Pirimicarb

Structural formula
General
Surname	Pirimicarb
other names	5,6-dimethyl-2-dimethylaminopyrimidin-4-yl- N , N -dimethyl-carbamate Pirimor
Molecular formula	C 11 H 18 N 4 O 2
Brief description	colorless solid
External identifiers / databases
CAS number 23103-98-2 EC number 245-430-1 ECHA InfoCard 100.041.285 PubChem 31645 Wikidata Q419705
properties
Molar mass	238.29 g mol −1
Physical state	firmly
density	1.18 g cm −3
Melting point	91.6 ° C
boiling point	Decomposes before boiling point
Vapor pressure	2.1 mPa (30 ° C)
pK s value	4.34
solubility	bad in water (3 g l −1 )
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 301-331-317-351-410 P: 273-501
Toxicological data	100 mg kg −1 ( LD 50 ,  rat ,  oral ) 500 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 .

Pirimicarb is an active ingredient for crop protection and a chemical compound from the group of carbamates .

Extraction and presentation

Pirimicarb can be obtained by reacting the intermediate products in the reaction of 2-methylethylacetoacetate with N , N- dimethylguanidine sulfate , and phosgene with dimethylamine .

properties

Pirimicarb is a colorless solid that is poorly soluble in water.

use

Pirimicarb is used as an active ingredient in crop protection products. It is used as a selective aphicide ( insecticide against tube aphids ) in a large number of cereals and other crops and works by inhibiting acetylcholinesterase . It was first approved in 1970. With pirimicarb-desmethyl (CAS number: 30614-22-3) and pirimicarb-desmethyl-formamido (27218-04-8) there are two derivatives with similar properties.

Admission

Pirimicarb was approved as an insecticidal active ingredient in the European Union in 2006. In Germany, Austria and Switzerland, pesticide products with this active ingredient are approved.

Others

In Switzerland, there were 2019 with Fipronil contaminated pirimicarb, which in Landi had been sold -Agrarmärkten to a bee deaths .

Individual evidence

1. ↑ Entry on Pirimicarb in the Hazardous Substances Data Bank , accessed July 29, 2012.
2. ↑ ^{a b c d e f g h i} Entry on pirimicarb in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
3. ^ ^{A b c} Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 57 ( limited preview in Google Book search).
4. ↑ Entry on Pirimicarb 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 .
5. ↑ Data sheet Pirimicarb, PESTANAL at Sigma-Aldrich , accessed on February 15, 2017 ( PDF ).
6. ↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 91 ( limited preview in Google Book search).
7. ^ World Health Organization, Food and Agriculture Organization: Pesticide Residues in Food 2004 . WHO, 2006, ISBN 978-92-4166520-9 , pp. 207 ( limited preview in Google Book search).
8. ↑ Horst Börner, Klaus Schlueter, Jens Aumann: Plant diseases and plant protection . Springer, 2009, p. 556 ( limited preview in Google Book search).
9. ↑ Directive 2006/39 / EC of the Commission of April 12, 2006 amending Directive 91/414 / EEC of the Council to include the active substances clodinafop, pirimicarb, rimsulfuron, tolclofos-methyl and triticonazole (PDF) .
10. ↑ Directorate-General for Health and Food Safety of the European Commission: entry on pirimicarb in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.
11. ↑ Illegal material: bee deaths in Aargau. In: schweizerbauer.ch . October 20, 2019, accessed October 20, 2019 .