Propachlor

Last updated
Propachlor
Propachlor (edited last pic to remove CH3 labels).png
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.016.036 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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
  • CC(C)N(c1ccccc1)C(=O)CCl
Properties
C11H14ClNO
Molar mass 211.69 g·mol−1
Appearancelight 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).

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]

Contents

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]

Current manufacturers

It is currently being produced by Makhteshim Agan Group and Shenzhen Qinfeng Pesticides Co., Ltd. [9]

References

  1. 1 2 Warholic, DT; Gutenmann, WH; Lisk, DJ (1983). "Propachlor herbicide residue studies in cabbage using modified analytical procedure". Bulletin of Environmental Contamination and Toxicology. 31 (5): 585–7. Bibcode:1983BuECT..31..585W. doi:10.1007/bf01605479. PMID   6640157.
  2. ↑ "Propachlor (Ramrod, Bexton) Herbicide Profile 2/85". Cornell University . Retrieved 2009-09-09.
  3. 1 2 "Propachlor - Reregistration Eligibility Decision (R.E.D.) Facts" (PDF). US Environmental Protection Agency. November 1998. Retrieved 12 January 2025.
  4. 1 2 "Reregistration Eligibility Decision (RED) - Propachlor" (PDF). U.S. Environmental Protection Agency. Archived from the original (PDF) on October 2, 2000. Retrieved 2009-09-09.
  5. ↑ "Illinois Pesticide Review". University of Illinois Extension Service. Retrieved 2009-09-09.
  6. ↑ "Toxics Release Inventory (TRI) Chemicals in TOXMAP". Archived from the original on September 17, 2005. Retrieved 2009-09-09.
  7. ↑ "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". European Commission . Retrieved 2009-09-09.
  8. ↑ "CHEMICALS KNOWN TO THE STATE TO CAUSE CANCER OR REPRODUCTIVE TOXICITY AUGUST 7, 2009" (PDF). State of California Environmental Protection Agency. Retrieved 2009-09-09.
  9. ↑ Farm Chemicals International (2012-03-12). "Propachlor" . Retrieved 2012-06-27.
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