Acetochlor

Structural formula
	Simplified structural formula - 1: 1 mixture of two atropisomers
General
Surname	Acetochlor
other names	2-chloro- N - (ethoxymethyl) - N - (2-ethyl-6-methylphenyl) acetamide; Acetochlor;
Molecular formula	C 14 H 20 ClNO 2
Brief description	light yellow liquid
External identifiers / databases
EC number	251-899-3
ECHA InfoCard	100.047.166
PubChem	1988
ChemSpider	1911
Wikidata	Q419732
properties
Molar mass	269.77 g mol −1
Physical state	liquid
density	1.135 g cm −3
boiling point	134 ° C at 0.5 hPa
solubility	slightly soluble in water (0.2 g l −1 at 20 ° C)
Refractive index	1.5272 (20 ° C)
safety instructions
H and P phrases	H: 332-315-317-335-351-361f-373-410
	P: 261-273-280-501
Toxicological data	763 mg kg −1 ( LD 50 , rat , oral ) ; 4166 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

Acetochlor is a chemical compound from the group of carboxamides and organic chlorine compounds .

Isomerism

Because of the limited rotation around the bond between the nitrogen atom and the aromatic radical, there are two atropisomers of acetochlorine. Most acetochlor is a mixture of the two isomers.

history

Acetochlor was first marketed in the United States in 1994 by a marketing company now owned by Monsanto and Dow AgroSciences .

Extraction and presentation

Acetochlor can be obtained by reacting chloromethyl ethyl ether and an intermediate product which is formed in the reaction of 6-ethyl-2-toluidine and chloroacetic acid chloride .

use

Estimated US application volume in 2012

Acetochlor, like the related chloroacetamides alachlor , butachlor and metolachlor, is used as a pre-emergence herbicide . The effect comes about by inhibiting the synthesis of very long-chain fatty acids (VLCFA). In 2012, over 15,000 tons of acetochlor were used in the USA - almost exclusively in corn cultivation.

Admission

In the EU countries such as Germany and Austria as well as in Switzerland, no agent is approved that contains this active ingredient. Nevertheless, acetochlor can be manufactured in the EU for export .

hazards

One case of poisoning with extreme swelling of the genitals as a result was described after skin contact.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Acetochlor data sheet from Sigma-Aldrich , accessed on February 15, 2017 ( PDF ).

↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-4.

↑ ^a ^b Entry on acetochlor in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

↑ Entry on 2-chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methylphenyl) acetamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 20, 2018. Manufacturers or distributors can use the expand harmonized classification and labeling .

^ Robert Irving Krieger, Handbook of Pesticide Toxicology: Principles, p. 1547; ISBN 978-0124262607 .

↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 7 ( limited preview in Google Book search).

↑ Entry on acetochlor. In: Römpp Online . Georg Thieme Verlag, accessed on February 16, 2014.

↑ General Directorate Health and Food Safety of the European Commission: Entry on acetochlor in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.

↑ Maurin Jost: Export of harmful pesticides: A lot of poison for abroad. In: taz.de . September 29, 2019, accessed October 1, 2019 .

^ R. Tian, L. Liu, Z. Liang, K. Guo: Acetochlor poisoning presenting as acute genital edema: A case report. In: Urology case reports. Volume 22, January 2019, pp. 47-48, doi : 10.1016 / j.eucr.2018.10.014 , PMID 30406020 , PMC 6214889 (free full text).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f Acetochlor data sheet from Sigma-Aldrich , accessed on February 15, 2017 ( PDF ).

[CRC90_3_4-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-4.

[GESTIS-3] Entry on acetochlor in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[CLP_100.047.166-4] Entry on 2-chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methylphenyl) acetamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 20, 2018. Manufacturers or distributors can use the expand harmonized classification and labeling .

[5] Robert Irving Krieger, Handbook of Pesticide Toxicology: Principles, p. 1547; ISBN 978-0124262607 .

[unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 7 ( limited preview in Google Book search).

[7] Entry on acetochlor. In: Römpp Online . Georg Thieme Verlag, accessed on February 16, 2014.

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

[9] Maurin Jost: Export of harmful pesticides: A lot of poison for abroad. In: taz.de . September 29, 2019, accessed October 1, 2019 .

[10] R. Tian, L. Liu, Z. Liang, K. Guo: Acetochlor poisoning presenting as acute genital edema: A case report. In: Urology case reports. Volume 22, January 2019, pp. 47-48, doi : 10.1016 / j.eucr.2018.10.014 , PMID 30406020 , PMC 6214889 (free full text).