1-Naphthylphthalamic acid

291.306

291.30

306R88V86P

204421

DTXSID6032437

CRYSTALLINE SOLID POWDER, PURPLE

29242990

66.4

3.86330

1.40 g/cm³ @ Temp: 20 °C

203 °C

433.31°C (rough estimate)

226.4ºC

1.4800 (estimate)

Sol in alkaline soln, but decomp above pH 9.5

Less than 133 Pascals at 20 deg C

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).

UNPLEASANT

NON-CORROSIVE

UN3077 (solid); UN3082 (liquid)

2

R36/37/38:Irritating to eyes, respiratory system and skin .

26-36/37/39

TH7350000

Xn

Stable. Incompatible with strong oxidizing agents.

P273

H412

H412 (97.44%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory.

Flammability: None, a water solution.

INHALATION HAS BEEN REPORTED TO CAUSE SLIGHT IRRITATION.|NO SKIN IRRITATION DESCRIBED IN MAN ... .

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.

LD50 Rabbit percutaneous > 2000 mg/kg|LC50 Rat inhalation > 2.07 mg/l|LD50 Rat oral 1770 mg/kg /Naptalam-sodium/|LD50 Rat oral > 8.5 g/kg

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.

... Photo-stable /in soil/.

BCF = 0.5 (calculated from water solubility by regression equations) /From table/

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.

NON-VOLATILE /IN SOIL/ ...

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)|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. (See all compounds classified as Plant Growth Regulators.)

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.

... 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.

... 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.

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.

1-N-naphthylphtalamic acid

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).

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/

Product analysis is by UV spectrometry. Residues may be determined by hydrolysis to 1-naphthylamine, a deriv of which is measured by colorimetry.|THE DETECTION & QUANTIFICATION OF PESTICIDES INCL NAPTALAM ON SILICA GEL CHROMATOGRAMS BY IN SITU FLUOROMETRY IS DESCRIBED.|ANALYSIS OF ALANAP RESIDUES IN FOOD & ENVIRONMENTAL SAMPLES WITH GC IS DESCRIBED.|Analysis of residues: Boiling in 40% sodium hydroxide, distilling off the cleaved 1-naphthylamine, coupling with diazotized sulfanilic acid, and determination of the red color complex spectrophotometrically.

Agrochemicals -> Herbicides