NO330409B1 - Anvendelse av triazolopyrimidinderivater som mikrobiocider for beskyttelse av materialer, fremgangsmate for beskyttelse av tekniske materialer samt tekniske materialer inneholdende de nevnte derivatene. - Google Patents
Anvendelse av triazolopyrimidinderivater som mikrobiocider for beskyttelse av materialer, fremgangsmate for beskyttelse av tekniske materialer samt tekniske materialer inneholdende de nevnte derivatene. Download PDFInfo
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- NO330409B1 NO330409B1 NO20035012A NO20035012A NO330409B1 NO 330409 B1 NO330409 B1 NO 330409B1 NO 20035012 A NO20035012 A NO 20035012A NO 20035012 A NO20035012 A NO 20035012A NO 330409 B1 NO330409 B1 NO 330409B1
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- Norway
- Prior art keywords
- protection
- technical materials
- wood
- methyl
- materials
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- 239000000463 material Substances 0.000 title claims abstract description 39
- 230000003641 microbiacidal effect Effects 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract description 9
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 17
- 229910052751 metal Inorganic materials 0.000 claims abstract description 15
- 239000002184 metal Substances 0.000 claims abstract description 15
- 244000005700 microbiome Species 0.000 claims abstract description 15
- 230000006378 damage Effects 0.000 claims abstract description 6
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
- -1 trimethylcyclopentyl Chemical group 0.000 claims description 105
- 239000002023 wood Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000003973 paint Substances 0.000 claims description 12
- 241000233866 Fungi Species 0.000 claims description 10
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 7
- 239000004744 fabric Substances 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- 239000000123 paper Substances 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
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
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- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 230000000845 anti-microbial effect Effects 0.000 abstract 1
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- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
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- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 229960002026 pyrithione Drugs 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- 229960003811 pyrithione disulfide Drugs 0.000 description 1
- 239000010453 quartz Substances 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
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-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
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 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
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 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
- 229940014213 spinosad Drugs 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- AJKIRUJIDFJUKJ-UHFFFAOYSA-N taurolidine Chemical compound C1NS(=O)(=O)CCN1CN1CNS(=O)(=O)CC1 AJKIRUJIDFJUKJ-UHFFFAOYSA-N 0.000 description 1
- 229960004267 taurolidine Drugs 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 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
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone 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
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 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
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Lubricants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Foreliggende oppfinnelse vedrører ny anvendelse av kjente triazolopyrimidinderivater som mikrobiocider for beskyttelse av tekniske materialer, en fremgangsmåte for beskyttelse av tekniske materialer mot angrep og/eller ødeleggelse forårsaket av mikroorganismer samt tekniske materialer som inneholder de nevnte derivatene.
Fra EP-A 550113 er det allerede kjent triazolopyrimidinderivater, hvis pyrimidinring i 7-stilling er substituert med en aminogruppe -NR<1>!?<2>, i 6-stilling med eventuelt substituert fenyl eller naftyl og i 5-stilling med halogen eller en rest -NR<5>R<6>. De der beskrevne forbindelsene egner seg for beskyttelse av planter mot angrep av fytopatogene sopper.
US-A-5985883 beskriver likeledes triazolopyrimidinderivater som i 6-stilling av pyrimidinringen er substituert med 2,4,6-triklorofenyl, for beskyttelse av planter mot angrep av fytopatogene sopper.
WO 02/083676 Al, som er publisert etter prioritetsdatoen for foreliggende søknad, beskriver triazolopyrimidinderivater med trifluorpropylaminogrupper for beskyttelse av tre, papir, dispersjonsmalinger, fibre og vevnader.
Det er nå overraskende funnet at de ovenfor omtalte triazolopyrimidinderivatene viser en meget god og bred mikrobiocid virkning mot de for beskyttelse av tekniske materialer relevante mikroorganismene. Dette funnet er spesielt overraskende siden for det første de aktuelle organismene er fundamentalt forskjellige fra de fytopatogene soppene og, for det andre, krever beskyttelsen av tekniske materialer fundamentalt forskjellige standarder av stoffet med hensyn til dets stabilitet, utlekkingsoppførsel, farge og kompatibilitet med andre mulige formuleringshjelpemidler.
Videre er det funnet at forbindelsene som anvendes ifølge oppfinnelsen oppviser en høy stabilitet i tekniske medier.
Gjenstand for foreliggende oppfinnelse er anvendelsen av triazolopyrimidinderivater med formelen (I)
hvori
R<1>står for metyl, etyl, propyl, trifluorpropyl, 2-(l,l,l-trifluorpropyl), benzyl, pentenyl, propinyl, cyklopropyl, cyklopentyl, trimetylcyklopentyl, cykloheksyl, trimetylcykloheksyl eller cyklooktyl,
R<2>står for hydrogen, metyl eller etyl,
eller
R<1>og R2 står sammen med nitrogenatomet som de er bundet til for en piperidyl, fenylpiperidyl, metylpiperidyl eller azepinyl,
R<3>står for fenyl, 2-fluorfenyl, 3-fluorfenyl, 4-fluorfenyl, 2-klorfenyl, 3-klorfenyl, 4-klorfenyl, 2-bromfenyl, 3-bromfenyl, 4-bromfenyl, 2-klor-6-fluorfenyl, 2,4-difluorfenyl, 3,4-difluorfenyl, 2-6-difluorfenyl, 2,4,6-trifluorfenyl, 2,3,6-trifluorfenyl, 2,4-diklorfenyl, 3,4-diklorfenyl, 2,6-diklorfenyl, 2,4,6-diklorfenyl, 2-metylfenyl, 3-metylfenyl, 4-metylfenyl, 3-butylfenyl, 4-butylfenyl, 2-metoksyfenyl, 3-metoksyfenyl, 4-metoksyfenyl, 3,4-dimetoksyfenyl eller 2-6-difluor-4-metoksyfenyl, og R<4>står for klor,
deres metallsalter, syreaddisjonsforbindelser, N-oksider, (R)- og (S)-isomerer samt deres racemater, såfremt et chiralsentrum er til stede i forbindelsene med formel (I),
som mikrobiocid for beskyttelse av tekniske materialer, under den forutsetning at ved beskyttelsen av tre, papir, malingsdispersjoner, fibre og vevnader står R<1>ikke for trifluorpropyl.
