NO176088B - Trevirkebeskyttelsesmiddel og anvendelse derav - Google Patents
Trevirkebeskyttelsesmiddel og anvendelse derav Download PDFInfo
- Publication number
- NO176088B NO176088B NO884758A NO884758A NO176088B NO 176088 B NO176088 B NO 176088B NO 884758 A NO884758 A NO 884758A NO 884758 A NO884758 A NO 884758A NO 176088 B NO176088 B NO 176088B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- water
- wood
- wood preservative
- benzimidazole
- Prior art date
Links
- 239000003171 wood protecting agent Substances 0.000 title claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002023 wood Substances 0.000 claims description 30
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 14
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- -1 dimethyl alkylamine Chemical class 0.000 claims description 6
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 claims description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229920000847 nonoxynol Polymers 0.000 claims description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 2
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 abstract 1
- LKUBWDNDGBVKFK-UHFFFAOYSA-N methyl 1h-benzimidazole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)=NC2=C1 LKUBWDNDGBVKFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 241000233866 Fungi Species 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005470 impregnation Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RYAUSSKQMZRMAI-YESZJQIVSA-N (S)-fenpropimorph Chemical compound C([C@@H](C)CC=1C=CC(=CC=1)C(C)(C)C)N1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-YESZJQIVSA-N 0.000 description 1
- TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- LWPLSMSFAZPBGO-UHFFFAOYSA-N 1-dodecyl-2h-pyridine;hydrochloride Chemical compound Cl.CCCCCCCCCCCCN1CC=CC=C1 LWPLSMSFAZPBGO-UHFFFAOYSA-N 0.000 description 1
- HILAYQUKKYWPJW-UHFFFAOYSA-N 1-dodecylguanidine Chemical compound CCCCCCCCCCCCN=C(N)N HILAYQUKKYWPJW-UHFFFAOYSA-N 0.000 description 1
- LEHNQGSPRXHYRT-UHFFFAOYSA-N 2-dodecyl-1h-imidazole Chemical compound CCCCCCCCCCCCC1=NC=CN1 LEHNQGSPRXHYRT-UHFFFAOYSA-N 0.000 description 1
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 description 1
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 1
- SBUKOHLFHYSZNG-UHFFFAOYSA-N 4-dodecyl-2,6-dimethylmorpholine Chemical compound CCCCCCCCCCCCN1CC(C)OC(C)C1 SBUKOHLFHYSZNG-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241001515917 Chaetomium globosum Species 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- QTDRLOKFLJJHTG-UHFFFAOYSA-N Furmecyclox Chemical compound C1=C(C)OC(C)=C1C(=O)N(OC)C1CCCCC1 QTDRLOKFLJJHTG-UHFFFAOYSA-N 0.000 description 1
- DYMNZCGFRHLNMT-UHFFFAOYSA-N Glyodin Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCC1=NCCN1 DYMNZCGFRHLNMT-UHFFFAOYSA-N 0.000 description 1
- 239000005795 Imazalil Substances 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241001674251 Serpula lacrymans Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BAZMYXGARXYAEQ-UHFFFAOYSA-N alpha-ethyl valeric acid Chemical compound CCCC(CC)C(O)=O BAZMYXGARXYAEQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- LJOZMWRYMKECFF-UHFFFAOYSA-N benodanil Chemical compound IC1=CC=CC=C1C(=O)NC1=CC=CC=C1 LJOZMWRYMKECFF-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- QQWAGMBIDPBJRR-UHFFFAOYSA-N cyclohexyldiazene Chemical compound N=NC1CCCCC1 QQWAGMBIDPBJRR-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229960002125 enilconazole Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 229960002809 lindane Drugs 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
- 238000004519 manufacturing process Methods 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 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
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000010257 thawing Methods 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
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- 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
- B27K3/16—Inorganic impregnating agents
- B27K3/166—Compounds of phosphorus
-
- 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
- B27K3/38—Aromatic 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
-
- 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
- B27K3/52—Impregnating agents containing mixtures of inorganic and organic compounds
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Trevirkebeskyttelsesmiddel.
Foreliggende oppfinnelse vedrører et trevirkebeskyttelsesmiddel på grunnlag av et dimetyl-alkylamin og en syre og anvendelse derav, for beskyttelse av trevirke, spesielt av friskt trevirke, f.eks. friskt oppsaget sagvirke i sagbruk eller nettopp felte trestammer i skogen.
