132-66-1

Basic information

• Product Name: NAPTALAM
• Synonyms: 2-((1-naphthalenylamino)carbonyl)-benzoicaci;2-((1-naphthalenylamino)carbonyl)benzoicacid;6q8;acp322;alanap1;alanap10g;alanap10gat;alanap-2
• CAS NO: 132-66-1
• Molecular Formula: C₁₈H₁₃NO₃
• Molecular Weight: 291.3
• EINECS: 205-073-4
• Mol File: 132-66-1.mol

Chemical Properties

• Melting Point: 185-190 °C
• Boiling Point: 433.31°C (rough estimate)
• Flash Point: 226.4°C
• Appearance: solid with an unpleasant odour
• Density: d420 1.40
• Vapor Pressure: 6.51E-09mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: 0-6°C
• PKA: 3.45±0.36(Predicted)
• Water Solubility: 0.2g/L(room temperature)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,6418
• BRN: 2814102
• CAS DataBase Reference: NAPTALAM(CAS DataBase Reference)
• NIST Chemistry Reference: NAPTALAM(132-66-1)
• EPA Substance Registry System: NAPTALAM(132-66-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN3077 (solid); UN3082 (liquid)
• WGK Germany: 2
• RTECS: TH7350000
• Hazardous Substances Data: 132-66-1(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Naptalam is used as a selective pre-emergence herbicide for controlling some grasses and many broadleaf weeds in crops such as soybeans, cucurbits, asparagus, groundnuts, potatoes, and established woody ornamentals. It acts as an auxin-transport inhibitor in plants, resulting in the attenuation of root growth through decreasing the cell production rate. However, it is not currently registered for use in the U.S. or EU countries.

Trade name

N-1-naphthyl- Trade Names: ALANAP?[C]; ALANAPE?; ANCRACK?; DYANAP?; GRELUTIN?; MORCRAN ?; NAPTRO?; NIP-A-THIN?; PEACH-THIN?; RESCUE?[C]; 6Q8?; SOLO?

Environmental Fate

Soil/Plant. Degrades in soils and plants forming 1-naphthylamine and phthalic acid (Hartley and Kidd, 1987; Humburg et al., 1989). Residual activity in soil is limited to approximately 3 to 4 months (Hartley and Kidd, 1987).Chemical/Physical. Forms N-(1-naphthyl)phthalimide at elevated temperatures (Worthing and Hance, 1991). Naptalam will precipitate as the free acid in very acidic waters or in extremely hard waters (Humburg et al., 1989).

Purification Methods

Crystallise the herbicide from EtOH (m 183-185o). The Na salt has m 185o. [Beilstein 12 H 1236, 12 I 525, 12 III 2876.]

InChI:InChI=1/C18H13NO3/c20-17(14-9-3-4-10-15(14)18(21)22)19-16-11-5-7-12-6-1-2-8-13(12)16/h1-11H,(H,19,20)(H,21,22)/p-1

Upstream product

• 85-44-9 phthalic anhydride 
• 134-32-7 1-amino-naphthalene 
• 4727-29-1 phthalanilic acid 
• 5333-99-3 2-(naphthalen-1-yl)isoindoline-1,3-dione 

Downstream Products

• 134-32-7 1-amino-naphthalene 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 1122445-09-3 RuCl₂(PPh₃)2(2-[(1-naphthylamino)carbonyl]benzoate) 
• 5333-99-3 2-(naphthalen-1-yl)isoindoline-1,3-dione 
• 38228-99-8 N,N'-dibenzylphthalamide 
• 7554-84-9 β-naptalam 

Related news

Determination of the pesticide NAPTALAM (cas 132-66-1) and its degradation products by positive and negative ion mass spectrometry09/30/2019

N-1-Naphthylphtalamic acid (naptalam) and its degradation products, 1-naphthylamine and N-(1-naphthyl) phthalimide were simultaneously determined in river water by two independent mass spectrometric (MS) methods. These were negative ion MS (NIMS) and programmable temperature vaporizer gas chroma...detailed

Study of the pesticide NAPTALAM (cas 132-66-1) degradation; theoretical and experimental09/29/2019

Two different processes for degradation of N-1-naphthylphthalamic acid (naptalam, Nap) are known. Formation of 1-naphthylamine (Na) and phthalic acid (Pha) is one of the degradation processes. Another degradation product of Nap is N-(1-naphthyl) phthalimide (Nad). The HPLC results show that the ...detailed

A facile flow-through phosphorimetric sensing device for simultaneous determination of NAPTALAM (cas 132-66-1) and its metabolite 1-naphthylamine10/01/2019

This paper presents the development of a single flow-through phosphorescence optosensor for simultaneous determination of pesticide N-1-naphthylphthlamic acid (NAP) and its metabolite 1-naphthylamine (NNA). The system works as a simple and rapid phosphorimetry-biparameter sensor. It is based in ...detailed

Relevant articles and documents

Kinetic Study on the Hydrolysis of 1-N-Naphthylphthalamic Acid (Naptalam)

The hydrolysis rate of 1-N naphthylphthalamic acid (Nap) was measured as a function of pH in the range of 0.9-5 and proceeds via undissociated neighboring carboxyl group participation as was proposed for other phthalamic acid derivatives.One of the main h

Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.

Process of improving activity of herbicides and fertilizers using N-(2-hydroxyethyl)-acetamide or -propanamide

The invention is related to the use of certain water-soluble compounds known as such and having the Formula for the modulation of membrane dependent metabolism processes within living cells, in particular with relation to transport phenomena and cell procedures which are induced or influenced by active agents supplied from outside the cell, products containing these substances for the above described uses and processes using these products.

Preparation and Characterisation of Chromium(III) Complexes of Maleanilic and Phthalanilic Acids

The complexes of the type , where A-A - maleanilic and phthalanilic acids, and their 4-methyl, 4-chloro, 4-nitro and 1-naphthyl derivatives have been prepared.The magnetic, conductance, ir and electronic spectral studies indicate their octahedral structure.

Morphanthridines: Part II - Syntheses of 5,6-Dihydro-6,11-dioxomorphanthridine, 1 (or 2)-Substituted 6,11-Dioxo-5,6-dihydromorphanthridines and 7H-12,13-Dihydro-7,12-dioxobenzonaphthazepine

A novel method for the synthesis of substituted 5,6-dihydro-6,11-dioxomorphanthridines (IV) involving the cyclization of anilic acids (III) with PPA has been developed.A new heterocyclic system, 7H-12,13-dihydro-7,12-dioxobenzonaphthazepine (VII), has also been synthesized.

Ternary Complexes of Some Metal Ions with 2,2'-Bipyridyl or 1,10-Phenanthroline as Primary Ligand and Naptalam as a Secondary Ligand

In order to explore complexation as a possible mode of action of some pesticides, the binary and ternary complexes of the type MAL+, where M=Co(II), Ni(II), Cu(II), or Zn(II), A=2,2'-bipyridyl (bpy) or 1,10-phenanthroline (phen) and L=naptalam, have been studied potentiometrically in solution.Protonation constant of naptalam and the stability constants of its binary as well as ternary complexes have been reported at constant ionic strength (0.1 M KNO3) and temperature (25 deg).The values of characterising constant (Δ log K) have been found to be positive, zero or small negative.These values have been used to interpret the extent of M->N-base ?-interactions in these systems.On the basis of formation of considerably stable binary and ternary metal complexes of these pesticides, a new mechanism for their mode of action has been proposed.

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.