Acetochlor

Acetochlor is an herbicide developed by Monsanto Company and Zeneca. It is a member of the class of herbicides known as chloroacetanilides. Its mode of action is elongase inhibition, and inhibition of geranylgeranyl pyrophosphate (GGPP) cyclization enzymes, part of the gibberellin pathway. It carries high risks of environmental contamination.^[2]

Acetochlor^[1]

Names
Preferred IUPAC name 2-Chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide
Other names Azetochlor CP55097 ICIA-5676
Identifiers
CAS Number	34256-82-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2394 Y
ChEMBL	ChEMBL1517425 Y
ChemSpider	1911 Y
ECHA InfoCard	100.047.166
KEGG	C10925 Y
PubChem CID	1988
UNII	8L08WMO94K Y
CompTox Dashboard (EPA)	DTXSID8023848
InChI InChI=1S/C14H20ClNO2/c1-4-12-8-6-7-11(3)14(12)16(10-18-5-2)13(17)9-15/h6-8H,4-5,9-10H2,1-3H3 Y Key: VTNQPKFIQCLBDU-UHFFFAOYSA-N Y InChI=1/C14H20ClNO2/c1-4-12-8-6-7-11(3)14(12)16(10-18-5-2)13(17)9-15/h6-8H,4-5,9-10H2,1-3H3 Key: VTNQPKFIQCLBDU-UHFFFAOYAJ
SMILES ClCC(=O)N(c1c(cccc1CC)C)COCC
Properties
Chemical formula	C14H20ClNO2
Molar mass	269.77 g·mol−1
Density	1.100 at 30 °C 1.136 at 20 °C
Melting point	< 0 °C (32 °F; 273 K)
Solubility in water	223 ppm
Hazards
Flash point	> 100 °C (212 °F; 373 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Manufacture

Acetochlor is manufactured in two steps from 2-ethyl-6-methylaniline. A reaction with chloroacetyl chloride gives an anilide which is treated with chloromethyl ethyl ether and sodium hydroxide to form the herbicide.^[3]

Uses

In the United States, acetochlor was registered by the EPA as a direct substitute for many herbicides of known concern. The EPA imposed several restrictions and conditions on the use of acetochlor.^[4]

It is approved for pre-emergence application or for pre-planting application with soil incorporation, in corn. (maize) at 5 litres / hectare (1835g / hectare of a.i.)^[5] It is the main active ingredient in Acenit, Keystone, Guardian, Harness, Relay, Sacemid, Surpass, Top-Hand, Trophy and Winner.

It is used to control weeds in corn, and is particularly useful as a replacement for atrazine in the case of some important weeds.

Safety

Acetochlor has been classified as a probable human carcinogen.^[1][4] Acetochlor, as alachlor, can cause nasal turbinate tumors via the generation of a common tissue reactive metabolite that leads to cytotoxicity and regenerative proliferation in the nasal epithelium.^[6]

It is a thyroid disruptor.^{[7][non-primary source needed]}

Human health effects from acetochlor at low environmental doses or at biomonitored levels from low environmental exposures are unknown.^[8] A case of poisoning with extremely swollen genitals as a symptom was reported after contact.^[9]

Ecologic effects

In the United States, acetochlor is the third most frequently detected herbicide in natural waters.^[10]

Acetochlor can accelerate metamorphosis in amphibians.^[11] It can also affect the development of fish.^[11]

See also

• Metolachlor