1-Naphthaleneacetic acid

186.20700

186.21

201-705-8

33T7G7757C

15772

DTXSID8020915

Needles from water|White crystals|Colorless crystals

2916399090

37.30000

2.46690

Solid

1.263 g/cm3

134.5-135.5 °C

352ºC

>100ºC

1.652

Slightly soluble in water, ethanol, acetone, chloroform and ether.

2-8ºC

LD50 orally in Rabbit: 1000 mg/kg LD50 dermal Rabbit > 5000 mg/kg

Odorless

4.23(at 25 °C)

4.23 (at 25 °C)|pKa = 4.23

Alkali metal and amine salts are readily soluble in water.

NONH for all modes of transport

3

R22

S24/25

QJ0876000

Xn

Some evidence of ultraviolet degradation.

P261-P273-P280-P305 + P351 + P338

H302-H315-H318-H335-H412

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Solutions of the heavy-metal salts of other acids form sparingly-soluble salts of 1-naphthylacetic acid.

|Danger|H302 (96.2%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 80 companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Wear rubber gloves.

NONFLAMMABLE

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Do not get on skin or in eyes. ... Do not spray in strong sunlight; preferably spray in late afternoon, evening, or at dusk.

A skin, mucous membrane, and severe eye irritant.|Dusts may cause nasal irritation.

The major hazards encountered in the use and handling of 1-naphthaleneacetic acid stem from its toxicologic properties. Toxic primarily via inhalation and dermal contact. Exposure to this odorless, white, crystalline substance (or colorless solution) may occur from its production or application as a herbicide and plant growth regulator. Effects from exposure include nasal, skin, and eye irritation. Wear gloves when handling this substance. This nonflammable, noncorrosive material should be stored in a cool, dry, dark area (to prevent the possibility of ultraviolet degradation). Before implementing land disposal of waste 1-naphthaleneacetic acid, consult with environmental regulatory agencies for guidance.

The inhibition of wheat coleoptile extension growth by concn of NC 9634 at about 260 muM was completely overcome by 50 uM naphthaleneacetic acid (NAA). Extension growth of intact apple shoots was inhibited by NAA, which was lethal at about 6.25X10-4 M. NC 9634 applied in combination with NAA reduced this growth inhibiting effect and prevented death of shoots sprayed with high auxin concn.

LD50 Mouse ip 609 mg/kg|LD50 Mouse oral 743 mg/kg|LD50 Rat ip 100 mg/kg|LD50 Rat oral 1000 mg/kg|LD50 Rabbit percutaneous greater than 5000 mg/kg

/OTHER TERRESTRIAL SPECIES/ Nontoxic to bees

1-Naphthaleneacetic acid's production may result in its release to the environment through various waste streams; it's use as a plant growth regulator(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a log Kow of 2.24(2) and a regression-derived equation(3), indicates that 1-naphthaleneacetic acid is expected to have moderate mobility in soil(SRC). The pKa of 1-naphthaleneacetic acid is 4.23(4), indicating that this compound will exist as an anion in the environment and anions typically have greater mobility in soils than do neutral species(5). Volatilization of 1-naphthaleneacetic acid from moist soil surfaces is not expected to be an important fate process(SRC) because anions do not volatilize. 1-Naphthaleneacetic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-5 mm Hg(SRC), determined from a fragment constant method(6). 1-Naphthaleneacetic acid has a reported half-life in soil of 10 days, attributed to microbial degradation(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a log Kow of 2.24(2) and a regression-derived equation(3), indicates that 1-naphthaleneacetic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected based upon a pKa of 1-naphthaleneacetic acid of 4.23(4), indicating that this compound will primarily exist in the dissociated form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5). According to a classification scheme(6), a BCF range of 0.5-4.2(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation is not expected to be a fast environmental fate process in water based upon a 0% theoretical BOD using activated sludge and the MITI test(7). Photolysis may be an important environmental fate process as indicated by the detection of photolysis products 1-naphthoic and phthalic acids following exposure of an aqueous solution of 1-naphthaleneacetic acid to sunlight(8,9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-naphthaleneacetic acid, which has an estimated vapor pressure of 1.6X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1-naphthaleneacetic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 hrs(SRC), calculated from its rate constant of 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1-naphthaleneacetic acid may be removed from the air by wet and dry deposition(SRC). Photolysis may be an important environmental fate process in the atmosphere as indicated by the detection of photolysis products 1-naphthoic and phthalic acids during analysis of a sunlight exposed aqueous solution of 1-naphthaleneacetic acid(4,5).