Gjenstand for foreliggende oppfinnelse er likeledes metallsaltene, syreaddisjonsforbindelsene, N-oksidene, og, dersom et chiralitetssentrum er tilstede, de eventuelt anrikede (R)- og (S)-isomerene og også deres racemater, av forbindelsene med generell formel (I) som mikrobiocid for beskyttelse av tekniske materialer.
Som metallsalt kommer fortrinnsvis salter av metaller fra andre til fjerde hovedgruppe og første til andre, samt fjerde til åttende sidegruppe, av det periodiske systemet på tale, som eksempler kan nevnes kobber, sink, mangan, magnesium, tinn, jern, kalsium, aluminium, bly, krom, kobolt og nikkel.
Som anioner av saltene kommer slike i betraktning som fortrinnsvis er avledet fra følgende syrer: halogenhydrogensyrer som for eksempel klorhydrogensyre og bromhydrogensyre, videre fosforsyre, salpetersyre og svovelsyre.
Metallsaltkompleksene av forbindelsene med generell formel (I) kan oppnås på enkel måte ved vanlige fremgangsmåter som eksempelvis ved oppløsning av metallsalter i alkohol, for eksempel etanol og tilsetning til forbindelser med generell formel (I). Man kan isolere metallsaltkompleksene på kjent måte, for eksempel ved frafiltrering og eventuelt rense ved omkrystallisering.
For fremstilling av syreaddisjonsforbindelser av forbindelser med generell formel (I) kommer fortrinnsvis følgende syrer på tale: halogenhydrogensyrene, som for eksempel klorhydrogensyre og bromhydrogensyre, spesielt klorhydrogensyre, videre fosforsyre, salpetersyre, svovelsyre, mono- og bifunksjonelle karboksylsyrer og hydroksykarboksylsyrer, som for eksempel eddiksyre, propionsyre, 2-etylheksansyre, smørsyre, mandelsyre, oksalsyre, ravsyre, 2-hydroksy-etan-dikarboksylsyre, maleinsyre, fumarsyre, vinsyre, sitronsyre, salisylsyre, sorbinsyre, melkesyre samt sulfonsyrer, som for eksempel p-toluensulfonsyre, 1,5-naftalindisulfonsyre, alkansulfonsyrer, benzosyrer og eventuelt substituerte benzosyrer.
Syreaddisjonssaltene av forbindelser med generell formel (I) kan oppnås på enkel måte ved vanlige saltdannelsesmetoder, for eksempel ved oppløsning av en forbindelse med generell formel (I) i et egnet, inert oppløsningsmiddel og tilsetning av syren, for eksempel klorhydrogensyre, og på kjent måte isoleres, for eksempel ved frafiltrering, og eventuelt renses ved vasking med et inert, organisk oppløsningsmiddel.
De ifølge oppfinnelsen anvendbare stoffene med formel (I) oppviser overraskende en sterk mikrobiocidisk virkning og kan anvendes for bekjempelse av uønskede mikroorganismer, som sopp og bakterier, ved materialbeskyttelse.
Ved materialbeskyttelse lar stoffene ifølge oppfinnelsen seg anvende for beskyttelse av tekniske materialer mot angrep og ødeleggelse ved uønskede mikroorganismer. Under tekniske materialer forstås i foreliggende sammenheng ikke-levende materialer, som er fremstilt for anvendelse innen det tekniske området. Eksempelvis kan tekniske materialer, som skal beskyttes ved hjelp av foreliggende oppfinnelse mot mikrobiell forandring eller ødeleggelse, være klebestoffer, lim, papir og kartong, tekstiler, lær, tre, malingsmidler og plastgjenstander, kjølesmøremidler og andre materialer som kan angripes eller ødelegges av mikroorganismer. Innenfor rammen av materialene som skal beskyttes skal også nevnes deler av produksjonsanlegg, eksempelvis kjølevannskretsløp, som kan påvirkes ved formering av mikroorganismer. Innenfor rammen av foreliggende oppfinnelse skal som tekniske materialer fortrinnsvis nevnes klebestoffer, lim, papir og kartong, lær, tre, malingsmidler, kjølesmøremidler og varmeoverføringsvæsker.
Virkestoffene med formel (I), samt midler, henholdsvis konsentrater, inneholdende disse samt blandinger anvendes fortrinnsvis for beskyttelse av tre eller trematerialer mot mikroorganismer, for eksempel mot treødeleggende eller tre-misfargende organismer, spesielt sopp.
Under tre, som kan beskyttes ved hjelp av forbindelsene med formel (I) henholdsvis blandinger inneholdende disse, forstås eksempelvis bygningstre, trebjelker, jernbanesviller, brodeler, moloer, trefartøy, kister, palletter, beholdere, telefonmaster, tregjerder, trekledninger, trevinduer og dører, kryssfiner, sponplater, snekkerarbeider og treprodukter, som finner anvendelse innenfor husholdning eller innenfor snekkervirksomhet.
En spesielt effektiv trebeskyttelse oppnås ved storteknisk
impregneringsfremgangsmåter, for eksempel vakuum, dobbeltvakuum- eller trykkfremgangsmåter.
Som mikroorganismer som kan bevirke nedbrytning eller en forandring av de tekniske materialene skal eksempelvis nevnes bakterier, sopper, gjær, alger og slimorganismer. Fortrinnsvis virker de virksomme stoffene ifølge oppfinnelsen mot sopper, spesielt muggsopper samt tre-misfargende og tre-ødeleggende sopper.
Det skal eksempelvis nevnes mikroorganismer av følgende slekter:
Aspergillus, som aspergillus niger,
Chaetomium, som chaetomium globosum,
Coniophora, som coniophora puetana,
Lentinus, som lentinus tigrinus,
Penicillium, som penicillium glaucum,
Polyporus, som polyporus versicolor,
Aureobasidium, som aureobasidium pullulans,
Sclerophoma, som sclerophoma pityophila,
Trichoderma, som trichoderma viride,
Escherichia, som eschericihia coli,
Pseudomonas, som pseudomonas aeruginosa,
Staphylococcus, som staphylococcus aureus.
