NO321617B1 - Anvendelse av cyproconazoler og fremgangsmate til beskyttelse av tekniske materialer, samt tekniske materialer inneholdende cyproconazoler - Google Patents
Anvendelse av cyproconazoler og fremgangsmate til beskyttelse av tekniske materialer, samt tekniske materialer inneholdende cyproconazoler Download PDFInfo
- Publication number
- NO321617B1 NO321617B1 NO19996481A NO996481A NO321617B1 NO 321617 B1 NO321617 B1 NO 321617B1 NO 19996481 A NO19996481 A NO 19996481A NO 996481 A NO996481 A NO 996481A NO 321617 B1 NO321617 B1 NO 321617B1
- Authority
- NO
- Norway
- Prior art keywords
- technical materials
- cyproconazoles
- acid
- protection
- wood
- Prior art date
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- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000028644 hyphal growth Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- MOQRZWSWPNIGMP-UHFFFAOYSA-N pentyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCC MOQRZWSWPNIGMP-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920006215 polyvinyl ketone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 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
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003171 wood protecting agent 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, 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
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, 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
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/343—Heterocyclic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, 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
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/50—Mixtures of different organic impregnating agents
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Saccharide Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Pyridine Compounds (AREA)
Abstract
Det er beskrevet anvendelsen av cyprokonazoler av formelen deres metallsalter eller syreaddisjonsforbindelser som mikrobicid til beskyttelse av tekniske materialer mot innenfor materialbeskyttelse relevante mikroorganismer, hvor tekniske materialer ikke omfatter tre og murverk.
Description
Den foreliggende oppfinnelsen vedrører anvendelse av cyproconazoler, en fremgangsmåte til beskyttelse av tekniske materialer, samt tekniske materialer inneholdende cyproconazoler, hvor tre og murverk er unntatt som tekniske materialer.
Det er kjent at azolderivatene som er beskrevet i DE-OS 3406993 kan bli anvendt til beskyttelse av planter.
Gjenstand for foreliggende oppfinnelse er anvendelse av et cyproconazoler med formelen (I)
dens metallsalter eller syreaddisjonsforbindelser som mikrobicid for beskyttelse av tekniske materialer, mot innenfor materialbeskyttelse relevante mikroorganismer, hvor som tekniske materialer tre og murverk er unntatt.
Cyproconazolene som er azolderivater kan ikke bare foreligge i form av fri base, men også i form av et metallsaltkompleks eller som syreaddisjonssalt. Som metallsalt er det fortrinnsvis aktuelt med salter av metaller fra II. til IV.-hovedgruppe og I. og II. så vel som IV. til Vn.-bigruppe i det periodiske system, som eksempel kan nevnes kobber, sink, mangan, magnesium, tinn, jern, kalsium, aluminium, bly, krom, kobolt og nikkel.
Som anioner av salter er det aktuelt med slike som fortrinnsvis avledes fra følgende syrer: halogenhydrogensyrer, som for eksempel hydrogenklorid og hydrogenbromid, videre fosforsyre, salpetersyre og svovelsyre.
Metallsaltkompleksene av azolderivater kan oppnås på enkel måte via vanlige fremgangsmåter, som for eksempel ved oppløsning av metallsalt i alkohol, for eksempel etanol og tilsetning av azolfungicid. Man kan isolere metallsaltkompleksene på kjent måte, f.eks. ved avfiltrering og eventuelt rensing ved omkrystallisering.
For fremstilling av syreaddisjonssaltene av azolderivatene er det fortrinnsvis aktuelt med følgende syrer: halogenhydrogensyrene, som f.eks. hydrogenklorid og hydrogenbromid, særlig hydrogenklorid, videre fosforsyre, salpetersyre, svovelsyre, mono- og bifunksjonelle karboksylsyrer og hydroksykarboksylsyrer, som f.eks. eddiksyre, propionsyre, 2-etylheksansyre, smørsyre, mandelsyre, oksalsyre, ravsyre, 2-hydroksyetan-dikarboksylsyre, maleinsyre, fumarsyre, vinsyre, sitronsyre, salicylsyre, sorbinsyre, melkesyre så vel som sulfonsyrer, som f.eks. p-toluensulfonsyre, p-decyl-fenylsulfonsyre, p-dodecyl-fenylsulfonsyre, 1,4-naftalindisulfonsyre, alkansulfonsyrer, benzosyre og eventuelt substituerte benzosyrer.
