Thiophanate-methyl

Structural formula
General
Surname	Thiophanate-methyl
other names	Methyl thiophanate; Thiophanate methyl; 4,4'- o -phenylenebis (3-thioallophanoic acid) dimethyl ester; Dimethyl-4,4'- o -phenylen-bis (3-thioallophanate);
Molecular formula	C 12 H 14 N 4 O 4 S 2
Brief description	light brown solid with a faint odor of sulfur dioxide
External identifiers / databases
EC number	245-740-7
ECHA InfoCard	100,041,567
PubChem	3032791
ChemSpider	2297683
Wikidata	Q126625
properties
Molar mass	342.40 g mol −1
Physical state	firmly
density	1.45 g cm −3
Melting point	162–163 ° C (decomposition)
solubility	practically insoluble in water; soluble in acetone; slightly soluble in acetonitrile, chloroform, ethyl acetate and methanol;
safety instructions
H and P phrases	H: 317-332-341-410
	P: 261-280
Toxicological data	6,640 mg kg −1 ( LD 50 , rat , oral ) ; 10,000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Thiophanate-methyl is a chemical compound from the group of carbamates and benzimidazole derivatives . It was brought to market by Soda in 1970/1971 .

Extraction and presentation

Thiophanate-methyl can be obtained by reacting methyl chloroformate with potassium thiocyanate and then reacting the intermediate product with o- phenylenediamine . If the ethyl ester is used instead of the methyl ester in the reaction, the related thiophanate ethyl is formed .

properties

Thiophanate-methyl is a flammable, light brown solid with a faint odor of sulfur dioxide, which is practically insoluble in water. At room temperature it is resistant to air and light and it is stable in an acidic environment. However, it decomposes in alkaline conditions and under the action of strong oxidizing agents and peroxides .

use

Thiophanate-methyl is used as an active ingredient in crop protection products. It is a fungicidal active ingredient and has been approved in Germany since 2009 for the indication of ear fusariosis in wheat and triticale . Its primary effect is caused by the breakdown product carbendazim , which acts as a β-tubulin inhibitor and disrupts cell division.

Admission

Thiophanate-methyl has been in the FRG since 1972 and was approved in the GDR since 1974. In 2005, only one plant protection product containing thiophanate methyl (Cercobin FL) was approved for pre-harvest treatment against fungal storage rot on pome fruit in Germany.

In the European Union, the active ingredient thiophanate methyl was approved for use as a fungicide with effect from March 1, 2006.

In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved.

safety instructions

Thiophanate-methyl leads to thyroid hyperplasias through the reduction of thyroid hormones and an increased TSH concentration .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on thiophanate methyl in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ Entry on Thiphanate-methyl in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on June 5, 2019.
↑ ^a ^b BUND: Residue Analysis of Plant Protection Products ( Memento from January 30, 2016 in the Internet Archive ) (PDF file; 338 kB), ISSN 0930-4657

↑ Entry on Thiophanate-methyl in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

↑ Entry on thiophanate-methyl. In: Römpp Online . Georg Thieme Verlag, accessed on June 5, 2019.

↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 211 ( limited preview in Google Book search).

↑ Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 ( limited preview in Google Book Search).

↑ T. Hirschfeld, FM Ellner, H. Buschhaus, M. Goßmann, C. Büttner (Institute for Ecochemistry): Investigations into the mechanism of action of thiophanate-methyl in Fusarium spp. (PDF file; 133 kB)

↑ Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer DE, 2010, ISBN 3-0348-0028-2 , pp. 27 ( limited preview in Google Book search).

↑ Peter Brandt: Reports on Food Safety 2005: Food Monitoring . Springer, 2007, ISBN 3-7643-8346-1 , p. 39 ( limited preview in Google Book search).

↑ Directive 2005/53 / EC of the Commission of September 16, 2005 amending Council Directive 91/414 / EEC to include the active substances chlorthalonil, chlorotoluron, cypermethrin, daminozide and thiophanate methyl (PDF)

↑ General Directorate Health and Food Safety of the European Commission: Entry on Thiophanate-methyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

↑ Hans-Werner Vohr: Toxicology: Volume 1: Fundamentals of Toxicology . John Wiley & Sons, 2012, ISBN 3-527-66003-8 ( limited preview in Google Book Search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on thiophanate methyl in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[2] Entry on Thiphanate-methyl in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on June 5, 2019.

[bund-3] BUND: Residue Analysis of Plant Protection Products ( Memento from January 30, 2016 in the Internet Archive ) (PDF file; 338 kB), ISSN 0930-4657

[CLP_100.041.567-4] Entry on Thiophanate-methyl in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[roempp-5] Entry on thiophanate-methyl. In: Römpp Online . Georg Thieme Verlag, accessed on June 5, 2019.

[Thomas_A._Unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 211 ( limited preview in Google Book search).

[kalyani-7] Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 ( limited preview in Google Book Search).

[Institute_for_Ecochemistry-8] T. Hirschfeld, FM Ellner, H. Buschhaus, M. Goßmann, C. Büttner (Institute for Ecochemistry): Investigations into the mechanism of action of thiophanate-methyl in Fusarium spp. (PDF file; 133 kB)

[Brandt_S27-9] Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer DE, 2010, ISBN 3-0348-0028-2 , pp. 27 ( limited preview in Google Book search).

[Brandt_S39-10] Peter Brandt: Reports on Food Safety 2005: Food Monitoring . Springer, 2007, ISBN 3-7643-8346-1 , p. 39 ( limited preview in Google Book search).

[11] Directive 2005/53 / EC of the Commission of September 16, 2005 amending Council Directive 91/414 / EEC to include the active substances chlorthalonil, chlorotoluron, cypermethrin, daminozide and thiophanate methyl (PDF)

[PSM-12] General Directorate Health and Food Safety of the European Commission: Entry on Thiophanate-methyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

[Hans-Werner_Vohr-13] Hans-Werner Vohr: Toxicology: Volume 1: Fundamentals of Toxicology . John Wiley & Sons, 2012, ISBN 3-527-66003-8 ( limited preview in Google Book Search).