US20040138217A1 - Fungicidally active compound combinations - Google Patents
Fungicidally active compound combinations Download PDFInfo
- Publication number
- US20040138217A1 US20040138217A1 US10/688,466 US68846603A US2004138217A1 US 20040138217 A1 US20040138217 A1 US 20040138217A1 US 68846603 A US68846603 A US 68846603A US 2004138217 A1 US2004138217 A1 US 2004138217A1
- Authority
- US
- United States
- Prior art keywords
- active compound
- group
- industrial materials
- wood
- ipconazole
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 239000012770 industrial material Substances 0.000 claims abstract description 16
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 244000005700 microbiome Species 0.000 claims abstract description 14
- 239000005796 Ipconazole Substances 0.000 claims abstract description 13
- 230000006378 damage Effects 0.000 claims abstract description 3
- 239000002023 wood Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 230000003641 microbiacidal effect Effects 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
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- 239000004033 plastic Substances 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000003619 algicide Substances 0.000 claims description 4
- 239000005068 cooling lubricant Substances 0.000 claims description 4
- VUWCWMOCWKCZTA-UHFFFAOYSA-N 1,2-thiazol-4-one Chemical class O=C1CSN=C1 VUWCWMOCWKCZTA-UHFFFAOYSA-N 0.000 claims description 3
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- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 3
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- 229940124561 microbicide Drugs 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
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- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 3
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- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 3
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- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000005877 Alpha-Cypermethrin Substances 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
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- 239000005839 Tebuconazole Substances 0.000 description 3
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- 239000005846 Triadimenol Substances 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Chemical class 0.000 description 3
- 229960000686 benzalkonium chloride Drugs 0.000 description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 3
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 3
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 3
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- 239000003995 emulsifying agent Substances 0.000 description 3
- 229940013764 fipronil Drugs 0.000 description 3
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 description 3
- 229940056881 imidacloprid Drugs 0.000 description 3
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
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- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 2
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- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- A01N43/64—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
Definitions
- the present invention relates to synergistic active compound mixtures comprising ipconazole and at least one further fungicidally active compound, microbicidal compositions based on these active compound mixtures and the use of these active compound mixtures, as well as compositions for protecting industrial materials.
- ipconazole has fungicidal properties and can be used for protecting industrial materials (cf. EP-A 341954).
- EP-A 341954 the antifungal action of ipconazole has been found to be insufficient against all wood-destroying organisms. Accordingly, it is an object of the present invention to improve the activity of ipconazole in the protection of industrial materials, in particular wood and wood composites.
- the present invention provides novel active compound mixtures comprising
- the compounds of formula (I) can be present in the form of different stereoisomers. Accordingly, the present invention encompasses mixtures comprising the isomerically pure or isomerically enriched compounds of the formula (I) or the enantiomerically pure or enantiomerically enriched compound of the formula (I) or the racemate of the formula (I).
- active compound mixtures comprising, as further fungicidally active compound b), selected from the group of the metal salts or metal oxides, sulphamides, triazoles, imidazoles, benzimidazoles, morpholine derivatives, benzothiazoles, isothiazolinones, thiocyanates, quatemary ammonium compounds and guanidines, iodine derivatives, phenols, pyridines, methoxyacrylates and quinolines.
- active compound mixtures comprising, as further fungicidally active compound b), selected from the group of the metal salts or metal oxides, sulphamides, triazoles, imidazoles, benzimidazoles, morpholine derivatives, benzothiazoles, isothiazolinones, thiocyanates, quatemary ammonium compounds and guanidines, iodine derivatives, phenols, pyridines, methoxyacrylates and quinolines.
- Preferred compounds b) of the mixture from the group of the metal salts and oxides are, for example, salts of the metals, copper and zinc, such as, for example, copper hydroxycarbonate, copper sulphate, copper chloride, copper borate, zinc fluorosilicate, or oxides, such as, for example, oxides of the metals copper and zinc, such as, for example, Cu 2 O, CuO, ZnO.
- Preferred components b) of the mixture from the group of the sulphamides are, for example, dichlofluanid, tolylfluanid or fluorfolpet.
