Metiram

Structural formula
	Structural example: The order of the zinc units and dithiocarbamate structures is not uniform and random. The illustration only shows the correct ratio of 3: 4.
General
Surname	Metiram
other names	Zinc ammonia ethylene bis (dithiocarbamate) poly [ethylene bis (thiuram disulfide)]
Molecular formula	(C 16 H 33 N 11 S 16 Zn 3 ) n
Brief description	yellow solid
External identifiers / databases
EC number	618-430-8
ECHA InfoCard	100.116.508
Wikidata	Q15632902
properties
Molar mass	(1088.70) n g mol −1
Physical state	firmly
density	1.86 g cm −3
Melting point	156 ° C (decomposition)
Vapor pressure	1 · 10 −5 Pa (20 ° C)
solubility	almost insoluble in water; insoluble in organic solvents;
safety instructions
H and P phrases	H: 317-373-410
	EUH: 401
	P: 101-102-260-272-280-303-352-333-311-362 + 364-391-501
Toxicological data	2850 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Metiram is a chemical compound from the group of dithiocarbamates .

Extraction and presentation

During the manufacturing process, ethylene diamine is reacted with carbon disulphide in an ammonia solution to form ammonium ethylene bisdithiocarbamate . This intermediate product is further reacted with zinc chloride and then with hydrogen peroxide to form the polymeric product.

properties

Metiram is a yellow solid that melts at 156 ° C with decomposition. The compound is insoluble in water or sparingly soluble in n-hexane , dichloromethane , chloroform , methanol , acetone and ethyl acetate . It is soluble in pyridine , with slow degradation. Metiram is unstable in strongly acidic or strongly alkaline media. The compound hydrolyzes in water at pH7 and 22 ° C with a half-life of 17.4 hours. The compound decomposes when exposed to UV light .

use

Estimated application rate in the USA

Metiram was used as a fungicide, for example against scab in pome fruit and downy mildew in wine and hops. It attacks at certain points of the pyruvate dehydrogenase system one, by combining with dithio groups of lipoic acid - dehydrogenase connects.

Admission

Metiram was launched in 1958 and has been in the FRG since 1971 and was approved in the GDR between 1974 and 1994.

Metiram has been an approved active ingredient in plant protection products in the European Union since July 2006. In Germany, Austria and Switzerland, plant protection products (e.g. Cabrio Top and Polyram WG) with this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e Metiram data sheet at Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).

↑ ^a ^b ^c ^d ^e ^f ^g ^h Müller, F .; Ackermann, P .; Margot, P .: Agricultural Fungicides. 2. Individual Fungicides in Ullmann's Encyclopedia of Industrial Chemistry , 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.o12_o06 .

^ Entry on Metiram. In: Römpp Online . Georg Thieme Verlag, accessed on March 25, 2013.

↑ ^a ^b Entry on Metiram in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.

↑ ^a ^b BASF: POLYRAM WG ( page no longer available , search in web archives ) Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. (PDF; 64 kB).@1@ 2

↑ ^a ^b FAO: Metiram (PDF; 267 kB).

↑ ^a ^b M. Bahadir, H. Parlar, Michael Spiteller: Springer Umweltlexikon . Springer, 2000, ISBN 978-3-540-63561-1 , pp. 764 ( limited preview in Google Book search).

↑ Peter Brandt (Ed.): Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer, 2010, ISBN 978-3-0348-0028-0 , pp. 21 ( limited preview in Google Book search).

↑ Directive 2005/72 / EC of the Commission of October 21, 2005 amending Directive 91/414 / EEC of the Council for the inclusion of the active substances chlorpyrifos, chlorpyrifos-methyl, Mancozeb, Maneb and Metiram (PDF) .

↑ General Directorate Health and Food Safety of the European Commission: Entry on Metiram in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[Sigma-1] Metiram data sheet at Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).

[Ullmann-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Müller, F .; Ackermann, P .; Margot, P .: Agricultural Fungicides. 2. Individual Fungicides in Ullmann's Encyclopedia of Industrial Chemistry , 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.o12_o06 .

[Römpp-3] Entry on Metiram. In: Römpp Online . Georg Thieme Verlag, accessed on March 25, 2013.

[ppdb-4] Entry on Metiram in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.

[BASF-5] BASF: POLYRAM WG ( page no longer available , search in web archives ) Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. (PDF; 64 kB).@1@ 2

[fao-6] FAO: Metiram (PDF; 267 kB).

[Springer-7] M. Bahadir, H. Parlar, Michael Spiteller: Springer Umweltlexikon . Springer, 2000, ISBN 978-3-540-63561-1 , pp. 764 ( limited preview in Google Book search).

[Peter_Brandt-8] Peter Brandt (Ed.): Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer, 2010, ISBN 978-3-0348-0028-0 , pp. 21 ( limited preview in Google Book search).

[9] Directive 2005/72 / EC of the Commission of October 21, 2005 amending Directive 91/414 / EEC of the Council for the inclusion of the active substances chlorpyrifos, chlorpyrifos-methyl, Mancozeb, Maneb and Metiram (PDF) .

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on Metiram in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.