Syreaddisjonssaltene av forbindelsene kan oppnås på enkel måte via vanlige saltdannelsesmetoder, f.eks. ved oppløsning av en forbindelse i et egnet inert oppløsningsmiddel og tilførsel av syre, f.eks. hydrogenklorid, og de kan bli isolert på kjent måte, f.eks. ved avfiltrering og eventuelt kan de bli renset via vasking med et inert organisk oppløsningsmiddel.
Spesielt foretrukket er forbindelsen (R<*>, R<*>)-a-(4-klorfenyl)-a-(l-cyklopropyletyl)lH-1,2,4-triazol-l-etanol (cyproconazol).
Videre angår oppfinnelsen en fremgangsmåte for beskyttelse av tekniske materialer unntatt tre og murverk, kjennetegnet ved at man behandler disse materialer med cyproconazoler av formelen (I)
Foreliggende oppfinnelse angår også tekniske materialer unntatt tre og murverk, kjennetegnet ved at de inneholder en forbindelse av formelen (I)
På overraskende måte viser disse forbindelsene en spesielt høy mikrobicid, særlig fungicid virkning, forbundet med et bredt virkningsspektrum mot relevante mikroorganismer innenfor materialbeskyttelse; de er fremfor virksomme mot muggsopper, sopper som misfarger og ødelegger tre. Beskyttelse av tre og murverk er ikke omfattet av foreliggende oppfinnelse. Det kan for eksempel nevnes følgende grupper av mikroorganismer, uten å være begrenset til disse:
A: tremisfargende sopper:
Al: Ascomyceter:
Ceratocystis som Ceratocystis minor
A2: Deuteromyceter:
Aspergillus som Aspergillus niger
Aureobasidium som Aureobasidium pullulans
Dactylium som Dactylium fusarioides
Penicillium som Penicillium brevicaule eller
Penicillium variabile
Sclerophoma som Schlerophoma pithyophila
Scopularia som Scopularia phycomyces
Trichoderma som Trichoderma viride eller
Trichoderma lignorum
A3: Zygomyceter:
Mucor som Mucor spinorus
B: Treødeleggende sopper:
Bl: Ascomyceter:
Chaetomium som Chaetomium globusum eller
Chaetomium alba-arenulum
Humicola som Humicola grisea
Petriella som Petriella setifera
Trichurus som Trichurus spiralis
B2: Basidiomyceter:
Coniophora som Coniophora puteana
Coriolus som Coriolus versicolor
Donkioporia som Donkioporia expansa
Glenospora som Glenospora graphii
Gloeophyllum som Gloeophyllum abietinum eller
Gloeophyllum adoratum eller Gl. protactum eller
Gloeophyllum sepiarium eller Gl. trabeum
Lentinus som Lentinus cyathiformes eller
Lentinus edodes eller Lentinus lepideus eller
Lentinus grinus eller L. squarrolosus
Paxillus som Paxillus panuoides
Pleurotus som Pleurotis ostreatus
Poria som Poria monticola eller Poria placenta
eller Poria vaillantii eller Poria vaporaria
Serpula som Serpula himantoides eller Serpula
lacrymans
Stereum som Stereum hirsutum
Tyromyces som Tyromyces palustris
B3: Deuteromyceter
Altemaria som Alternaria tenius
Cladosporium som Cladosporium herbarum
Mengden av det anvendte virkestoffet er avhengig av type og den forekommende mikroorganismens kimtall og mediet. Den optimale anvendelsesmengden kan bli bestemt ved anvendelse av testrekker. Generelt er det imidlertid tilstrekkelig å anvende 0,001 til 20 vekt-%, fortrinnsvis 0,05 til 10 vekt-% av virkestoffet, med hensyn til materialet som skal beskyttes.
