나프틸아세트산

Attractants

Active substance -> EU Pesticides database: Approved

Pesticides -> Plant Growth Regulators

Environmental transformation -> Pesticides (parent, predecessor)

log Kow = 2.24

2.24

Needles from water

White crystals

Colorless crystals

Slightly soluble in ethanol, trifluoroacetic acid; soluble in benzene and acetic acid; very soluble in ethyl ether, acetone, and chloroform.

10.6 mg/l in carbon tetrachloride @ 26 °C; 55 mg/l in xylene at 26 °C

About 30 parts in alcohol

Very sol in isopropanol

In water, 420 mg/l @ 20 °C

134.5-135.5 °C

Melting point of 125-128 °C /Technical grade/

134.5 - 135.5 °C

This chemical does not meet GHS hazard criteria for 0.9% (1 of 112) of reports.

Danger

H302 (97.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 112 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: 1-Naphthaleneacetic acid

Commission Regulation (EC) No 33/2008

Napthalene Acetates is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/941/EC, Reg. (EU) 2023/2592, Reg. (EU) No 2019/291, Reg. (EU) No 540/2011, Reg. (EU) No 787/2011

1-Naphthylacetic acid: Does not have an individual approval but may be used under an appropriate group standard

A skin and mucous membrane irritant; A severe eye irritant; High-dose animal studies: reduce food intake, decreased hemoglobin, increased liver enzymes; [HSDB] The naphthalene acetates are metabolized in the body and excreted as glycine and glucoronic acid conjugates within 48 hours of exposure; The most common effect seen in high-dose animal studies is a reduction in body weight; 1-naphthaleneacetic acid derivatives covered in the RED are the acetamide (CAS # 86-86-2), potassium salt (CAS # 15165-79-4), ammonium salt (CAS # 25545-89-5), sodium salt (CAS # 61-31-4), and ethyl ester (CAS # 2122-70-5);[Reference #1]

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.

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. 1-Naphthaleneacetic acid 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 '88. Case No: 0379; Pesticide type: growth regulator; Registration Standard Date: 08/31/81; 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 RED document.; Active ingredient (AI): 1-naphthaleneacetic acid; Data Call-in (DCI) Date(s): 09/11/90; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner..

Tolerances are established for residues of the plant growth regulator 1-naphthaleneacetic acid in or on the following raw agricultural commodities: apple; cherry, sweet; olive; orange, sweet; pear; pineaple (from the application of the sodium salt to the growing crop); quince; and tangerine.

A skin, mucous membrane, and severe eye irritant.

Dusts may cause nasal irritation.

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.

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.

Tolerances are established for residues of the plant growth regulator 1-naphthaleneacetic acid in or on the following raw agricultural commodities: apple, 1 ppm; cherry, sweet, 0.1 ppm; olive, 0.1ppm (negligible residues); orange, sweet, 0.1 ppm; pear, 1 ppm; pineaple (from the application of the sodium salt to the growing crop), 0.05 ppm; quince, 1 ppm; and tangerine, 0.1 ppm.

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.

LC50 Mallard duck (8 days) >10,000 mg/kg

LC50 Bobwhite quail (8 days) >10,000 mg/kg

LC50 Rainbow trout 57 mg active ingredient /L / 96 hr /Conditions of bioassay not specified/

LC50 Bluegill sunfish 82 mg active ingredient/L/96 hr /Conditions of bioassay not specified/

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).

1-Naphthaleneacetic acid was shown to be readily absorbed in tomato fruit cuticles(1). Lipophilic in nature, 1-naphthaleneacetic acid applied as a spray concn of 1 g/l to maize, rape, strawberry, and sugar beet resulted in plant uptake rates of 26, 98, 96, and 61% of amount applied, respectively, after 24 hrs; plants characterized by waxy leaves exhibited more rapid uptake(2). Use of a surfactant (NP8, nonylphenol) decreased the rate of absorption to 17, 15, 35, and 13%, respectively(2).

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).

/HUMAN EXPOSURE STUDIES/ Dusts may cause nasal irritation.

/HUMAN EXPOSURE STUDIES/ A skin, mucous membrane, and severe eye irritant.

AEROBIC: 1-Naphthaleneacetic acid, present at 30 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 100 mg/l and the Japanese MITI test(1). 1-Naphthaleneacetic acid has a reported half-life in soil of 10 days, attributed to microbial degradation(2).

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. 1-Naphthaleneacetic acid 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 '88. Case No: 0379; Pesticide type: growth regulator; Registration Standard Date: 08/31/81; 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 RED document.; Active ingredient (AI): 1-naphthaleneacetic acid; Data Call-in (DCI) Date(s): 09/11/90; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner..

Tolerances are established for residues of the plant growth regulator 1-naphthaleneacetic acid in or on the following raw agricultural commodities: apple; cherry, sweet; olive; orange, sweet; pear; pineaple (from the application of the sodium salt to the growing crop); quince; and tangerine.

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.

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.

Used as a plant growth regulator, abscission promoter, and substrate for auxin inducers of specific plant enzymes; Stimulates root formation in cuttings of woody, herbaceous plants, and vines; Prevents premature flower and fruit drop; Controls regrowth of tree sprouts after trimming; Inhibits sprouting in stored potato, turnip, and ornamental bulbs; [HSDB] Registered for use on fruit crops and ornamentals; [Reference #1]

See Reference #1.

Farming (Pesticides) [Category: Industry]

For 1-naphthaleneacetic acid (USEPA/OPP Pesticide Code: 056002) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Plant growth regulator.

Stimulates root formation in cuttings of woody, herbaceous plants, vines. Prevents premature flower, fruit drop in apples, pears, grapes, guavas, mangoes, watermelons, pawpaws, pineapples, citrus, aubergines, cucumbers, cotton, soya. Controls regrowth of tree sprouts after trimming of apple, fig, lemon, olive, pear, pomegranate, prune, pyracantha, walnut. Inhibits sprouting in stored potato, turnip, ornamental bulbs.

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.

Environmental transformation -> Pesticides (parent, predecessor)

HERBICIDES

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.