EXPOSURE OF NAPHTHALENEACETIC ACID TO ULTRAVIOLET LIGHT & SUNLIGHT PRODUCED 1-HYDROXMETHYL NAPHTHALENE, 1-NAPHTHALDEHYDE, NAPHTHALENE-1-CARBOXYLIC ACID & 1-METHYL NAPHTHALENE UNDER AEROBIC CONDITIONS. ANAEROBICALLY, ONLY THE 1-METHYL ANALOG WAS OBSERVED. PHTHALIC ACID HAS ALSO BEEN OBSERVED.|A METABOLIC PRODUCT OF NAPHTHALENEACETIC ACID FROM WHEAT COLEOPTILES WAS IDENTIFIED AS THE 5-HYDROXY ANALOG. ON THE /APPLE/ LEAF, UV RADIATION DEGRADED NAA WITH LOSS OF THE CARBOXYL GROUP.|The rate constant for the vapor-phase reaction of 1-naphthaleneacetic acid with photochemically-produced hydroxyl radicals has been estimated as 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Naphthaleneacetic acid is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Photolysis in air and water were identified as the major degradation process for carboxylic acid plant growth regulators(3). 1-Naphthoic and phthalic acids were identified as the photolysis products of 1-naphthaleneacetic acid in sunlight exposed aqueous solution(4,5).

2.95|BCFs of 0.15-0.59 and <1.7-4.2 were measured in carp (Cyprinus carpio) for 1-naphthaleneacetic acid at test chemical concns of 0.5 and 0.05 mg/l, respectively(1). According to a classification scheme(2), these BCFs suggest the potential for bioconcentration in aquatic organisms is low(SRC).

158.49 L/kg|The Koc of 1-naphthaleneacetic acid is estimated as 390(SRC), using a log Kow of 2.24(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-naphthaleneacetic acid is expected to have moderate mobility in soil. The pKa of 1-naphthaleneacetic acid is 4.23(4), indicating that this compound will primarily exist in the dissociated form in the environment and anions generally have greater mobility than their neutral counterparts(5).

The pKa of 1-naphthaleneacetic acid is 4.23(1), which indicates this compound will exist as an anion in the environment. Volatilization from water and moist soil surfaces will not occur since anions do not volatilize. Volatilization from dry soil is not expected(SRC), based on its estimated vapor pressure of 1.6X10-9 mm Hg at 25 °C determined from a fragment constant method(2).

1-Naphthaleneacetic acid was detected in 1 of 2,363 domestic apple samples collected between October 1, 1985 and September 30, 1991, analyzed as part of the EPA Total Diet Study(1). The maximum residue measured was 0.02 ppm(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 3,732 workers (574 of these are female) are potentially exposed to 1-naphthaleneacetic acid in the US(1). The NOES Survey does not include farm workers. Occupational exposure to 1-naphthaleneacetic acid may occur through inhalation and dermal contact with this compound at workplaces where 1-naphthaleneacetic acid is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 1-naphthaleneacetic acid via inhalation of ingestion of contaminated fruits(SRC).

After oral administration /0.1-1.0 mg/ ...of (14)C-naphthaleneacetic acid /(14)C-NAA/ to rats ...83-90% ...was excreted in urine, mostly in 24 hr and 3-10% in feces in 48 hr. After larger doses, excretion of (14)C in urine was prolonged and more was excreted in feces. Thus, after dose of about 100 mg /(14)C-NAA/ rat excreted 55% in 24-hr urine, 16% in 2nd day and 21% in 48-hr feces, whereas, after dose of about 250 mg, rat excreted 25% in 24-hr urine, 42% in 2nd day, 10% in 3rd day, and 18% in 48-hr feces and 3% in 3rd day.|Experiments in rats with cannulated bile ducts showed that fecal /(14)C-naphthaleneacetic acid/ was probably due to material excreted in bile. In rat receiving a lower dose (about 0.1 mg), excretion in urine (38%) was 4-fold more than in bile (9%), whereas in rat receiving a higher dose (about 100 mg), excretion in bile (12%) was 3-fold more than in urine (4%). The pattern applied whether bile was collected for 2 or 6 hr. The portion of /(14)C-NAA/ excreted in bile was greater than that excreted in feces suggesting that entero-hepatic circulation occurred thus, (14)C-compound excreted in bile were partly reabsorbed from intestines (after possible modification, such as deconjugation of conjugates) to be excreted by kidneys. Thus, naphthaleneacetic acid was rapidly and completely absorbed after oral dose to rats and its excretion was dose-dependent, but was rapid after lower doses.|Thin apple and pear blossoms: foliar absorption characteristics: surplus washes off easily; physiological action results from absorbed and translocated portion. Translocation characteristics: mobile; accumulates in meristems.

