S -ethyl- N , N -dipropylthiocarbamate

Structural formula
General
Surname	S -ethyl- N , N -dipropylthiocarbamate
other names	S -Ethyl- N , N -dipropylcarbamothioate ( IUPAC ) ; EPTC;
Molecular formula	C 9 H 19 NOS
Brief description	colorless liquid
External identifiers / databases
EC number	212-073-8
ECHA InfoCard	100.010.976
PubChem	12968
ChemSpider	12428
Wikidata	Q424784
properties
Molar mass	189.32 g mol −1
Physical state	liquid
density	0.955 g cm −3
boiling point	127 ° C (26.6 mbar)
Vapor pressure	0.032 hPa (25 ° C)
solubility	almost insoluble in water; miscible with organic solvents such as acetone, ethyl alcohol, MIBK and xylene;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	916 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 .

S -Ethyl- N , N -dipropylthiocarbamate ( EPTC for short) is a chemical compound from the group of dithiocarbamates .

Extraction and presentation

S -Ethyl- N , N- dipropylthiocarbamate can be obtained starting from phosgene , which is reacted with ethyl mercaptan to form ethyl thiochloroformate and this is then reacted with dipropylamine to form EPTC.

properties

S -Ethyl- N , N -dipropylthiocarbamate is a colorless liquid that is insoluble in water.

use

Estimated US application rate in 2011

S -Ethyl- N , N -dipropylthiocarbamate is a selective thiocarbamate herbicide brought onto the market in 1969 for use in pre- emergence control of certain grasses and weeds in vegetables, fruit and ornamentals. It works by inhibiting lipid synthesis .

In the EU states such as Germany and Austria as well as in Switzerland, no pesticides are permitted that contain this compound as an active ingredient.

The amount applied in the USA has decreased continuously over the last few decades.

Trade names

S -Ethyl- N , N- dipropylthiocarbamate was sold under the trade names Alirox, Eptam, Eradicane, Genep, Niptan and Witox.

Web links

Degradation of the Thiocarbamate Herbicide EPTC ; JOURNAL OF BACTERIOLOGY; PMC 176643 (free full text, PDF)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry for CAS no. 759-94-4 in the GESTIS substance database of the IFA , accessed on September 23, 2011(JavaScript required) .
↑ ^a ^b ^c ^d data sheet EPTC, PESTANAL ^® , analytical standard at Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
↑ Entry EPTC at Extoxnet.
↑ Entry on EPTC 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 .
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 0-8155-1401-8 ( page 106 in the Google book search).
↑ Cornell: EPTC (Eptam) Herbicide Profile 10/83
^ Terence Robert Roberts, DH (David Herd) Hutson, Royal Society of Chemistry: Metabolic pathways of agrochemicals, Part 2 . 1998, ISBN 0-85404-494-9 , pp. 593 ( limited preview in Google Book search).
↑ General Directorate Health and Food Safety of the European Commission: Entry on EPTC (S-dipropylthiocarbamate) 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 for CAS no. 759-94-4 in the GESTIS substance database of the IFA , accessed on September 23, 2011(JavaScript required) .

[Sigma-2] ta sheet EPTC, PESTANAL ^® , analytical standard at Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).

[EXT-3] Entry EPTC at Extoxnet.

[CLP_100.010.976-4] Entry on EPTC 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 .

[unger-5] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 0-8155-1401-8 ( page 106 in the Google book search).

[Corn-6] Cornell: EPTC (Eptam) Herbicide Profile 10/83

[mpw-7] Terence Robert Roberts, DH (David Herd) Hutson, Royal Society of Chemistry: Metabolic pathways of agrochemicals, Part 2 . 1998, ISBN 0-85404-494-9 , pp. 593 ( limited preview in Google Book search).

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on EPTC (S-dipropylthiocarbamate) in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.