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
CAS Number	52570-16-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:7475;
ChemSpider	36918;
ECHA InfoCard	100.108.762
EC Number	610-862-5;
KEGG	C10954;
PubChem CID	40413;
CompTox Dashboard (EPA)	DTXSID8058118 ;
	InChI 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;
	SMILES CC(C(=O)NC1=CC=CC=C1)OC2=CC3=CC=CC=C3C=C2;
Properties
Chemical formula	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). Infobox references

Naproanilide is a selective acetamide herbicide,^[1] used on rice paddies to control dicotyl weeds, and many annual or perennial weeds.^[2] It was introduced in the 1970s.^[3]

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

One metabolic product of naproanilide is naphthoxypropionic acid (NPA).^[3]

References

1 2 "naproanilide data sheet". www.bcpcpesticidecompendium.org.
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.
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.