Propachlor

Propachlor (2-chloro-N-isopropylacetanilide)^[1] is an anilide used primarily as an herbicide first marketed by Monsanto under the tradename Ramrod. It was initially registered for use in the United States in 1964.^[2][3]

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Propachlor

Names
Preferred IUPAC name 2-Chloro-N-phenyl-N-(propan-2-yl)acetamide
Other names 2-Chloro-N-isopropylacetanilide N-Isopropyl-2-chloroacetanilide Ramrod (trade name) Bexton (trade name) Nitacid (trade name) Satecid (trade name)
Identifiers
CAS Number	1918-16-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1394829
ChemSpider	4762
ECHA InfoCard	100.016.036
PubChem CID	4931
UNII	015443A483 Y
CompTox Dashboard (EPA)	DTXSID4024274
InChI InChI=1S/C11H14ClNO/c1-9(2)13(11(14)8-12)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3 Key: MFOUDYKPLGXPGO-UHFFFAOYSA-N InChI=1/C11H14ClNO/c1-9(2)13(11(14)8-12)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3 Key: MFOUDYKPLGXPGO-UHFFFAOYAZ
SMILES CC(C)N(c1ccccc1)C(=O)CCl
Properties
Chemical formula	C11H14ClNO
Molar mass	211.69 g·mol−1
Appearance	light tan solid
Density	1.139 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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The preparation acts on annual grasses and on some broadleaf weeds ^[1] and was briefly sold in the UK as a germination inhibitor under the name Murphy Covershield. Propachlor was sold in flake, pelletized, and concentrated liquid formulations, which contained Propachlor as the main ingredient, or as a mixture with Atrazine or Propazine. Propazine-only formulations typically included instructions for mixing with Atrazine.^[3]

Between 1987 and 1996, about 2.1 million pounds of its active ingredient were used in the United States.^[4] 75% was applied to sorghum crops and 24% to maize.^[4]

Monsanto voluntarily discontinued its manufacture in 1998.^[5] It is currently listed in the U.S. Environmental Protection Agency's Toxics Release Inventory.^[6] In 2008, the European Commission issued a decision withdrawing its approval for use as of March 18, 2009, citing the presence of its metabolites in groundwater.^[7] Propachlor was added to California's Proposition 65 list as a carcinogen in 2001.^[8]