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Naptalam

HCID 8594
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Basic information

CAS
132-66-1
Standard SMILES
O=C(O)c1ccccc1C(=O)Nc1cccc2ccccc12
InChIKey
JXTHEWSKYLZVJC-UHFFFAOYSA-N
Molecular formula
C18H13NO3
Average molar mass
291.3 g/mol
Monoisotopic mass
291.08954328

Overview

Naptalam is a dicarboxylic acid monoamide which results from addition of one equivalent of 1-naphthylamine to phthalic anhydride. It has a role as a herbicide. It is a carboxylic acid, a dicarboxylic acid monoamide and a N-(1-naphthyl)carboxamide. It is a conjugate acid of a naptalamate.

Names & identifiers

Preferred name
Naptalam
IUPAC
2-(naphthalen-1-ylcarbamoyl)benzoic acid
English name
NAPTALAM
Molecular formula
C18H13NO3
Molecular weight
291.3

Names & synonyms

NAPTALAM132-66-1GrelutinN-1-Naphthylphthalamic acidN-(1-Naphthyl)phthalamic acidAlanapeAnalapeDyanapPeach-ThinMor-CranNaphthalamAlanap 1
Show more names
NPANAPHTHYLPHTHALAMIC ACIDn-1-naphthalenephthalamicacidALANAP1-N-NAPHTHYLPHTHALAMIC ACID (NPA)6q8soloacp322
Alanap 3Alanap 10G atAlanap-2NaptalameCyanapNaptro1-N-Naphthylphthalamic acidAlanap Plus

Database identifiers

CAS
132-66-1
PubChem CID
8594
DTXSID
DTXSID6032437
ChEMBL
CHEMBL2447888
ChEBI
CHEBI:60833
UNII
306R88V86P
EC Number
625-029-1
Nikkaji
J4.410E

Properties

Computed structural propertiesFilling in

XLogP
3.5
Topological polar surface area
66.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
22
Formal charge
0
Complexity
423

Experimental & physicochemical properties

Pesticides · 4 items

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Other

Pesticide (Naptalam) -> USDA PDB

LogP3.0
OdorUNPLEASANT
Density1.40 @ 20 °C/4 °C
Color/FormCRYSTALLINE SOLID POWDER, PURPLE
Solubility · 4 items

INSOL IN HEXANE, XYLENE, BENZENE; PPM @ 25 °C: ACETONE 5,000; ISOPROPANOL 2,100; CARBON TETRACHLORIDE 100; WATER 200; DIMETHYLFORMAMIDE 39,400; DIMETHYL SULFOXIDE 43,100; METHYLETHYL KETONE 3,700

SLIGHTLY SOL IN ETHANOL

INSOL IN SOLVENT NAPHTHA

Sol in alkaline soln, but decomp above pH 9.5

CorrosivityNON-CORROSIVE
Melting Point · 2 items

203 °C

MP: 175-180 °C /TECHNICAL/

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

H412 (98.5%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 68 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information2002/2076
Other Safety InformationIMAP assessments - Benzoic acid, 2-[(1-naphthalenylamino)carbonyl]-: Environment tier I assessment
Fire PotentialFlammability: None, a water solution.
Hazards Summary · 1 item

May cause respiratory irritation and permanent eye injury; No adverse effects in a 90-day feeding study of rats at 1000 ppm in daily diet; Not tumorigenic in mice; 15 mg/kg/day was NOEL for maternal and fetotoxic effects in a study of rats; [HSDB] May cause irritation; [MSDSonline]

FIFRA Requirements · 2 items

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Naptalam is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0183; Pesticide type: Herbicide; Registration Standard Date: 03/30/85; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): N-1-Naphthylphthalamic acid; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

... Naptalam may act by affecting the transport of auxin within the plant.

