DK146065B - Dithiocarbamater med baktericid virkning - Google Patents
Dithiocarbamater med baktericid virkning Download PDFInfo
- Publication number
- DK146065B DK146065B DK080473AA DK80473A DK146065B DK 146065 B DK146065 B DK 146065B DK 080473A A DK080473A A DK 080473AA DK 80473 A DK80473 A DK 80473A DK 146065 B DK146065 B DK 146065B
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- Denmark
- Prior art keywords
- compounds
- dithiocarbamates
- solid
- potassium
- bactericide effect
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N47/14—Di-thio analogues thereof
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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Description
i 146065
Opfindelsen angår hidtil ukendte N-hydroxyme-thyl-N-methyl-dithiocarbamater. De kan anvendes som bactericider og herunder til jorddesinfektion i industri og landbrug.
5 De omhandlede dithiocarbamater er ejendommeli ge ved at de har den i kravet angivne . formel.
Et stort antal dithiocarbaminsyresalte er beskrevet i den kemiske litteratur som kommercielle, 10 industrielle og agrikulturkemiske mikrobicider og nematocider. Det har nu vist sig, at de omhandlede forbindelser har en særlig kraftig baktericid virkning.
Forbindelserne ifølge opfindelsen er egnede til bekæmpelse'af slim og slam ved pulp- og papirfa-15 brikation, ved behandling af ferskvand til industrielle processer og i køletåme. Forbindelserne er endvidere egnede som landbrugsbaktericider og jorddesinfektionsmidler. Endvidere er forbindelserne stabile i alkaliske systemer, hvorfor de er egnede som konserveringsmidler 20 til klæbestoffer, fugemasser, mørtler, spartelmasser, sammensatte cementer, detergenter, voksemulsioner til gulve og gulvpolitur, blæk, latexemulsioner, stivelse til vasketøj, skærevæskeemulsioner, latexmalinger, overtræk, færdigbehandlingsmidler og trykfarver base-25 ret på stivelse og latex til pulp og papir, spinde-emulsioner samt færdigbehandlingsopløsninger og trykpastaer til anvendelse i tekstilindustrien. Forbindelserne er også effektive over for sulfatreducerende bakterier og jernbakterier.
30 De omhandlede forbindelser kan fremstilles ved omsætning af Na- eller K-N-methyldithiocarbamat med formaldehyd og monomethylamin.
Mængden af natrium- eller kaliumdithiocarbamat, der skal tilsættes i vandige systemer, kan passende 35 være fra ca. 0,01 til 10.000 dele pr. million del vand (ppm). Det vil imidlertid forstås, at der kan anvendes større mængder uden skadelig virkning, men sådanne større mængder forøger udgifterne, samtidig med at der 146065 2 kun opnås begrænset fordel. Når forbindelserne ifølge opfindelsen anvendes som jorddesinfektionsmiddel andrager egnede mængder fra 11-330 kg/hektar. Som nævnt ovenfor, kan der anvendes større mængder uden skadelig virk-5 ning.
Det foretrækkes at fremstille de omhandlede forbindelser ved først at fremstille natrium- eller kaliumsaltene af methyldithiocarbaminsyre og derpå tilsætte aldehydet efterfulgt af aminen. Tilfredsstillende pro-10 dukter kan også fås ved at sætte aminen til dithiocar-bamatet efterfulgt af tilsætning af aldehydet eller ved at blande aminen og aldehydet og sætte blandingen til dithiocarbamatet.
Forbindelserne ifølge opfindelsen anvendes i almindelighed 15 uden isolering, eftersan alkalimetalsalte af dithiocarbamin-syre er ekstremt opløselige i vand, er hygroskopiske og dekomponeres af syre og varme, og de oxideres af luften, når der gøres forsøg på at isolere forbindelserne.
20
Eksempel
Isolering og prøvning af den aktive bestanddel.
2000 g 56%rs kalium-N-methyldithiocarbamat, 25 634 g 37%'s formaldehyd, 486 g 50%'s mrøetnethylamin alt i vandig opløsning og 272 g vand omsattes til opnåelse af en opløsning.
