(±)-2-(3-Chlorophenoxy)propionic acid

200.619

200.62

202-915-2

DTXSID9034232

Colorless crystals

2918990028

46.53000

2.52

white to off-white crystalline powder

1.3±0.1 g/cm3

113-114 °C

318.5±17.0 °C at 760 mmHg

146.4±20.9 °C

1.547

In water, 1,200 mg/L at 22 deg C

0-6ºC

2.28X10-4 mm Hg at 25 deg C (est)

Henry's Law constant = 1.65X10-8 atm-cu m/mol at 25 °C (est)

pKa = 3.62 (hydroxyl) (est)

Hydroxyl radical reaction rate constant = 2.47X10-11 cu cm/molec-sec at 25 °C (est)

Non-corrosive

3.2

NONH for all modes of transport

2

R36/37/38

S26-S36

UE9285000

Xi:Irritant;

Highly stable

P261-P305 + P351 + P338

H302-H315-H319-H335

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.|Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

WHO; Environ Health Criteria: Phenoxyherbicides (1984).|Nat'l Research Council Canada; Phenoxyherbicides NRCC No: 16075 (1978).

|Warning|H302 (96.36%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 110 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

The maximum degradation rate of 2-(3-chlorophenoxy)propionic acid, present at 40-45 mg/L, using an activated sludge from a municipal wastewater treatment plant and an ultimate biodegradability test, ISO 7287, was 12 and 18 umol/hr, following a 16-day lag phase and being completely removed after 25 days; the study was conducted using a racemic mixture of five chiral phenoxyalkanoic acids.

For several good reasons, .... herbicides ... should be handled and applied only with full attention to safety measures that minimize personal contact. Many formulations contain adjuvants (stabilizers, penetrants, surfactants) that may have significant irritating and toxic effects. A number of premixed formulations contain two or more active ingredients; the companion pesticides may be more toxic than the principal herbicide. Good hygienic practice should not be disregarded just because a pesticide is reported to have a high LD50 in laboratory rodents.|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.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Irritating to eyes.|Irritate skin and mucous membranes /Chlorophenoxy compounds; from table/

LD50 Rat oral 750 mg/kg

LD50 Rat oral > 750 mg/kg

2-(3-Chlorophenoxy)propionic acid's former production and use as a plant growth regulator(1) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 88(SRC), determined from a water solubility of 1,200 mg/L(2) and a regression-derived equation(3), indicates that 2-(3-chlorophenoxy)propionic acid is expected to have high mobility in soil(SRC). The estimated pKa of 2-(3-chlorophenoxy)propionic acid is 3.62(4), indicating that this compound will exit almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize. 2-(3-Chlorophenoxy)propionic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-4 mm Hg(SRC), determined from a fragment constant method(6). 2-(3-Chlorophenoxy)propionic acid was completely degraded in 25 days following a 16-day lag period using activated sludge(7), indicating that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 88(SRC), determined from a water solubility of 1,200 mg/L(2) and a regression-derived equation(3), indicates that 2-(3-chlorophenoxy)propionic acid is not expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 3.62(4) indicates 2-(3-chlorophenoxy)propionic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 11(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2-(3-Chlorophenoxy)propionic acid was completely degraded in 25 days following a 16-day lag period using activated sludge(7), indicating that|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-(3-chlorophenoxy)propionic acid, which has an estimated vapor pressure of 2.3X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-(3-chlorophenoxy)propionic 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 16 hours(SRC), calculated from its rate constant of 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-(3-Chlorophenoxy)propionic acid contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Phenoxy herbicides have an ultraviolet absorption maximum in water in the 280-290 nm range, they ... can absorb radiation and be photochemically degraded. /Phenoxy herbicides/|The rate constant for the vapor-phase reaction of 2-(3-chlorophenoxy)propionic acid with photochemically-produced hydroxyl radicals has been estimated as 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-(3-Chlorophenoxy)propionic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2-(3-Chlorophenoxy)propionic acid does contain chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 11 was calculated in fish for 2-(3-chlorophenoxy)propionic acid(SRC), using water solubility of 1,200 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of 2-(3-chlorophenoxy)propionic acid is estimated as 88(SRC), using a water solubility of 1,200 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-(3-chlorophenoxy)propionic acid is expected to have high mobility in soil. The pKa of 2-(3-chlorophenoxy)propionic acid is 3.62(4), indicating that this compound will exist entirely in the anion form in the environment and anions generally do not adsorb) more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

An estimated pKa of 3.62(1) indicates 2-(3-chlorophenoxy)propionic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces or moist soil is not expected to be an important fate process(2). 2-(3-Chlorophenoxy)propionic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(3).