Virkestoffet kan anvendes slik det er, i form av konsentrat eller generelt vanlige formuleringer som pulver, granulater, oppløsninger, suspensjoner, emulsjoner eller pastaer.
De nevnte formuleringene kan bli fremstilt på i og for seg kjent måte, for eksempel ved blanding av virkestoffet med minst et oppløsnings- henholdsvis fortynningsmiddel, emulgator, dispergerings- og/eller binde- eller fikseringsmiddel, vann-frastøter, eventuelle sikkativer og UV-stabilisatorer og eventuelle fargestoffer og pigmenter så vel som ytterligere bearbeidingshjelpemidler.
Når det gjelder oppløsnings- henholdsvis fortynningsmidler, er det aktuelt med organisk-kjemiske oppløsningsmidler eller oppløsningsmiddelblandinger og/eller et polart organisk oppløsningsmiddel eller oppløsningsmiddelblandinger og/eller et oljeaktig henholdsvis oljeaktig organisk-kjemisk oppløsningsmiddel eller oppløsningsmiddelblanding og/eller vann med eventuelt en emulgator og/eller tverrbindingsmiddel. Som vanlige tungtflyktige vannuløselige oljer eller oljeaktige oppløsningsmidler blir det fortrinnsvis anvendt de vanlige mineraloljene/- mineraloljeholdige oppløsningsmiddelblandingene eller deres aromatfraksjoner. Fortrinnsvis skal det nevnes testbensin, petroleum eller alkylbenzoler, ved siden av spindelolje og monoklomaftalin. Kokeområdene til disse tungtflyktige oppløsningsmiddel(blandingene) strekker seg over et område fra ca. 170°C til maksimalt 350°C.
De foran beskrevne tungtflyktige oljene eller oljeaktige opp løsningsmidlene kan bli delvis erstattet ved lett flyktige organisk-kjemiske oppløsningsmidler.
For fremstilling av et trebeskyttelsesmiddel kan en del av de ovenfor beskrevne oppløsningsmidlene eller oppløsningsmiddelblandingene erstattes med et polart organisk-kjemisk oppløsningsmiddel eller oppløsningsmiddelblanding. Fortrinnsvis anvendes oppløsningsmidler som inneholder hydroksylgrupper, estergrupper, etergrupper eller blandinger som inneholder disse funksjonaliteten og det kan for eksempel nevnes at man kan benytte ester eller glukoleter. Som bindemiddel forstår man ifølge oppfinnelsen vannfortynnbare henholdsvis i organiskkjemisk oppløsningsmiddelløselige, disperger- eller emulgerbare kunstharpikser, bindende tørkende oljer, for eksempel på basis av akrylharpikser, vinylharpikser, polyesterharpikser, polyuretanharpikser, alkydharpikser, fenolharpikser, hydrokarbonharpikser, silikonharpikser. Det benyttende oppløsningsmiddel kan anvendes som løsning, emulsjon eller dispersjon. Fortrinnsvis blir det anvendt blandinger av alkylharpikser og tørkede plantehoIdige oljer. Spesielt foretrukket er alkydharpikser med en oljeandel mellom 45 og 70%.
Det nevnte bindemiddel kan erstatter helt eller delvis med et fikseringsmiddel(blanding) eller en mykgjører(blanding). Disse tilsetningsstoffene skal forebygge en flyktiggjøring av virkestoffet så vel som en krystallisasjon henholdsvis utfelling. De kan erstatte 0,01 til 30 vekt-% bindemiddel (med hensyn på 100% av anvendt bindemiddel). Mykgjøreren stammer fråden kjemiske klassen av ftalsyreester som dibutyl-, dioktyl-eller benzylbutylftalat, fosforsyreester som tributylfosfat, adipinsyreester som di-(2-etylheksyl)-adipat, stearat som butylstearat og amylstearat, oleat som butyloleat, glycerineter eller høyeremolekylær glykoleter, glycerinester så vel som p-toluensulfon-syreester.
