Napropamide

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]

Napropamide

Skeletal formula of napropamide
Names
Preferred IUPAC name N,N-Diethyl-2-naphthalen-1-yloxypropanamide
Identifiers
CAS Number	15299-99-7
3D model (JSmol)	Interactive image
Beilstein Reference	2217870
ChEBI	CHEBI:83771
ChEMBL	ChEMBL1877460
ChemSpider	25304
ECHA InfoCard	100.035.742
EC Number	239-333-3
KEGG	C18868
PubChem CID	27189
UNII	B56M9401K6
CompTox Dashboard (EPA)	DTXSID5024211
InChI 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
SMILES CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21
Properties
Chemical formula	C17H21NO2
Molar mass	271.360 g·mol−1
Density	1.18[1]
Melting point	74.5 °C (166.1 °F; 347.6 K)[1]
Solubility in water	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

"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]