Dimethyl sulfamide
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| General | |||||||||||||||||||
| Surname | Dimethyl sulfamide | ||||||||||||||||||
| other names |
N , N -dimethylsulfamide |
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| Molecular formula | C 2 H 8 N 2 O 2 S | ||||||||||||||||||
| Brief description |
white crystals |
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| properties | |||||||||||||||||||
| Molar mass | 124.16 g mol −1 | ||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
97 ° C |
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| solubility |
sparingly soluble in water: 1.8 g l −1 (20 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Dimethyl sulfamide (short: DMS ; not to be confused with dimethyl sulfide or dimethyl sulfate , which are also abbreviated as DMS) is a chemical compound from the group of sulfonamides . It arises as a metabolite of the fungicides dichlofluanid and tolylfluanid .
history
The pollution of drinking water with dimethyl sulfamide made headlines in Ravensburg and Oberkirch , among others . There is a breakdown product of the pesticide tolylfluanid which until the fall of 2006 was unknown. It can also be released from the fungicide dichlofluanid. Although dimethylsulfamide itself is not toxic, is in the treatment of so polluted water with ozone is a risk that it the carcinogenic dimethylnitrosamine is formed.
Presentation and extraction
The synthesis is carried out by converting sulfamic acid with dimethylamine in ethylene glycol dimethyl ether .
literature
- Carsten K. Schmidt: Transformation products of plant protection product metabolites: Activated carbon for the enrichment of N, N-dimethylsulfamide and NDMA from aqueous matrices . In: GIT . tape 51 , no. 10 , ISSN 0016-3538 , p. 817-819 .
Web links
- PAN Pesticides Database - Chemicals: N, N-Dimethylsulfamide (metabolite of tolylfluanid).
- Bayer CropScience: Temporary ban on the use of pesticides containing tolylfluanid in the field. News from March 16, 2007
Individual evidence
- ^ Jie Li, Adriaan J. Minnaard, Robertus JM Klein Gebbink, Gerard van Koten: P'CP'-Pincer palladium complex-catalyzed allylation of N, N-dimethylsulfamoyl-protected aldimines . In: Tetrahedron Letters . tape 50 , no. 19 , May 13, 2009, pp. 2232-2235 , doi : 10.1016 / j.tetlet.2009.02.187 .
- ↑ Entry on N, N-Dimethylsulfamide at TCI Europe, accessed on June 27, 2011.
- ↑ Directive 98/8 / EC concerning the placing of biocidal products on the market, Assessment Report Dichlofluanid
- ↑ There is not yet a harmonized classification for this substance . A labeling of (dimethylsulfamoyl) amine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on November 30, 2018, is reproduced from a self-classification by the distributor .
- ↑ Our drinking water, the best controlled food. (PDF) Technical Works Schussental (Ravensburg), accessed on November 22, 2017 .
- ↑ Stadtwerke Oberkirch: Information event organized by the “Wasserversorgung Vorderes Renchtal” association on water quality. ( Memento from January 15, 2010 in the Internet Archive ).
- ↑ S. Hauswirth: Dimethyl sulfamide in groundwater and drinking water - the pollutant of the year? In: Healthcare . tape 70 , no. 3 , 2008, 38, doi : 10.1055 / s-2008-1076545 .
- ↑ JM McManus, JW McFarland, CF Gerber, WM McLamore, GD Laubach: Sulfamylurea Hypoglycemic Agents. I. Synthesis and Screening . In: J. Med. Chem. Volume 8 , no. 6 , 1965, pp. 766-776 , doi : 10.1021 / jm00330a009 .