- Preferred components b) of the mixture from the group of the triazoles are, for example, azaconazoles, bitertanol, bromuconazole, cyproconazole, epoxyconazole, fluquinconazole, hexaconazole, metconazole, penconazole, propioconazole, tebuconazole, tetraconazole or triadimenol and their metal salts and acid adducts.
- Preferred components b) of the mixture from the group of the imidazoles are, for example, clotrimazole, climbazole, imazalil, ketoconazole or prochloraz and their metal salts and acid adducts.
- Preferred components b) of the mixture from the group of the benzimidazoles are, for example, carbendazim or thiabendazole or their salts.
- Preferred components b) of the mixture from the group of the morpholine derivatives are, for example, dodemorph, fenpropimorph, tridemorph, and their salts with arylsulphonic acids, such as, for example, p-toluenesulphonic acid and p-dodecylphenylsulphonic acid.
- Preferred components b) of the mixture from the group of the benzothiazoles are, for example, 2-mercaptobenzothiazole and benzothiophenes, such as, for example, N-cyclohexyl-benzo[b]thiophenecarboxamide S,S-dioxide or bethoxazin.
- Preferred components b) of the mixture from the group of the isothiazolinones are, for example, 4,5-dichloro-N-octylisothiazolin-3-one, N-octylisothiazolin-3-one or benzisothiazolinone.
- Preferred components b) of the mixture from the group of the thiocyanates are, for example, thiocyanatomethylthiobenzothiazole or methylenebisthiocyanate.
- Preferred components b) of the mixture from the group of the quatemary ammonium compounds and guanidines are, for example, benzalkonium chloride, benzyldimethyltetradecylammonium chloride, benzyldimethyl-dodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, didecyldimethylammonium chloride, dioctyldimethylammonium chloride, N-hexadecyltrimethylammonium chloride, didecylmethyl-poly(oxyethyl)ammonium propionate.
- Preferred components b) of the mixture from the group of the iodine derivatives are, for example, diiodomethyl-p-tolyl sulphone or 3-iodo-2-propynyl n-butylcarbamate.
- Preferred components b) of the mixture from the group of the phenols are, for example, tribromophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, dichlorophen, 2-benzyl4-chlorophenol, triclosan, diclosan, hexachlorophen, p-hydroxybenzoic esters, o-phenylphenol and their alkali metal and alkaline earth metal salts.
- Preferred components b) of the mixture from the group of the pyridines are, for example, 1-hydroxy-2-pyridinethione (and its Cu, Na, Fe, Mn, Zn salts) or tetrachloro-4-methylsulphonylpyridine.
- Preferred components b) of the mixture from the group of the methoxyacrylates are, for example, azoxystrobin or trifloxystrobin.
- Preferred components b) of the mixture from the group of the quinolines are, for example, quinoxyfen, 8-hydroxyquinoline and their Cu salts.
- the weight ratios of the active compounds a) and b) in the active compound mixture according to the invention can be varied within a relatively wide range.
- the present invention provides active compound mixtures comprising a synergistically effective amount of a) ipconazole of the formula (I) and a synergistically effective amount of at least one further fungicidally active compound b).
- weight ratios of fungicidally active compound b) to a) ipconazole of from 1:20 to 20:1, particularly preferably from 1:4 to 4:1.
- the mixtures according to the invention may additionally comprise one or more of the following active compounds c):
- active compound mixtures comprising, as further active compound c), at least one of the following insecticides and/or algicides:
- active compound mixtures according to the invention which, as further active compound c), comprise at least one of the following insecticides:
- the active compounds c) are generally present in an amount of from 0.00001% by weight to 10% by weight, preferably from 0.0001% by weight to 5% by weight and particularly preferably from 0.001% by weight to 1% by weight.
- the active compound mixtures according to the invention can be prepared by mixing the individual components a) and b) and, if appropriate, c) with one another in a customary manner, if appropriate with addition of solvents and processing auxiliaries.
- the active compound mixtures according to the invention have strong microbicidal action and can be used for controlling microorganisms, such as, for example, fungi, bacteria and algae, in the protection of materials.
- the active compound combinations are preferably used for controlling microorganisms in the protection of wood.