Fikseringsmidler baserer seg kjemisk på polyvinylalkyletere som for eksempel polyvinylmetyleter eller ketoner som benzofenon, etylenbenzofenon.
Som oppløsningsmiddel henholdsvis fortynningsmiddel er det aktuelt med vann, eventuelt i blanding med et eller flere av de ovenfor nevnte løsnings- henholdsvis fortynningsmidler, emulgatorer og dispergatorer.
Tekniske materialer er ifølge oppfinnelsen ikke levende materialer, som er blitt bearbeidet for anvendelse innenfor teknikken, dog unntatt tre og murverk. Eksempler på tekniske materialer som skal beskyttes av virkestoffet mot mikrobiologisk forandring eller ødeleggelse, er klebestoffer, lim, papir og kartong, tekstiler, lær, overflatebeskyttelsesmidler og kunststoffartikler, kjølesmøremidler og andre materialer, som kan bli angrepet av mikroorganismer eller som kan bli ødelagt. Innenfor rammen av de materialer som skal beskyttes kan det også nevnes deler av produksjonsanlegg, for eksempel kjølevannskretsløp, som kan bli påvirket av formering av mikroorganismer. Foretrukne tekniske materialer i forbindelse med foreliggende oppfinnelse er klebestoffer, lim, papir og kartong, lær, overflatebeskyttelsesmidler, kjølesmøremiddel, vandige hydraulikkvæsker og kjølekretsløp.
Virkestoffet med formel (I) kan blandes med minst ett videre antimikrobiologisk virksomt stoff, fungicid og særlig med andre virkestoffer for å forsterke virkespekteret eller for å oppnå spesielle effekter. I flere tilfeller oppnår man derved synergistisk effekt, dvs. virkningen til blandingen er større enn virkningen til enkeltkomponentene. Spesielt fordelaktige blandingspartnere er følgende forbindelser: Sulfenamider som diklorfluanid, tolylfluanid, folpet, fluorfolpet;
benzimidazoler som karbendazim, benomyl, fuberidazol, tiabendazol eller deres salter;
tiocyanater som tiocyanatometyltiobenzotiazol, metylenbistiocyanat;
kvartere ammoniumforbindelser som benzyldimetyltetradecylammoniumklorid, benzyldimetyldodecylairunoniumklorid, didecyldimerylainmoniumklorid;
morfolinderivater som tridemorf, fenpropimorf, falimorf;
azoler som triadimefon, triadimenol, bitertanol, tebuconazoler, propikonazoler, azakonazoler, heksakonazoler, prokloraz, bromukonazoler, metkonazoler, penkonazoler, difenokonazoler, fenbendazoler, opus, fensilazoler;
2- (l-klorcyklopropyl)-l-(2-klorfenyl)-3-(l,2,4-triazol-l-yl)-propan-2-ol;
jodderivater som dijodmetyl-p-tolylsulfon, 3-jod-2-propionyl-alkohol, 4-klorfenyl-3-jodpropargylformal, 3-brom-2,3-dijod-2-propenyletylkarbonat, 2,3,3-trijodallylalkohol, 3- brom-2,3-dij od-2-propenylalkohol, 3-jod-2-propinyl-n-butyIkarbamat, 3-jod-2-propinyl-n-heksylkarbamat, 3-jod-2-propinyl-cykloheksylkarbamat, 3-jod-2-propinyl-fenylkarbamat, O-1 -(6-jodo-3-okso-heks-5-inyl)butylkarbamat, O-1 -(6-j odo-3 -okso-heks-5-inyl)fenylkarbamat, napkocider;
fenolderivater som tribromfenol, tetraklorfenol, 3-metyl-4-klorfenol, diklorofen, o-fenylfenol, m-fenylfenol, p-fenylfenol, 2-benzyl-4-klorfenol;
