Propachlor

Propachlor

Names
IUPAC name 2-Chloro-N-isopropyl-N-phenylacetamide
Other names 2-Chloro-N-isopropylacetanilide
Identifiers
CAS Number	1918-16-7
ChEMBL	ChEMBL1394829
ChemSpider	4762
Jmol interactive 3D	Image
PubChem	4931
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

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 plants ^[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

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

References

1. 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. PMID 6640157.
2. "Propachlor (Ramrod, Bexton) Herbicide Profile 2/85". Cornell University. Retrieved 2009-09-09.
3. "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. "Propachlor". Retrieved 2012-06-27.

External Links

• Propachlor in the Pesticide Properties DataBase (PPDB)