Napropamide

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Napropamide
Skeletal formula of napropamide Napropamide.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 239-333-3
KEGG
PubChem CID
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]
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).

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. 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.
  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.
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