Til en roterende vakuumfordamper blev der ledt 1080 g af opløsningen, hvorpå der blev opvarmet til 50-30 55°C til opnåelse af konstant vægt. Remanensen var en blanding af en tyk sirup og et krystallinsk fast stof, og den havde en vægt på 459,6 g (46,6% af den oprindelige vægt). Denne remanens blev blandet med 300 ml iso-propanol, og der blev opnået en opløsning indeholdende 35 et krystallinsk fast stof. Blandingen blev filtreret i Buchner-tragt, og det faste stof blev vasket med iso-propanol og tørret i vakuumdesiccator. Dette stof blev opslæmmet i 700 ml ether og filtreret. Efter tørring 146065 3 vejede det faste stof (A) 247 g. Det etheriske filtrat blev inddampet, hvorved der blev opnået en flydende remanens på 7,4 g. Analyse af det faste stof for svovl og nitrogen dannede ikke i sig selv basis for nogen slut-5 ninger, men forholdet mellem S og N var 1:1, hvilket angav, at der var fremkommet reaktionsprodukter mellem dithiocarbamat, formaldehyd og monoethylamin. Forsøg på at adskille denne blanding og identificeret komponenterne mislykkedes. Det blev vist, at det faste stof 10 var en blanding af dithiocarbaminsyresalte ved opløseligheden i vand, tilstedeværelsen af kalium (ca. 24%) og det infrarøde spektrum.
Isopropanolfiltratet blev sammenblandet med vaskevæskerne og der udskiltes 20 g fast stof ved hen-15 stand. Den tilbageværende isopropanolopløsning blev inddampet til opnåelse af 174 g af en tyk gul sirup.
Når siruppen blev opløst i 500 ml methanol og opløsningen fortyndet med 1000 ml ether, blev der opnået et hvidt fast stof identisk med de 20 g, der allerede var 20 opnået, i en mængde på 55 g (efter tørring). Dette faste stof blev betegnet (B) og blev tørret i en vakuum-desiccator. Analyse viste 23,3% kalium, 36,5% svovl og 8,5% nitrogen, hvilket sammen med det infrarøde spektrum antydede, at forbindelsen var kalium-25 N-hydroxymethyl-N-methyldithiocarbamat (teoretisk analyse for denne forbindelse: K 23,5 ; S 38,7; N 8,4).
Forbindelserne (A) og (B) blev prøvet mod Aero-bacter aerogenes ved pulpsubstratmetoden ved en pH-vær-di på 5,5 efter 18 timers kontakt. Resultaterne er an-30 ført i tabel 2.
Til sammenligning og identifikation er spektrene for forbindelsen (B) (fig. 1) og kalium-N-methyl-di-thiocarbamat (fig. 2) vedlagt.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00246961A US3856851A (en) | 1972-04-24 | 1972-04-24 | Potassium n-hydroxylmethyl-n-methyldithiocarbamate |
US24696172 | 1972-04-24 |
Publications (2)
Publication Number | Publication Date |
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DK146065B true DK146065B (da) | 1983-06-20 |
DK146065C DK146065C (da) | 1983-11-14 |
Family
ID=22932937
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DK80473A DK146065C (da) | 1972-04-24 | 1973-02-14 | Dithiocarbamater med baktericid virkning |
Country Status (21)
Country | Link |
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US (1) | US3856851A (da) |
JP (1) | JPS5419444B2 (da) |
AR (1) | AR195699A1 (da) |
AT (2) | AT322572B (da) |
AU (1) | AU467626B2 (da) |
BE (1) | BE796216A (da) |
BR (1) | BR7302041D0 (da) |
CA (1) | CA978998A (da) |
CH (1) | CH590832A5 (da) |
DE (2) | DE2308807C2 (da) |
DK (1) | DK146065C (da) |
ES (1) | ES412021A1 (da) |
FI (1) | FI55749C (da) |
FR (2) | FR2181815B1 (da) |
GB (2) | GB1420028A (da) |
IT (1) | IT983023B (da) |
NL (2) | NL172116C (da) |
NO (1) | NO137122C (da) |
PH (1) | PH10937A (da) |
SE (1) | SE418142B (da) |
ZA (1) | ZA731003B (da) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS52108021A (en) * | 1976-03-05 | 1977-09-10 | Buckman Labor Inc | Stabilized insecticide and its usage |
US4185113A (en) * | 1976-03-10 | 1980-01-22 | Roussel Uclaf | Stabilized metal salts of ethylene bis dithiocarbamic acid |