- the active compound combinations according to the invention can be used for protecting industrial materials against colonization and destruction by microorganisms.
- the present invention furthermore provides the use of the mixtures according to the invention as microbicide for protecting industrial materials.
- industrial materials are to be understood as meaning non-living materials which have been prepared for use in industry.
- the industrial materials are, for example, adhesives, sizes, paper and board, textiles, leather, wood, woodbased materials, paints and plastic articles, cooling lubricants and other materials which can be colonized or destroyed by microorganisms.
- industrial materials are also to be understood as meaning parts of production plants, for example cooling-water circuits, which may be impaired by the proliferation of microorganisms.
- Industrial materials which are preferably protected are adhesives, sizes, paper and board, leather, wood, woodbased materials, paints, plastic articles, cooling lubricants and heat-transfer liquids.
- the active compound combinations according to the invention are particularly suitable for protecting wood, woodbased materials, plastics, cooling lubricants and coating systems, such as paints, varnishes or plaster, against colonization by microorganisms.
- the active compound combinations according to the invention are particularly preferably suitable for protecting wood, woodbased materials, plastics and coating systems, such as paints, varnishes or plaster, against colonization by microorganisms.
- Microorganisms capable of degrading or changing the industrial materials are, for example, bacteria, fungi, yeasts, algae and slime organisms.
- the active compound combinations according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and insects and against slime organisms and algae. Especially preferred is the action of the active compound combinations against wood-destroying fungi and insects.
- Wood which can be protected by the active compound combinations according to the invention or compositions comprising them is to be understood as meaning, for example: construction timber, wooden beams, railway sleepers, bridge components, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden claddings, windows and doors made from wood, plywood, chipboard, joiner's wood or woodbased materials which are quite generally used in domestic construction or in joinery.
- the synergistic combinations claimed have particularly high microbicidal, in particular fungicidal, action, together with a broad activity spectrum against microorganisms encountered in the protection of materials; they are particularly effective against moulds, wood-discolouring and wood-destroying fungi.
- A1 Ascomycetes Ceratocystis, such as Ceratocystis minor
- A2 Deuteromycetes
- Aspergillus such as Aspergillus niger
- Aureobasidium such as Aureobasidium pullulans
- Dactylium such as Dactylium fusarioides
- Penicillium such as Penicillium brevicaule or
- Sclerophoma such as Sclerophoma pithyophila
- Scopularia such as Scopularia phycomyces
- Trichoderma such as Trichoderma viride or
- Mucor such as Mucor spinorus
- B1 Chaetomium, such as Chaetomium globosum or
- Petriella such as Petriella setifera
- Trichurus such as Trichurus spiralis
- Coniophora such as Coniophora tenuum
- Coriolus such as Coriolus versicolor
- Donkioporia such as Donkioporia expans
- Gloeophyllum such as Gloeophyllum abietinum or
- Gloeophyllum adoratum or
- Lentinus such as Lentinus cyathiformes or
- Paxillus such as Paxillus panuoides
- Pleurotus such as Pleurotus ostreatus
- Poria such as Poria monticola or
- Serpula such as Serpula himantoides or
- Stereum such as Stereum hirsutum
- Tyromyces such as Tyromyces palustris
- the combinations according to the invention are highly suitable for protecting wood and woodbased materials against attack by wood-destroying insects, such as, for example,
- Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucilugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus
- the active compound mixtures can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances.
- formulations can be produced in a known manner, for example by mixing the active compound mixture or the individual active compounds a) and b) and, if appropriate, c) with extenders, that is liquid solvents, liquefied gases under pressure and/or solid carriers, if appropriate 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, for example, 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 mineral oil fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
- aromatics such as xylene, toluene or alkylnaphthalenes
- chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
- 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, and also 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 natrual rocks, such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic materials 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, alkyl sulphates, arylsulphonates, and also protein hydrolysates.
- Suitable dispersants are, for example lignosulphite waste liquors and methylcellulose.
- Tackifiers such as carboxymethylcellulose and 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 be used in the formulations.
- Other possible additives are mineral and vegetable oils.
- colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- inorganic pigments for example iron oxide, titanium oxide and Prussian Blue
- organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
- trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- the formulations generally comprise between 0.1 and 95% by weight of active compound mixture, preferably between 0.5 and 25% by weight.
- the present invention furthermore provides microbicidal compositions based on the active compound combinations according to the invention, which compositions comprise at least one solvent or diluent and, if appropriate, processing auxiliaries and, if appropriate, further antimicrobially active compounds.
- microbicidal compositions or concentrates used for protecting the industrial materials comprise the active compound mixture according to the invention in a concentration of from 0.01 to 95% by weight, in particular from 0.1 to 25% by weight.
- concentrations of the active compound mixture to be used according to the invention depend on the nature and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
- the optimum application rate can be determined by test series.
- the use concentrations are in the range of from 0.001 to 5% by weight, preferably from 0.01 to 1.5% by weight, based on the material to be protected.
- the active compound mixtures or compositions according to the invention have, compared to the microbicidal compositions known from the prior art, improved microbicidal activity. Furthermore, they have good stability and cover, in an advantageous manner, a broad activity spectrum.
- the active compound mixtures can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, pastes, soluble powders.
- the application is carried out in a customary manner, for example by spraying, spreading, dipping and industrial impregnation processes, for example vacuum, double-vacuum or pressure processes.
Abstract
Active compound mixtures comprising ipconazole and at least one further fungicidally active compound are highly suitable for protecting industrial materials against colonization and destruction by microorganisms.
Description
- 1. Field of the Invention
- The present invention relates to synergistic active compound mixtures comprising ipconazole and at least one further fungicidally active compound, microbicidal compositions based on these active compound mixtures and the use of these active compound mixtures, as well as compositions for protecting industrial materials.
- 2. Brief Description of the Prior Art
- From the literature, it is known that ipconazole has fungicidal properties and can be used for protecting industrial materials (cf. EP-A 341954). However, in protecting wood and wood composites, the antifungal action of ipconazole has been found to be insufficient against all wood-destroying organisms. Accordingly, it is an object of the present invention to improve the activity of ipconazole in the protection of industrial materials, in particular wood and wood composites.
- Surprisingly, it has now been found that mixtures of ipconazole with certain other fungicides have better microbicidal activity, in particular against wood-destroying organisms, compared with the activity of the sum of the individual active compounds.
- Accordingly, the present invention provides novel active compound mixtures comprising
-
- and
- b) at least one further fungicidally active compound.
- As can be seen from formula (I), the compounds of formula (I) can be present in the form of different stereoisomers. Accordingly, the present invention encompasses mixtures comprising the isomerically pure or isomerically enriched compounds of the formula (I) or the enantiomerically pure or enantiomerically enriched compound of the formula (I) or the racemate of the formula (I).
- The invention is described more fully hereunder with particular reference, but without limitation to its preferred embodiments. Preference is given to active compound mixtures according to the invention comprising, as further fungicidally active compound b), selected from the group of the metal salts or metal oxides, sulphamides, triazoles, imidazoles, benzimidazoles, morpholine derivatives, benzothiazoles, isothiazolinones, thiocyanates, quatemary ammonium compounds and guanidines, iodine derivatives, phenols, pyridines, methoxyacrylates and quinolines.
- Preferred compounds b) of the mixture from the group of the metal salts and oxides are, for example, salts of the metals, copper and zinc, such as, for example, copper hydroxycarbonate, copper sulphate, copper chloride, copper borate, zinc fluorosilicate, or oxides, such as, for example, oxides of the metals copper and zinc, such as, for example, Cu2O, CuO, ZnO.
- Preferred components b) of the mixture from the group of the sulphamides are, for example, dichlofluanid, tolylfluanid or fluorfolpet.
- Preferred components b) of the mixture from the group of the triazoles are, for example, azaconazoles, bitertanol, bromuconazole, cyproconazole, epoxyconazole, fluquinconazole, hexaconazole, metconazole, penconazole, propioconazole, tebuconazole, tetraconazole or triadimenol and their metal salts and acid adducts.