bromderivater som 2-brom-2-nitro-l,3-propandiol, 2-brom-2-brommetyl-glutardinitriI;
isotiazolinoner som N-metylisotiazoIin-3-on, 5-kloro-N-rnetyl-isotiazolin-3-on} 4,5-diklor-N-oktylisotiazolin-3-on, N-oktyl-isotiazolin-3-on;
benzisotiazolinoner som 4,5-trimetylen-N-meetylisotiazol-3-on;
pyridiner som l-hydroksy-2-pyridintion (og deres Na-, Fe-, Mn-, Zn-salter), tetraklor-4-metylsulfonylpyridin;
metallsåper som tinn-, kobber-, sinknaftenat, -oktoat, -2-etylheksanoat, -oleat, -fosfat, - benzoat;
metallsalter og -oksider som tributyltinnoksid, CU2O, CuO, ZnO, CUSO4, CuCl2, kobberborater, kobberfluorsilikater, natriumdikromat, kaliumdikromat, kobberhydroksy-karbonat;
dialkylditiokarbamater som Na- og Zn-salter av dialkyl-ditiokarbamater, tetrametyltiuramdisulfid;
nitriler som 2,4,5,6-tetrakloirsoftalodintril;
benztiazoler som 2-merkaptobenzotiazol;
kinoliner som 8-hydroksykinolin og deres Cu-salter;
borforbindelser som borsyre, borsyreester, boraks;
formaldehyd og formaldehydavspaltende forbindelser som benzylalkoholmono(poly)-hemiformal, oksazolidiner, heksahydro-S-triaziner, N-metylolkloracetamid, para-formaldehyd;
tris-N-(cykloheksyldiazeruumdioksy)-alumiruum,N-(cykloheksyldiazeruumdioksy)-tributyltinn henholdsvis K-salter, Bis-N-(cykloheksyldiazeniumdioksy)-kobber.
Som insekticider kan det anvendes:
fosforsyreester som azinofs-etyl, azinfos-metyl, l-84-klorfenyl)-4-(0-etyl, S-propyl)fosforyloksy-pyrazol, klorpyrifos, økoumafos, demeton, demeton-S-metyl, diazinon, diklorfos, dimetoater, etoprofos, etrimfos, fenitrotion, fention, heptenofos, paration, paration-metyl, fosaloner, foksim, pirimifos-etyl, pirimifos-metyl, profenofos, protiofos, sulfprofos, triazofos og trikloron;
karbamagter som aldikarb, bendiokarb, 2-(l-metylpropyl)-fenylmetylkarbamat, butokarboksim, butoksykarboksim, karbaryl, karbofuran, karbosulfan, kloetokarb, isoprokarb, metomyl, oksamyl, pirimikarb, promekarb, propoksur og tiodikarb;
organosilisiumforbindelser, fortrinnsvis dimetyl(fenyl)silyl-metyl-3-fenoksybenzyleter som dimetyl(4-etoksyfenyl)-silylmetyl-3-fenoksybenzyleter eller (dimetylfenyl)-silyl-metyl-2-fenoksy-6-pyridylmetyleter som for eksempel dimetyl(9-etoksyfenyl)-silylmetyl-2-fenoksy-6-pyridylmetyleter eller [{fenyl)-3-(3-fenoksyfenyl)-propyl]-(dimetyl)-silaner som for eksempel (4-etoksyfenyl)-[3-(4-fiuoro-3-fenoksyfenyl-propyl]-dimetylsilan,
pyretroider som alletrin, alfametrin, bioresmetrin, byfentrin, cykloprotrin, cyflutrin, dekaametrin, cyhalotrin, cypermetrin, deltametrin, alfa-cyano-3 - fenyl-2 -metylbenzyl-2,2-mmetyl-3-(2-klor-2-trifiuor-metylvinyl)cyklopropankarb fenpropatrin, fenflutrin, fenvaleratr, flucytrinater, fiumetrin, fluvalinater, permetrin, resmetrin og tralometrin;
nitroiminer og nitrometylener som l-Kå-klor-S-pyridinylJ-metylJ-^S-dihydro-N-nitro-1 H-imidazol-2 -amin (imidakloprid), N- [(6-kor-3 -pyridnyl) -metyl- ]N2-cyano-N 1 - metylacetamid.
