Napropamide
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{chembox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| Name = Napropamide
| ImageFile = Napropamide.svg
| ImageSize = 200px
| ImageName = Skeletal formula of napropamide
| ImageFile1 =
| ImageSize1 = 200px
| ImageName1 =
| PIN = N,N-Diethyl-2-naphthalen-1-yloxypropanamide
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 15299-99-7
| CASNo_Ref =
| Beilstein = 2217870
| IUPHAR_ligand =
| ChEBI = 83771
| ChemSpiderID = 25304
| KEGG = C18868
| PubChem = 27189
| ChEMBL_Ref =
| ChEMBL = 1877460
| EINECS = 239-333-3
| UNII = B56M9401K6
| StdInChI = 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
| StdInChIKey = WXZVAROIGSFCFJ-UHFFFAOYSA-N
| SMILES = CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21
}}
| Section2 = {{Chembox Properties
| C=17 | H=21 | N=1 | O=2
| Appearance =
| Odor =
| Density =
| Solubility =
| SolubleOther =
| MeltingPtC =
| MeltingPt_ref =
| BoilingPtC =
| BoilingPt_ref =
| Viscosity =
| VaporPressure =
| ThermalConductivity =
| LogP =
| pKa =
| RefractIndex =
}}
| Section3 = {{Chembox Thermochemistry
| DeltaHc =
| HeatCapacity =
| DeltaHf =
}}
| Section4 = {{Chembox Hazards
| ExternalSDS =
| MainHazards =
| FlashPtC =
| FlashPt_ref =
| NFPA_ref =
| LD50 =
}}
}}
Napropamide is an acetamide chemical herbicide. Its formula is {{chem2|C17H21NO2}}. It is sold under the trade name of Devrinol,{{Cite web|url=https://content.ces.ncsu.edu/devrinol-napropamide |title=Devrinol (napropamide) |first=Joe |last=Neal |date= November 18, 2014 |website=NC State Extension |access-date=November 26, 2024}} and was first manufactured in 1969.{{Citation |last=Wendeborn |first=S. |title=1.8 Chirality in Agrochemicals |date=2012 |work=Comprehensive Chirality |pages=120–166 |url=https://linkinghub.elsevier.com/retrieve/pii/B9780080951676001026 |access-date=2024-11-26 |publisher=Elsevier |language=en |doi=10.1016/b978-0-08-095167-6.00102-6 |isbn=978-0-08-095168-3 |last2=Godineau |first2=E. |last3=Mondière |first3=R. |last4=Smejkal |first4=T. |last5=Smits |first5=H.|url-access=subscription }}
"Devrinol 50" is a wettable powder containing 50% napropamide.{{cite journal |last1=Williams |first1=H.h. |title=Effects of certain preemergence herbicides on Diochondra spp. |journal=Proceedings of the Second International Turfgrass Research Conference |date=1974 |pages=410–417 |doi=10.2135/1974.proc2ndintlturfgrass.c60}}
Use
Napropamide is used as a herbicide by inhibiting the growth of roots. 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.