2-(p-Carbethoxyphenyl)-1,3(2H,4H)-isoquinolinedione, an experimental herbicide, caused effects on geotropism, which are often indicative of an effect on auxin transport, in a whole plant herbicidal screen. However, it showed little or no activity in an in vitro binding assay in corn coleoptiles for the auxin transport inhibitor, N-1-naphthylphthalamic acid. Other active isoquinolinedione analogues of this compound did, however, exhibit significant in vitro activity. Direct measurements of auxin transport in corn coleoptiles were undertaken in an attempt to resolve the apparent discrepancy between herbicidal and binding activities. In all cases examined, compounds that were highly active on whole plants were good inhibitors of auxin transport, and compounds that were weak as herbicides showed little or no effect on auxin transport. Therefore, it is concluded that the mode of action of these isoquinolinedione herbicides is the inhibition of auxin transport. Ring-opened analogues of several isoquinolinediones were synthesized and assayed in both the transport and binding assays, in order to test whether compounds in this class express their herbicidal activity by undergoing ring-opening in vivo, yielding products that are more straightforward analogues of N-1-naphthylphthalamic acid with free carboxyl groups. The homophthalamic acids had little or no activity in both assays. On the other hand, the p-ethyl- and p-ethoxy-phenyl phthalamic acids showed auxin transport inhibition comparable to the parent isoquinolinediones, but with markedly increased binding activity. These results support the possible role of ring-opening in the generation of biological activity. However, the p-carbethoxyphenyl phthalamic acid, analogous to 2-(p-carbethoxyphenyl)-1,3(2H,4H)-isoquinolinedione, was very weak in both assays. Thus, ring-opening in vivo cannot alone account for the biological activity of this class of compounds.

Metabolism/Metabolites · 2 items

... NAPTALAM APPEARS TO BREAK DOWN RATHER RAPIDLY INTO ... /ALPHA-NAPHTHYLAMINE & PHTHALIC ACID IN PLANTS/.

WHEN UNSTERILIZED SOIL WAS EXTRACTED AFTER FIVE DAYS OF INCUBATION WITH 500 PPM OF NAPTALAM, 9 OR 10 METABOLITES WERE FOUND. THE MAIN METABOLITE WAS 2-AMINO-4-METHYL-5-CHLOROTHIAZOLE & TWO DECHLORINATED METABOLITES WERE ALSO IDENTIFIED.

MeSH Pharmacological Classification

Related reactions

2 records
New reaction record
HRID 240237 reaction equation
HRID 240237As reactantuspto-grants-2014_02
HRID 1460269 reaction equation
HRID 1460269As productuspto-grants-1991_12

Compound notes

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Vapor Pressure
Less than 133 Pascals at 20 °C
Physical DescriptionColorless solid; [Hawley] Purple solid with an unpleasant odor; [HSDB] Solid with an unpleasant odor; [MSDSonline]
Stability/Shelf Life · 2 items

SHELF STORAGE OF 4 TO 5 YR HAS BEEN OBSERVED WITHOUT CHANGE IN THE ACTIVE PRODUCT. THE FORMULATION WILL FREEZE & ACTIVE INGREDIENT WILL PPT @ -1 °C ... UPON WARMING WITH MILD AGITATION IT WILL REDISSOLVE. TEMPERATURE OF 60 TO 65 °C FOR ... OVER 2 HR SHOULD BE AVOIDED OR RING CLOSURE WILL OCCUR & IMIDE FORM OF ACTIVE INGREDIENT WILL BE FORMED AND PRECIPITATE.

RAPIDLY HYDROLYZED @ PH OF 9.5 OR GREATER, IS UNSTABLE @ 200 °C OR GREATER

Collision Cross Section168.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6032437]

Physicochemical properties

Melting point
185 · 185-190 °C
Boiling point
433.31 °C · 433.31°C (rough estimate)
Density
420 · d420 1.40
refractive index
1.48 · 1.4800 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
25 mg/ml; · DMF: 25 mg/ml; DMF:PBS (pH 7.2) (1:3): 0.25 mg/ml; DMSO: 15 mg/ml
form
Solid
pka
3.45 · 3.45±0.36(Predicted)
color
White to Gray to Dark blue
biological source
rabbit
Water Solubility
0.2 g/L · 0.2g/L(room temperature)
Merck
14 · 14,6418
BRN
2814102 · 2814102
Henry's Law Constant
2.3 · 2.3×1010 mol/(m3Pa) at 25℃, MacBean (2012)
Stability
Stable. Incompatible with strong oxidizing agents.
Major Application
agricultureenvironmental
InChI
1S/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)
InChIKey
JXTHEWSKYLZVJC-UHFFFAOYSA-N
SMILES
OC(=O)c1ccccc1C(=O)Nc2cccc3ccccc23
CAS DataBase Reference
132 · 132-66-1(CAS DataBase Reference)
FDA UNII
306 R88V86P · 306R88V86P
EPA Substance Registry System
Naptalam (132-66-1)
UNSPSC Code
41116107 · 41116107
NACRES
41 · NA.41
Hazard statements
412 · H412
Precautionary statements
273 · P273
PPE
Eyeshields, Gloves
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36/37/39
RIDADR
3077 · UN3077 (solid); UN3082 (liquid)
WGK Germany
2 · 2
RTECS
7350000 · TH7350000
HS Code
29242990 · 29242990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
3 · Aquatic Chronic 3
Hazardous Substances Data
132 · 132-66-1(Hazardous Substances Data)
Toxicity
50 · LC50 (96-hour) for bluegill sunfish 354 mg/L and rainbow trout 76 mg/L (Hartley and Kidd, 1987); acute oral LD50 of the free acid and sodium salt for rats >8,200 and 1,800 mg/kg, respectively (Ashton and Monaco, 1991).

