Napropamide

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| Name = Napropamide

| ImageFile = Napropamide.svg

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| ImageName = Skeletal formula of napropamide

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| PIN = N,N-Diethyl-2-naphthalen-1-yloxypropanamide

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| Section1 = {{Chembox Identifiers

| CASNo = 15299-99-7

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| Beilstein = 2217870

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| 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

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| Section2 = {{Chembox Properties

| C=17 | H=21 | N=1 | O=2

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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.

See also

References