Napropamide

Napropamide
Skeletal formula of napropamide
Skeletal formula of napropamide
Names
Preferred IUPAC name
N,N-Diethyl-2-naphthalen-1-yloxypropanamide
Identifiers
3D model (JSmol)
2217870
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.035.742 Edit this at Wikidata
EC Number
  • 239-333-3
KEGG
UNII
  • InChI=1S/C17H21NO2/c1-4-18(5-2)17(19)13(3)20-16-12-8-10-14-9-6-7-11-15(14)16/h6-13H,4-5H2,1-3H3
    Key: WXZVAROIGSFCFJ-UHFFFAOYSA-N
  • CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21
Properties
C17H21NO2
Molar mass 271.360 g·mol−1
Density 1.18
Melting point 74.5 °C (166.1 °F; 347.6 K)
63 mg/L
Vapor pressure 0.167 mPa
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Napropamide is an acetamide herbicide. It was first sold under the trade name Devrinol, and was first manufactured in 1969. It is widely used in the European Union, and in Australia.

"Devrinol 50" is a wettable powder containing 50% napropamide.

Napropamide's mode of action is unknown, therefore the HRAC classification system calls it equivalently Group Z or Group 0, although it was formerly classified as Group K (Group K3 or 15).

Chemistry

Napropamide inhibits root growth. It is used against annual grasses and broadleaf weeds. The d-isomer is noted as being significantly more effective than the racemic mixture against certain weeds. Its formula is C17H21NO2.

Tradenames

Napropamide has been sold as "Devrinol", "Jouster" and "Naprop".

References

  1. 1 2 3 4 5 6 Lewis KA, Tzilivakis J, Warner DJ, Green A (18 May 2016). "An international database for pesticide risk assessments and management". Human and Ecological Risk Assessment: An International Journal. 22 (4): 1050–1064. doi:10.1080/10807039.2015.1133242. hdl:2299/17565.
  2. 1 2 3 Neal J (November 18, 2014). "Devrinol (napropamide)". NC State Extension. Retrieved November 26, 2024.
  3. 1 2 Wendeborn S, Godineau E, Mondière R, Smejkal T, Smits H (2012), "1.8 Chirality in Agrochemicals", Comprehensive Chirality, Elsevier, pp. 120–166, doi:10.1016/b978-0-08-095167-6.00102-6, ISBN 978-0-08-095168-3, retrieved 2024-11-26
  4. ↑ "Devrinol 500WG Napropamide".
  5. 1 2 Williams H (1974). "Effects of certain preemergence herbicides on Diochondra spp". Proceedings of the Second International Turfgrass Research Conference: 410–417. doi:10.2135/1974.proc2ndintlturfgrass.c60.
  6. ↑ "Australia Herbicide Classification Lookup". Herbicide Resistance Action Committee.