Slike blandinger, konsentrater og formuleringer viser virkning ikke bare mot de forannevnte soppene, men også mot materialødeleggende insekter, dersom et insekticid er tilsatt. Som eksempler, uten å begrense, skal det som materialødeleggende insekter nevnes:
A: årevingede insekter:
Sirex juvencus
Urocerus augur
Urocerus gigas
Urocerus gigas taignus
B: Biller:
Anobium punctatum
Apate monachus
Bostrychus capucins
Chlorophores pilosus
Dendrobium pertinex
Dinoderus minutus
Ernobius mollis
Heterobostrychus brunneus
Hylotrupes bajulus
Lyctus afncanus
Lyctus brunneus
Lyctus linearis
Lyctus planicollis
Lyctus pubescens
Minthea rugicollis
Priobium carpini
Ptilinus pecticornis
Sinoxylon spee.
Trogoxylon aequale
Trypto dendron spee.
Xestobium rufovillosum
Xyleborus spee.
C: Termitter:
Coptotermes formosanus
Cryptotermes brevis
Heterotermes indicola
Kalotermes flavicolHs
Mastotermes darwiniensis
Reticulitermes flavipes
Reticulitermes lucifugus
Reticulitermes santonensis
Zootermopsis nevadensis
Andre virkestoffer som kommer i betraktning er algicider, moUuskicider, virkestoffer mot sjødyr, som slår seg ned for eksempel på skipsbunnmalinger.
Spesielt foretrukket er følgende blandingspartnere:
diklofluanid, tolylfluanid,
benzyldimetyldodecylammoniumklorid, didecyldimetylammoniumklorid,
tebukonazoler, propikonazoler, azakonazoler, heksakonazoler,
3-brom-2,3-dijod-2-propenylalkohol, 3-(jod-3-propinyl-n-butylkarbamat,
a-fenylfenol, m-fenylfenol, p-fenylfenol, 3-meryl-4-klorfenol,
tiocyanatometyltiobenzotiazol,
N-metylisotiazolin-3-on, 5-kloro-N-metylisotiazolin-3on, 4,5-dikloro-N-oktylisotiazolin-3 -on, N-oktyl-isotiazolin-3-on,
benzylalkoholmono(poly)-hemiformal, N-metylolkloracetamid,
foksim,
cyflutrin, permetrin, cypermetrin, deltameterin, imidakloprid.
Mikrobiocidmidler som anvendes til beskyttelse av tekniske materialer eller konsentrater kan inneholde virkestoffet med formel (I) i en konsentrasjon fra 0,01 til 95 vekt-%, særlig 0,01 til 60 vekt-%, ved siden av 0,001 til 95 vekt-% av en eller flere ytterligere egnede fungicider, insekticider eller andre virkestoffer som nevnt over.
Midlene gjør det mulig på fordelaktig måte å erstatte de til nå anvendte mikrobiocid-midlene på en effektiv måte. De viser en god stabilitet og har på fordelaktig måte et bredt virkningsspektrum.
Eksempel 1
Hemmingstest på store kolonier av basidiomyceter
Fra koloner av Gloeophyllum trabeum, Coniophora puteana, Poria placenta, Lentinus tigrinus, Coriolus versicolor og Stereum sanguinolentum blir det stanset ut mycelstykker og disse blir inkubert på et maltekstrakt-pepton-holdig agamæringsmaterialer ved 26°C. Hemmingen av hyfevekst på det materialholdige næringsgulvet blir sammenlignet med lengdevekst på næringsgulvet uten materialtilsetning og bonitert som prosentuell hemming.
Ved en konsentrasjon på 10 ppm oppnår man med forbindelsen cyproconazol en 100% hemming.
Claims (4)
1.
Anvendelse av cyproconazoler av formelen (I)
deres metallsalter eller syreaddisjonsforbindelser som mikrobicid til beskyttelse av tekniske materialer mot innenfor materialbeskyttelse relevante mikroorganismer, hvor som tekniske materialer tre og murverk er unntatt.
2.
