Pirimiphos-methyl

Structural formula
General
Surname	Pirimiphos-methyl
other names	O - (2-Diethylamino-6-methylpyrimidin-4-yl) - O , O -dimethyl thiophosphate Fernex
Molecular formula	C 11 H 20 N 3 O 3 PS
Brief description	clear to yellowish liquid
External identifiers / databases
CAS number 29232-93-7 EC number 249-528-5 ECHA InfoCard 100.045.011 PubChem 34526 Wikidata Q415867
properties
Molar mass	305.34 g mol −1
Physical state	liquid
density	1.17 g cm −3
Melting point	20.8 ° C
boiling point	Decomposition before boiling point is reached (around 162 ° C)
Vapor pressure	negligible (2.0 × 10 −6  kPa at 20 ° C)
solubility	practically insoluble in water (8.6 mg l −1 at 20 ° C) miscible with most organic solvents
Refractive index	1.527 (at 25 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 302-410 P: 273-501
Toxicological data	1250 mg kg −1 ( LD 50 ,  rat ,  oral ) > 2000 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 . Refractive index: Na-D line , 20 ° C

Pirimiphos-methyl is a chemical compound from the group of thiophosphoric acid esters .

Extraction and presentation

Pirimiphos-methyl can be obtained by reacting N , N- diethylguanidine with acetoacetic ester and reacting the intermediate product formed with O , O -dimethylphosphorochlorothioate .

properties

Pirimiphos-methyl is a liquid that is practically insoluble in water. Pirimiphos-methyl is moderately persistent in the soil with a half-life of 39 days, but is rapidly degraded under the influence of UV light (half-life of 0.2 days).

use

Pirimiphos-methyl is used as active ingredient in pesticides used. It is a post-harvest insecticide used in the United States on stored corn, millet and seeds. It is used to control various insects such as mealybugs and flies (in cattle) and cigarette beetles, rice flour beetles, cadaver beetles, moths (on corn and grain) and others. The chemically related ethyl derivative ( pirimiphos-ethyl ) is also used as an insecticide. Pirimiphos-methyl was approved as an insecticide in the United States in 1978 and approximately 12,000 pounds (5.4 tons) were used in 2006 . It works by inhibiting acetylcholinesterase .

Admission

Pirimiphos-methyl was approved in the European Union in 2007 as an insecticide for applications on stored crops.

Plant protection products with this active ingredient are not permitted in Germany, Austria or Switzerland.

Individual evidence

1. ↑ ^{a b c d} Entry on Pirimiphos-methyl in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 24, 2019.
2. ↑ ^{a b c d e f g h i} Entry on pirimiphos-methyl in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
3. ↑ WHO SPECIFICATIONS AND EVALUATIONS FOR PUBLIC HEALTH PESTICIDES - Pirimiphos-methyl. (PDF) In: World Health Organization. Retrieved July 24, 2019 . 
4. ^ Joint Meeting on Pesticide Residues (JMPR), Monograph for PIRIMIPHOS-METHYL , accessed December 9, 2014.
5. ↑ Entry on Pirimiphos-methyl in the Hazardous Substances Data Bank , accessed on July 24, 2019.
6. ↑ Entry on Pirimiphos-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 .
7. ↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 561 ( limited preview in Google Book search).
8. ↑ EPA: Pirimiphos-methyl IRED Facts
9. ↑ External identifiers of or database links to Pirimiphos-ethyl : CAS number: 23505-41-1, EC number: 245-704-0, ECHA InfoCard: 100.041.534 , GESTIS substance database : 510351 , PubChem : 31957 , ChemSpider : 29635 , Wikidata : Q22808666 .
10. ↑ EPA: Reregistration Eligibility Decision for Pirimiphos-methyl (PDF; 649 kB)
11. ^ Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 451 ( limited preview in Google Book search).
12. ↑ Directive 2007/52 / EC of the Commission of August 16, 2007 amending Council Directive 91/414 / EEC to include the active substances Ethoprophos, Pirimiphos-Methyl and Fipronil (PDF)
13. ↑ General Directorate Health and Food Safety of the European Commission: Entry on pirimiphos-methyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.