Det er kjent å anvende dimetylalkylaminer, 2-(metoksy-karbonylamino)benzimidazol (BCM) eller N-tridecyl-2,6-dimetyl-morfolin (tridemorf), f.eks. i form av deres salter, til beskyttelse av trevirke (EP-147 976, DE-3 138 575.3, DE-3 507 4 2 0.5). Virkningen av disse midlene er imidlertid ikke tilfredsstillende.
Det ble funnet at trevirkebeskyttelsesmidler som inneholder a) et dimetylalkylamin, b) en vannløselig syre og c) en vannuløselig syre eller BCM eller c) en vannuløselig syre og 2-(metoksykarbonylamino)-benzimidazol, bortsett fra en blanding av N-tridecyl-2,6-dimetylmorfolin, dimetyl-C12-alkylamin, etoksylert nonylfenol (9 etylenoksyd pr. fenol), propylenglykol, fluorborsyre, fosforsyre, isooktansyre og vann, har en svært god virkning mot treparasitter, spesielt mot sopp, som er bedre enn virkningen av de kjente trevirkebeskyttelsesmidlene. De nye trevirkebeskyttelsesmidlene er vannløselige. De anvendes i form av vandige impregnerings-løsninger som fremstilles fra trevirkebeskyttelsesmidlene (konsentratene) ved fortynning med vann. Den foreliggende oppfinnelsen omfatter såvel konsentratene som også de fortynnede vandige løsningene (impregnerings-løsningene) som kan fremstilles derav ved fortynning med vann. De nye trevirkebeskyttelsesmidlene egner seg til beskyttelse av trevirke, spesielt av friskt trevirke, slik som det forekommer f.eks. som friskt oppsaget trevirke i sagbruk eller som nettopp felte trestammer i skogen.
Et dimetylalkylamin er et N,N-dimetyl-N-alkylamin med en alkylrest som inneholder eksempelvis 6 til 20 C-atomer. Dimetylalkylaminer med 12 til 14 C-atomer i alkylresten blir foretrukket. Ved siden av de rene dimetylalkylaminene kan også anvendes blandinger, f.eks. blandinger av dimetyl-C12-alkylamin og dimetyl-C14-alkylamin (dimetylalkyl (C12/C14-aiuin) .
En vannløselig syre er eksempelvis en vannløselig uorganisk syre, f.eks. en syre av fosfor, spesielt fosfonsyre (H3PO3) , fosfinsyre (H3P02) , sure fosforsyreestere (f.eks. fosforsyre-mono- (eller -di)-alkylester, eksempelvis fosfor-syremonobutylester, fosforsyre-di-butylester), fosfonsyre-mono-alkylester eller en syre av svovel, f.eks. en sulfonsyre, eksempelvis benzo 1-mono- (eller -di)-sulfonsyre, sulfaminsyre, 4-fenolsulfonsyre. Dessuten en organisk C2-C4-karboksyl-syre, f.eks. monokarboksylsyre, eksempelvis eddiksyre, propionsyre, metoksyeddiksyre, melkesyre, glykolsyre eller polykarboksylsyre, f.eks. fumarsyre, citronsyre, maleinsyre.
En vannuløselig syre er f.eks. en alifatisk C5-C20-karboksylsyre, eksempelvis en monokarboksylsyre, heksansyre, heptansyre, oktansyre, nonansyre, dekansyre, 2-etylpentansyre, 2-etylheksansyre, 2-etylheptansyre, isooktansyre, isononan-syre, versatikksyrér (sterkt forgrenede monokarbokylsyrer), eller en dikarbokylsyre, f.eks. dekandikarboksylsyre.
Syrene kan også anvendes i form av sine salter, f.eks. dimetylalkylaminsaltene. De BCM inneholdende midlene kan også ved siden av den vannløselige syren dessuten inneholde en vannuløselig syre.
Trevirkebeskyttelsesmidlene er blandbare med vann, danner klare løsninger med vann og har i den vanlige anvendelses-konsentrasjonen (0,5 til 10,0 vekt-%, beregnet på konsen-tratet), en pH-verdi lavere enn 7,0 ved utelukkende anvendelse av dimetylalkylamin, ved blandinger av dimetylalkylamin med tridemorf, en pH-verdi lavere enn 6, og ved blandinger av dimetylalkylamin med BCM, en pH-verdi lavere enn 3,5. De fremstilles ved blanding av de enkelte komponentene med hverandre.
