Acetochlor

• 2-chloro- N-( ethoxymethyl )-N- (2-ethyl -6 -methylphenyl ) acetamide
• Azetochlor

Light yellow liquid

Liquid

1.135 g · cm -3

134 ° C at 0.5 hPa

Slightly soluble in water (0.2 g · l-1 at 20 ° C)

1.5272 (20 ° C)

Attention

• 763 mg · kg -1 ( LD50, rat, oral)
• 4166 mg · kg -1 ( LD50, Rabbit, transdermal)

Template: Infobox chemical / molecular formula search available

Acetochlor is a mixture of two isomeric chemical compounds from the group of carboxylic acid amides and organic chlorine compounds.

History

Acetochlor was brought to the USA in 1994 by a marketing company to market, which is now part Monsanto and Dow AgroSciences.

Production and representation

Acetochlor can be obtained by the reaction of chloromethyl ethyl ether and an intermediate product, which results from the reaction of 2-ethyl -6-methyl -aniline and chloroacetyl chloride.

Isomerism

Due to the limited rotation around the bond of the nitrogen atom to the aromatic radical has two atropisomers of acetochlor.

Use

Acetochlor is like the related chloroacetamides alachlor, butachlor and metolachlor used as a pre-emergence herbicide. The effect is produced by inhibition of the synthesis of very long chain fatty acids ( VLCFA ). In Germany, Austria and Switzerland no means is admitted that contains this ingredient.

In the U.S. in 2011 were 15,000 tons acetochlor - used - almost exclusively in corn cultivation.