NZ189120A (en) * | 1977-12-16 | 1981-12-15 | Borax Holdings Ltd | Wood-preservative containing an alkali metal boate and a dithiocarbamate |
JPS58947B2 (ja) * | 1978-07-06 | 1983-01-08 | 日産自動車株式会社 | 耐熱羽根車のダイカスト装置 |
US4203999A (en) * | 1978-10-16 | 1980-05-20 | The Dow Chemical Company | Bis(dithiocarbamate) salts |
EP0037861A1 (en) * | 1980-03-24 | 1981-10-21 | Tokyo Organic Chemical Industries, Ltd. | Salts of alkylenebisdithiocarbamic acid derivatives, processes for their preparation, fungicidal compositions containing them and methods of combating fungi |
US4315846A (en) * | 1980-03-26 | 1982-02-16 | Tokyo Organic Chemical Industries, Ltd. | Metal salt of N-substituted alkylenebisdithiocarbamic acid |
DE3426078A1 (de) * | 1984-07-14 | 1986-01-23 | Basf Ag, 6700 Ludwigshafen | Verfahren zur stabilisierung von zineb |
US5100915A (en) * | 1990-06-06 | 1992-03-31 | Pennwalt France S.A. | Reduction and inhibition of etu content in alkylenebisdithiocarbamates |
ES2681975T3 (es) * | 2012-09-25 | 2018-09-17 | Buckman Laboratories International, Inc. | Método para la potenciación de la eficacia biocida de sales de monoalquilditiocarbamato |
MX368322B (es) * | 2014-08-01 | 2019-09-26 | Buckman Laboratories Int Inc | Microbicidas y usos de los mismos. |
US10793451B2 (en) * | 2015-06-30 | 2020-10-06 | Bulk Chemical Services, LLC. | Method for treating water used in oil field applications to inhibit bacterial growth with methylammonium monomethyldithiocarbamate |
CN106336075B (zh) * | 2016-09-14 | 2019-08-02 | 清华大学 | 一种处理电厂循环冷却排污水的方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US2589209A (en) * | 1948-09-04 | 1952-03-18 | Hanson Van Winkle Munning Co | Dithiocarbamate-aldehyde condensation polymers |
US2609389A (en) * | 1949-05-14 | 1952-09-02 | Du Pont | Preparation of certain salts of alkylene bis-dithiocarbamic acids |
US3084095A (en) * | 1958-08-01 | 1963-04-02 | Vondelingen Plaat Bv | Fungicidal dithiocarbamic acid derivatives |
-
1972
- 1972-04-24 US US00246961A patent/US3856851A/en not_active Expired - Lifetime
-
1973
- 1973-02-08 AR AR246503A patent/AR195699A1/es active
- 1973-02-12 CA CA163,545A patent/CA978998A/en not_active Expired
- 1973-02-13 ZA ZA731003A patent/ZA731003B/xx unknown
- 1973-02-13 AU AU52096/73A patent/AU467626B2/en not_active Expired
- 1973-02-14 DK DK80473A patent/DK146065C/da not_active IP Right Cessation
- 1973-02-22 DE DE2308807A patent/DE2308807C2/de not_active Expired
- 1973-02-23 NL NLAANVRAGE7302546,A patent/NL172116C/xx not_active IP Right Cessation
- 1973-02-23 FI FI559/73A patent/FI55749C/fi active
- 1973-02-23 AT AT162073A patent/AT322572B/de not_active IP Right Cessation
- 1973-02-24 ES ES412021A patent/ES412021A1/es not_active Expired
- 1973-03-02 BE BE128321A patent/BE796216A/xx not_active IP Right Cessation
- 1973-03-13 FR FR7308936A patent/FR2181815B1/fr not_active Expired
- 1973-03-22 BR BR732041A patent/BR7302041D0/pt unknown
- 1973-03-30 PH PH14473A patent/PH10937A/en unknown
- 1973-04-06 JP JP3884973A patent/JPS5419444B2/ja not_active Expired
- 1973-04-09 IT IT49307/73A patent/IT983023B/it active
- 1973-04-18 SE SE7305549A patent/SE418142B/xx unknown
- 1973-04-18 NO NO1664/73A patent/NO137122C/no unknown
- 1973-04-19 GB GB1907873A patent/GB1420028A/en not_active Expired
- 1973-04-24 CH CH579073A patent/CH590832A5/xx not_active IP Right Cessation
-
1976
- 1976-02-23 AT AT129476A patent/AT339666B/de not_active IP Right Cessation
- 1976-02-27 DE DE19762608135 patent/DE2608135A1/de not_active Ceased
- 1976-03-04 FR FR7606151A patent/FR2342662A1/fr active Granted
- 1976-03-10 NL NLAANVRAGE7602496,A patent/NL175019C/xx not_active IP Right Cessation
- 1976-04-29 GB GB17552/76A patent/GB1486174A/en not_active Expired
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