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
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[1]
Melting point 74.5 °C (166.1 °F; 347.6 K)[1]
Boiling point 77.4 °C (171.3 °F; 350.5 K)[1]
63 mg/L[1]
Vapor pressure 0.167 mPa[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Napropamide is an acetamide herbicide. It was first sold under the trade name Devrinol,[2] and was first manufactured in 1969.[3] It is widely used in the European Union,[1] and in Australia.[4]

"Devrinol 50" is a wettable powder containing 50% napropamide.[5]

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).[6]

Chemistry

Napropamide inhibits root growth. It is used against annual grasses and broadleaf weeds.[2] The d-isomer is noted as being significantly more effective than the racemic mixture against certain weeds.[3] Its formula is C17H21NO2.[2]

Tradenames

Napropamide has been sold as "Devrinol", "Jouster" and "Naprop".[5][1]

References

  1. ^ a b c d e f g 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.
  2. ^ a b c Neal J (November 18, 2014). "Devrinol (napropamide)". NC State Extension. Retrieved November 26, 2024.
  3. ^ a b 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. ^ a b 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.
  • Napropamide in the Pesticide Properties DataBase (PPDB)
  • Napropamide in the Pesticide Properties DataBase (PPDB) (Napropamide-M)
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