CA1174005A - Fungicidal composition - Google Patents
Fungicidal compositionInfo
- Publication number
- CA1174005A CA1174005A CA000400641A CA400641A CA1174005A CA 1174005 A CA1174005 A CA 1174005A CA 000400641 A CA000400641 A CA 000400641A CA 400641 A CA400641 A CA 400641A CA 1174005 A CA1174005 A CA 1174005A
- Authority
- CA
- Canada
- Prior art keywords
- group
- tin
- iodopropargyl
- fungicidal composition
- tributyl
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 44
- -1 halogenated phenol compound Chemical class 0.000 claims abstract description 58
- 239000002904 solvent Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- ODOPKAJVFRHHGM-UHFFFAOYSA-N phenyltin Chemical compound [Sn]C1=CC=CC=C1 ODOPKAJVFRHHGM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003381 stabilizer Substances 0.000 claims abstract description 8
- 239000004094 surface-active agent Substances 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 claims description 20
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 claims description 13
- KPFPEXKMIDAQNO-UHFFFAOYSA-N 3-chloro-2-phenylphenol Chemical compound OC1=CC=CC(Cl)=C1C1=CC=CC=C1 KPFPEXKMIDAQNO-UHFFFAOYSA-N 0.000 claims description 13
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 claims description 13
- 239000003350 kerosene Substances 0.000 claims description 13
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 235000002639 sodium chloride Nutrition 0.000 claims description 8
- GGSUJMOTNBEZHS-UHFFFAOYSA-M tripropylstannanylium;hydroxide Chemical compound [OH-].CCC[Sn+](CCC)CCC GGSUJMOTNBEZHS-UHFFFAOYSA-M 0.000 claims description 8
- VAFVPAKNJFBOFX-HKIWRJGFSA-M (z)-octadec-9-enoate;tributylstannanylium Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)O[Sn](CCCC)(CCCC)CCCC VAFVPAKNJFBOFX-HKIWRJGFSA-M 0.000 claims description 7
- LKYMWFDXBHLYNJ-UHFFFAOYSA-N 3-iodo-3-(1-iodoprop-2-ynoxy)prop-1-yne Chemical compound C#CC(I)OC(I)C#C LKYMWFDXBHLYNJ-UHFFFAOYSA-N 0.000 claims description 7
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- FVFLIQMADUVDSP-UHFFFAOYSA-M chloro(tripropyl)stannane Chemical compound CCC[Sn](Cl)(CCC)CCC FVFLIQMADUVDSP-UHFFFAOYSA-M 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- WOUNUBHOYKWRNA-UHFFFAOYSA-M triethylstannyl acetate Chemical compound CC[Sn](CC)(CC)OC(C)=O WOUNUBHOYKWRNA-UHFFFAOYSA-M 0.000 claims description 7
- LSBFRYCHYLHPSU-UHFFFAOYSA-M tripropylstannyl acetate Chemical compound CCC[Sn](CCC)(CCC)OC(C)=O LSBFRYCHYLHPSU-UHFFFAOYSA-M 0.000 claims description 7
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 claims description 6
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims description 5
- 229910052939 potassium sulfate Inorganic materials 0.000 claims description 5
- 235000011151 potassium sulphates Nutrition 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
- 235000011152 sodium sulphate Nutrition 0.000 claims description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 229940043237 diethanolamine Drugs 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229930182478 glucoside Natural products 0.000 claims description 3
- 150000008131 glucosides Chemical class 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 235000010333 potassium nitrate Nutrition 0.000 claims description 2
- 239000004323 potassium nitrate Substances 0.000 claims description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 2
- 235000011009 potassium phosphates Nutrition 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 235000010344 sodium nitrate Nutrition 0.000 claims description 2
- 239000004317 sodium nitrate Substances 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- 235000011008 sodium phosphates Nutrition 0.000 claims description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- 239000000306 component Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000008233 hard water Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000002649 leather substitute Substances 0.000 description 3
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 3
- NRHFWOJROOQKBK-UHFFFAOYSA-N triphenyltin;hydrate Chemical compound O.C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 NRHFWOJROOQKBK-UHFFFAOYSA-N 0.000 description 3