Anvendelse ifølge krav 1 til beskyttelse av klebemidler, lim, papir og kartong, tekstiler, lær, malinger og plastartikler, kjølesmøremidler, vandige hydraulikvæsker og kjølekretsløp.
3.
Fremgangsmåte til beskyttelse av tekniske materialer unntatt tre og murverk, karakterisert ved at man behandler disse materialer med cyproconazoler av formelen (I)
4.
Tekniske materialer unntatt tre og murverk, karakterisert ved at de inneholder en forbindelse av formelen (I)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4233337A DE4233337A1 (de) | 1992-10-05 | 1992-10-05 | Mikrobizide Mittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO996481L NO996481L (no) | 1994-04-06 |
| NO996481D0 NO996481D0 (no) | 1999-12-27 |
| NO321617B1 true NO321617B1 (no) | 2006-06-12 |
Family
ID=6469595
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19933352A NO306971B1 (no) | 1992-10-05 | 1993-09-21 | Kombinasjon av cyprokonazol med tebukonazol eller propikonazol, anvendelse herav og middel og tekniske materialer inneholdende kombinasjonen samt fremgangsmåte for beskyttelse av tekniske materialer |
| NO19996482A NO321618B1 (no) | 1992-10-05 | 1999-12-27 | Anvendelse av en kombinasjon inneholdende cyproconazoler, en fremgangsmate til beskyttelse av tekniske materialer, middel inneholdende cyproconazoler, samt tekniske materialer. |
| NO19996481A NO321617B1 (no) | 1992-10-05 | 1999-12-27 | Anvendelse av cyproconazoler og fremgangsmate til beskyttelse av tekniske materialer, samt tekniske materialer inneholdende cyproconazoler |
| NO19996480A NO321616B1 (no) | 1992-10-05 | 1999-12-27 | Anvendelse av en synergistisk effektiv blanding omfattende cyproconazol, blandinger omfattende cyproconazol, fremgangsmate for beskyttelse av tekniske materialer, samt tekniske materialer og midler inneholdende en slik blanding. |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19933352A NO306971B1 (no) | 1992-10-05 | 1993-09-21 | Kombinasjon av cyprokonazol med tebukonazol eller propikonazol, anvendelse herav og middel og tekniske materialer inneholdende kombinasjonen samt fremgangsmåte for beskyttelse av tekniske materialer |
| NO19996482A NO321618B1 (no) | 1992-10-05 | 1999-12-27 | Anvendelse av en kombinasjon inneholdende cyproconazoler, en fremgangsmate til beskyttelse av tekniske materialer, middel inneholdende cyproconazoler, samt tekniske materialer. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19996480A NO321616B1 (no) | 1992-10-05 | 1999-12-27 | Anvendelse av en synergistisk effektiv blanding omfattende cyproconazol, blandinger omfattende cyproconazol, fremgangsmate for beskyttelse av tekniske materialer, samt tekniske materialer og midler inneholdende en slik blanding. |
Country Status (11)
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| US (3) | US20010051649A1 (no) |
| EP (4) | EP0884149B1 (no) |
| JP (1) | JP3216946B2 (no) |
| AT (3) | ATE320891T1 (no) |
| CA (1) | CA2107502C (no) |
| DE (5) | DE4233337A1 (no) |
| DK (3) | DK0591764T3 (no) |
| ES (3) | ES2133342T5 (no) |
| FI (1) | FI111794B (no) |
| NO (4) | NO306971B1 (no) |
| PT (2) | PT884149E (no) |
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| AU689480B2 (en) * | 1993-06-21 | 1998-04-02 | Bayer Aktiengesellschaft | Fungicidal active-substance combination |
| DE4426753A1 (de) | 1994-07-28 | 1996-02-01 | Bayer Ag | Mittel zur Bekämpfung von Pflanzenschädlingen |