De virksomme stoffene med formel (I) kan, avhengig av de fysikalske og/eller kjemiske egenskapene, overføres til vanlige formuleringer som oppløsninger, emulsjoner, suspensjoner, pulver, skum, pastaer, granulater, aerosoler, mikroinnkapslinger i polymere stoffer, som ULV-kald- og varmtåkeformuleringer.
Formuleringene, henholdsvis midlene, for beskyttelse av tekniske materialer fremstilles på kjent måte, for eksempel ved blanding av de virksomme stoffene med drøyemidler, det vil si flytende oppløsningsmidler, undertrykkstående, flytendegjorte gasser og/eller faste bærestoffer, eventuelt under anvendelse av overflateaktive midler, det vil si emulgeringsmidler og/eller dispergeringsmidler og/eller skumfremkallende midler. I tilfelle anvendelse av vann som drøyemiddel kan for eksempel også organiske oppløsningsmidler anvendes som hjelpeoppløsningsmidler. Som flytende oppløsningsmidler kommer i det vesentlige på tale: aromater, som xylen, toluen eller alkylnaftalin, klorerte aromater eller klorerte alifatiske hydrokarboner, som klorbenzener, kloretylener eller metylenklorid, alifatiske hydrokarboner, som cykloheksan eller parafiner, for eksempel råoljefraksjoner, alkoholer, som butanol eller glyserol samt deres etere og estere, ketoner, som aceton, metyletylketon, metylisobutylketon eller cykloheksanon, sterkt polare oppløsningsmidler, som dimetylformamid og dimetylsulfoksid, samt vann. Med flytendegjorte gassformige drøyemidler eller bærestoffer menes slike væsker som er gassformige ved normal temperatur og normalt trykk, for eksempel aerosol-drivgasser, som halogenhydrokarboner samt butan, propan, nitrogen og karbondioksid. Som faste bærere kommer på tale: for eksempel naturlig steinmel, som kaoliner, leirer, talkum, kritt, kvarts, attapulgitt, montmorillonitt eller diatomejord og syntetisk steinmel som høydispers kiselsyre, aluminiumoksid og silikater. Som faste bærestoffer for granulater på tale: for eksempel oppbrutte og fraksjonerte naturlige bergarter som kalsitt, marmor, pimpstein, sepiolitt, dolomitt samt syntetiske granulater av uorganiske og organiske mel, samt granulater av organisk materiale som sagflis, kokosnøttskall, maiskolber og tobakkstengler. Som emulgerings- og/eller skumfrembringende middel kommer på tale: for eksempel ikke-ionogene og anionogene emulgatorer, som polyoksyetylen-fettsyreester, polyoksyetylen-fettalkoholeter, for eksempel akylaryl-polyglykoleter, alkylsulfonater, akylsulfater, arylsulfonater samt eggehvitehydrolysater. Som dispergeringsmiddel kommer på tale: for eksempel ligninsulfittavluter og metylcellulose.
Det kan i formuleringene anvendes vedheftingsmidler som karboksymetylcellulose, naturlige og syntetiske, pulverformige, kornformige eller lateksformige polymerer, som gummi arabicum, polyvinylalkohol, polyvinylacetat, samt naturlige fosfolipider, som kefaliner og lecitiner og syntetiske fosfolipider. Ytterligere additiver kan være mineralske og vegetabilske oljer.
Det kan anvendes fargestoffer som uorganiske pigmenter, for eksempel jernoksid, titanoksid, jerncyanblått og organiske fargestoffer som alizarin-, azo- og metallftalocyaninfargestoffer og spornæringsstoffer, som salt eller jern, mangan, bor, kobber, kobolt, molybden og sink.
Formuleringene inneholder generelt mellom 0,1 og 95 vektprosent virkestoff, fortrinnsvis mellom 0,5 og 90%.
Foreliggende oppfinnelse vedrører videre en fremgangsmåte for beskyttelse av tekniske materialer mot angrep og/eller ødeleggelse forårsaket av mikroorganismer, kjennetegnet ved at man lar minst en forbindelse med formel (I) virke inn på mikroorganismen eller dens livsrom, under den forutsetning at ved beskyttelse av tre, papir, malingsdispersjoner, fibre eller vevnader er R<1>ikke trifluorpropyl.
Foreliggende oppfinnelse vedrører videre tekniske materialer, kjennetegnet ved at de inneholder minst en forbindelse (I), under den forutsetning at ved beskyttelsen av tre, papir, malingsdispersjoner, fibre og vevnader er R<1>ikke trifluorpropyl.
Virkestoffene ifølge oppfinnelsen kan som sådanne eller i form av deres formulering også anvendes i blanding med kjente fungicider, baktericider, akaricider, nematicider eller insekticider, for dermed for eksempel å utvide virkningsspekteret eller forebygge resistensutvikling. I mange tilfeller oppnår man derved synergistiske effekter, det vil si virksomheten av blandingen er større enn virksomheten av enkeltkomponentene.
I forbindelse med oppfinnelsen viser følgende blandingspartnere seg som spesielt gunstige:
Triazoler som:
Azaconazol, azocyklotin, bitertanol, bromuconazol, cyproconazol, diclobutrazol, difenoconazol, diniconazol, epoksyconazol, etaconazol, fenbuconazol, fenklorazol, fenetanil, fluquinconazol, flusilazol, flutriafol, furconazol, heksaconazol, imibenconazle, ipconazol, isozofos, myklobutianil, metconazol, paclobutrazol, penconazole, propioconazol, (±)-cis-1 -(4-klorfenyl)-2-( 1H-1,2,4-triazol-1 -yl)-cykloheptanol, 2-( 1 -tert.-butyl)-1-1 (2-klorofenyl)-3-( 1,2,4-triazol-1 -yl)-propan-2-og lignende, tebuconazol, tetraconazol, triadimefon, triadimenol, triapentenol, triflumizol, triticonazol, uniconazol samt deres metallsalter og syreaddukter;
Imidazoler som:
Clotrimazol, bifonazol, climbazol, econazol, fenapamil, imazalil, isoconazol, ketoconazol, lombazol, miconazol, pefurazoat, prokloras, trifluizol, thiazolcar, 1-imidazolyl-l-(4'-klorfenoksy)-3,3-dimetylbutan-2-on samt deres metallsalter og syreaddukter;
Pyridiner og pyrimidiner som:
Ancymidol, butiobat, fenarimol, mepanipyrin, nuarimol, pyroksyfur, triamirol;
Succinat-dehydrogenaseinhibitorer som:
Benodanil, karboksim, karboksimsulfoksid, syklafluramid, fenfuram, flutanil, furcabanil, furmecykloks, mebenil, mepronil, metfuroxam, metsulfovaks, pyrokarbolid, oskykarboksi, shirlan, seedvax;
Naftalinderivater som:
Terbinafin, naftifin, butenafin, 3-kloro-7(2-aza-2,7,7-trimetyl-oct-3-en-f-in);
Sulfenamider som:
Diklofiuanid, tolyfluanid, folpet, flourfolpet; captan, captofol;
Benzimidalzoler som:
Carendazim, benomyl, fuberidazol, thiabendazol eller deres salter;
Morfolinderviater som:
Aldimorf, dimetomorf, dodenmorf, falimorf, fenpropidin, fenpropimorf, tridemorf, triomorfamid og deres arylsulfonsyresalter, som for eksempel p-toluensulfonsyre og p-dodesylfenylsulfonsyre;
Benztiazoler som:
2-merkaptobenzotiazol;
Benziofendioksider som:
Benzo[b]tiofen-S,S-dioksid-karbonsyrecykloheksylamid;
Benzamider som:
2,6-Dikloro-N-(4-trifluorometylbenzyl)-benzamid, tekloftalam;
Borforbindelser som:
Borsyre, borsyreester, boraks;
Formaldehyd og formaldehydavspaltende forbindelser som: Benzylalkoholmono-(poly)-hemiformal, n-butanol-hemiformal, dazomet, etylenglykolhemiformal, heksa-hydro-S-triazin, heksametylentetramin, N-hydroksy-metyl-N'-metyltiourea, N-metylolklaracetamid, oksazolidin, paraformaldehyd, taurolin, tetrahydro-1,3-oksazin, N-(2-hydroksypropyl)-amin-metanol;
Isotiazolinoner som:
N-metylisotiazolin-3-on, 5-klor-N-metylisotiazolin-3-on, 4,5-dikloro-N-oktylisotiazolin-3-on, 5-klor-N-oktylisotiazoliner, N-oktyl-isotiazolin-3-on, 4,5-trimetylen-isotiazolinon, 4-5-benzisotiazolinon;
Aldehyder som:
Kanelaldehyder, formaldehyd, glutardialdehyd, P-bromkanelaldehyd;
Tiocyanater som:
Tiocyanatometyltiobenzotiazol, metylenbistiocyanater;
Kvartære ammoniumforbindelser og guanidiner som:
Benzalkoniumklorid, benzyldimentyltetradecylammoniumklorid, benzyldmetyldodecylammoniumklorid, diklorbenzyl-dimetyl-alkyl-ammoniumklorid, didecyldimethylammoniumklorid, dioktyl-dimetyl-ammoniumklorid, N-heksadecyltrimetyl-ammoniumklorid, 1 -heksadecyl-pyridinum-klorid, iminoctadintirs(albesilat);
Jodderviater som:
Diodmetyl-p-tolysulfon, 3-jod-2-proinyl-alkohol, 4-klorfenyl-3-jodpropargyl-format, 3-brom-2,3-dijod-2-propenylalkohol, 3-jod-2-propinyl-n-butylkarbamat, 3-jod-2-propinyl-n-heksykarbamat, 3-jod-2-propinyl-cykloheksylkarbamat, 3-jod-2-propinyl-fenylkarbamat;
Fenoler som:
Tribromfenol, tetraklorfenol, 3-metyl-4-klorfenol, 3,5-dimetyl-4-klorfenol, fenoksyetanol, diklorfen, 2-benzyl-4-klorfenol, 5-klor-2-(2,4-diklorfenoksy)-fenol, heksaklorofen, p-hydroksybenzosyrer, o-fenylfenol, m-fenylfenol, p-fenylfenol og deres alkali- og jordalkalimetallsalter;
Mikrobicider med aktiverte halogengrupper som:
