| Identification | Back Directory | [Name]
NAPROANILIDE | [CAS]
52570-16-8 | [Synonyms]
mt101
MT-101
uribest
Urigbest
NAPROANILIDE
Naproanilide-D5
naproanilide (jmaf)
Naproanilide,10ug/ml
NAPROANILIDE STANDARD
naproanilide (JMAF only)
2-(2-naphthyloxy)propionanilide
2-（2-naphtyloxy) propionanilide
alpha-(2-naphthoxy)propionanilide
Naproanilide@100 μg/mL in Acetone
Naproanilide, 100 μg /μL in Acetone
alpha-(beta-naphthoxy)propionanilide
2-(2-Naphtyloxy)-N-phenylpropanamide
N-Phenyl-2-(2-naphtyloxy)propionamide
2-(2-Naphthyloxy)-N-phenylpropanamide
2-(2-naphthalenyloxy)-n-phenyl-propanamid
2-(2-naphthalenyloxy)-n-phenylpropanamide
Propanamide, 2-(2-naphthalenyloxy)-N-phenyl-
[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 | [Molecular Formula]
C19H17NO2 | [MDL Number]
MFCD01310442 | [MOL File]
52570-16-8.mol | [Molecular Weight]
291.34 |
| Chemical Properties | Back Directory | [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) | [Henry's Law Constant]
1.6×105 mol/(m3Pa) at 25℃, Hilal et al. (2008) |
| Hazard Information | Back Directory | [Description]
Naproanilide is a rice herbicide. Itself it has no herbicidal activity however its major metabolite 2-(2-naphthoxy)propionic acid does. It is only slightly toxic. Photodegradation appears to be the main degradation pathway in paddy fields. Little is known about the toxicity of this substance to wildlife. | [Chemical Properties]
The pure product is white, odorless crystals. MPa is 128°C, relative density is 1.256 (25°C), and vapor pressure is 66.66 Pa (110°C). Solubility at 27°C is: acetone 171 g/L, benzene 36 g/L, toluene 42 g/L, ethanol 17 g/L, and water 0.74 mg/L. It is stable in neutral and weakly acidic solutions, but unstable in alkaline or hot strongly acidic solutions. The original drug is stable to water, but the solution is unstable to water. The half-life in soil is 2 to 7 days, and the drug disappears within 1 month. | [Uses]
Naproanilide is used as a herbicide. | [Definition]
ChEBI: Naproanilide is a member of naphthalenes. | [Production Methods]
Naproanilide is synthesised through a three-step process starting from 2-chloropropanoic acid, aniline, and 2-naphthol. First, 2-chloropropanoic acid undergoes a nucleophilic substitution with aniline, where the amine group replaces the chlorine atom, forming an amide intermediate. In the second step, this intermediate reacts with 2-naphthol in the presence of a base, such as sodium hydroxide, which activates the phenolic oxygen to act as a nucleophile. This leads to the formation of a naphthyl ether linkage, completing the structure of naproanilide. | [Mechanism of action]
Stimulates RNA synthesis. Absorbed through stems and roots. No herbicidal activity itself but is rapidly hydrolysed to an active metabolite | [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. | [Pesticide Type]
Herbicide |
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