CA2012308A1 - Antifouling agent for fishnets - Google Patents
Antifouling agent for fishnetsInfo
- Publication number
- CA2012308A1 CA2012308A1 CA 2012308 CA2012308A CA2012308A1 CA 2012308 A1 CA2012308 A1 CA 2012308A1 CA 2012308 CA2012308 CA 2012308 CA 2012308 A CA2012308 A CA 2012308A CA 2012308 A1 CA2012308 A1 CA 2012308A1
- Authority
- CA
- Canada
- Prior art keywords
- halogen
- group
- alkyl group
- general formula
- compound represented
- 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
- 239000002519 antifouling agent Substances 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- -1 phenoxy, hydroxy Chemical group 0.000 claims abstract description 11
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 239000004615 ingredient Substances 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 abstract description 5
- 241000251468 Actinopterygii Species 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 28
- 239000008096 xylene Substances 0.000 description 28
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 14
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 12
- 239000004925 Acrylic resin Substances 0.000 description 11
- 229920000178 Acrylic resin Polymers 0.000 description 11
- 230000003373 anti-fouling effect Effects 0.000 description 9
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- GTYVCFZGYDUDAF-UHFFFAOYSA-N 4,5-dichloro-2-(4-chlorophenyl)-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1C1=CC=C(Cl)C=C1 GTYVCFZGYDUDAF-UHFFFAOYSA-N 0.000 description 2
- GYXRKHGSQNXWRZ-UHFFFAOYSA-N 4,5-dichloro-2-[(4-chlorophenyl)methyl]-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1CC1=CC=C(Cl)C=C1 GYXRKHGSQNXWRZ-UHFFFAOYSA-N 0.000 description 2
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 description 2
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AZJUIUPNFDKSHM-UHFFFAOYSA-N (ethylpentasulfanyl)ethane Chemical compound CCSSSSSCC AZJUIUPNFDKSHM-UHFFFAOYSA-N 0.000 description 1
- CVKMVKOPUGPBSF-UHFFFAOYSA-N 1-(hexylpentasulfanyl)hexane Chemical compound CCCCCCSSSSSCCCCCC CVKMVKOPUGPBSF-UHFFFAOYSA-N 0.000 description 1
- WKTPUCFPNFPXJQ-UHFFFAOYSA-N 1-(tetradecyltetrasulfanyl)tetradecane Chemical compound C(CCCCCCCCCCCCC)SSSSCCCCCCCCCCCCCC WKTPUCFPNFPXJQ-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- PQIJDRCKMJCOFO-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-1,2-thiazol-3-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C=CS1 PQIJDRCKMJCOFO-UHFFFAOYSA-N 0.000 description 1
- UOCWVEPGKJFCMS-UHFFFAOYSA-N 4,5-dichloro-2-(3-chloro-2-methoxyphenyl)-1,2-thiazol-3-one Chemical compound COC1=C(Cl)C=CC=C1N1C(=O)C(Cl)=C(Cl)S1 UOCWVEPGKJFCMS-UHFFFAOYSA-N 0.000 description 1
- JSPDPUAKFJOUDW-UHFFFAOYSA-N 4,5-dichloro-2-hexyl-1,2-thiazol-3-one Chemical compound CCCCCCN1SC(Cl)=C(Cl)C1=O JSPDPUAKFJOUDW-UHFFFAOYSA-N 0.000 description 1
- KTMKFPKXLMTLSP-UHFFFAOYSA-N 5-chloro-4-(2-phenylethyl)-1,2-thiazol-3-one Chemical compound ClC1=C(C(NS1)=O)CCC1=CC=CC=C1 KTMKFPKXLMTLSP-UHFFFAOYSA-N 0.000 description 1
- 241000331231 Amorphocerini gen. n. 1 DAD-2008 Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- UAWAZHKAWGRMAY-UHFFFAOYSA-N ClC=1C(N(SC1Cl)CCCCCCCCCCCCC)=O Chemical compound ClC=1C(N(SC1Cl)CCCCCCCCCCCCC)=O UAWAZHKAWGRMAY-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 241000131858 Siboglinidae Species 0.000 description 1
