Propargite

Structural formula
Simplified structural formula without stereochemistry
General
Surname	Propargite
other names	2- (4- tert- butylphenoxy) cyclohexylprop-2-ynyl sulfite Omite Committee Uniroyal D014
Molecular formula	C 19 H 26 O 4 S
Brief description	Solid, technical grade liquid
External identifiers / databases
CAS number 2312-35-8 (mixture of stereoisomers) EC number 219-006-1 ECHA InfoCard 100.017.279 PubChem 4936 ChemSpider 4767 Wikidata Q168065
properties
Molar mass	350.48 g mol −1
Physical state	solid or liquid
density	1.113 g cm −3
boiling point	210 ° C (decomposition)
Vapor pressure	0.00404 mPa (25 ° C)
solubility	practically insoluble in water (0.215 mg l −1 at 20 ° C) miscible with organic solvents such as acetone, benzene and ethanol
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 331-315-318-351-410 P: 261-273-280-304 + 340 + 311-305 + 351 + 338-403 + 233
Toxicological data	2800 mg kg −1 ( LD 50 ,  rat ,  oral ) 10,300 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 .

Propargit is a mixture of several isomeric chemical compounds from the group of organosulphites ( esters of sulphurous acid ).

Extraction and presentation

Propargitol can be prepared by reacting 4- tert- butylphenol with the 1,2-epoxycyclohexane , followed by reaction with thionyl chloride and propargyl alcohol in the presence of a base.

properties

As a technical product, propargite is a yellowish brown liquid that is practically insoluble in water.

use

Propargit is used outside Europe as a plant protection product ( acaricide ) under the brand names Omite and Comite .

Admission

The approval of the active ingredient in the European Union was withdrawn in 2011, the use-by period ended at the end of 2012.

No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

It was first approved in the USA in 1969.

Hazard assessment

Propargit was included by the EU in 2015 in accordance with Regulation (EC) No. 1907/2006 (REACH) in the context of substance evaluation in the Community's ongoing action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the inclusion of propargite were concerns regarding the dangers arising from a possible assignment to the group of PBT / vPvB substances and as a potential endocrine disruptor . The re-evaluation has been running since 2019 and is carried out by the Netherlands .

further reading

• S. Sarkar, S. Seenivasan, RP Asir: Biodegradation of propargite by Pseudomonas putida, isolated from tea rhizosphere. In: Journal of hazardous materials. Volume 174, Numbers 1-3, February 2010, pp. 295-298, ISSN  1873-3336 . doi : 10.1016 / j.jhazmat.2009.09.050 . PMID 19892461 .
• BK Kang, G. Jyot et al. a .: Dissipation kinetics of propargite in brinjal fruits under subtropical conditions of Punjab, India. In: Bulletin of Environmental Contamination and Toxicology . Volume 82, Number 2, February 2009, pp. 248-250, doi : 10.1007 / s00128-008-9610-7 . PMID 19009222 .
• V. Kumar, C. Sood, et al. a .: Dissipation behavior of propargite – an acaricide residues in soil, apple (Malus pumila) and tea (Camellia sinensis). In: Chemosphere . Volume 58, Number 6, February 2005, pp. 837-843, doi : 10.1016 / j.chemosphere.2004.06.032 . PMID 15621197 .
• L. Yu, R. Schoen et al. a .: Determination of o-phenylphenol, diphenylamine, and propargite pesticide residues in selected fruits and vegetables by gas chromatography / mass spectrometry. In: Journal of AOAC International . Volume 80, Number 3, 1997, pp. 651-656, PMID 9170661 .

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on propargite in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
2. ↑ ^{a b} Entry on Propargite in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.
3. ^ Cornell University: propargite (Omite, Comite) Chemical Fact Sheet 9/86
4. ↑ Entry on Propargite 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. ^ Entry on Propargite in the Hazardous Substances Data Bank , accessed July 29, 2012.
6. ↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 991 ( limited preview in Google Book Search).
7. ↑ EU: Implementing Regulation (EU) No. 943/2011 of the Commission of September 22, 2011 on the non-approval of the active substance propargite according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending the Commission Decision 2008/934 / EC
8. ↑ General Directorate Health and Food Safety of the European Commission: Entry on propargite in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 27, 2016.
9. ↑ EPA: Propargite RED Facts
10. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Propargite , accessed on March 26, 2019.