propachlor

{{Chembox

| ImageFile = File:Propachlor (edited last pic to remove CH3 labels).png

| ImageSize = 200px

| PIN = 2-Chloro-N-phenyl-N-(propan-2-yl)acetamide

| OtherNames = {{Unbulleted list

| 2-Chloro-N-isopropylacetanilide

| N-Isopropyl-2-chloroacetanilide

| Ramrod (trade name)

| Bexton (trade name)

| Nitacid (trade name)

| Satecid (trade name)

}}

|Section1={{Chembox Identifiers

| CASNo = 1918-16-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 015443A483

| PubChem = 4931

| ChemSpiderID = 4762

| ChEMBL = 1394829

| SMILES = CC(C)N(c1ccccc1)C(=O)CCl

| InChI = 1/C11H14ClNO/c1-9(2)13(11(14)8-12)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3

| InChIKey = MFOUDYKPLGXPGO-UHFFFAOYAZ

| StdInChI = 1S/C11H14ClNO/c1-9(2)13(11(14)8-12)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3

| StdInChIKey = MFOUDYKPLGXPGO-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=11 | H=14 | Cl=1 | N=1 | O=1

| Appearance = light tan solid

| Density = 1.139 g/mL

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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}}

Propachlor (2-chloro-N-isopropylacetanilide) 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.{{cite web|title=Propachlor (Ramrod, Bexton) Herbicide Profile 2/85|url=http://pmep.cce.cornell.edu/profiles/herb-growthreg/naa-rimsulfuron/propachlor/propach_prf_0285.html|publisher=Cornell University|accessdate=2009-09-09}}{{cite web | title=Propachlor - Reregistration Eligibility Decision (R.E.D.) Facts | url=https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-019101_1-Nov-98.pdf | publisher=US Environmental Protection Agency | date=November 1998 |access-date=12 January 2025}}

The preparation acts on annual grasses and on some broadleaf weeds {{cite journal | pmid = 6640157 | year = 1983 | last1 = Warholic | first1 = DT | last2 = Gutenmann | first2 = WH | last3 = Lisk | first3 = DJ | title = Propachlor herbicide residue studies in cabbage using modified analytical procedure | volume = 31 | issue = 5 | pages = 585–7 | journal = Bulletin of Environmental Contamination and Toxicology| doi = 10.1007/bf01605479 | bibcode = 1983BuECT..31..585W }} 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.

Between 1987 and 1996, about 2.1 million pounds of its active ingredient were used in the United States.{{cite web|title=Reregistration Eligibility Decision (RED) - Propachlor|url=http://www.epa.gov/oppsrrd1/REDs/0177red.pdf|publisher=U.S. Environmental Protection Agency|accessdate=2009-09-09}} 75% was applied to sorghum crops and 24% to maize.

Monsanto voluntarily discontinued its manufacture in 1998.{{cite web|title=Illinois Pesticide Review|url=http://web.extension.uiuc.edu/ipr/i4189_829.html|publisher=University of Illinois Extension Service|accessdate=2009-09-09}} It is currently listed in the U.S. Environmental Protection Agency's Toxics Release Inventory.{{cite web|title=Toxics Release Inventory (TRI) Chemicals in TOXMAP|url=http://toxmap.nlm.nih.gov/toxmap/main/chemicals.jsp|accessdate=2009-09-09}} 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.{{cite web|title=COMMISSION DECISION of 18 September 2008 concerning the non-inclusion of propachlor in Annex I to Council Directive 91/414/EEC and the withdrawal of authorisations for plant protection products containing that substance|url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2008:251:0039:0040:EN:PDF|publisher=European Commission|accessdate=2009-09-09}} Propachlor was added to California's Proposition 65 list as a carcinogen in 2001.{{cite web|url=http://www.oehha.ca.gov/prop65/prop65_list/files/P65single080709.pdf|publisher=State of California Environmental Protection Agency|title=CHEMICALS KNOWN TO THE STATE TO CAUSE CANCER OR REPRODUCTIVE TOXICITY AUGUST 7, 2009|accessdate=2009-09-09}}