Thiram

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Structural formula
Structure of thiram
General
Surname Thiram
other names
  • TMTD
  • Tetramethylthiuram disulfide
  • Pomarsol
  • Thianosan
  • Tetramethylthioperoxydicarbondiamide
  • Tutan
  • Bis (dimethylthiocarbamoyl) disulfide
Molecular formula C 6 H 12 N 2 S 4
Brief description

colorless, odorless, flammable crystals

External identifiers / databases
CAS number 137-26-8
EC number 205-286-2
ECHA InfoCard 100.004.806
PubChem 5455
Wikidata Q416572
Drug information
ATC code

P03 AA05

properties
Molar mass 240.44 g · mol -1
Physical state

firmly

density

1.3 g cm −3

Melting point

148-152 ° C

boiling point

129 ° C (at 26.6 h Pa )

Vapor pressure

0.00133 Pa (25 ° C)

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
08 - Dangerous to health 07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-332-315-317-319-373-410
P: 273-280-305 + 351 + 338-501
MAK

DFG / Switzerland: 1 mg m −3 (measured as inhalable dust )

Toxicological data

560 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Thiram ( TMTD in Russia, Thiuram in Japan) is a chemical compound from the group of dithiocarbamates , more precisely a dimethyl dithiocarbamate. It is in the form of a colorless and odorless powder.

history

Thiram was introduced by DuPont in the USA as a crop protection product in 1931 . The first research into the effects of thiram took place in the 1960s. It is produced and used in large quantities today. It is subject to the Rotterdam Convention .

Extraction and presentation

Thiram is represented on the basis of carbon disulfide and dimethylamine . These react with sodium hydroxide to form sodium dimethyldithiocarbonate . This is dimerized to thiram with hydrogen peroxide .

properties

Thiram decomposes into sulfur, nitrogen and carbon oxides above the melting point.

use

Thiram is a broad spectrum fungicide and is used against fungal pathogens in pome fruit ( scab , rotting), strawberry, vine, vegetable and ornamental plant cultivation ( botrytis ) and as a dressing agent. It is sometimes used in combination with other substances such as B. Tecoram , Dimethomorph or Metalaxyl are used.

Thiram also acts as a repellent against birds and rodents.

Thiram is also used in the rubber industry as a vulcanization accelerator.

Admission

In Germany, thiram-containing preparations could be used against the so-called emergence diseases . In Switzerland, in addition to the use against fungal diseases of the seedling, there are approvals as a wound closure agent for fruit trees, against scabs on fruit and as a game repellent . Thiram-containing preparations were also approved in Austria.

The routine extension of approval in the EU was rejected in October 2018 by the European Commission because of the risk to workers and consumers from spraying foliage as well as the risk to birds and mammals in all forms of use, so that use as a plant protection product in the EU from 31. January 2020 is no longer permitted. Despite this, Thiram remains approved in seven EU member states. In addition, the active ingredient manufactured by Bayer is also sold on the Brazilian market.

Safety instructions / risk assessment

Thiram is only slightly toxic, but in large doses or with prolonged contact it can cause allergies and damage the liver. Acetaldehyde syndrome occurs when exposed to alcohol . When thiram reacts with nitrosating agents, carcinogenic N -nitrosamines can be formed. Long-term traces (100–500 ppm) of thiram in the feed of birds lead to soft eggshells, reduced laying performance and deformities in poultry.

Thiram was included by the EU in 2012 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation in the Community's rolling action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the inclusion of thiram were concerns about high (aggregated) tonnage and widespread use and as a potential endocrine disruptor . The re-evaluation took place from 2014 and was carried out by Sweden . A final report was then published.

See also

Individual evidence

  1. ↑ a b c d e f g h i Entry on Thiram in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  2. ↑ Donald Mackay, Wan Ying Shiu, Kuo-Ching Ma, Sum Chi Lee: Handbook of physical-chemical properties and environmental fate for organic chemicals , Vol. IV, 2nd Edition, CRC Press, 2006, ISBN 978-1-56670-687 -2 , p. 4097.
  3. ↑ a b Entry Thiram at Extoxnet.
  4. ↑ Entry on Thiram in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 137-26-8 or Thiram ), accessed on November 2, 2015.
  6. ↑ a b Entry on Thiram. In: Römpp Online . Georg Thieme Verlag, accessed on May 3, 2015.
  7. ↑ United States Environmental Protection Agency: Thiram Factsheet (PDF; 167 kB).
  8. ^ Joint Meeting on Pesticide Residues (JMPR), Monograph for Thiram , accessed December 9, 2014.
  9. ↑ a b Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 129 ( limited preview in Google Book search).
  10. ↑ Saat- und Erntetechnik GmbH: seeds encrusted with fungicides ( Memento from April 6, 2005 in the Internet Archive )
  11. ↑ MAK Value Documentation in German language, 2007, doi : 10.1002 / 3527600418.mb13726d0043
  12. ↑ a b Directorate-General for Health and Food Safety of the European Commission: Entry on thiram in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.
  13. ↑ Implementing Regulation (EU) 2018/1500 of the Commission of 9 October 2018 on the non-renewal of the approval for the active substance thiram and the ban on the use and sale of seeds that have been treated with plant protection products containing thiram, in accordance with Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending the Commission Implementing Regulation (EU) No. 540/2011 . 32018R1500, October 10, 2018 ( europa.eu [accessed October 25, 2018]).
  14. Jump up ↑ Benjamin Luig, Fran Paula de Castro and Alan Tygel (both Campanha Permanente Contra os Agrotóxicos e Pela Vida), Lena Luig (INKOTA network), Simphiwe Dada (Khanyisa), Sarah Schneider (MISEREOR) and Jan Urhahn (Rosa-Luxemburg- Foundation): Dangerous pesticides. (PDF; 2.4 MB) from Bayer and BASF - a global business with double standards. Rosa Luxemburg Foundation , INKOTA network , Episcopal Aid Organization Misereor u. a., April 2020, accessed on April 25, 2020 .
  15. ↑ Veterinary pharmacology and toxicology Zurich via Thiam
  16. ↑ Clinipharm: Toxikologie-Dithiocarbamate
  17. ↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
  18. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Thiram , accessed on March 26, 2019.