Tolerances are established for residues of the herbicide N-1-naphthyl phthalamic acid from application of its sodium salt in or on the following agricultural commodities: peanut hulls, cantaloups, cranberries, cucumbers, muskmelons, peanuts, peanut hay, soybeans, soybean hay, and watermelons.

Hazard Classes and CategoriesAquatic Chronic 3 (98.5%)
Skin, Eye, and Respiratory Irritations · 2 items

INHALATION HAS BEEN REPORTED TO CAUSE SLIGHT IRRITATION.

NO SKIN IRRITATION DESCRIBED IN MAN ... .

Safety & protection

Allowable Tolerances · 1 item

Tolerances are established for residues of the herbicide N-1-naphthyl phthalamic acid from application of its sodium salt in or on the following agricultural commodities: peanut hulls, 0.1 ppm; and cantaloups, cranberries, cucumbers, muskmelons, peanuts, peanut hay, soybeans, soybean hay, and watermelons, 0.1 ppm (negligible residues).

Toxicology

Interactions · 2 items

In the greenhouse, naptalamat 1.1 to 4.5 kg ai/ha antagonized activity of paraquat at 0.04 to 0.14 kg ai/ha in 14 of 16 rate combinations when applied to sicklepod. Sicklepod shoot fresh weight reduction was less compared to that obtained with paraquat alone when paraquat at 0.04 kg/ha was mixed with bentazon at 0.42 to 0.84 kg ai/ha or monocarbamide dihydrogensulfate at 14 to 58 kg ai/ha. Paraquat activity on Florida beggarweed was antagonized by mixtures of paraquat at 0.04 to 0.14 kg/ha with naptalam at 3.4 or 4.5 kg/ha.

Laboratory studies demonstrated that naptalam safens cucumber against the phytotoxic effects of chloramben. In petri dish studies, cucumber seedlings grown from seeds exposed to chloramben plus naptalam had greater shoot growth, root growth, and dry weight than seedlings grown from seeds exposed to chloramben alone. Naptalam also partially reversed the reduction in dry weight of various plant parts caused by exposure of roots of hydroponically grown seedlings to chloramben. More radioactivity from root-applied (14)C chloramben remained in cucumber roots and less was translocated to shoots wih a (14)C chloramben plus naptalam treatment than with a (14)C chloramben alone treatment. Naptalam appeared to influence chloramben metabolism. In various plant parts, concn of chloramben and its metabolites differed between the two treatments.

Ecotoxicity Values · 4 items

LD50 Anas platyrhynchos (Mallard) oral > 10000 mg/kg/8 days

LD50 Colinus virginianus (Bobwhite quail) oral > 10000 mg/kg/8 days

LC50 Lepomis macrochirus (Bluegill) 354 mg/l/96 hr

LC50 Salmo gairdneri (Rainbow trout) 76 mg/l/96 hr

Environmental Fate · 2 items

Terrestrial Fate: In ... soil, degradation to 1-naphthylamine and phthalic acid.