- Preferred components b) of the mixture from the group of the imidazoles are, for example, clotrimazole, climbazole, imazalil, ketoconazole or prochloraz and their metal salts and acid adducts.
- Preferred components b) of the mixture from the group of the benzimidazoles are, for example, carbendazim or thiabendazole or their salts.
- Preferred components b) of the mixture from the group of the morpholine derivatives are, for example, dodemorph, fenpropimorph, tridemorph, and their salts with arylsulphonic acids, such as, for example, p-toluenesulphonic acid and p-dodecylphenylsulphonic acid.
- Preferred components b) of the mixture from the group of the benzothiazoles are, for example, 2-mercaptobenzothiazole and benzothiophenes, such as, for example, N-cyclohexyl-benzo[b]thiophenecarboxamide S,S-dioxide or bethoxazin.
- Preferred components b) of the mixture from the group of the isothiazolinones are, for example, 4,5-dichloro-N-octylisothiazolin-3-one, N-octylisothiazolin-3-one or benzisothiazolinone.
- Preferred components b) of the mixture from the group of the thiocyanates are, for example, thiocyanatomethylthiobenzothiazole or methylenebisthiocyanate.
- Preferred components b) of the mixture from the group of the quatemary ammonium compounds and guanidines are, for example, benzalkonium chloride, benzyldimethyltetradecylammonium chloride, benzyldimethyl-dodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, didecyldimethylammonium chloride, dioctyldimethylammonium chloride, N-hexadecyltrimethylammonium chloride, didecylmethyl-poly(oxyethyl)ammonium propionate.
- Preferred components b) of the mixture from the group of the iodine derivatives are, for example, diiodomethyl-p-tolyl sulphone or 3-iodo-2-propynyl n-butylcarbamate.
- Preferred components b) of the mixture from the group of the phenols are, for example, tribromophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, dichlorophen, 2-benzyl4-chlorophenol, triclosan, diclosan, hexachlorophen, p-hydroxybenzoic esters, o-phenylphenol and their alkali metal and alkaline earth metal salts.
- Preferred components b) of the mixture from the group of the pyridines are, for example, 1-hydroxy-2-pyridinethione (and its Cu, Na, Fe, Mn, Zn salts) or tetrachloro-4-methylsulphonylpyridine.
- Preferred components b) of the mixture from the group of the methoxyacrylates are, for example, azoxystrobin or trifloxystrobin.
- Preferred components b) of the mixture from the group of the quinolines are, for example, quinoxyfen, 8-hydroxyquinoline and their Cu salts.
- Particularly preferred are mixtures of a) ipconazole of the formula (I) with at least one fungicidally active compound b) from the group consisting of:
- azaconazole, cyproconazole, fluquinconazole, hexaconazole, propioconazole, tebuconazole, triadimenol, climbazole, imazalil, prochloraz, dichlofluanid, tolylfluanid, thiabendazole, fenpropimorph, tridemorph, N-cyclohexyl-benzo[b]thiophenecarboxamide S,S-dioxide, bethoxazin, thiocyanatomethylthiobenzothiazole, benzalkonium chloride, didecyldimethylammonium chloride, didecylmethylpoly(oxyethyl)-ammonium propionate, 3-iodo-2-propynyl butylcarbamate, and trifloxystrobin.
- Especially preferred are mixtures of a) ipconazole of the formula (I) with at least one fungicidally action compound b) selected from the group consisting of:
- cyproconazole, fluquinconazole, tebuconazole, triadimenol, prochloraz, tolylfluanid, bethoxazin, benzalkonium chloride, didecyldimethylammonium chloride, didecyl-methylpoly(oxyethyl)ammonium propionate, 3-iodo-2-propynyl butylcarbamate.
- The weight ratios of the active compounds a) and b) in the active compound mixture according to the invention can be varied within a relatively wide range.
- However, if the active compounds a) and b) in the active compound mixtures according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. Accordingly, the present invention provides active compound mixtures comprising a synergistically effective amount of a) ipconazole of the formula (I) and a synergistically effective amount of at least one further fungicidally active compound b).