- 244000191761 Sida cordifolia Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- OATNQHYJXLHTEW-UHFFFAOYSA-N benzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C=C1 OATNQHYJXLHTEW-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- ZUYREEAWHZRZDX-UHFFFAOYSA-N di(propan-2-yl)carbamothioylsulfanyl n,n-di(propan-2-yl)carbamodithioate Chemical compound CC(C)N(C(C)C)C(=S)SSC(=S)N(C(C)C)C(C)C ZUYREEAWHZRZDX-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RFUABQNZKSSKRX-UHFFFAOYSA-N methyl 4-(trifluoromethyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CN=CC=C1C(F)(F)F RFUABQNZKSSKRX-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical class C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
-
- 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
- A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/26—Oxidation products of dithiocarbamic acid derivatives, e.g. thiuram sulfides
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1074924A JP2790309B2 (ja) | 1989-03-29 | 1989-03-29 | 水棲汚損生物付着防止剤 |
| JP89/74924 | 1989-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2012308A1 true CA2012308A1 (en) | 1990-09-29 |
Family
ID=13561403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2012308 Abandoned CA2012308A1 (en) | 1989-03-29 | 1990-03-15 | Antifouling agent for fishnets |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2790309B2 (ko) |
| KR (1) | KR0143560B1 (ko) |
| CA (1) | CA2012308A1 (ko) |
| GB (1) | GB2234250B (ko) |
| SG (1) | SG64892G (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3084073B2 (ja) * | 1991-01-31 | 2000-09-04 | ローム・アンド・ハース・ジャパン株式会社 | 防汚薬剤の溶出速度制御方法 |
| US5472483A (en) * | 1994-11-18 | 1995-12-05 | Asahi Denka Kogyo Kabushiki Kaisha | Antifouling agent |
| DE69426117T2 (de) * | 1994-11-21 | 2001-03-01 | Asahi Denka Kogyo Kk | Antifouling Wirkstoff |
| CN115340626B (zh) * | 2022-10-07 | 2024-05-24 | 广东省漆色彩新型材料有限公司 | 一种接枝酚异噻唑啉酮丙烯酸酯单体的杀菌防污树脂及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127687A (en) * | 1976-07-19 | 1978-11-28 | Rohm And Haas Company | Prevention of fouling of marine structures such as boat hulls |
| JPS5634604A (en) * | 1979-08-29 | 1981-04-06 | Yoshitomi Pharmaceut Ind Ltd | Antifouling agent |
| JPS5681505A (en) * | 1979-12-06 | 1981-07-03 | Yoshitomi Pharmaceut Ind Ltd | Antifouling solution for fishing net |
| JPS56118006A (en) * | 1980-02-23 | 1981-09-16 | Yoshitomi Pharmaceut Ind Ltd | Antifouling solution for fish net |
| JPS62115072A (ja) * | 1985-11-13 | 1987-05-26 | Nippon Paint Co Ltd | 水中防汚塗料 |
-
1989
- 1989-03-29 JP JP1074924A patent/JP2790309B2/ja not_active Expired - Lifetime
-
1990
- 1990-03-15 CA CA 2012308 patent/CA2012308A1/en not_active Abandoned
- 1990-03-22 KR KR1019900003898A patent/KR0143560B1/ko not_active IP Right Cessation
- 1990-03-28 GB GB9006932A patent/GB2234250B/en not_active Expired - Fee Related
-
1992
- 1992-06-27 SG SG64892A patent/SG64892G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SG64892G (en) | 1992-10-02 |
| JPH02255605A (ja) | 1990-10-16 |
| JP2790309B2 (ja) | 1998-08-27 |
| GB2234250B (en) | 1992-04-08 |
| KR0143560B1 (ko) | 1998-07-15 |
| GB9006932D0 (en) | 1990-05-23 |
| KR900013853A (ko) | 1990-10-22 |
| GB2234250A (en) | 1991-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |