Monocrotophos

Structural formula
	cis -Monocrotophos (top) and trans -Monocrotophos (bottom)
General
Surname	Monocrotophos
other names	Azodrine; Bilobran; Nuvacron; 3-dimethoxyphosphoryloxy- N -methylbut-2-enamide; O , O -dimethyl- O- (2- N -methylcarbamoyl-1-methyl) vinyl phosphate; Dimethyl- ( E ) -1-methyl-2- (methylcarbamoyl) vinyl phosphate ( IUPAC ) ;
Molecular formula	C 7 H 14 NO 5 P
Brief description	colorless, flammable solid; in technical quality: brown, semi-solid mass;
External identifiers / databases
EC number	230-042-7
ECHA InfoCard	100.027.311
PubChem	5371562
Wikidata	Q412441
properties
Molar mass	223.17 g mol −1
Physical state	firmly
density	1.22 g cm −3
Melting point	54–55 ° C ( trans -Monocrotophos)
boiling point	125 ° C (0.067 Pascal )
Vapor pressure	0.29 mPa (20 ° C)
solubility	Soluble in water; soluble in acetone and aliphatic alcohols; slightly soluble in mineral oils;
safety instructions
H and P phrases	H: 300-311-330-341-410
	P: 260-264-273-280-284-301 + 310
MAK	Switzerland: 0.25 mg m −3
Toxicological data	14 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 .

Monocrotophos is an unsaturated chemical compound and an insecticide from the group of carboxamides and phosphoric acid esters . Monocrotophos was introduced by Ciba in 1965 .

Extraction and presentation

Monocrotophos is no longer patent-protected and is produced by several companies without a license.

Synthesis of Monocrotophos (mixture of cis and trans isomers)

Monocrotophos can be synthesized from diketene . The addition of methylamine initially results in methylacetoacetamide , which after reaction with sulfuryl chloride and subsequent Perkow reaction of the product with trimethyl phosphite leads to monocrotophos.

The technical synthesis provides a mixture of cis - and trans -Monocrotophos, the cis - isomer usually predominates.

properties

Pure monocrotophos forms colorless crystals. Technical Monocrotophos contains at least 75% of the compound and is a red-brown mixture of solid and liquid components with a melting point between 25 and 35 ° C and a mild ester odor. It is unstable in short chain alcohols and glycols . It hydrolyzes slowly in water , at temperatures above 38 ° C it begins to decompose. The isomers cis and trans monocrotophos differ not only in toxicological terms, but also in their storage stability.

use

Monocrotophos is used as a broad-spectrum and fast-acting insecticide (for example against Lepidoptera , Homoptera , mites and Coleoptera ). It works as a cholinesterase inhibitor.

Admission

In the USA, the use of potatoes and tomatoes was banned in 1985 and generally in 1988. Monocrotophos has not been included in the list of active ingredients in plant protection products approved in Europe . There is consequently no approval of a plant protection product containing monocrotophos in Germany and Austria, and no such product is approved in Switzerland either.

safety instructions

Monocrotophos is highly toxic, especially for birds ( LD ₅₀ 0.9–6.7 mg / kg) and bees.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on Monocrotophos in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b Entry on Monocrotophos. In: Römpp Online . Georg Thieme Verlag, accessed on November 30, 2014.
↑ Seema and A. Panvar, Acta Ciencia Indica, Chemistry 2007, 33 , 467-472.
↑ ^a ^b ^c ^d Health and Safety Guide (HSG) for Monocrotophos , accessed on November 30, 2014.
↑ Entry on Monocrotophos 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 .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values , accessed on November 2, 2015.
^ ^A ^b Health implications from monocrotophos use: a review of the evidence in India ( Memento of September 6, 2009 in the Internet Archive ).
↑ Thomas A. Unger: Pesticide synthesis handbook , ISBN 0-8155-1401-8 .
↑ N. Ismail, M. Vairamani and R. Nageswara Rao, Journal of Chromatography A , 2000, 903 , 255-260.
↑ E. Neuenschwander, Rev. Environ. Contam. Toxicol. 1994, 139 , 41.
↑ Monocrotophos (Toxipedia) ( Memento from October 15, 2009 in the Internet Archive ).
↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on Monocrotophos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f Entry on Monocrotophos in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[roempp-2] Entry on Monocrotophos. In: Römpp Online . Georg Thieme Verlag, accessed on November 30, 2014.

[Seema-3] Seema and A. Panvar, Acta Ciencia Indica, Chemistry 2007, 33 , 467-472.

[inchem-4] Health and Safety Guide (HSG) for Monocrotophos , accessed on November 30, 2014.

[CLP_100.027.311-5] Entry on Monocrotophos 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 .

[6] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values , accessed on November 2, 2015.

[searo-7] A ^b Health implications from monocrotophos use: a review of the evidence in India ( Memento of September 6, 2009 in the Internet Archive ).

[8] Thomas A. Unger: Pesticide synthesis handbook , ISBN 0-8155-1401-8 .

[Ismail-9] N. Ismail, M. Vairamani and R. Nageswara Rao, Journal of Chromatography A , 2000, 903 , 255-260.

[Neuenschwander-10] E. Neuenschwander, Rev. Environ. Contam. Toxicol. 1994, 139 , 41.

[11] Monocrotophos (Toxipedia) ( Memento from October 15, 2009 in the Internet Archive ).

[12] Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.

[PSM-13] Directorate-General for Health and Food Safety of the European Commission: Entry on Monocrotophos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.