| NZ523237A (en) * | 2002-12-18 | 2005-10-28 | Lanxess Deutschland Gmbh | Improvements in preservatives for wood-based products |
| JP4644238B2 (ja) * | 2007-10-09 | 2011-03-02 | タイメイテック株式会社 | 防汚塗料 |
| 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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| RU2620650C2 (ru) * | 2015-11-19 | 2017-05-29 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Башкирский государственный университет" | Антисептик нефтяной для пропитки древесины |
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| DK0556157T3 (da) * | 1992-02-13 | 1998-08-10 | Novartis Ag | Fungicide blandinger på basis af triazol-fungicider og et 4,6-dimethyl-N-phenyl-2-pyrimidinamin. |
| GB9204878D0 (en) † | 1992-03-05 | 1992-04-22 | Sandoz Ltd | Fungicidal compositions |
| DE4228793A1 (de) * | 1992-08-29 | 1994-03-10 | Hoechst Ag | 2-Arylhydrazono-3-ketosäure-piperidide, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel, insbesondere Fungizide |
| DE4233337A1 (de) * | 1992-10-05 | 1994-04-07 | Bayer Ag | Mikrobizide Mittel |
| AU689480B2 (en) * | 1993-06-21 | 1998-04-02 | Bayer Aktiengesellschaft | Fungicidal active-substance combination |
| US5373934A (en) | 1993-12-10 | 1994-12-20 | Aluminum Company Of America | Bottle-gripping insert element |
-
1992
- 1992-10-05 DE DE4233337A patent/DE4233337A1/de not_active Withdrawn
-
1993
- 1993-09-21 NO NO19933352A patent/NO306971B1/no not_active IP Right Cessation
- 1993-09-22 AT AT98113739T patent/ATE320891T1/de active
- 1993-09-22 PT PT98113739T patent/PT884149E/pt unknown
- 1993-09-22 EP EP98113739A patent/EP0884149B1/de not_active Expired - Lifetime
- 1993-09-22 ES ES93115261T patent/ES2133342T5/es not_active Expired - Lifetime
- 1993-09-22 DE DE59310387T patent/DE59310387D1/de not_active Expired - Lifetime
- 1993-09-22 AT AT98113740T patent/ATE320892T1/de active
- 1993-09-22 ES ES98113740T patent/ES2259195T3/es not_active Expired - Lifetime
- 1993-09-22 EP EP93115261A patent/EP0591764B2/de not_active Expired - Lifetime
- 1993-09-22 PT PT98113740T patent/PT884150E/pt unknown
- 1993-09-22 DE DE59309573T patent/DE59309573D1/de not_active Expired - Lifetime
- 1993-09-22 DK DK93115261T patent/DK0591764T3/da active
- 1993-09-22 EP EP98113740A patent/EP0884150B1/de not_active Expired - Lifetime
- 1993-09-22 DK DK98113739T patent/DK0884149T3/da active
- 1993-09-22 AT AT93115261T patent/ATE179922T1/de active
- 1993-09-22 DE DE59310388T patent/DE59310388D1/de not_active Expired - Lifetime
- 1993-09-22 DE DE59310386T patent/DE59310386D1/de not_active Expired - Lifetime
- 1993-09-22 ES ES98113739T patent/ES2260811T3/es not_active Expired - Lifetime
- 1993-09-22 DK DK98113740T patent/DK0884150T3/da active
- 1993-09-22 EP EP98113741A patent/EP0878281B1/de not_active Expired - Lifetime
- 1993-09-30 JP JP26555993A patent/JP3216946B2/ja not_active Expired - Lifetime
- 1993-10-01 CA CA002107502A patent/CA2107502C/en not_active Expired - Lifetime
- 1993-10-01 FI FI934318A patent/FI111794B/fi not_active IP Right Cessation
-
1999
- 1999-12-27 NO NO19996482A patent/NO321618B1/no unknown
- 1999-12-27 NO NO19996481A patent/NO321617B1/no unknown
- 1999-12-27 NO NO19996480A patent/NO321616B1/no unknown
-
2001
- 2001-07-10 US US09/902,328 patent/US20010051649A1/en not_active Abandoned
- 2001-07-10 US US09/901,979 patent/US7307070B2/en not_active Expired - Fee Related
-
2007
- 2007-10-31 US US11/932,337 patent/US20080044492A1/en not_active Abandoned
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