Naproanilide

Naproanilide
Names
IUPAC name
(2RS)-2-(2-naphthyloxy)propananilide
Preferred IUPAC name
rac-2-(naphthalen-2-yloxy)-N-phenylpropanamide
Other names
  • (RS)-2-(2-naphthyloxy)propionanilide
  • 2-(2 -naphthy1oxy)propionanilide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.108.762 Edit this at Wikidata
EC Number
  • 610-862-5
KEGG
  • InChI=1S/C19H17NO2/c1-14(19(21)20-17-9-3-2-4-10-17)22-18-12-11-15-7-5-6-8-16(15)13-18/h2-14H,1H3,(H,20,21)
    Key: LVKTWOXHRYGDMM-UHFFFAOYSA-N
  • CC(C(=O)NC1=CC=CC=C1)OC2=CC3=CC=CC=C3C=C2
Properties
C19H17NO2
Molar mass 291.350 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Naproanilide is a selective acetamide herbicide, used on rice paddies to control dicotyl weeds, and many annual or perennial weeds. It was introduced in the 1970s.

Its normal application rate is 1-2 kg/Ha. It is extremely safe on rice, producing little effect even at 32 kg/Ha.

One metabolic product of naproanilide is naphthoxypropionic acid (NPA).

References

  1. 1 2 "naproanilide data sheet". www.bcpcpesticidecompendium.org.
  2. 1 2 Wang, Yei-Shung; Hwang, Kuan-Liang; Chen, Yuh-Lin (1994). "Absorption, translocation and metabolism of the herbicide naproanilide in tobacco". Pesticide Science. 42 (1): 53–58. doi:10.1002/ps.27804201099.
  3. 1 2 Nagayoshi, E; Shiga, N; Matano, O; Goto, S. "Microdetermination of a Herbicide, α-(2-naphthoxy)propionanilide". Journal of Pesticide Science (in Japanese). doi:10.1584/jpestics.2.445.