TERRESTRIAL FATE: THE ANNUAL APPLICATION OF NAPTALAM TO CRANBERRY BOGS RESULTED IN A BUILD-UP OF NAPTALAM IN BOG SOIL. THE BOG SOILS THAT HAD RECEIVED ANNUAL APPLICATIONS OF 8-12 LB NAPTALAM/ACRE SHOWED THE MOST RESIDUE AT THE 0-4 INCH DEPTHS. FOR 8-10 LB NAPTALAM/ACRE, A STEADY STATE BETWEEN THE PERSISTENCE & BREAKDOWN OF NAPTALAM WAS REACHED AFTER 2 YEARS.

Soil Adsorption/Mobility · 3 items

LEACHES RAPIDLY IN HIGHLY POROUS OR SILT LOAM SOILS OF EXTREMELY FINE TEXTURE. HEAVY RAINS IMMEDIATELY AFTER APPLICATION WILL CAUSE ... LEACHING ... .

Koc = 4 (calculated from water solubility by regression equations) /From table/

Terrestrial Fate: Absorption and leaching characteristics: Incomplete data indicate that naptalam is very mobile in a fine sand, a sandy loam, and a silt loam soil, and slightly mobile in muck soil. Retention of naptalam by soil is correlated with /cation exchange capacity/ CEC and organic matter content.

Human Toxicity Excerpts · 3 items

INHALATION HAS BEEN REPORTED TO CAUSE SLIGHT IRRITATION.

NO SKIN IRRITATION DESCRIBED IN MAN ... .

Hazards to humans statement: DANGER. Harmful if swallowed. Corrosive. Causes irreversible eye damage. Do not get in eyes or on clothing.

Environmental BiodegradationSUBJECT TO SLOW MICROBIAL BREAKDOWN.
Environmental BioconcentrationBCF = 0.5 (calculated from water solubility by regression equations) /From table/
Volatilization from Water/SoilNON-VOLATILE /IN SOIL/ ...
Non-Human Toxicity Excerpts · 5 items

... LOW ACUTE TOXICITY IN RATS ... NO SKIN IRRITATION DESCRIBED IN ... ANIMALS.

SUBACUTE TOXICITY: 90 DAY FEEDING STUDY SHOWED NO ADVERSE EFFECTS @ 1000 PPM IN DAILY DIET OF RATS & NO ADVERSE EFFECT LEVEL OF GREATER THAN 5000 PPM IN DAILY DIET OF DOGS.

NAPTALAM WAS NOT TUMORIGENIC WHEN ADMIN ORALLY TO MICE (64-215 MG/KG/DAY). /FROM TABLE/

NO EVIDENCE OF MUTAGENICITY TO ESCHERICHIA COLI WAS FOUND FOR A VARIETY OF COMMERCIAL PRODUCTS INCL NAPTALAM.

For more Non-Human Toxicity Excerpts (Complete) data for NAPTALAM (11 total), please visit the HSDB record page.

Evidence for CarcinogenicityCancer Classification: Group D Not Classifiable as to Human Carcinogenicity
Environmental Abiotic Degradation... Photo-stable /in soil/.
Toxicity DataLC50 (rat) > 2,070 mg/m3

Regulatory information

FIFRA Requirements · 2 items

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Naptalam is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0183; Pesticide type: Herbicide; Registration Standard Date: 03/30/85; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): N-1-Naphthylphthalamic acid; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Tolerances are established for residues of the herbicide N-1-naphthyl phthalamic acid from application of its sodium salt in or on the following agricultural commodities: peanut hulls, cantaloups, cranberries, cucumbers, muskmelons, peanuts, peanut hay, soybeans, soybean hay, and watermelons.

Safety data

PPE
Eyeshields, Gloves
wgk
2
rtecs
TH7350000
ridadr
UN3077 (solid); UN3082 (liquid)
hs_code
29242990
Toxicity
LC50 (96-hour) for bluegill sunfish 354 mg/L and rainbow trout 76 mg/L (Hartley and Kidd, 1987); acute oral LD50 of the free acid and sodium salt for rats >8,200 and 1,800 mg/kg, respectively (Ashton and Monaco, 1991).
risk_code
36/37/38
safety_code
26-36/37/39
Storage Class
11 - Combustible Solids
Hazard statements
H412
Hazard Classifications
Aquatic Chronic 3
Precautionary statements
P273
Hazardous Substances Data
132-66-1(Hazardous Substances Data)
· 2 items

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.