Trevirkebeskyttelsesmidlene (konsentratene) er mer eller mindre viskøse løsninger, med en viskositet som kan reduseres ved tilsetning av polare løsningsmidler. Som polare løsnings-midler kan anvendes f.eks. dimetylformamid, dietylformamid, N-metylpyrrolidon, dimetylsulfoksyd, glykoler, polyglykoler, glykoleter, glykoleteracetater og alkoholer. I disse tilfellene foreligger BCM-saltet for det meste i pastaform.
Konsentratene inneholder vanligvis (vekt-%).
hvorved summen alltid skal være 100 vekt-%.
Blandingsforholdet (vekt-deler) av BCM til dimetylalkylamin ligger f.eks. mellom 1:50 til 2:1, fortrinnsvis 1:20 til 1:2.
Dessuten kan vann være tilstede, som f.eks. inneholdes i de handelsvanlige formene av syrene. I tilleg kan tilsettes: fuktemidler, korrosjonsinhibitorer, fargestoffer og eventuelt bindemiddel.
For å forbedre virkningsbredden av trevirkebeskyttelsesmidlene, kan de dessuten også inneholde nitrogenholdige organiske fungicider, f.eks. ytterligere morfolinderivater, som f.eks. fenpropemorf, aldimorf; guanidinderivater, som f.eks. dodecylguanidin, klorheksadin, guazatin, f.eks. imidazolderivater, f.eks. imazalil, dodecylimidazol, glyodin; pyrimidinderivater, f.eks. heksatidin, kvartære ammonium-forbindelser, f.eks. N-dodecylpyridinklorid. Dessuten kan andre fungicider anvendes i tillegg, som f.eks. 2-(tiocyan-metyltio)benzotiazol, 3-jod-2-propynylbutylkarbamat, 2-(4-tiazolyl)benzimidazol, vannløselige salter (f.eks. kalium-saltet) av N-cykloheksyl'diazeniumdioksydet.
Også andre fungicider, som f.eks. furmecykloks eller benodanil, eller insekticider, som lindan eller permetrin, kan tilsettes til formuleringene, de må eventuelt innarbeides under tilsetning av emulgatorer, f.eks. etoksylerte nonyl-fenoler.
Anvendelsen av beskyttelsesmiddelet for treverket kan, alt etter hvor utsatt treverket er, foregå f.eks.:
a) ved påsprøytning av treverket med oppløsningen,
b) ved neddykking av treverket i oppløsningen,
c) ved impregnering av treverket ved hjelp av
trykkforskjeller,
f.eks. kjeletrykk- eller dobbelvakuumimpregnering,
d) ved påstrykning av treverket.
Ved følgeprodukter av tre, f.eks. oppsaget treverk,
cellestoff, såvel som videre tekniske produkter eller også celluloseholdige materialer som utsettes for soppangrep, f.eks. mellomprodukter ved papirfremstillingen, treaktige ettårsplanter (bagasse, raps) må anvendelsen tilpasses til de tekniske mulighetene.
Virkningen av midlene på trevirkebeskyttelsesområdet omfatter eksempelvis:
a) muggsopp (f.eks. aspergillus niger),
b) forråtnelsessopp (f.eks. chaetomium globosum),
c) blåsopp (f.eks. pullularia pullulans),
d) treødeleggende basidiomyceter (f.eks. serpula lacrymans), spesielt er virkningen svært god mot blåsopp.
Trevirkebeskyttelsesmidlene har en svært god fungicid virkning, som det fremgår av følgende forsøk.
Til forsøkene ble anvendt saftfriske, nettopp oppsagede stykker av ytterved av bartre med målene 200 x 50 x 15 mm, som var dypfryst til forsøkende begynte.
Etter opptining, (omlag 6 timer) ble trestykkene dykket ned i de løsningene som skulle anvendes i ca. 10 sekunder, stillet svakt på skrå for avdrypping og etter en mellomlagring på ca. 24 timer under normale klimabetingelser, plassert i forsøkslandskapet. Med de enkelte forsøksløsningene ble 10 prøvebrett impregnert av gangen på den ovenfor beskrevne måten. Kontrolltrestykker uten impregnering ble neddykket i rent vann.
Som prøvelandskap ble valgt ut en skyggefull eng, der gressvollen ble snauklippet før utleggingen av prøvestykkene. Prøvestykkene ble lagt ut på to kunststoffskinner i en høyde
av ca. 1 cm over gressvollen.
