52570-16-8

Basic information

• Product Name: NAPROANILIDE
• Synonyms: 2-(2-naphthalenyloxy)-n-phenyl-propanamid;2-(2-naphthalenyloxy)-n-phenylpropanamide;2-(2-naphthyloxy)propionanilide;alpha-(2-naphthoxy)propionanilide;alpha-(beta-naphthoxy)propionanilide;mt101;MT-101;uribest
• CAS NO: 52570-16-8
• Molecular Formula: C₁₉H₁₇NO₂
• Molecular Weight: 291.34
• Mol File: 52570-16-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 433.35°C (rough estimate)
• Flash Point: 275.5oC
• Appearance: /
• Density: 1.1552 (rough estimate)
• Vapor Pressure: 2.16E-11mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 0-6°C
• PKA: 13.46±0.70(Predicted)
• CAS DataBase Reference: NAPROANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: NAPROANILIDE(52570-16-8)
• EPA Substance Registry System: NAPROANILIDE(52570-16-8)

Safety Data

• Hazardous Substances Data: 52570-16-8(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/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)

Upstream product

• 201230-82-2 carbon monoxide 
• 7309-03-7 2-vinyloxynaphthalene 
• 62-53-3 aniline 
• 42308-20-3 2-bromopropionanilide 
• 135-19-3 β-naphthol 

Downstream Products

• 135-88-6 N-Phenyl-2-naphthylamine 

Relevant articles and documents

Palladium-catalyzed highly regioselective hydroaminocarbonylation of aromatic alkenes to branched amides

Pd(t-Bu3P)2 has been successfully identified as an efficient catalyst for the hydroaminocarbonylation of aromatic alkenes to branched amides under relatively mild reaction conditions. With hydroxylamine hydrochloride as an additive,

Synergistic herbicidal mixtures

PCT No. PCT/EP96/04935 Sec. 371 Date May 1, 1998 Sec. 102(e) Date May 1, 1998 PCT Filed Nov. 12, 1996 PCT Pub. No. WO97/17852 PCT Pub. Date May 22, 1997A synergistically active herbicidal composition which comprises, as active components, a mixture of 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile [Component (A)] and a herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor, pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin, bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb, cinosulfuron, thenylchlor, cumyluron, MK 243, naproanilide, anilofos, benfuresate, bifenox, CH-900, MCPA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (ICIA0051), trifluralin, piperophos, pyributicarb, ethoxysulfuron, bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap, cyclosulfamuron, cyhalofop-butyl, NBA-061, azimsulfuron, propanil or imazosulfuron [Component (B)] and which are suitable for controlling undesirable plants in rice cultivation.

Sulphonylaminophenyluracil herbicides for paddy field

A herbicide for paddy field comprising sulphonylaminophenyluracil derivative as an active ingredient which is represented by the formula (I): STR1 wherein R1 represents hydrogen or methyl, R2 represents C1-5 alkyl, fluro-substituted C1-2 alkyl or C3-6 cycloalkyl, optionally applied in combination with another herbicide.