Occupational exposure and general population exposure should be low or non-existent since 2-(3-chlorophenoxy)propionic acid is no longer produced or used in the US and was voluntarily cancelled as of Sept, 2006(1). In the past, 2-(3-chlorophenoxy)propionic acid was formulated as a soluble concentrate and exposure to this compound was primarily dermal and in the field where it was applied(SRC).|... Occupational exposure to chlorophenoxy herbicides ... is known to have occurred during their production, formulation, application & disposal. /Chlorophenoxy herbicides/

The chlorophenoxy compounds are absorbed across the gut wall, lung, and skin. They are not significantly fat storable. Excretion occurs almost entirely by way of the urine. /Chlorophenoxy herbicides/

In plants, these chemicals /chlorophenoxy compounds/ mimic the action of auxins, hormones chemically related to indoleacetic acid that stimulate growth. ... Target organ toxicity that can be associated with the pharmacokinetics, biotransformation, and/or elimination of these chemicals, their mechanism(s) of toxic action are poorly understood. /Chlorophenoxy compounds/

/SIGNS AND SYMPTOMS/ When ingested, high concentrations of chlorophenoxy compounds may irritate the mouth & throat, & GI tract. ... chest pain (from esophagitis), abdominal pain & diarrhea commonly ensue. ... absorbed chlorophenoxy compounds have caused fibrillary muscle twitching, skeletal muscle tenderness, & myotonia ... ingestion of very large amounts has produced metabolic acidosis, fever, tachycardia, hyperventilation, vasodilatation & sweating. Particular cases have been characterized by coma & convulsions. /Chlorophenoxy compounds/|/SIGNS AND SYMPTOMS/ Generally low systemic toxicity, May contain dioxins as contaminants, which have caused chloracne and neurologic damage to chemical plant workers; causes headache, dizziness. /Chlorophenoxy compounds; from table/|/SIGNS AND SYMPTOMS/ Workers involved in the manufacture of this class of herbicides, ... experienced a severe type of contact dermatitis called "chemical worker chloroacne." Herbicide sprayers of a few decades ago developed a persistent condition known as "weed bumps" /SRP: probably due to dioxin contamination/ following daily and seasonal exposure to chlorophenoxy herbicides. /Chlorophenoxy compound/|/SIGNS AND SYMPTOMS/ Ingestion of large amounts of chlorophenoxy acids has resulted in severe metabolic acidosis in humans. Such cases have been associated with electrocardiographic changes, myotonia, muscle weakness, myoglobinuria, and elevated serum creatine phosphokinase, all reflecting injury to striated muscle. Because chlorophenoxy acids are weak uncouplers of oxidative phosphorylation, extraordinary doses may produce hyperthermia from increased production of body heat. /Chlorophenoxy acids/|For more Human Toxicity Excerpts (Complete) data for 2-(3-CHLOROPHENOXY)PROPIONIC ACID (14 total), please visit the HSDB record page.

2-(3-chlorophenoxy)propionic acid

Wettable powder|Soluble concentrate.|Fruitone CPA

Propanoic acid, 2-(3-chlorophenoxy)-: INACTIVE|Chlorophenoxy herbicides are applied alone or as mixtures with other herbicides, in solutions, dispersions, or emulsions in water &/or oil, using equipment that produces large droplets to avoid spray drift. /Chlorophenoxy herbicides/|New Zealand: The spraying of phenoxyherbicides is restricted within prescribed distances of vineyards. /Phenoxyherbicides/

A PROCEDURE FOR DETECTING CHLOROPHENOXY HERBICIDES IN WATER IS DESCRIBED. EXTRACTED WITH BENZENE, THE EXTRACT IS DILUTED WITH ACETONE TO A SUITABLE VOLUME FOR GAS-LIQUID CHROMATOGRAPHY. THE RESULTS INDICATE THAT THE EXTRACTION METHOD WOULD BE APPLICABLE FOR DETERMINING POSSIBLE WATER CONTAMINATION BY CHLOROPHENOXY ESTERS. /CHLOROPHENOXY HERBICIDES/|By hplc with u.v. detection.