De prøvebrettene som var utsatt for den ytre påvirkningen (regn) ble prøvet etter 2 mnd. (august/september).
Den fungicide virkningen ble klassifisert i fire kate-gorier på grunn av den opptredende fargingen og forandringen av treoverflaten:
0 ingen vekst
+ svak punktvis overflatevekst
++ sterkere punktvis vekst
+++ store flater inntil fullstendig bevokst.
Sammenligningseksempel:
50, 00% dimetylalkylamin (C12/C1A)
17,50% fosfonsyre
22,50% propylenglykol
Sammenligningseksempel: 50,00% tridemorf 3 0,00% fosfonsyre 20,00% propylenglykol
Eksempel 1 (ifølge oppfinnelsen):
Eksempel 2:
30,00% dimetylalkylamin (C12/Cu) 2 0,00% tridemorf 25,00% fosfonsyre 25,00% propylenglykol
Eksempel 3:
35,00% dimetylalkylamin (C12/Cu)
20,00% tridemorf
10,00% isooktansyre
35,00% melkesyre 85% (15% vann)
Sammenligning:
25,00% 2-(metoksykarbonylamino)-benzimidazol 37,50% fosfonsyre
37,50% vann
Eksempel 4:
Sammenligningseksempel BCM:
50% 2-(metoksy-karbonylamino)-benzimidazol 50% sulfaminsyre
(omsatt i vakuum-knamaskin)
Eksempel 5 (ifølge oppfinnelsen):
Eksempel 6:
Alle prøvetrestykkene uten behandling var bevokst og farget med blåsopp (+++).
Ytterligere en blanding med god fungicid virkning er følgende blanding:
Claims (5)
1. Trevirkebeskyttelsesmiddel på grunnlag av et dimetyl-alkylamin og en syre,
karakterisert ved at trevirkebeskyttelses-middelet inneholder a) et dimetylalkylamin, b) en vannløselig syre og c) en vannuløselig syre eller 2-(metoksykarbonyl-amino)-benzimidazol eller c) en vannuløselig syre og 2-(metoksykarbonylamino)-benzimidazol, bortsett fra en blanding av N-tridecyl-2,6-dimetylmorfolin, dimetyl-C12-alkylamin, etoksylert nonylfenol (9 etylenoksyd pr. fenol), propylenglykol, fluorborsyre, fosforsyre, isooktansyre og vann.
2. Trevirkebeskyttelsesmiddel ifølge krav 1, karakterisert ved at det i tillegg inneholder N-tridecyl-2,6-dimetylmorfolin.
3. Trevirkebeskyttelsesmiddel ifølge krav 1, karakterisert ved at inneholder en fosfonsyre som vannløselig syre.
4. Trevirkebeskyttelsesmiddel ifølge krav 1, karakterisert ved at det inneholder 2-etylheksansyre som vannuløselig syre.
5. Anvendelse av trevirkebeskyttelsmiddel ifølge krav 1 for behandling av trevirke.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873736298 DE3736298A1 (de) | 1987-10-27 | 1987-10-27 | Holzschutzmittel |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO884758D0 NO884758D0 (no) | 1988-10-26 |
| NO884758L NO884758L (no) | 1989-04-28 |
| NO176088B true NO176088B (no) | 1994-10-24 |
| NO176088C NO176088C (no) | 1995-02-01 |
Family
ID=6339153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO884758A NO176088C (no) | 1987-10-27 | 1988-10-26 | Trevirkebeskyttelsesmiddel og anvendelse derav |
Country Status (10)
| Country | Link |
|---|---|
| EP (2) | EP0466206B1 (no) |
| AT (2) | ATE90611T1 (no) |
| AU (1) | AU605639B2 (no) |
| CA (1) | CA1327428C (no) |
| DE (3) | DE3736298A1 (no) |
| ES (2) | ES2040810T3 (no) |
| FI (1) | FI98797C (no) |
| NO (1) | NO176088C (no) |
| NZ (1) | NZ226721A (no) |
| PT (1) | PT88855B (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3839640A1 (de) * | 1988-11-24 | 1990-05-31 | Wolman Gmbh Dr | Holzschutzmittel |
| DE3918978A1 (de) * | 1989-06-10 | 1990-12-13 | Wolman Gmbh Dr | Mischung fuer den holzschutz |
| DE4009740A1 (de) * | 1990-03-27 | 1991-10-02 | Desowag Materialschutz Gmbh | Mittel oder konzentrat zum schutz von schnittholz gegen holzverfaerbende pilze |
| DE4441672A1 (de) * | 1994-11-23 | 1996-05-30 | Basf Ag | Holzschutzmittel |
| DE19517811C2 (de) * | 1995-05-17 | 1999-02-25 | Baden Chemie Gmbh | Verwendung eines Beschichtungsstoffes zur Reduzierung bzw. Vermeidung der Biozidabgabe |
| AU3541499A (en) | 1998-04-17 | 1999-11-08 | Mattersmiths Holdings Limited | A biocidal composition containing phosphite ions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3138575A1 (de) * | 1981-09-28 | 1983-04-07 | Basf Ag, 6700 Ludwigshafen | Fungizid |
| GB8333228D0 (en) * | 1983-12-13 | 1984-01-18 | Hicksons Timber Products Ltd | Antifungal compositions |
| DE3502939A1 (de) * | 1985-01-30 | 1986-07-31 | Dr. Wolman Gmbh, 7573 Sinzheim | Fungizides mittel |
| DE3507420A1 (de) * | 1985-03-02 | 1986-09-04 | Basf Ag, 6700 Ludwigshafen | Holzschutzmittel |
| DE3605007A1 (de) * | 1986-02-18 | 1987-08-20 | Wolman Gmbh Dr | Salz eines substituierten morpholins mit fluoroborsaeure und holzschutzmittel |
| DE3613254A1 (de) * | 1986-04-19 | 1987-10-22 | Wolman Gmbh Dr | Holzschutzmittel mit dimethylalkylamin und borsaeure |
-
1987
- 1987-10-27 DE DE19873736298 patent/DE3736298A1/de not_active Withdrawn
-
1988
- 1988-10-19 ES ES198888117433T patent/ES2040810T3/es not_active Expired - Lifetime
- 1988-10-19 AT AT88117433T patent/ATE90611T1/de not_active IP Right Cessation
- 1988-10-19 DE DE3852704T patent/DE3852704D1/de not_active Expired - Fee Related
- 1988-10-19 EP EP91115260A patent/EP0466206B1/de not_active Expired - Lifetime
- 1988-10-19 DE DE8888117433T patent/DE3881831D1/de not_active Expired - Lifetime
- 1988-10-19 AT AT91115260T patent/ATE116591T1/de active
- 1988-10-19 EP EP88117433A patent/EP0316602B1/de not_active Expired - Lifetime
- 1988-10-19 ES ES91115260T patent/ES2067109T3/es not_active Expired - Lifetime
- 1988-10-20 FI FI884848A patent/FI98797C/fi not_active IP Right Cessation
- 1988-10-25 CA CA000581222A patent/CA1327428C/en not_active Expired - Lifetime
- 1988-10-26 AU AU24347/88A patent/AU605639B2/en not_active Expired
- 1988-10-26 NZ NZ226721A patent/NZ226721A/en unknown
- 1988-10-26 NO NO884758A patent/NO176088C/no not_active IP Right Cessation
- 1988-10-26 PT PT88855A patent/PT88855B/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3852704D1 (de) | 1995-02-16 |
| AU605639B2 (en) | 1991-01-17 |
| ATE116591T1 (de) | 1995-01-15 |
| ES2040810T3 (es) | 1993-11-01 |
| EP0466206B1 (de) | 1995-01-04 |
| ATE90611T1 (de) | 1993-07-15 |
| EP0466206A1 (de) | 1992-01-15 |
| NZ226721A (en) | 1990-01-29 |
| NO884758D0 (no) | 1988-10-26 |
| FI884848A (fi) | 1989-04-28 |
| NO176088C (no) | 1995-02-01 |
| EP0316602A3 (en) | 1990-09-12 |
| DE3736298A1 (de) | 1989-05-11 |
| ES2067109T3 (es) | 1995-03-16 |
| EP0316602B1 (de) | 1993-06-16 |
| AU2434788A (en) | 1989-04-27 |
| CA1327428C (en) | 1994-03-08 |
| EP0316602A2 (de) | 1989-05-24 |
| FI884848A0 (fi) | 1988-10-20 |
| PT88855B (pt) | 1993-01-29 |
| FI98797B (fi) | 1997-05-15 |
| NO884758L (no) | 1989-04-28 |
| FI98797C (fi) | 1997-08-25 |
| DE3881831D1 (de) | 1993-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |