NO812579L - Mikrobicid middel. - Google Patents
Mikrobicid middel.Info
- Publication number
- NO812579L NO812579L NO812579A NO812579A NO812579L NO 812579 L NO812579 L NO 812579L NO 812579 A NO812579 A NO 812579A NO 812579 A NO812579 A NO 812579A NO 812579 L NO812579 L NO 812579L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- agent
- formula
- microbicid
- microbicidal
- Prior art date
Links
- 239000002855 microbicide agent Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 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 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000013543 active substance Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- -1 aromatic alcohols Chemical class 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AGULWIQIYWWFBJ-UHFFFAOYSA-N 3,4-dichlorofuran-2,5-dione Chemical compound ClC1=C(Cl)C(=O)OC1=O AGULWIQIYWWFBJ-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000223259 Trichoderma Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KVBAKSQRUXXHCK-UHFFFAOYSA-N 3,4-Dichloro-5-hydroxy-2H-pyrrol-2-one Chemical class ClC1=C(Cl)C(=O)NC1=O KVBAKSQRUXXHCK-UHFFFAOYSA-N 0.000 description 1
- YNDDOOKQQGEOFR-UHFFFAOYSA-N 3,4-dichloro-1-(2-fluorophenyl)pyrrole-2,5-dione Chemical class FC1=CC=CC=C1N1C(=O)C(Cl)=C(Cl)C1=O YNDDOOKQQGEOFR-UHFFFAOYSA-N 0.000 description 1
- RQCLKJICDPMGDH-UHFFFAOYSA-N 7-(dichloromethyl)-2-fluoro-3-sulfanylideneisoindol-1-one Chemical compound S=C1N(F)C(=O)C2=C1C=CC=C2C(Cl)Cl RQCLKJICDPMGDH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000223602 Alternaria alternata Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000221955 Chaetomium Species 0.000 description 1
- 241001515917 Chaetomium globosum Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241001600093 Coniophora Species 0.000 description 1
- 241001626940 Coniophora cerebella Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000222418 Lentinus Species 0.000 description 1
- 241000222451 Lentinus tigrinus Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241001123663 Penicillium expansum Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000222640 Polyporus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000907561 Sydowia polyspora Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 241000222355 Trametes versicolor Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000005068 cooling lubricant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- IPENDKRRWFURRE-UHFFFAOYSA-N fluoroimide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(Cl)=C(Cl)C1=O IPENDKRRWFURRE-UHFFFAOYSA-N 0.000 description 1
- 238000004362 fungal culture Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/456—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Steroid Compounds (AREA)
Description
Oppfinnelsen vedrører mikrobicide midler som inneholder N-alkyl-2,3-diklor-maleinimider.
Fra U.S. patent nr. 2.865.730 er det kjent at halogen-maleinimider har herbicid virkning. I britisk patent nr. 1.094.802 omtales anvendelsen av halogen-maleinimider som vekststoffer.
Det er dessuten kjent (DE-OS 2.156.967 og U.S. patent nr. 3.734.927) at N-(p-fluorfenyl)-2,3-diklormalein-imid er et virksomt stoff mot sitrusskurv. Fra Japan Kokai 73/39, 638 er det kjent anvendelse av N-(fluorfenyl)-2,3-di-klormaleinimider til bekjempelse av Trichoderma viridei sopp-kulturer.
Det er funnet nye mikrobicide midler som inneholder N-alkyl-2,3-diklormaleinimider med formel
hvori
R"<*>" betyr en eventuelt substituert alkyl eller cykloalkyl.
De nye N-alkyl- resp. -cykloalkylsubstituerte di-klormaleinimider har overraskende større mikrobicid virkning enn de tilsvarende N-fenylsubstituer te forbindelser.
Alkyl er fortrinnsvis en rettlinjet eller forgrenet hydrokarbonrest med 1-16 karbonatomer. Spesielt foretrukket er en lavere alkylrest med inntil ca. 6 karbonatomer. Eksempelvis skal det nevnes følgende alkylrester: metyl, etyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, heksyl og isoheksyl.
Cykloalkyl er fortrinnsvis en cyklisk hydrokarbonrest med 3-10 karbonatomer. Spesielt foretrukket er cyklopentyl- og cykloheksylresten.
Som substituenter av resten R^" skal det nevnes i mikrobicide midler vanlige substi tuenter . Eksempelvis, kan det nevnes følgende rester: halogen som fluor, klor. brom og jod (fortrinnsvis fluor og klorl, tiocyanat, C^-C^-alkok-sy, C^-C^-alkyltio og fenyl.
Som foretrukket mikrobicid middel med formel (I) skal det nevnes N-alkyl-2,3-diklormaleinimid med formel
hvori
R 2 betyr en lavere alkyl-, cyklopentyl- eller cykloheksylrest.
N-alkyl-2,3-diklormaleinimidene ifølge oppfinnelsen kan fremstilles på i og for seg kjent måte (britisk patent 818-192). Eksempelvis kan aminer med formel
hvor i
R^ har ovennevnte betydning,
omsettes med diklormaleinsyreanhydrid ved forhøyede tempe-raturer, eksempelvis 70 - 120°C i nærvær av syrer, eksempelvis iseddik eller saltsyre.
N-alkyl-2,3-diklormaleinimidene ifølge oppfinnelsen kan fortrinnsvis anvendes som virksomme stoffer til bekjempelse av mikroorganismer i tekniske materialer.
Tekniske materialer som skal beskyttes ved hjelp av de virksomme stoffer ifølge oppfinnelsen mot en mikrobi-ell endring og ødeleggelse er eksempelvis klebestoffer, lim, papir og kartong, tekstiler, lær, tre, påstrykningsmidler, puss, emulsjoner og kunststoffartikler som kan angripes og/ eller ødelegges av mikroorganismer. Innen rammen av materialer som skal beskyttes kan det også nevnes deler av produk-sjonsanlegg, eksempelvis kjølevanns-og kjølesmøremiddel-kretsløp som kan påvirkes av mikroorganismer.
Mikroorganismer som kan bevirke en nedbygning eller en endring av de tekniske materialer er eksempelvis bakterier, sopp, gjær, alger, slim og virer. Fortrinnsvis anvendes N-alkyl-2,3-diklormaleinimidene ifølge oppfinnelsen mot sopp, spesielt mot tremisfargende og treødeleggende sopp og muggsopp.
Som mikroorganismer kan eksempelvis nevnes føl-gende slekter:
Alternaria, som Alternaria tenuis,
Aspergillus, som Aspergillus niger,
Chaetomium, som Chaetomium globosum,.
Coniophora, som Coniophora cerebella,
Lentinus, som Lentinus tigrinus,
Penicillium, som Penicillium glaucum,
Polyporus, som Polyporus versicolor,
Pullularia, som Pullularia pullulans,
Scerophoma, som Sclerophoma pityophila, Trichoderma, som Tr'ichoderma viride, Staphylococcus, som Staphylococcus aureus.
Alt etter anvendelsesområdet kan N-alkyl-2,3-di-klormaleinimidene ifølge oppfinnelsen overføres i de vanlige formuleringer som oppløsninger, emulsjoner, suspensjon-er, pulvere, pastaer og granulater. Disse kan fremstilles på i og for seg kjent måte f.eks. ved sammenblanding av de virksomme stoffer med et drøyemiddel av flytende oppløs-ningsmiddel og/eller faste bærestoffer, eventuelt under anvendelse av overflateaktive midler som emulgatorer og/eller dispergeringsmidler idet eksempelvis ved anvendelse av vann-drøyemidler eventuelt kan anvendes organiske oppløsnings-midler som hjelpeoppløsningsmidler.
Flytende oppløsningsmidler av de virksomme stoffer kan f.eks. være vann, alkohol, eksempelvis lavere alifatisk alkohol, fortrinnsvis etanol og isopropanol, og aromatiske alkoholer som benzylalkohol, flytende hydrokarboner sqm bensinfraksjoner, klorerte hydrokarboner som 1,2-dikloretan.
Faste bærestoffer som kan tilsettes ved fremstil-lingen av de ferdige anvendelsesformer av det virksomme stoff kan eksempelvis være talkum, kiselgur, bentonitt, kao-lin, diatomenjord og syntetisk stenmel.
Overflateaktive midler kan være handelsvanlige emulgatorer som alkylsulfonat, alkylarylsulfonater, aryl-sulfonater, alkylamidsulfonater, alkylarylpolyeteralkoholer, polyoksyetylen-fettsyreestere eller dispergeringsmidler som lignin, metylcellulose , polyoksyetylenpolyoksypropylenblokk-^ polymer.
Anvendelsesformen av det mikrobicide middel ifølge oppfinnelsen inneholder vanligvis 0,1 - 95 vekt-%, fortrinnsvis 0,5 - 90 vekt-%, av N-alkyl-2,3-diklormaleinimidet iføl-ge oppfinnelsen som virksomt stoff.
De for beskyttelse av tekniske materialer nødven-dige virksomme stoffmenger kan varieres innen store områder. Vanligvis ligger de i området på 0,0001 - 5 vekt-%, fortrinnsvis i området på 0,01 - 2 vekt-% referert til den samlede mengde av materialet som skal beskyttes.
De virksomme stoffer ifølge oppfinnelsen kan fore-ligge i formuleringer i blanding med andre kjente virksomme stoffer. Eksempelvis skal det nevnes følgende virksomme stoffer: Benzimidazolyl-metylkarbamat, tetrametyl-tiuramdisulfid, N-fluordiklormetyltioftalimid og N,N'-dimetyl-N'-fenyl-(N-fluordiklormetyltio)-sulfamid.
A) Fremstillingseksempel
Til en oppløsning av 334 g (2,0 mol) diklormaleinsyreanhydrid i 1400 ml iseddik settes 146 g (2,0 mol) n-butyl-amin oppløst i 300 ml iseddik. Etter 2 timers omrøring ved 80°C lar man det avkjøle og blander reaksjonsblandingen med isvann. De utfelte gulaktige krystaller frasuges, vaskes med vann og tørkes. Utbytte: 390,0 g (88% av det. teoretiske), smeltepunkt 37°C.
B) Bestemmelse av den minimale hemmekonsentrasjon ( MHK); En agar som fremstilles av ølvørter og pepton blandes med det virksomme stoff i konsentrasjoner på 0,1 mg/l til 2000 mg/l. Etter stivning av agaren foregår kontaminer-ing med renkulturene av de i tabell 1 oppførte prøveorganis-mer. Etter 2 ukers lagring ved 28°C og 60 - 70% relativ luftfuktighet bestemmes MHK. MHK er den laveste konsen-trasjon av virksomt stoff hvor veksten av den angitte mikro-betype hemmes. Den er angitt i følgende tabell 1.
Claims (4)
1. Mikrobicid middel inneholdende N-alkyl-2,3-diklor-maleinimider med formel
hvori
R" <*> " betyr eventuelt substituert alkyl eller cykloalkyl.
2. Mikrobicid middel ifølge krav 1, inneholdende N-alkyl-2,3-diklormaleinimider med formel
hvor
R 2betyr en lavere alkyl- eller cykloheksylrest.
3. Anvendelse av mikrobicide midler ifølge krav 1 til beskyttelse av tekniske materialer.
4. Mikrobicid middel ifølge krav 1 og 2 inneholdende 0,1 - 55 vekt-% N-alkyl-2,3-diklormaleinimid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803030481 DE3030481A1 (de) | 1980-08-12 | 1980-08-12 | Mikrobizides mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO812579L true NO812579L (no) | 1982-02-15 |
Family
ID=6109456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO812579A NO812579L (no) | 1980-08-12 | 1981-07-28 | Mikrobicid middel. |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0045907A1 (no) |
| JP (1) | JPS5754102A (no) |
| DE (1) | DE3030481A1 (no) |
| DK (1) | DK356781A (no) |
| FI (1) | FI812471L (no) |
| NO (1) | NO812579L (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3222152A1 (de) * | 1982-06-12 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Substituierte maleinsaeureimide, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3306697A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Substituierte maleinsaeureimide |
| DE3306844A1 (de) * | 1983-02-26 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Fungizide mittel auf maleinsaeureimid-basis |
| US4709052A (en) * | 1983-05-31 | 1987-11-24 | Sumitomo Chemical Company, Limited | Soil disease-controlling imides |
| DE3415532A1 (de) * | 1984-04-26 | 1985-10-31 | Bayer Ag, 5090 Leverkusen | N-(dichlorfluormethylthio)-3,4-dimethylmaleinimid, ein verfahren zu seiner herstellung und seine verwendung |
| DE3738591A1 (de) * | 1987-11-13 | 1989-05-24 | Bayer Ag | N-substituierte dichlormaleinimide |
| CN103113280B (zh) * | 2013-02-06 | 2015-08-26 | 浙江工业大学 | 一种3,4-二氯顺丁烯二酰亚胺化合物及其制备与应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2865730A (en) * | 1955-07-25 | 1958-12-23 | Fmc Corp | Method of regulating plant growth |
| DE1108224B (de) * | 1956-12-19 | 1961-06-08 | Ici Ltd | Verfahren zur Herstellung von N-substituierten Halogenmaleinimiden |
| DE1146694B (de) * | 1960-09-10 | 1963-04-04 | Basf Ag | Insektenbekaempfungsmittel |
| JPS4817052B1 (no) * | 1970-01-10 | 1973-05-26 | ||
| US3890270A (en) * | 1974-04-10 | 1975-06-17 | Tenneco Chem | Polyvinyl halide resin compositions |
-
1980
- 1980-08-12 DE DE19803030481 patent/DE3030481A1/de not_active Withdrawn
-
1981
- 1981-07-28 NO NO812579A patent/NO812579L/no unknown
- 1981-07-30 EP EP81105997A patent/EP0045907A1/de not_active Withdrawn
- 1981-08-10 FI FI812471A patent/FI812471L/fi not_active Application Discontinuation
- 1981-08-11 DK DK356781A patent/DK356781A/da unknown
- 1981-08-11 JP JP56124854A patent/JPS5754102A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK356781A (da) | 1982-02-13 |
| FI812471L (fi) | 1982-02-13 |
| DE3030481A1 (de) | 1982-03-11 |
| EP0045907A1 (de) | 1982-02-17 |
| JPS5754102A (no) | 1982-03-31 |
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