When naphthaleneacetic acid was incubated with aspergillus niger, major metabolite was found to be 5-hydroxy analog. 4- and 6-hydroxy analogs were also observed.|A metabolic product of naphthaleneacetic acid from wheat coleoptiles was identified as the 5-hydroxy analog.|When kinnow mandarin fruits were dipped in aq soln of naphthaleneacetic acid, 4 metabolites were formed. Two of these were not identified. Other two, in larger amt, were identified as the Alpha-NAA-aspartate and alpha-naphthylacetyl-beta-d-glucose (na-glucose).|Hydrolysis of the methyl ester of naphthaleneacetic acid was observed during storage of treated potatoes. When winesap and stayman cultivars were exposed to naphthaleneacetic acid ...some decarboxylation occurred and 6 conjugates were formed. Pea roots exposed to NAA produced NAA-aspartate... .|After single oral doses ... /to/ rats, 4 metabolites were found in urine. Two were identified as naphthaceturic acid and naphthacetylglucosiduronic acid. 3rd compound was apparently as a sulfate, indicating possible hydroxylation. The 4th was unidentified.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Naphthalene and Related Compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Start an IV with lactated Ringer's. Adequate hydration must be maintained to prevent renal failure secondary to myoglobinuria unless signs of cerebral or pulmonary edema are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Naphthalene and related compounds/|Maintain an open air way and assist ventilation if necessary. Treat coma and seizures if they occur. Treat hemolysis and resulting hemoglobinuria if they occur by intravenous hydration and urinary alkalinization. There is no specific antidote. Administer activated charcoal if available. Do not induce vomiting, because of the risk of lethargy and seizures. Do not administer milk, fats or oils, which may enhance absorption /Naphthalene/|NAPHTHALENE toxicosis caused by vapor inhalation can usually be managed simply by removing the individual to fresh air. Skin contamination should be removed promptly by washing with soap and water. Eye contamination should be removed by flushing with copious amounts of clear water. Irritation may be severe, and if it persists, should receive medical attention. SRP: /It may be helpful to empty stomach and administer dose of activated charcoal/ Examine the plasma for evidence of hemolysis: a reddish-brown tinge. Examine the blood smear for "ghosts" and Heinz bodies. If /hemolysis is/ present, monitor red blood cell count and hematocrit for anemia, urine for protein, and cells. Measure direct- and indirect-reacting bilirubin in the plasma. Monitor fluid balance and blood electrolytes. If possible, monitor urinary excretion of naphthol to assess severity of poisoning and clinical progress. If hemolysis is clinically significnt, administer intravenous fluids to accelerate urinary excretion of the naphthol metabolite and protect the kidney from products of hemolysis. Use Ringer's-lactate or sodium bicarbonate to keep urine pH above 7.5. Consider use of mannitol, or furosemide, to promote diuresis. If urine flow declines, intravenous infusions must be carefully monitored to avoid fluid overload. Institute hemodialysis. Consider charcoal hemoperfusion in tandem to extract naphthalene and end-products. If anemia is severe, blood transfusions may be needed. Hydrocortisone may be of some benefit if significant hemolysis is present. /Fumigant poisoning/

/HUMAN EXPOSURE STUDIES/ Dusts may cause nasal irritation.|/HUMAN EXPOSURE STUDIES/ A skin, mucous membrane, and severe eye irritant.

1-naphthaleneacetic acid

1997. U.S. 1-Naphthaleneacetic acid 10,486 lbs active ingredient applied per year.|1992. U.S. 1-Naphthaleneacetic acid 13,146 lbs active ingredient applied per year.

Fruitone-N, SL (35 g sodium 2-(1-naphthyl)acetate/l); NAA-800, SP (201 g 2-(1-naphthyl)acetic acid/kg); Phyomone, WP (182 g 2-(1-naphthyl)acetic acid/kg); Planofix; tipoff, EC ... Mixtures include: Keriroot, (2-(1-naphthyl)acetic aicd + captan) ...|Rootone F, (4-indol-3-ylbutyric acid + 1-naphthylacetic acid)|Aqueous liquid, aerosol, liquid spray concentrate, powder, water soluble poder (agronaa).|Sol concentrate; water-sol powder; wettable powder; emulsifiable concentrate; dustable powder; tablet.|For more Formulations/Preparations (Complete) data for 1-NAPHTHALENEACETIC ACID (32 total), please visit the HSDB record page.

1-Naphthaleneacetic acid: ACTIVE|Application methods: Dip basal end of cuttings before placing in rooting medium. Otherwise, foliar spray is the usual application method. For blossom thinning spray apples 14 to 21 days after calyx period; pears, 5 to 7 days after petal fall. To reduce preharvest fruit drop, spray at the first sign of sound mature fruit drop. Rates: Rooting cutting, 1000 to 4000 ppm. Blossom thinning, 5 to 50 ppm. Preharvest drop control, 5 to 10 ppm. Usual carrier: Rooting cmpd, talc. Water is the primary carrier for other naphthyleneacetic acid formulations.

Method: AOAC 970.54, Naphthyleneacetic Acid Pesticide Residues, Spectrophotometric Method; Analyte: Naphthyleneacetic acid; Matrix: Apples and potatoes.|A method using high-performance liquid chromatography with fluorescence detection is described for the quantitative measurement of 1-naphthaleneacetic acid in grapes. Sensitivity of method is 0.05 ppm.|Product analysis by glc of a derivative. Residues determined by uv spectrophotometry ... or by hplc.|Analysis of residues: (1) By UV spectrophotometry ... (2) By Gas Chromatography Liquid ... (3) By spectrofluorometric determination in citrus fruits ... (4) By colorimetry ...

Agrochemicals -> Plant Growth Regulators|Environmental transformation -> Pesticides (parent, predecessor)|HERBICIDES

1-naphthylacetic acid has known environmental transformation products that include 1-methylnaphthalene, 1-naphthalenemethanol, 1-naphthoic acid (M2), and naphthaldehyde.