- Preferred are weight ratios of fungicidally active compound b) to a) ipconazole of from 1:20 to 20:1, particularly preferably from 1:4 to 4:1. If appropriate, the mixtures according to the invention may additionally comprise one or more of the following active compounds c):
- Insecticides:
- acetamiprid, allethrin, alpha-cypermethrin, beta-cyfluthrin, bifenthrin, bioallethrin, 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone (CAS-RN: 120955-77-3), chlorfenapyr, chlorpyrifos, clothianidin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, ethofenprox, fenoxycarb, fipronil, flufenoxuron, hexaflumuron, imidacloprid, nitenpyram, permethrin, pyriproxifen, silafluofen, tebufenozide, thiamethoxam, tralomethrin, triflumuron;
- Algicides:
- benzthiazuron, cybutrin, difenoxuron, diuron, dazomet, ethoxyfen, fluometuron, methabenzthiazuron, terbutryn.
- Preference is given to active compound mixtures according to the invention comprising, as further active compound c), at least one of the following insecticides and/or algicides:
- alpha-cypermethrin, bifenthrin, chlorfenapyr, clothianidin, cyfluthrin, cypermethrin, deltamethrin, fipronil, imidacloprid, permethrin, cybutrin, diuron, terbutryn.
- Particular preference is given to active compound mixtures according to the invention which, as further active compound c), comprise at least one of the following insecticides:
- alpha-cypermethrin, bifenthrin, chlorfenapyr, cypermethrin, fipronil, imidacloprid, permethrin;
- In the active compound mixture according to the invention, the active compounds c) are generally present in an amount of from 0.00001% by weight to 10% by weight, preferably from 0.0001% by weight to 5% by weight and particularly preferably from 0.001% by weight to 1% by weight.
- The active compound mixtures according to the invention can be prepared by mixing the individual components a) and b) and, if appropriate, c) with one another in a customary manner, if appropriate with addition of solvents and processing auxiliaries.
- The active compound mixtures according to the invention have strong microbicidal action and can be used for controlling microorganisms, such as, for example, fungi, bacteria and algae, in the protection of materials. The active compound combinations are preferably used for controlling microorganisms in the protection of wood.
- In the protection of materials, the active compound combinations according to the invention can be used for protecting industrial materials against colonization and destruction by microorganisms.
- The present invention furthermore provides the use of the mixtures according to the invention as microbicide for protecting industrial materials.
- In the present context, industrial materials are to be understood as meaning non-living materials which have been prepared for use in industry. The industrial materials are, for example, adhesives, sizes, paper and board, textiles, leather, wood, woodbased materials, paints and plastic articles, cooling lubricants and other materials which can be colonized or destroyed by microorganisms. Furthermore, in the context of the present invention, industrial materials are also to be understood as meaning parts of production plants, for example cooling-water circuits, which may be impaired by the proliferation of microorganisms. Industrial materials which are preferably protected are adhesives, sizes, paper and board, leather, wood, woodbased materials, paints, plastic articles, cooling lubricants and heat-transfer liquids.
- The active compound combinations according to the invention are particularly suitable for protecting wood, woodbased materials, plastics, cooling lubricants and coating systems, such as paints, varnishes or plaster, against colonization by microorganisms. The active compound combinations according to the invention are particularly preferably suitable for protecting wood, woodbased materials, plastics and coating systems, such as paints, varnishes or plaster, against colonization by microorganisms.
- Microorganisms capable of degrading or changing the industrial materials which may be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms. The active compound combinations according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and insects and against slime organisms and algae. Especially preferred is the action of the active compound combinations against wood-destroying fungi and insects.
- Wood which can be protected by the active compound combinations according to the invention or compositions comprising them is to be understood as meaning, for example: construction timber, wooden beams, railway sleepers, bridge components, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden claddings, windows and doors made from wood, plywood, chipboard, joiner's wood or woodbased materials which are quite generally used in domestic construction or in joinery.
- Particularly effective protection of wood is achieved by industrial-scale impregnating processes, for example vacuum, double-vacuum or pressure processes.
- The synergistic combinations claimed have particularly high microbicidal, in particular fungicidal, action, together with a broad activity spectrum against microorganisms encountered in the protection of materials; they are particularly effective against moulds, wood-discolouring and wood-destroying fungi.
