Mecarbam

Structural formula
General
Surname	Mecarbam
other names	N -ethoxycarbonyl- N -methylcarbamoylmethyl- O , O -diethyldithiophosphate; Murotox; Murfotox; Pestan; Afos;
Molecular formula	C 10 H 20 NO 5 PS 2
Brief description	colorless liquid
External identifiers / databases
EC number	219-993-9
ECHA InfoCard	100.018.177
PubChem	17434
ChemSpider	16491
Wikidata	Q27117958
properties
Molar mass	329.38 g · mol -1
Physical state	liquid
density	1.222 g cm −3
Melting point	9 ° C
boiling point	144 ° C (0.026 hPa)
Vapor pressure	1 · 10 −10 Pa (25 ° C)
solubility	heavy in water (1 g l −1 at 20 ° C)
safety instructions
H and P phrases	H: 301 + 311-330-410
	P: 273-280-301 + 310 + 330-302 + 352 + 312-304 + 340 + 310
Toxicological data	31 mg kg −1 ( LD 50 , rat , oral ) ; 380 mg kg −1 ( LD 50 , rat , transdermal ) ; 0.004 mg l −1 ( LC 50 , fish , 96 hours ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mecarbam is an insecticide from the active ingredient group of organophosphates . The compound was introduced in 1961 by Murphy Chemicals Ltd. developed.

Extraction and presentation

Mecarbam can be obtained through a multi-stage reaction. For this purpose, phosgene and ethanol are first reacted with methylamine to form N -methylethyl carbamate, which is then reacted with chloroacetic acid chloride . The resulting molecule then reacts with O , O -diethyldithiophosphate to form mecarbam.

properties

Mecarbam is an oily liquid that is colorless in its pure form and in technical form can have a pale yellow to brownish color. It freezes at temperatures below 9 ° C and is non-volatile due to its low vapor pressure. It is poorly in water, but readily soluble in organic solvents. With a half-life of 35 days in the soil, it is moderately persistent. Mecarbam hydrolyzes slowly in an aqueous acidic medium and quickly under alkaline conditions. Mecarbam decomposes at a temperature of 338 ° C.

Mode of action

Like all organophosphates and phosphoric acid esters, the effect of mecarbam is based on the irreversible inhibition of acetylcholine esterase in nerve cells . This has the effect that the transmission of stimuli in the nervous system is disturbed or comes to a standstill, which in turn can lead to paralysis, respiratory failure and ultimately death.

Areas of application

Mecarbam is an insecticide and acaricide that can be used against sucking and chewing pests. It also works as an ovicide . Typical areas of application are the control of aphids , white flies and red spiders , as well as grease insects and scale insects on fruit trees. In rice cultivation it can be used against fruit flies , cicadas and leaf miners .

Analytics

Both liquid and gas chromatographic methods can be used for reliable detection and quantification of mecarbam . A mass spectrometer can be used for identification after the chromatographic separation .

Admission

In the European Union and Switzerland are no pesticides registered with the drug Mecarbam.

Individual evidence

↑ ^a ^b ^c ^d Hayes, Wayland J. ,, Laws, Edward R.,: Handbook of pesticide toxicology. Volume 3, Classes of pesticides . San Diego, California 2013, ISBN 978-1-4832-8863-5 ( limited preview in Google Book Search [accessed May 23, 2019]).

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on Mecarbam in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

↑ ^a ^b ^c Entry on Mecarbam in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on November 12, 2018.

↑ Entry on Mecarbam in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 12, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .

↑ Wegler, Richard .: Chemistry of pesticides . Springer Berlin Heidelberg, Berlin, Heidelberg 1970, ISBN 3-642-46210-3 ( limited preview in the Google book search).

↑ Thomas A. Unger: Pesticide synthesis handbook . Noyes Publications, 1996, ISBN 0-8155-1401-8 , pp. 360 ( limited preview in Google Book Search).

↑ Zweig, Gunter., Sherma, Joseph .: Government regulations, pheromone analysis, additional pesticides . Academic Press, New York 1976, ISBN 1-4832-2085-0 ( limited preview in Google Book Search [accessed November 12, 2018]).

↑ Emad R. Atallah, et al .: QuEChERS analytical method for determination of 93 pesticide residues in apples and potatoes using LC-MS / MS . In: Journal of Applied Sciences Research . tape 8 , no. December 12 , 2012, ISSN 1819-544X , p. 5690-5697 (English, researchgate.net ).

↑ Zeying He et al .: QuEChERS Combined with Agilent 7000 Series Triple Quadrupole GC / MS System for the Analysis of Over 200 Pesticide Residues in Cereals - Application Note. (PDF) In: agilent.com. Agilent Technologies, Inc., March 2, 2015, accessed May 23, 2019 .

↑ Directorate-General for Health and Food Safety of the European Commission: Entry on Mecarbam in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on July 26, 2019.

[wayland-1] Hayes, Wayland J. ,, Laws, Edward R.,: Handbook of pesticide toxicology. Volume 3, Classes of pesticides . San Diego, California 2013, ISBN 978-1-4832-8863-5 ( limited preview in Google Book Search [accessed May 23, 2019]).

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on Mecarbam in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[PPDB-3] Entry on Mecarbam in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on November 12, 2018.

[CLP_100.018.177-4] Entry on Mecarbam in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 12, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Wegler, Richard .: Chemistry of pesticides . Springer Berlin Heidelberg, Berlin, Heidelberg 1970, ISBN 3-642-46210-3 ( limited preview in the Google book search).

[Unger-6] Thomas A. Unger: Pesticide synthesis handbook . Noyes Publications, 1996, ISBN 0-8155-1401-8 , pp. 360 ( limited preview in Google Book Search).

[7] Zweig, Gunter., Sherma, Joseph .: Government regulations, pheromone analysis, additional pesticides . Academic Press, New York 1976, ISBN 1-4832-2085-0 ( limited preview in Google Book Search [accessed November 12, 2018]).