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Propachlor

Propachlor
Names
Preferred IUPAC name
2-Chloro-N-phenyl-N-(propan-2-yl)acetamide
Other names
2-Chloro-N-isopropylacetanilide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.016.036 Edit this at Wikidata
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
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).

Propachlor (2-chloro-N-isopropylacetanilide)[1] is an herbicide first marketed by Monsanto. It was registered for use in the United States during 1965.[2]

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.

Between 1987 and 1996, about 2.1 million pounds of its active ingredient were used in the United States.[3] 75% was applied to sorghum crops and 24% to maize.[3]

Monsanto voluntarily discontinued its manufacture in 1998.[4] It is currently listed in the U.S. Environmental Protection Agency's Toxics Release Inventory.[5] 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.[6] Propachlor was added to California's Proposition 65 list as a carcinogen in 2001.[7]

Current manufacturers

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It is currently being produced by Makhteshim Agan Group and Shenzhen Qinfeng Pesticides Co., Ltd.[8]

References

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  1. ^ a b 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. doi:10.1007/bf01605479. PMID 6640157.
  2. ^ "Propachlor (Ramrod, Bexton) Herbicide Profile 2/85". Cornell University. Retrieved 2009-09-09.
  3. ^ a b "Reregistration Eligibility Decision (RED) - Propachlor" (PDF). U.S. Environmental Protection Agency. Retrieved 2009-09-09.
  4. ^ "Illinois Pesticide Review". University of Illinois Extension Service. Retrieved 2009-09-09.
  5. ^ "Toxics Release Inventory (TRI) Chemicals in TOXMAP". Retrieved 2009-09-09.
  6. ^ "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.
  7. ^ "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.
  8. ^ Farm Chemicals International (2012-03-12). "Propachlor". Retrieved 2012-06-27.
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