- The following groups of microorganisms may be mentioned by way of example, but not by way of limitation:
- A. Wood-discolouring fungi:
- A1: Ascomycetes Ceratocystis, such asCeratocystis minor
- A2: Deuteromycetes:
- Aspergillus, such asAspergillus niger
- Aureobasidium, such asAureobasidium pullulans
- Dactylium, such asDactylium fusarioides
- Penicillium, such asPenicillium brevicaule or
-
- Sclerophoma, such asSclerophoma pithyophila
- Scopularia, such asScopularia phycomyces
- Trichoderma, such asTrichoderma viride or
-
- A3: Zygomycetes:
- Mucor, such asMucor spinorus
- Wood-destroying fungi:
- B1: Chaetomium, such asChaetomium globosum or
-
-
- Petriella, such asPetriella setifera
- Trichurus, such asTrichurus spiralis
- B2: Basidiomycetes
- Coniophora, such asConiophora puteana
- Coriolus, such asCoriolus versicolor
- Donkioporia, such asDonkioporia expans
- Glenospora, such asGlenospora graphii
- Gloeophyllum, such asGloeophyllum abietinum or
-
-
-
-
- Lentinus, such asLentinus cyathiformes or
-
-
-
-
- Paxillus, such asPaxillus panuoides
- Pleurotus, such asPleurotus ostreatus
- Poria, such asPoria monticola or
-
-
-
- Serpula, such asSerpula himantoides or
-
- Stereum, such asStereum hirsutum
- Tyromyces, such asTyromyces palustris
- The combinations according to the invention are highly suitable for protecting wood and woodbased materials against attack by wood-destroying insects, such as, for example,
- 1. Beetles
-
- 2. Hymenoptera
-
- 3. Termites
-
- Depending on their particular physical and/or chemical properties, the active compound mixtures can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances.
- These formulations can be produced in a known manner, for example by mixing the active compound mixture or the individual active compounds a) and b) and, if appropriate, c) with extenders, that is liquid solvents, liquefied gases under pressure and/or solid carriers, if appropriate 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, for example, organic solvents as auxiliary solvents. Essentially, 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 mineral oil fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water. 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, and also 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 natrual rocks, such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic materials 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, alkyl sulphates, arylsulphonates, and also protein hydrolysates. Suitable dispersants are, for example lignosulphite waste liquors and methylcellulose.
- Tackifiers such as carboxymethylcellulose and 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 be used in the formulations. Other possible additives are mineral and vegetable oils.
- It is possible to use colorants, such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- The formulations generally comprise between 0.1 and 95% by weight of active compound mixture, preferably between 0.5 and 25% by weight.
- The present invention furthermore provides microbicidal compositions based on the active compound combinations according to the invention, which compositions comprise at least one solvent or diluent and, if appropriate, processing auxiliaries and, if appropriate, further antimicrobially active compounds.
- The microbicidal compositions or concentrates used for protecting the industrial materials comprise the active compound mixture according to the invention in a concentration of from 0.01 to 95% by weight, in particular from 0.1 to 25% by weight.
- The concentrations of the active compound mixture to be used according to the invention depend on the nature and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimum application rate can be determined by test series. In general, the use concentrations are in the range of from 0.001 to 5% by weight, preferably from 0.01 to 1.5% by weight, based on the material to be protected.
- The active compound mixtures or compositions according to the invention have, compared to the microbicidal compositions known from the prior art, improved microbicidal activity. Furthermore, they have good stability and cover, in an advantageous manner, a broad activity spectrum.
- The active compound mixtures can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, pastes, soluble powders. The application is carried out in a customary manner, for example by spraying, spreading, dipping and industrial impregnation processes, for example vacuum, double-vacuum or pressure processes.
- Although the invention has been described in detail in the foregoing for the purpose of illustration, it is to be understood that such detail is solely for that purpose and that variations can be made therein by those skilled in the art without departing from the spirit and scope of the invention except as it may be limited by the claims.