Bronidoks, 2-brom-2-nitro-l,3 propandiol, 2-brom-4'-hydroksy-acetofenon, l-brom-3-klor-4,4,5,5-tetrametyl-2-imidazoldinon, P-brom-P-nitrostyren, kloracetamid, kloramin T, l,3-dibrom-4,4,5,5-tetrametyl-2-imidazoldinon, dikloramin T, 3,4-diklor-(3H)-l,2-ditiol-3-on, 2,2-dibrom-3-nitril-propionamid, l,2-dibrom-2,4-dicyanobutan, halan, halazon, mucoklorsyre, fenyl-(2-klor-cyan-vinyl)sulfon, fenyl-(l,2 diklor-2-syanvinyl)sulfon, triklorisocyanusyre;
Pyridiner som:
l-hydroksy-2-pyridintion (og deres Na-, Fe-, Mn-, Zn-salter), tetraklor-4-metyl-sulfinylpyridin, pyrimetanol, mepanipyrim, dipyrition, l-hydroksy-4-metyl-6-(2,4,4-trimetylpentyl)-2( lH)-pyridin;
Metoksyakrylater eller lignende som:
Azoksystrobin,
Metyl-(E)-metoksimino[alfa-(o-tolyloksy)-o-tolyl]acetat, (E)-2-metoksyirnino-N-metyl-2-(2-fenoksyfenyl)acetamid, (E)-2-{2-[-cyanofenoksy)pyrimidin-4-yloksy]fenyl} -3-metoksyakrylat,
0-me1yl-2-[[[[[[3-metoksimino-2-butyl]imino]oksy]metyl]-alfa-(metoksimino)-N-metylbenzenacetamid,
2-[[[[l-(2,5-dime1ylfenyl)etyliden]amino]oksy]me1yl]-alfa-(metoksimino)-N-metylbenzenacetamid,
alfa-(metoksyimmo)-N-metyl-2-[[[[l-[3-trifluorometyl)fenyl]-etyliden]-amino] oksy]mety 1] -benzenacetamid,
trifluoksystrobin,
alfa-(metoksymetylen)-2-[[[[l-[trilfuorometyl)fenyl]etyliden]amino]-oksy]metyl]benzeneddiksyre-metylester,
2-[[[5-kloro-3-(trilfuorme1<y>l)-2-pr<y>idin<y>l]oks<y>]me1<y>l]-alfa-(rnetoksyimino)-N-metylbenzenacetamid,
2-[[[cyklopropyl[4-etoksyfenyl)imino]metyl]tio]metyl]-alfa-rnetoksy-irnino)-benzeneddiksyre-metylester,
alfa-(metoksyimino)-N-metyl-2-)4-rnetyl-4-fenyl-2,7-dioksa-3,6-diazaokta-3-5-dien-l-yl)benzenacetamid,
alfa-(metoksymetylen)-2-(4-metyl-5-fenyl-2,7-dioksa-3,6-diazaookta-3,5-dien-l-yl-benzeneddiksyre-metylester,
alfa(-metoksimino)-N-metyl-2 - [ [[ 1 - [e-trifluorometyl)fenyl]etoksy] imino] -metyl] - benzenacetamid,
2-[[3,5-dikloro-2-pyridinyl)-oksy]metyl]-alfa-(metoksyimino)-N-metyl-benzenacetamid,
2-[[3,5-dikloro-2-pyridinyl)-oksy]metyl]-alfa-(metoksyimino)-N-metyl-benzenacetamid,
2-[4,5-dimetyl-9-(4-morfolinyl)-2,7-dioksa-3,6-diazanona-3,5-dien-l-yl]-alfa-(metoksymetylen)-benzeneddiksyremetylester,
Kresoksim-metyl;
Metallsåper som:
Tinn, kobber, sinknaftenat,- oktonat, 2-etylheksanoat, -oleat, -fosfat, -benzoat;
Metallsalter som:
Kobberhydroksykarbonat, natriumdikromat, kaliumdikromat, kaliumkromat, kobbersulfat, kobberklorid, kobberborat, sinkfluorsilikat, kobberfluorsilikat;
Oksider som:
Tributyltinnoksid, C112O, CuO, ZnO;
Ditiokarbamater som:
Kufraneb, ferban, kalium-N-hydroksymetyl-N'-metyl-ditiobarbamat, Na- eller K-dimetylditiokarbamat, macozeb, maneb, metam, metiram, tiram, zineb, ziram;
Nitriler som:
2,4,5,6-tetraklorisoftalodinitril, dinatrium-cyano-ditioimidokarbamat,
Kinoliner som:
8-hydroksykinolin og deres Cu-salter;
Øvrige fungicider og baktericider som:
5-hydroksy-2-(5H)-furanon; 4,5-benzditiazolinon, 4,5-trimetylenditiazolinon, N-(2-p-klorbenzoyletyl)-heksaminiumklorid, 2-okso-2-(4-hydroksy-fenyl)acethydroksimsyrer, tris-N-(cykloheksyldiazeniumdioksy)-aluminium, N-(cykloheksyldiazeniumdioksy)-tri-butyltinn hhv. K-salter, bis-N-(cykloheksyldiazeniumdioksy)-kobber, iprovalicarb, fenheksamid, spiroksamin, karpropamid, diflumetorin, quinoksyfen, famoksadon, polyoksorim, acibenzolar-S-metyl, furametpyr, tifluzamid, metalaksy-M, Ag, Zn eller Cu-holdige zeolitter alene eller innbefattet i polymere materialer.
Helt spesielt foretrukket er blandingen med
Azaconazol, bromuconazol, cyproconazol, diklobutrazol, heksaconazol, metaconazol, penconazol, propiconazol, tebuconazol, diklofulanid, tolylfluanid, fluorfolpet, metfuroksam, karboksin, benzo([b]tiofen-S,S-dioksidkarboksysyrecykloheksylamid, fenpiclonil, 4-(2,2-difluoro-l,3-benzodioksol-4-yl)-lH-pyrrol-3-karbonitril, butenafin, imazalil, N-metyl-isotiazolin-3-on, 5-klor-N-metylisotiazolin-3-on, N-oktylisotiazolin-3-on, diklor-N-oktylisotiazolinon, mercaptobentiazol, tiocyanatometyltiobenzotiazol, N-(2-hydroksypropyl)-amino-metanol, benzylalkohol-(hemi)-formal, N-metylolkloracetamid, N-(2-hydroksypropyl)-amin-metanol, glutaraldehyd, omadin, dimetyldicarbonat, 2-brom-2-nitro-l,3-propendiol og/eller 3-iodo-2-propinyl-n-butylkarbamat.