Absorption, Distribution and Excretion · 2 items

TRANSLOCATION CHARACTERISTICS: GIVES STRONG EPINASTIC RESPONSE (SRP: CURLING OF STEM) ON TOMATOES, APPLIED ON THE FOLIAGE OR THROUGH THE SOIL. APPEARS TO ACCUMULATE IN MERISTEMATIC TISSUE.

Absorption predominantly via the roots, but also, to some extent, via the foliage, with accumulation in meristemat8ic tissue.

Uses & manufacturing

Uses · 6 items

Used as selective pre-emergence herbicide and analytical reagent for thorium and zirconium; [Merck Index]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

AS ANALYTICAL REAGENT FOR THORIUM & ZIRCONIUM

GIVES CONTROL OF PIGWEED, PURSLANE, LAMBSQUARTER, QUICKWEED, RAGWEED, CHICKWEED, FOXTAIL, CRABGRASS.

Methods of ManufacturingBy the interaction of phthalic anhydride with 1-naphthylamine in benzene, xylene, or kerosene at room temp.
Formulations/Preparations · 5 items

ALANAP-3 /IS/ AQ SOLUTION OF SODIUM SALT CONTAINING EQUIVALENT OF 22% COMPOUND AS ACID. /SODIUM SALT/

IT IS FORMULATED AS EMULSIFIABLE CONCENTRATE, WETTABLE POWDER, & GRANULES.

Alanap Plus (mixt of naptalam plus chloropropham), Solo (mixt of naptalam plus chlorpropham), Mor-Cran (mixt of naptalam plus chlorpropham) ... The sodium salt is the active ingredient in liq and granular Alanap and Peach Thin 322. It is also one of the active materials in Solo, Alanap Plus, and Dyanap. The others are chlorpropham and sodium dinoseb.

Naptro (dinitrophenol + naptalam)

Wettable powder - containing 90% active ingredient; Alanap-2 - wettable powder containing 90% active ingredient as imide; Alanap 10G - granules containing 10% active ingredient; Cyanap - combination 20.8% Naptalam, 10.5% Dinoseb, (Uniroyal and Ansul) used for peanuts; Mor-cran - mixture of alanap and CIPC (Uniroyal) used for cranberries; Solo - mixture of alanap and and CIPC (Uniroyal) used for soybeans; Ancrack - 2 lb naptalam plus 1 lb Dinoseb (Ansul) used for soybeans and peanuts; Peachthin 322 - 17.2% sodium salt used for thinning peach trees (Amdal Co, Abbott Laboratories).

General Manufacturing Information · 3 items

WEED CONTROL USUALLY LASTS 3 TO 8 WK, DEPENDING ON SOIL & WEATHER CONDITIONS.

Year of initial registration: 1949.

Types and methods of application: Planter-mounted preemergence herbicide sprayer, aerial sprayer, or granular applicator. Applications may be preemergence, or postemergence in soybeans and cucurbits. One application per year, except on cucurbits, where there may be two. Application rates: For the liquid formulations, rates range from 2.0-6.0 lb. ai/acre, except on ornamental nursery stock, where 8.0 lb. ai/acre may be used. For the granular formulation, the rate is 4.3 lb ai/acre, except on cranberries, where 8.1 lb ai/acre may be used. Usual carriers: Water is the most common carrier for liquid formulations. /Former use/

Applications · 4 items

DescriptionNaptalam is a broad-spectrum herbicide. It is usually used as the sodium salt as this is more soluble. Whilst naptalam is not particularly toxic to humans its major metabolite 1-naphthylamine is a carcinogen. Its environmental fate is pH sensitive. It may pose a threat to groundwaters. Virtually non-toxic to mammals, birds, honeybees and most aquatic species. No data for earthworms has been identified.

UsesSelective preemergence herbicide used to control some grasses and many broadleaved weeds in soybeans, cucurbits, asparagus, groundnuts, potatoes and established woody ornamentals.

UsesN-(1-Naphthyl)phthalamic Acid is an auxin-transport inhibitor in plants resulting in the attenuation of root growth through decreasing the cell production rate.

General DescriptionNaptalam is a purple crystalline solid, which can be used as an anti-geotropic agent and as an auxin (IAA) antagonist in plants.

Additional notes

DefinitionChEBI: A dicarboxylic acid monoamide which results from addition of one equivalent of 1-naphthylamine to phthalic anhydride.