Claims (10)
2. Active compound mixture according to claim 1 , characterized in that it comprises, as fungicidally active compound b), selected from the group of the metal salts or metal oxides, sulphamides, triazoles, imidazoles, benzimidazoles, morpholine derivatives, benzothiazoles, isothiazolinones, thiocyanates, quaternary ammonium compounds and guanidines, iodine derivatives, phenols, pyridines, methoxyacrylates and quinolines.
3. Active compound mixture according to claim 1 , characterized in that the weight ratio of the fungicidally active compound b) to ipconazole a) is from 1:20 to 20:1.
4. Active compound mixture according to claim 1 , characterized in that it comprises at least one further active compound c) from the group of the insecticides and/or algicides.
5. A process for protecting industrial materials comprising applying thereto active compound mixtures according to claim 1 as micro bicides.
6. A process according to claim 5 , characterized in that the industrial materials are wood, woodbased materials, plastics, cooling lubricants and coating systems, such as paints, varnishes or plaster.
7. Method for protecting industrial materials against colonization and/or destruction by microorganisms, comprising contacting the microorganism or its habitat with an active compound combination according to claim 1 .
8. Microbicidal composition, comprising an active compound combination according to claim 1 and at least one solvent and/or diluent and, optionally processing auxiliaries and, optionally further antimicrobially active compounds.
9. Composition according to claim 8 , characterized in that it comprises at least one further antimicrobially active compound from the group of the algicides and/or insecticides.
10. An article of matter containing industrial materials, treated with an active compound mixture according to claim 1.
Priority Applications (2)
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US12/691,816 US8758788B2 (en) | 2002-10-17 | 2010-01-22 | Fungicidally active compound combinations |
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DE10248335A DE10248335A1 (en) | 2002-10-17 | 2002-10-17 | Fungicidal active ingredient combinations |
DE10248335.3 | 2002-10-17 |
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EP (1) | EP1410714B1 (en) |
JP (1) | JP2004277405A (en) |
AU (3) | AU2003255175A1 (en) |
DE (2) | DE10248335A1 (en) |
DK (1) | DK1410714T3 (en) |
NZ (1) | NZ528889A (en) |
PL (1) | PL362944A1 (en) |
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US20060252847A1 (en) * | 2002-12-18 | 2006-11-09 | Hayward Peter J | Preservatives for wood-based products |
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DE102005006420A1 (en) * | 2005-02-12 | 2006-08-31 | Lanxess Deutschland Gmbh | Fungicidal mixtures for wood protection |
CN100362919C (en) * | 2005-04-27 | 2008-01-23 | 鞍山科技大学 | Green trichodermin enoyl morpholine water dispersion tablet or granule and production thereof |
DE102005043428A1 (en) * | 2005-09-13 | 2007-03-15 | Lanxess Deutschland Gmbh | Use of triclosan for wood preservation |
DE102005043427A1 (en) * | 2005-09-13 | 2007-03-15 | Lanxess Deutschland Gmbh | Use of diclosan for wood preservation |
WO2007062802A2 (en) * | 2005-11-29 | 2007-06-07 | Syngenta Participations Ag | Synergistic fungicidal compositions comprising chlorothalonil and ipconazol |
GB201010439D0 (en) | 2010-06-21 | 2010-08-04 | Arch Timber Protection Ltd | A method |
GB201119139D0 (en) | 2011-11-04 | 2011-12-21 | Arch Timber Protection Ltd | Additives for use in wood preservation |
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DK1410714T3 (en) | 2007-01-02 |
US20100184757A1 (en) | 2010-07-22 |
AU2003255175A1 (en) | 2004-05-06 |
DE50304722D1 (en) | 2006-10-05 |
AU2009202330B2 (en) | 2012-03-08 |
AU2009202330A1 (en) | 2009-07-02 |
JP2004277405A (en) | 2004-10-07 |
NZ528889A (en) | 2005-07-29 |
EP1410714B1 (en) | 2006-08-23 |
EP1410714A1 (en) | 2004-04-21 |
AU2012203397A1 (en) | 2012-06-28 |
PL362944A1 (en) | 2004-04-19 |
US8758788B2 (en) | 2014-06-24 |
DE10248335A1 (en) | 2004-05-06 |
US20080108680A1 (en) | 2008-05-08 |
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