Videre fremstilles, bortsett fra de ovenfor nevnte fungicidene og baktericidene, også godt virksomme blandinger med andre virkestoffer:
Insekticider / akaricider / nematicider:
Abamectin, acefat, acetamiprid, acrinatrin, alanykarb, aldikarb, aldoksykarb, aldrin, alletrin, alfa-cypermetrin, amitraz, avermectin, AZ 60541, azadiraktin, azinfos A, azinfos M, azocyklotin,
Bacillus turingiensis, bartrin, 4-bromo-2(4-klorfenyl)-l-(etoksymetyl)-5-(trifluorometyl)-lA-pyrrol-3-karbonitril, bendiokarb, benfurakarb, bensultap, betacyflutrin, bioresmetrin, bioalletrin, bromofos, A, bromofos M, bufenkarb, buprofezin, butatiofos, butokarboksim, butoksykarboksim, kadusafos, karbaryl, karbofuran, karbofenotion, karbosulfan, kartap, chinometionat, chloetocarb, klordan, koretoksyfos, klorfenapyr, klorfenvinfos, klorfluazuron, klormefos, N-[(6-kloro-3-pyridinyl)-metyl]-N'n-cyano-N-metyl-etanimidamid, klorpicrin, klorpyrifos A, klorpyrifos M, Cis-resmetrin, klosytrin, sypofenotrin, klofentecin, coumafos, cyanofos, cykloprotrin, fyflutrin, cyhalotrin, cyheksatin, cypermetrin, cyromacin, decametrin, deltametrin, demeton M, demeton S, demeton-S-metyl, diafeniuron, dialifos, diacinon, l,2-dibenzoyl-l-(l,ldemetyl)-hydrasin, DNOC, deklofention, diklorvos, diklifos, difetialon, diflubenzuron, dimetoat, dimetyl-(fenyl)-silyl-metyl-3-fenoksybenzyleter, dirnetyl-(4-etoksyfenyl)-silylmetyl-3-fenoksybenzyleter, demetylvinfos, dioksation, disulfoton,
Eflusilanat, emamectin, empentrin, endosulfan, EPN, esefenvalert, etiofenkarb, etion, etofenproks, etrifos, etoksazol, etobenzanid,
Fenamifos, fenazaquin, fenbutatinocid, fenflutrin, fenitrotion, fenobukarb, fenotiokarb, fenoksykarb, fenpropatrin, fenpyrad, fenpyrocimat, fensulfotion, fention, fenvalerat, fipronil, fluazuron, flucykloksuron, flucytrinat, flufenoksuron, flupyrazofos, flufenzin, flumentrin, flufenproks, fluvalinat, fonofos, formetanate, formotion, fosmetilan, fostiazat, fubfenproks, furatiokarb, halofenocid, HCH, hetenofos, hexaflumuron, heksytiazoks, hydromethylnon, hydropren,
Imidakloprid, imiprotrin, indoksykarb, jodfenfos, iprinomectin, Iprobenfos, isaofos, isoamidofos, isofenfos, isoprokarb, isoprotiolane, isoksation, ivermectin, lamacyhalotrin, lufenuron,
Kaderin,
Lambda-cyhalotrin, lufenuron,
Malation, mekarbam, mervinfos, mesulfenfos, metaldehyd, metakrifos,
Metamidofos, metidation, metiokarb, metomyl, metalkarb, milbemektin, Monocrotophos, moksiektin,
Naled, NC 184, NI 125, nikotin, Nitenpyram,
Ometoat, oksamyl, oksydemeton, M, oksydeprofos,
Paration A, paration M, penfluron, permetrin, 2-4-fenoksyfenoksy)etyl-etylkarbamat, fentoat, for at, fosalon, fosmet, fosfamidon, foksim, pirimikarb, pirimifos M, pirimifos
A, pralletrin, profenofos, promekarb, prpafos, propksur, protiofos, protoat, pyemtrozin, pyraklofos, pyridafention, pyresmetrin, pyretrum, pyridaben, pyrimidifen, pyriproksifen, pyritiobac-natrium,
Quinalfos,
Resmetrin, RH-7988, rotenon,
Salition, sebufos, silafluofen, spinosad, sulfotep, sulprofos,
Tau-fluvalinate, taroils, tebufensozid, tebufenpyrad, tebupirimfos, teflubenzuron, teflutrin, temefos, terbam, terbufos, tetraklorvinfos, tetremetrin, tetrametakarb, tiakloprid, tiafenox, tiametoksam, tiapronil, tiodikarb, tiofanoks, tiazofos, tiocyclam, tiometon, tionazin, turingiensin, tralometrin, tranflurtrion, triaraten, triazofos, trazamate, triklorfon, triflumuron, trimetakarb,
Vamidotion, XMC, xylykarb, setametrin,
Molluskicider:
Fentinacetat, metaldehyd, metiokarb, niklosamid,
Herbicier og algicider:
Acetoklor, acifluorfen, aclonifen, acrolein, alaklor, alloksydim, ametryn, amidosulfuron, amitrol, ammoniumsulfamat, anilofos, asulam, atrazin, azafenidin, aziptrotryn, azimsulfuron,
Benazolin, benfluralin, benfuresat, bensulfuron, bensulfid, bentazon, benzofencap, benztiazuron, bifenoks, bispyribak, bispyribak-natrium, bispyribak-metyl, boraks, bromasil, bromobutid, bromofenoksium, bromoksynil, butaklor, butamisfos, butralin, butylat, bialafos, benzoyl-prop, bromobutide, butroksydim,
Karbetamid, karfentrazon-etyl, karfenstrol, klometoksyfen, kloramben, klorbromuron, klorfurenol, kloridazon, klorimuron klornitrofen, kloroeddiksyre, kloransulam-metyl, Sinidon-etyl, klorotoluron, kloroksuron, klorprofam, klorsulfuron, klortal, klortiamid, sinmetylin, sinofulsuron, klefoksydim, kletodim, klomazon, klomprop, klopyralid, cyanamid, cyanazin, cykloat, cykloksydim, kloroksynil, klodinafop-propargyl, cumyluron, klometoksyfen, cyhalofop-butyl, klopyrasuluron, cyklosulfamuron, Diklusulam, diklorprop, diklorprop-P, diklofop, dietatyl, difenoksuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperat, dometaklor, dimetipin, dinitramin, dinoseb, sinoseg, acetat, conterb, defenamid, dipropetry, diquat, ditiopyr, diduron, DNOC, DSMA, 2,4-d, aimuron, dalapun, dazomet, 2,4-DB, desmedifam, desmetryn, dikamba, diklobenil, dimetamid, ditiopyr, dimetametryn, englinazin, endotal, EPCT, esprokarb, etalfluralin, edidimuron, etofumesat, etobenzanid, etoksyfen, etametsulfuron, etoksysulfuron, fenoksaprop, fenoksaprop-P, fenuron, flamprop, flamprop-M, flasasulfuron, fluazifop, fluazifop-P, fluenaklor, flukloralin, flufenaset, fimeturon, fluorocglycofen, fluoronitrofen, flupropanat, flurenol, fluridon, flurokloridon, fluroksypyr, fomesafen, fosmin, flosemetin, flamprop-isopropyl, flamprop-isopropyl-L, Flumiklorak-pentyl, flumipropyn, flumiokszim, fluratom, flumiokszim, flupyrsulfuronmetyl, flutiasetmetyl, glyfosat, glufosinatammonium,
Haloksyfop, heksazinon,
Imasametabenz, isoproturon, isoksaben, isoksapyrifop, imazapyr, imazaquin, Imazetapyr, ioksynil, isopropalin, imazusulfuron, imazomoks, isoksaflutol, imazapik, Laktofen, lenasil, linuron,
MCPA, MCPA-tioetyl, MCPB, mekoprop-P, mefenaset, mefluidid,
Metam, metamitrin, metazaklor, metabenziazuron, metazol, metoropytryn, Metyldymrom, metylisotiocyanat, metobromuron, metoksuron, metribuzin, Metsulfuron, molinat, manolid, monolinuron, MSMA, metolaklor, metosulam, Metobenzuron, Naproanilid, napropamid, naptalm, neburon, nekosulfuron, Norflurazon, natriumklorat, oksadiazon, oksyfluorfen, oskysulfuron, orbenkarb, Oryzalin, oksadiargyl, propyzamid, prosulfokarb, pyrazolat, pyrazolsulfuron, Pyrazoksyfen, pyribenzoksim, pyributikarb, pyridat, paraquat, pebulat,
Pendimetalin, pentaklorofenol, pentoksazon, pentanoklor, petroleum, oljer, Fenmedifam, pkloram, piperofos, pretilaklor, primisulforon, prodiamin, prometrym, propaklor, propanil, propaquizafob, propazin, propham, propisoklor, pyriminobak-metyl, pelargonsyre, pyritiobak, pyraflufen-etyl, quinmerak, quinoklamin, quizalofop, quizalofop-P, quinklorak,
Rimsulfuron,
Setoksydim, sifuron, simazin, simetryn, sulfosulfuron, sulfometuron, sufentrazon, sulkontrion, sulfosate,
Tjæreoljer, TCA, tebutam, tebutiuron, terbasil, terbumeton, terbuthylazin, terbutryn, tiazafluoron, tifensulfuron, tiobenkarb, tiokarbazil, tralkoksydim, triallat, triasulfuron, tribenzuron, triclopyr, tridifan, trietazin, trifluoralin, tykor, thdiazimin, tiazopyr, triflusulfuron,
Vernolat.
