLAND GMBH reassignment LANXESS DEUTSCHLAND GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JAETSCH, THOMAS, KAULEN, JOHANNES, KUGLER, MARTIN, KOO9P, BERND, GERHARZ, TANJA
Publication of US20140088041A1 publication Critical patent/US20140088041A1/en
Assigned to LANXESS DEUTSCHLAND GMBH reassignment LANXESS DEUTSCHLAND GMBH CORRECTIVE ASSIGNMENT TO CORRECT THE SPELLING OF FIRST INVENTOR PREVIOUSLY RECORDED AT REEL: 032037 FRAME: 0400. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Assignors: JAETSCH, THOMAS, KAULEN, JOHANNES, KUGLER, MARTIN, KOOP, BERND, GERHARZ, TANJA
Abandoned legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/561,2-Diazoles; Hydrogenated 1,2-diazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08Oxygen or sulfur directly attached to an aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02Amines; Quaternary ammonium compounds
    • A01N33/04Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02Amines; Quaternary ammonium compounds
    • A01N33/12Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N55/00Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/08Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N59/00Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/14Boron; Compounds thereof
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B27WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27KPROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34Organic impregnating agents
    • B27K3/343Heterocyclic compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B27WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27KPROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34Organic impregnating agents
    • B27K3/38Aromatic compounds
    • B27K3/40Aromatic compounds halogenated
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B27WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27KPROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K2240/00Purpose of the treatment
    • B27K2240/20Removing fungi, molds or insects

Definitions

  • the invention relates to mixtures comprising penflufen, to the use of these mixtures for protecting industrial materials and to a method for treating industrial materials with the penflufen mixtures.
  • Penflufen N-(2-[1,3-dimethylbutylphenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide) is a pyrazolylcarboxanilide of the formula (I). In addition, penflufen is a fungicide.
  • Pyrazolylcarboxanilides are specific carboxamides and are known from WO 03/010149 for controlling unwanted microorganisms in crop protection and in the protection of materials.
  • WO 03/010149 mentions penflufen in a list of further pyrazolylcarboxanilides, and the action of penflufen as a crop protection agent is shown in one example. Specific mixtures with penflufen have not been described.
  • WO 2006/114212 discloses active compound combinations of carboxamides with known insecticidally active compounds for controlling unwanted animal pests and also unwanted phytopathogenic fungi. Mixtures of penflufen and insecticides have also been described.
  • Synergistic fungicidal active compound combinations comprising carboxamides with a wide variety of different mixing partners are known from WO 2005/041653.
  • penflufen is, among others, mentioned as a mixing partner.
  • the use described of the synergistic fungicidal active compound combinations is the control of phytopathogenic fungi.
  • WO 2005/058839 discloses a wide variety of different fungicides, bactericides and insecticides which may be used, optionally with an optically active carboxamide, for example an enantiomer of penflufen, for controlling unwanted microorganisms in crop protection and in the protection of industrial materials. Specific examples of mixtures are not mentioned.
  • an optically active enantiomer of penflufen for crop protection.
  • the known active compound combinations have the disadvantage that their activity against microorganisms is not always sufficient in the protection of materials.
  • compositions comprising
  • Penflufen may be employed as a racemate, in enantiomerically pure form or as an enriched enantiomer mixture.
  • a use as salt or acid addition compound is also possible, salts being understood as meaning in particular sodium, potassium, magnesium, calcium, zinc, aluminium, iron and copper salts, and acid addition compounds being understood as meaning in particular adducts with hydrohalic acids, for example hydrogen chloride and hydrogen bromide, carboxylic acids such as, for example, formic acid, acetic acid, tartaric acid and oxalic acid, sulphonic acids such as, for example, p-toluenesulphonic acid, and also sulphuric acid, phosphoric acid and nitric acid.