- 241000233732 Fusarium verticillioides Species 0.000 description 2
- 241000223259 Trichoderma Species 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 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 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- NSPWVJAKNXJHEP-UHFFFAOYSA-N tripropyltin Chemical compound CCC[Sn](CCC)CCC NSPWVJAKNXJHEP-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- HDAARJMMUUPRTI-UHFFFAOYSA-N (3-hydroxy-2-phenylphenyl) hypochlorite Chemical compound ClOC=1C(=C(C=CC1)O)C1=CC=CC=C1 HDAARJMMUUPRTI-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 1
- OUCSIUCEQVCDEL-UHFFFAOYSA-N 2,3,4-tribromophenol Chemical compound OC1=CC=C(Br)C(Br)=C1Br OUCSIUCEQVCDEL-UHFFFAOYSA-N 0.000 description 1
- 244000283070 Abies balsamea Species 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000006173 Larrea tridentata Nutrition 0.000 description 1
- 244000073231 Larrea tridentata Species 0.000 description 1
- 241000235546 Rhizopus stolonifer Species 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960002126 creosote Drugs 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229960003887 dichlorophen Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 235000019589 hardness Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- DZWGKMVDRPKMPD-UHFFFAOYSA-N tripropyl(tripropylstannyloxy)stannane Chemical compound CCC[Sn](CCC)(CCC)O[Sn](CCC)(CCC)CCC DZWGKMVDRPKMPD-UHFFFAOYSA-N 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56-51750 | 1981-04-08 | ||
| JP56051750A JPS57167905A (en) | 1981-04-08 | 1981-04-08 | Antimicrobial composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1174005A true CA1174005A (en) | 1984-09-11 |
Family
ID=12895601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000400641A Expired CA1174005A (en) | 1981-04-08 | 1982-04-07 | Fungicidal composition |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS57167905A (enrdf_load_stackoverflow) |
| CA (1) | CA1174005A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000071312A1 (en) * | 1999-05-24 | 2000-11-30 | Lonza Inc. | Amine oxide/iodine containing blends for wood preservation |
| US6340384B1 (en) | 1999-05-24 | 2002-01-22 | Lonza Inc. | Copper/amine oxide wood preservatives |
| US6448279B1 (en) | 1999-05-24 | 2002-09-10 | Lonza Inc. | Isothiazolone/amine oxide wood preservatives |
| US6508869B2 (en) | 2000-06-30 | 2003-01-21 | Lonza Inc. | Boron compound/amine oxide compositions |
| US6527981B1 (en) | 1999-05-24 | 2003-03-04 | Lonza Inc. | Azole/amine oxide preservatives |
| US6572788B2 (en) | 2000-05-24 | 2003-06-03 | Lonza, Inc. | Amine oxide wood preservatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2733006B2 (ja) | 1993-07-27 | 1998-03-30 | 株式会社神戸製鋼所 | 半導体用電極及びその製造方法並びに半導体用電極膜形成用スパッタリングターゲット |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5643243A (en) * | 1979-09-14 | 1981-04-21 | Sankyo Co Ltd | Iodopropargyl derivative, and antifungal and preservative agent containing said derivative as effective component |
-
1981
- 1981-04-08 JP JP56051750A patent/JPS57167905A/ja active Granted
-
1982
- 1982-04-07 CA CA000400641A patent/CA1174005A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000071312A1 (en) * | 1999-05-24 | 2000-11-30 | Lonza Inc. | Amine oxide/iodine containing blends for wood preservation |
| US6340384B1 (en) | 1999-05-24 | 2002-01-22 | Lonza Inc. | Copper/amine oxide wood preservatives |
| US6375727B1 (en) | 1999-05-24 | 2002-04-23 | Lonza Inc. | Amine oxide/iodine containing blends for wood preservation |
| US6448279B1 (en) | 1999-05-24 | 2002-09-10 | Lonza Inc. | Isothiazolone/amine oxide wood preservatives |
| US6527981B1 (en) | 1999-05-24 | 2003-03-04 | Lonza Inc. | Azole/amine oxide preservatives |
| US6572788B2 (en) | 2000-05-24 | 2003-06-03 | Lonza, Inc. | Amine oxide wood preservatives |
| US6508869B2 (en) | 2000-06-30 | 2003-01-21 | Lonza Inc. | Boron compound/amine oxide compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0113446B2 (enrdf_load_stackoverflow) | 1989-03-06 |
| JPS57167905A (en) | 1982-10-16 |
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