De virksomme stoffene kan anvendes sådanne, i form av konsentrater eller i form av deres formuleringer eller de derav tilbredte anvendelsesformene, som brukerferdige oppløsninger, suspensjoner, sprøytepulvere, pastaer, oppløselige pulvere, støvmidler og granulater.
De for beskyttelse av tekniske materialer anvendte midlene inneholder virkestoffer generelt i en mengde fra 1 til 95%, fortrinnsvis fra 10 til 75%.
Anvendelseskonsentrasj onene av de virksomme stoffene avhenger av typen og forekomsten av mikroorganismene som skal bekjempes, samt av sammensetningen av materialet som skal beskyttes. Den optimale anvendelsesmengden kan bestemmes ved forsøksrekker. Generelt ligger anvendelseskonsentrasjonene i området fra 0,001 til 5 vektprosent, fortrinnsvis fra 0,05 til 1,0 vektprosent, relativt til materialet som skal beskyttes.
Anvendelseseksempel
Hemmetest på meget store kolonier av basidiomyceter.
Fra kolonier av Gloeophyllum trabeum (Pl), Coniophora puteana (P2), Poria placenta (P3), Lentinus tigrinus (P4), Coriolus versicolor (P5) og Sterum anguinolentum (P6), ble det stukket ut mycelstykker og disse ble inkubert på en agarnæringsplate ved 26°C. Hemningen av veksten av sopptråder på næringsmediet inneholdende virksomt stoff (konsentrasjon av virksomt stoff 6 ppm) ble sammenlignet med lengdeveksten uten tilsats av virksomt stoff og bedømt som prosentvis hemning.
Claims (6)
1.
Anvendelse av forbindelser med formel (I)
hvori
R<1>står for metyl, etyl, propyl, trifluorpropyl, 2-( 1,1,1-trifluorpropyl), benzyl, pentenyl, propinyl, cyklopropyl, cyklopentyl, trimetylcyklopentyl, cykloheksyl, trimetylcykloheksyl eller cyklooktyl,
R<2>står for hydrogen, metyl eller etyl,
eller
R<1>og R2 står sammen med nitrogenatomet som de er bundet til for en piperidyl, fenylpiperidyl, metylpiperidyl eller azepinyl,
R<3>står for fenyl, 2-fluorfenyl, 3-fluorfenyl, 4-fluorfenyl, 2-klorfenyl, 3-klorfenyl, 4-klorfenyl, 2-bromfenyl, 3-bromfenyl, 4-bromfenyl, 2-klor-6-fluorfenyl, 2,4-difluorfenyl, 3,4-difluorfenyl, 2-6-difluorfenyl, 2,4,6-trifluorfenyl, 2,3,6-trifluorfenyl, 2,4-diklorfenyl, 3,4-diklorfenyl, 2,6-diklorfenyl, 2,4,6-diklorfenyl, 2-metylfenyl, 3-metylfenyl, 4-metylfenyl, 3-butylfenyl, 4-butylfenyl, 2-metoksyfenyl, 3-metoksyfenyl, 4-metoksyfenyl, 3,4-dimetoksyfenyl eller 2-6-difluor-4-metoksyfenyl, og
R<4>står for klor,
deres metallsalter, syreaddisjonsforbindelser, N-oksider, (R)- og (S)-isomerer samt deres racemater, såfremt et chiralsentrum er til stede i forbindelsene med formel (I), som mikrobiocid for beskyttelse av tekniske materialer, under den forutsetning at ved beskyttelsen av tre, papir, malingsdispersjoner, fibre og vevnader står R<1>ikke for trifluorpropyl.
2.
Anvendelse ifølge krav 1, hvor det som tekniske materialer beskyttes tre eller trematerialer mot angrep av treødeleggende sopper.
3.
Anvendelse ifølge krav 1, hvor det som tekniske materialer beskyttes malingsmidler, for eksempel trebeskyttelseslasurer eller malingsfilmer mot angrep ved misfargende eller malingsoverflateødeleggende sopp.
4.
Anvendelse ifølge krav 1, hvor det som teknisk materiale beskyttes plaster.
5.
Fremgangsmåte for beskyttelse av tekniske materialer mot angrep og/eller ødeleggelse forårsaket av mikroorganismer,karakterisert vedat man lar minst en forbindelse med formel (I) ifølge krav 1 virke inn på mikroorganismen eller dens livsrom, under den forutsetning at ved beskyttelsen av tre, papir, malingsdispersjoner, fibre og vevnader er R<1>ikke trifluorpropyl.
6.