  • hydrohalic acids for example hydrogen chloride and hydrogen bromide
  • carboxylic acids such as, for example, formic acid, acetic acid, tartaric acid and oxalic acid
  • sulphonic acids such as, for example, p-toluenesulphonic
  • the phenols are preferably tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, dichlorophen, 2-benzyl-4-chlorophenol, triclosan, diclosan, hexachlorophene, p-hydroxybenzoic esters, o-phenylphenol, m-phenylphenol, p-phenylphenol, 4-(2-tert-butyl-4-methylphenoxy)phenol, 4-(2-isopropyl-4-methylphenoxy)phenol, 4-(2,4-dimethylphenoxy)phenol and their alkali and alkaline earth metal salts, or mixtures of these compounds.
  • the phenols used are phenylphenols. Very particular preference is given to using o-phenylphenol.
  • the boron compounds are preferably inorganic boron compounds.
  • the boron compounds are alkali metal or alkaline earth metal borates such as, for example, sodium tetraborate, disodium tetraborate decahydrate (sodium borate, borax) or disodium octaborate tetrahydrate, or boric acid, boron oxide, boric hydrides, or boric esters or mixtures of these compounds.
  • alkali metal or alkaline earth metal borates such as, for example, sodium tetraborate, disodium tetraborate decahydrate (sodium borate, borax) or disodium octaborate tetrahydrate, or boric acid, boron oxide, boric hydrides, or boric esters or mixtures of these compounds.
  • sodium borate sodium borate
  • borax disodium tetraborate decahydrate
  • disodium octaborate tetrahydrate or bo
  • the compounds of the formula (II) are organic quarternary ammonium compounds.
  • the compounds of the formula (II) are benzalkonium chloride, benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, didecyldimethylammonium chloride, dioctyldimethylammonium chloride, hexadecyltrimethylammonium chloride, didecylmethylpoly(oxyethyl)ammonium propionate, didecyldimethylammonium carbonate, didecyldimethylammonium bicarbonate.
  • the radicals of the formula (IV) are derivatives of polyethylene glycols.
  • z is preferably 2, 3, 4 or 5.
  • R 1 and R 2 independently of one another preferably represent methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or n-pentyl. Particularly preferably, R 1 or R 2 represent methyl.
  • R 3 and R 4 independently of one another preferably represent phenyl, benzyl, o-, m-, p-xylene, o-, m-, p-trimethylphenyl, o-, p-, m-chlorobenzyl, —CH 2 —CH 2 —O—CH 2 —CH 2 —OH, —[CH 2 —CH 2 —O] 2 —CH 2 —CH 2 —OH, —[CH 2 —CH 2 —O] 3 —CH 2 —CH 2 —OH, —[CH 2 —CH 2 —O] 4 —CH 2 —CH 2 —OH, dichlorobenzyl, n-, isononyl, n-, isodecyl, n-, isododecyl, n-, isotetradecyl, n-, isohexadecyl, n-, isooctenyl, n
  • R 3 and R 4 independently of one another represent benzyl, —CH 2 —CH 2 —O—CH 2 —CH 2 —OH, —[CH 2 —CH 2 —O] 2 —CH 2 —CH 2 —OH, —[CH 2 —CH 2 —O] 3 —CH 2 —CH 2 —OH, —[CH 2 —CH 2 —O] 4 —CH 2 —CH 2 —OH, dichlorobenzyl, n-, isononyl, n-, isodecyl, n-, isododecyl, n-, isotetradecyl, n-, isohexadecyl, n-, isooctenyl, n-, isononenyl or n-, isodecenyl.
  • X preferably represents a halide, carbonate, bicarbonate, borate, sulphate, hydroxide or carboxylate. Particularly preferably, X represents a chloride, bicarbonate or carbonate.
  • n is preferably 1, 2 or 3.
  • the isothiazolinones are preferably N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one (DCOIT), 5-chloro-N-octylisothiazolinone, N-octylisothiazolin-3-one, 4,5-trimethyleneisothiazolinone and 4,5-benzisothiazolinone.
  • the isothiazolinone used is with particular preference 4,5-dichloro-N-octylisothiazolin-3-one (DCOIT).
  • 3-Iodo-2-propynyl alkylcarbamate preferably represents 3-iodo-2-propynyl N-butylcarbamate (IPBC) and 3-iodo-2-propynyl N-hexylcarbamate.
  • IPBC 3-iodo-2-propynyl alkylcarbamate
  • 3-Iodo-2-propynyl alkylcarbamate particularly preferably represents 3-iodo-2-propynyl N-butylcarbamate.
  • 3-Iodo-2-propynyl cycloalkylcarbamate preferably represents 3-iodo-2-propynyl cyclohexylcarbamate.
  • 3-Iodo-2-propynyl arylcarbamate preferably represents 3-iodo-2-propynyl N-phenylcarbamate.
  • the compounds of the formula (III) are tertiary amines.
  • the compounds of the formula (III) are N-(3-aminopropyl)-N-dodecyl-1,3-propanediamine, N-(3-aminopropyl)-N-decyl-1,3-propanediamine, N-(3-aminopropyl)-N-tetradecyl-1,3-propariediamine and their acid addition compounds.
  • Acid addition compounds of the compounds of the formula (III) are to be understood as meaning, in particular, adducts with hydrohalic acids, for example hydrogen chloride and hydrogen bromide, carboxylic acids such as, for example, formic acid, acetic acid, tartaric acid and oxalic acid, sulphonic acids such as, for example, p-toluenesulphonic acid, and also sulphuric acid, phosphoric acid and nitric acid.
  • hydrohalic acids for example hydrogen chloride and hydrogen bromide
  • carboxylic acids such as, for example, formic acid, acetic acid, tartaric acid and oxalic acid
  • sulphonic acids such as, for example, p-toluenesulphonic acid, and also sulphuric acid, phosphoric acid and nitric acid.
  • R 5 preferably represents n-, isooctyl, n-, isononyl, n-, isodecyl, n-, isododecyl, n-, isohexadecyl, n-, isooctenyl, n-, isononenyl, n-, isodecenyl, cyclopentyl or cyclohexyl.
  • R 5 represents dodecyl, tetradecyl or decyl.
  • m preferably represents 2, 3 or 4.
  • y preferably represents 2, 3 or 4.
  • Alkyl and alkenyl in each case independently represent straight-chain, cyclic or branched alkyl and alkenyl radicals, respectively.
  • C 1 -C 6 -Alkyl represents, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, neopentyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,
  • C 1 -C 6 -alkyl represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl and n-hexyl.
  • C 8 -C 18 -Alkyl and/or C 6 -C 22 -alkyl represent, by way of example and preferably, n-, isooctyl, n-, isononyl, n-, isodecyl, n-, isododecyl or n-, isohexadecyl.
  • C 8 -C 18 -alkenyl and/or C 6 -C 22 -alkenyl represent n-, isooctenyl, n-, isononenyl, n- or isodecenyl or else also represent polyunsaturated C 8 -C 18 -alkenyl radicals.
  • C 5 -C 20 -cycloalkyl represents cyclopentyl or cyclohexyl.
  • C 6 -C 24 -aryl represents a mono-, bi- or tricyclic carbocyclic aromatic radical which has preferably 6 to 24 aromatic carbon atoms and which may optionally be substituted further by halogens.
  • C 6 -C 24 -aryl represents biphenyl, phenyl, o-, p-, m-chlorobenzyl, dichlorobenzyl, naphthyl, o-, m-, p-benzyl, o-, m-, p-xylene or o-, m-, p-trimethylphenyl.
  • C 6 -C 24 -aryl represents o-, m-, p-benzyl, o-, p-, m-chlorobenzyl or dichlorobenzyl.
  • compositions comprising
  • compositions comprising
  • compositions are even more preferred:
  • Penflufen is preferably employed in a weight ratio of 50:1 to 1:50, in particular of from 20:1 to 1:20, preferably of from 10:1 to 1:10 to a compound of b) (Table 1).
  • composition of penflufen and 3-iodo-2-propynyl-N-butylcarbamate which comprises 85% by weight to 75% by weight of penflufen and 15% by weight to 25% by weight of 3-iodo-2-propynyl-N-butylcarbamate.
  • compositions of penflufen and isothiazolinones comprise more than 50% by weight of penflufen.
  • the mixtures comprise at least 50% by weight of penflufen and at least 10% by weight of 4,5-dichloro-N-octylisothiazolin-3-one.
  • compositions used in accordance with the invention can be employed in solid or liquid form. Suitable for this purpose are formulations such as solutions, emulsions, suspensions, powders, granules, pastes, aerosols and also very fine encapsulations in polymeric substances.
  • Such formulations can be produced in a known manner, for example by mixing the compositions with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to employ organic solvents as auxiliary solvents.
  • suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycerol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as
  • Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates.
  • Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic meals, and also granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
  • Suitable emulsifiers and/or foam formers are: for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates.
  • Suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
  • Tackifiers such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can additionally be used in the formulations. Further additives may be mineral and vegetable oils.
  • compositions may furthermore comprise colorants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian Blue, copper oxide and organic dyes, such as alizarin, azo and metallophthalocyanine dyes.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian Blue, copper oxide and organic dyes, such as alizarin, azo and metallophthalocyanine dyes.
  • composition used generally comprises preferably from 0.1 to 95 percent by weight of components a) and b), preferably from 0.5 to 90% by weight.
  • compositions according to the invention may also comprise other active compounds, for example fungicides, bactericides and/or insecticides, to broaden the activity spectrum or to prevent the development of resistance, for example.
  • active compounds for example fungicides, bactericides and/or insecticides
  • synergistic effects are obtained, i.e. the activity of combined active compounds is greater than the activity of the individual components.
  • imidazoles such as:
  • clotrimazole bifonazole, climbazole, econazole, fenapanil, imazalil, isoconazole, ketoconazole, lombazole, miconazole, pefurazoate, prochloraz, triflumizole and their metal salts and acid adducts;
  • pyridines and pyrimidines such as:
  • succinate dehydrogenase inhibitors such as:
  • naphthalene derivatives such as:
  • sulphenamides such as:
  • benzimidazoles such as:
  • aldimorph, dimethomorph, dodemorph, falimorph, fenpropidin fenpropimorph, tridemorph, trimorphamid and their arylsulphonate salts such as, for example, p-toluenesulphonic acid and p-dodecylphenyl-sulphonic acid;
  • benzothiazoles such as:
  • benzothiophene dioxides such as:
  • boric acid boric ester, borax
  • formaldehyde and formaldehyde-releasing compounds such as:
  • aldehydes such as:
  • cinnamaldehyde formaldehyde, glutardialdehyde, ⁇ -bromocinnamaldehyde, o-phthaldialdehyde; thiocyanates such as:
  • benzalkonium chloride benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, didecyldimethylammonium chloride, dioctyldimethylammonium chloride, N-hexadecyltrimethylammonium chloride, 1-hexadecylpyridinium chloride, iminoctadine tris(albesilate);
  • iodine derivatives such as:
  • diiodomethyl p-tolyl sulphone 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargylformal, 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynyl n-butylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate, 3-iodo-2-propynyl cyclohexylcarbamate, 3-iodo-2-propynyl phenylcarbamate;
  • microbicides with an activated halogen group such as:
  • bronopol bronidox
