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NAPROANILIDE

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NAPROANILIDE Basic information

Product Name:
NAPROANILIDE
Synonyms:
  • 2-(2-naphthalenyloxy)-n-phenyl-propanamid
  • 2-(2-naphthalenyloxy)-n-phenylpropanamide
  • 2-(2-naphthyloxy)propionanilide
  • 2-(2-naphtyloxy) propionanilide
  • [2S,(-)]-N-Phenyl-2-(2-naphthoxy)propionamide
  • [S,(-)]-2-(2-Naphtyloxy)-N-phenylpropionamide
  • [2R,(+)]-N-Phenyl-2-(2-naphthoxy)propionamide
  • [R,(+)]-2-(2-Naphtyloxy)-N-phenylpropionamide
CAS:
52570-16-8
MF:
C19H17NO2
MW:
291.34
Mol File:
52570-16-8.mol
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NAPROANILIDE Chemical Properties

Melting point:
128 °C
Boiling point:
433.35°C (rough estimate)
Density 
1.1552 (rough estimate)
refractive index 
1.5000 (estimate)
storage temp. 
0-6°C
pka
13.46±0.70(Predicted)
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NAPROANILIDE Usage And Synthesis

Uses

Naproanilide is used as a herbicide.

Metabolic pathway

In the rice paddy ecosystem, naproanilide is biodegraded by the rice plant and organisms in the paddy field and by soil organisms and is mainly hydrolyzed to 2-(2-naphthoxy)propionic acid (NOP) and its methyl ester (NOPM). In rice plants (Oryza sativa L.) and Sagittaria pygmaea MIQ, naproanilide is metabolized to phytotoxic NOP. In rice plants, NOP subsequently undergoes hydroxylation and rapid conjugation with glucose. Phytotoxic NOP is produced only in a small amount. In S. pygmaea, the amounts of NOP and NOPM are significantly greater than those in rice plants. The difference in metabolites of naproanilide shows a possible mechanism of their herbicidal selectivity. Naproanilide and NOP in aqueous solution are rapidly degraded under sunlight and UV light. The disappearance of naproanilide in the paddy field is largely attributed to photochemical degradation in the surface water.

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