Tekniske materialer,karakterisert vedat de inneholder minst en forbindelse (I) ifølge krav 1, under den forutsetning at ved beskyttelsen av tre, papir, malingsdispersjoner, fibre og vevnader er R<1>ikke trifluorpropyl.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10124208A DE10124208A1 (de) | 2001-05-18 | 2001-05-18 | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
PCT/EP2002/004965 WO2002094020A1 (de) | 2001-05-18 | 2002-05-06 | Verwendung von triazolopyrimidin-derivaten als mikrobizide im materialschutz |
Publications (3)
Publication Number | Publication Date |
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NO20035012D0 NO20035012D0 (no) | 2003-11-11 |
NO20035012L NO20035012L (no) | 2003-11-11 |
NO330409B1 true NO330409B1 (no) | 2011-04-04 |
Family
ID=7685242
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20035012A NO330409B1 (no) | 2001-05-18 | 2003-11-11 | Anvendelse av triazolopyrimidinderivater som mikrobiocider for beskyttelse av materialer, fremgangsmate for beskyttelse av tekniske materialer samt tekniske materialer inneholdende de nevnte derivatene. |
Country Status (21)
Country | Link |
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US (2) | US7888371B2 (no) |
EP (1) | EP1395117B2 (no) |
JP (1) | JP4593881B2 (no) |
CN (1) | CN100342786C (no) |
AT (1) | ATE333793T1 (no) |
AU (1) | AU2002255002B2 (no) |
BR (1) | BR0209830B1 (no) |
CA (1) | CA2447623C (no) |
CZ (1) | CZ20033129A3 (no) |
DE (2) | DE10124208A1 (no) |
DK (1) | DK1395117T4 (no) |
EE (1) | EE05437B1 (no) |
ES (1) | ES2269677T5 (no) |
HK (1) | HK1066148A1 (no) |
NO (1) | NO330409B1 (no) |
NZ (1) | NZ529567A (no) |
PL (1) | PL208003B1 (no) |
PT (1) | PT1395117E (no) |
RU (1) | RU2335128C2 (no) |
WO (1) | WO2002094020A1 (no) |
ZA (1) | ZA200308893B (no) |
Families Citing this family (21)
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DE10124208A1 (de) * | 2001-05-18 | 2002-11-21 | Bayer Ag | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
UA80304C2 (en) | 2002-11-07 | 2007-09-10 | Basf Ag | Substituted 6-(2-halogenphenyl)triazolopyrimidines |
WO2005027635A1 (en) * | 2003-09-19 | 2005-03-31 | Arch Chemicals, Inc. | Stabilized halopropynyl compositions as preservatives |
US7419982B2 (en) * | 2003-09-24 | 2008-09-02 | Wyeth Holdings Corporation | Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts |
DE602004004295T8 (de) * | 2003-09-24 | 2007-09-20 | Wyeth Holdings Corp. | 6-[(Substituiertes)]Triazolopyrimidine als Antikrebsmittel |
DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
WO2005112643A1 (de) * | 2004-05-07 | 2005-12-01 | Basf Aktiengesellschaft | Fungizide mischungen |
WO2006015728A1 (de) * | 2004-08-03 | 2006-02-16 | Basf Aktiengesellschaft | Fungizide synergistische mischungen aus triazolopyrmidin-derivate |
DE102005015677A1 (de) | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
CA2916460C (en) | 2005-06-09 | 2017-10-03 | Klaus Stenzel | Combinations comprising prothioconazole and gulfosinate |
DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
US9012360B2 (en) | 2009-03-25 | 2015-04-21 | Bayer Intellectual Property Gmbh | Synergistic combinations of active ingredients |
IN2012DN01345A (no) | 2009-07-16 | 2015-06-05 | Bayer Cropscience Ag | |
WO2011017190A2 (en) * | 2009-08-05 | 2011-02-10 | Dow Global Technologies Inc. | Synergistic antimicrobial composition |
JP5364936B2 (ja) * | 2010-11-09 | 2013-12-11 | ダウ グローバル テクノロジーズ エルエルシー | フルメツラムまたはジクロスラムとジヨードメチル−p−トリルスルホンとの相乗的組み合わせ |
JP5529833B2 (ja) * | 2010-12-22 | 2014-06-25 | ダウ グローバル テクノロジーズ エルエルシー | グリホサート化合物とdmitsとの相乗的組み合わせ |
RU2446686C1 (ru) * | 2010-12-22 | 2012-04-10 | Государственное учреждение "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Академии наук Республики Башкортостан" | Фунгицидное средство и способ его получения |
EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
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US5071937A (en) * | 1987-12-22 | 1991-12-10 | Mobay Corporation | Coating compositions based on blocked polyisocyanates and sterically hindered aromatic polyamines |
DE3811302A1 (de) * | 1988-04-02 | 1989-10-19 | Bayer Ag | Derivate des triazolylmethyl-cyclopropyl-carbinols als materialschutzmittel |
US5593996A (en) | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
TW224044B (no) * | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
DE4204816A1 (de) * | 1992-02-18 | 1993-08-19 | Bayer Ag | Triazolo-pyridin-derivate |
TWI252231B (en) † | 1997-04-14 | 2006-04-01 | American Cyanamid Co | Fungicidal trifluorophenyl-triazolopyrimidines |
US5985883A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trichlorophenyl-triazolopyrimidines |
JP2000103790A (ja) * | 1998-09-25 | 2000-04-11 | American Cyanamid Co | 殺菌・殺カビ性のトリハロフェニル―トリアゾロピリミジン類 |
US6559151B2 (en) * | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
SK18412002A3 (sk) | 2000-06-30 | 2003-06-03 | Wyeth | Použitie substituovaných triazolopyrimidínových derivátov a farmaceutický prostriedok s ich obsahom |
EP1368351A2 (de) * | 2000-11-13 | 2003-12-10 | Basf Aktiengesellschaft | 7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen |
DE10063115A1 (de) * | 2000-12-18 | 2002-06-27 | Bayer Ag | Triazolopyrimidine |
EE200300499A (et) * | 2001-04-11 | 2003-12-15 | Basf Aktiengesellschaft | 5-halogeen-6-fenüül-7-fluoroalküülaminotriasolopürimidiinid |
DE10124208A1 (de) * | 2001-05-18 | 2002-11-21 | Bayer Ag | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
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- 2002-05-06 AT AT02724307T patent/ATE333793T1/de active
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