  • 2-bromo-2-nitro-1,3-propanediol 2-bromo-4′-hydroxyacetophenone
  • 1-bromo-3-chloro-4,4,5,5-tetramethyl-2-imidazolidinone 1-bromo-3-chloro-4,4,5,5-tetramethyl-2-imidazolidinone
  • ⁇ -bromo- ⁇ -nitrostyrene chloroacetamide
  • chloramine T 1,3-dibromo-4,4,5,5-tetramethyl-2-imidazolidinone
  • dichloramine T 3,4-dichloro-(3H)-1,2-dithiol-3-one, 2,2-dibromo-3-nitrile-propionamide, 1,2-dibromo-2,4-dicyanobutane, halane, halazone, mucochloric acid, phenyl (2-chlorocyanovinyl)sulphone, phenyl (1
  • pyridines such as:
  • methoxyacrylates or similar such as:
  • azoxystrobin dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin;
  • metal soaps such as:
  • salts of the metals tin, copper and zinc with higher fatty acids, resin acids, naphthenoic acids and phosphoric acid such as, for example, tin naphthenate, tin octoate, tin 2-ethylhexanoate, tin oleate, tin phosphate, tin benzoate, copper naphthenate, copper octoate, copper 2-ethylhexanoate, copper oleate, copper phosphate, copper benzoate, zinc naphthenate, zinc octoate, zinc 2-ethylhexanoate, zinc oleate, zinc phosphate, zinc benzoate;
  • metal salts such as:
  • salts of the metals tin, copper, zinc, and also chromates and dichromates such as, for example, copper hydroxycarbonate, sodium dichromate, potassium dichromate, potassium chromate, copper sulphate, copper chloride, copper borate, zinc fluorosilicate, copper fluorosilicate;
  • oxides of the metals tin, copper and zinc such as, for example, tributyltin oxide, Cu 2 O, CuO, ZnO;
  • dithiocarbamates such as:
  • cufraneb ferban, potassium N-hydroxymethyl-N′-methyldithiocarbamate, sodium dimethyldithiocarbamate, potassium dimethyldithiocarbamate, mancozeb, maneb, metam, metiram, thiram, zineb, ziram;
  • nitriles such as:
  • bethozaxin 5-hydroxy-2(5H)-furanone, 4,5-benzodithiazolinone, 4,5-trimethylenedithiazolinone, N-(2-p-chlorobenzoylethyl)hexaminium chloride, 2-oxo-2-(4-hydroxyphenyl)acetohydroxycinnamoyl chloride, tris-N-(cyclohexyldiazeniumdioxy)aluminium, N-(cyclohexyldiazeniumdioxy)tributyltin or its potassium salts, bis-N-(cyclohexyldiazeniumdioxy)copper; iprovalicarb, fenhexamide, spiroxamine, carpropamid, diflumetorin, quinoxyfen, famoxadone, polyoxorim, acibenzolar S-methyl, furametpyr, thifluzamide, methalaxyl-M, be
  • Bacillus thuringiensis barthrin, 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, bioresmethrin, bioallethrin, bistrifluoron, bromophos A, bromophos M, bufencarb, buprofezin, butathiophos, butocarboxim, butoxycarboxim,
  • fenamiphos fenazaquin, fenbutatin oxide, fenfluthrin, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fensulphothion, fenthion, fenvalerate, fipronil, flonicamid, fluacrypyrim, fluazuron, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flupyrazofos, flufenzine, flumethrin, flufenprox, fluvalinate, fonophos, formethanate, formothion, fosmethilan, fosthiazate, fubfenprox, furathiocarb
  • HCH halofenocid
  • HCH CAS RN: 58-89-9
  • heptenophos hexaflumuron
  • hexythiazox hydramethylnon
  • hydroprene halofenocid
  • imidacloprid imiprothrin, indoxycarb, iodfenfos, iprinomectin, iprobenfos, isazophos, isoamidophos, isofenphos, isoprocarb, isoprothiolane, isoxathion, ivermectin, lama-cyhalothrin, lufenuron,
  • parathion A parathion M, penfluoron, permethrin, 2-(4-phenoxyphenoxy)-ethyl ethylcarbamate, phenthoate, phorate, phosalon, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, prallethrin, profenophos, promecarb, propaphos, propoxur, prothiophos, prothoate, pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyrimidifen, pyriproxifen, pyrithiobac-sodium,
  • tau-fluvalinate tau-fluvalinate, taroils, tebufenozide, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin, ternephos, terbam, terbufos, tetrachlorvinphos, tetramethrin, tetramethacarb, thiacloprid, thiafenox, thiamethoxam, thiapronil, thiodicarb, thiofanox, thiazophos, thiocyclam, thiomethon, thionazin, thuringiensin, tralomethrin, transfluthrin, triarathen, triazophos, triazamate, triazuron, trichlorfon, triflumuron, trimethacarb,
  • acetochlor acifluorfen, aclonifen, acrolein, alachlor, alloxydim, ametryn, amidosulphuron, amitrole, ammonium sulphamate, anilofos, asulam, atrazine, azafenidin, aziptrotryne, azimsulphuron,
  • eglinazine endothal
  • EPTC S-ethyl dipropylthiocarbamate
  • esprocarb ethalfluralin
  • ethidimuron ethofumesate
  • ethobenzanid ethoxyfen
  • ethametsulphuron ethoxysulphuron
  • fenoxaprop fenoxaprop-P, fenuron, flamprop, flamprop-M, flazasulphuron, fluazifop, fluazifop-P, fuenachior, fluchloralin, flufenacet, flumeturon, fluorocglycofen, fluoronitrofen, flupropanate, flurenol, fluridone, fluorochloridone, fluoroxypyr, fomesafen, fosamine, fosametine, flamprop-isopropyl, flamprop-isopropyl-L, flufenpyr, flumiclorac-pentyl, flumipropyn, flumioxzim, flurtamone, flumioxzim, flupyrsulphuron-methyl, fluthiacet-methyl,
  • imazamethabenz isoproturon, isoxaben, isoxapyrifop, imazapyr, imazaquin, imazethapyr, ioxynil, isopropalin, imazosulphuron, imazomox, isoxaflutole, imazapic,
  • MCPA (2-(4-chloro-2-methylphenoxy)acetic acid), MCPA-hydrazide, MCPA-thioethyl, MCPB (4-(4-chloro-2-methylphenoxy)butanoic acid), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulphuron, metam, metamifop, metamitron, metazachlor, methabenzthiazuron, methazole, methoroptryne, methyldymron, methyl isothiocyanate, metobromuron, metoxuron, metribuzin, metsulphuron, molinate, monalide, monalinuron, MSMA (monosodium methyl arsenate), metolachlor, metosulam, metobenzuron,
  • naproanilide napropamide, naptalam, neburon, nicosulphuron, norflurazon, sodium chlorate,
  • tar oils TCA (trichloroacetic acid), TCA-sodium, tebutam, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thiazafluoron, thifensuiphuron, thiobencarb, thiocarbazil, tralkoxydim, tri-allate, triasulphuron, tribenuron, triclopyr, tridiphane, trietazine, trifluralin, tycor, thidiazimin, thiazopyr, triflusulphuron,
  • the invention furthermore relates to the use of the compositions according to the invention for protecting industrial materials against attack and/or destruction by microorganisms.
  • Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry.
  • Industrial materials which are to be protected by the present invention against microbial change or destruction can be, for example, adhesives, sizes, paper and board, textiles, leather, wood, timber products, wood/plastic composites, paints, synthetic articles, cooling lubricants and other materials which can be attacked or destroyed by microorganisms.
  • the range of materials to be protected also includes parts of production plants, for example cooling water circuits, which may be impaired by the proliferation of microorganisms.
  • Industrial materials in the context of the present invention are preferably adhesives, sizes, papers and boards, leather, wood, timber products, wood-plastic composites, paints, cooling lubricants and heat transfer liquids; particularly preferred industrial materials are wood, timber products and wood-plastic composites (WPC).
  • WPC wood-plastic composites
  • Wood is to be understood as meaning, in particular: construction timber, wooden beams, railway sleepers, bridge components, jetties, vehicles made of wood, boxes, pallets, containers, telephone poles, wooden fences, wood lagging, windows and doors made of wood, joiners work and wood-based materials used in domestic construction or carpentry and joinery.
  • Timber products are to be understood as meaning, in particular: plywood, chipboard, fibre board, oriented strand board (OSB) or composite board.
  • OSB oriented strand board
  • Wood/plastic composite is to be understood as meaning, in particular: thermoplastically processable composites consisting of wood, plastic and additives.
  • Wood is particularly preferred.
  • Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the compositions according to the invention preferably act against wood-destroying basidiomycetes, preferably holobasidiomycetes.
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Polyporus such as Polyporus versicolor
  • Gloeophyllum such as Gloeophyllum trabeum
  • Poria such as Poria placenta
  • Coriolus such as Coriolus versicolor
  • Stereum such as Stereum sanguinolentum.
  • compositions according to the invention act against species of the genera Gloeophyllum, Coniophora, Coriolus, Stereum or Poria .
  • compositions according to the invention act against Gloeophyllum trabeum, Coriolus versicolor, Stereum sanguinolentum or Poria placenta.
  • compositions to be used according to the invention act against wood-destroying and soft rot-causing ascomycetes and associated deuteromycetes, such as, for example:
  • Glenospora species of the genus Glenospora , such as Glenospora graphii,
  • Chaetomium globosum species of the genus Chaetomium , such as Chaetomium globosum
  • Humicola grisea species of the genus Humicola , such as Humicola grisea,
  • Petriella species of the genus Petriella , such as Petriella setifera,
  • Trichurus spiralis species of the genus Trichurus , such as Trichurus spiralis
  • Lecythophora species of the genus Lecythophora , such as Lecythophora mutabilis
  • Sclerophoma species of the genus Sclerophoma , such as Sclerophoma pityophila
  • Aureobasidium species of the genus Aureobasidium , such as Aureobasidium pullulans.
  • the invention furthermore relates to industrial materials, in particular wood, a timber product or a wood/plastic composite, comprising
  • the invention furthermore relates to a process for protecting industrial materials against attack and/or destruction by microorganisms, characterized in that at least one composition comprising
  • compositions are applied to the industrial material preferably by painting, drenching, spraying, impregnating or in a different manner.
  • Wood-plastic composites can be prepared, for example, by mixing with input of thermal energy, in particular extruding or injection moulding, wood particles, a thermoplastic polymer and the compositions.
  • Wood composites can be treated, for example, by the glue incorporation method.
  • the composition according to the invention is, if appropriate, added in the form of a formulation of the glue liquor and this biocidally finished glue is applied in a customary manner to the chips, in particular applied using a nozzle (for example in the case of chip boards or OSB boards) or applied via rolls to the veneer (for example in the case of plywood).
  • the composition according to the invention is, if appropriate, sprayed in the form of a formulation to the timber product or applied using a roll.
  • the use concentrations of the compositions 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 rate of use can be determined by test series.
  • the use concentrations are in the range from 0.001 to 5% by weight, preferably from 0.005 to 1.0% by weight, of the composition and optionally other additives, based on the material to be protected.
  • Mycelium pieces were punched out of a colony of the wood-destroying fungus in question and incubated on a malt extract/peptone-containing nutrient agar at 26° C. The growth of the hyphae with and without active compound was compared. The minimum inhibitory concentration (MIC) stated was the concentration at which the radial hyphae growth was suppressed completely.
  • MIC minimum inhibitory concentration
  • SI>1 means antagonism
  • SI ⁇ 1 means synergism

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Forests & Forestry (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
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EP10188713A EP2443928A1 (de) 2010-10-25 2010-10-25 Fungizide Penflufen Mischungen
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PT2632267T (pt) 2016-11-16
US20160295863A1 (en) 2016-10-13
EP2632267A1 (de) 2013-09-04
AU2016200702A1 (en) 2016-02-25
NZ609633A (en) 2014-11-28
CL2013001127A1 (es) 2014-04-21
CN103179858A (zh) 2013-06-26
AU2016200702B2 (en) 2017-08-31
JP2013540786A (ja) 2013-11-07
BR112013009897A2 (pt) 2016-07-05
CL2015002928A1 (es) 2016-04-22
MX2013004570A (es) 2013-05-17
RU2013123767A (ru) 2014-12-10
CA2815033C (en) 2019-02-05
BR112013009897B1 (pt) 2018-11-13
CN105211069A (zh) 2016-01-06
CA3007180A1 (en) 2012-05-03

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