2,3,6-Trichlorobenzoic acid

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Soluble in ethyl ether

In water, 7.7X10+3 mg/L at 22 °C

0.00055 [mmHg]

5.5X10-4 mm Hg at 25 °C

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

H302 (98.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

2002/2076

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Trichlorobenzoic acid is found on List D. Case No: 4088; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI):Trichlorobenzoic acid; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled.".

Acute Tox. 4 (98.7%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 4 *

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that 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)./

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.

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.

LC50; Species: Lepomis macrochirus (Bluegill, fingerling, length 3-5 in); Conditions: freshwater, static, 25 °C, pH 6.7 (6.3-7.3), hardness 77.1 mg/L CaCO3 (17.0-176.0 mg/L CaCO3), dissolved oxygen 4.6 mg/L (1.3-7.8 mg/L); Concentration: 1,750,000 ug/L for 24 hr

LC50; Species: Lepomis macrochirus (Bluegill, fingerling, length 3-5 in); Conditions: freshwater, static, 25 °C, pH 7.0 (6.6-7.4), hardness 19.0 mg/L CaCO3, dissolved oxygen 7.3 mg/L (7.1-7.7 mg/L); Concentration: 1800000 ug/L for 24 hr

LC50; Species: Lepomis macrochirus (Bluegill, fingerling, length 3-5 in); Conditions: freshwater, static, 25 °C, pH 7.0 (6.6-7.4), hardness 19.0 mg/L CaCO3, dissolved oxygen 7.3 mg/L (7.1-7.7 mg/L); Concentration: 1750000 ug/L for 48 hr

LC50; Species: Micropterus salmoides (Largemouth bass, fingerling, length 3-5 in); Conditions: freshwater, static, 25 °C, pH 6.7 (6.3-7.3), hardness 77.1 mg/L CaCO3 (17.0-176.0 mg/L CaCO3), dissolved oxygen 4.6 mg/L (1.3-7.8 mg/L); Concentration: 1300000 ug/L for 24 hr

For more Ecotoxicity Values (Complete) data for 2,3,6-TRICHLOROBENZOIC ACID (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 65(SRC), determined from a structure estimation method(2), indicates that 2,3,6-trichlorobenzoic acid is expected to have high mobility in soil(SRC). The estimated pKa of 2,3,6-trichlorobenzoic acid is 1.8(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). 2,3,6-Trichlorobenzoic acid had high mobility based upon observations from laboratory and field studies that indicate that the 2,3,6-trichlorobenzoic acid readily leaches through soil(5-7). Volatilization from moist soil surfaces is not expected to be an important fate process because anions do not volatilize. 2,3,6-Trichlorobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.5X10-4 mm Hg(5). Screening studies have shown 2,3,6-trichlorobenzoic acid to be resistant to biodegradation; 2,3,6-trichlorobenzoic acid, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(8).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 65(SRC), determined from a structure estimation method(2), indicates that 2,3,6-trichlorobenzoic acid is expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 1.8(3) indicates 2,3,6-trichlorobenzoic 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(4). According to a classification scheme(5), BCFs of <3.5 in carp (Cypinus carpio), exposed over a 6-week period(6) suggest bioconcentration in aquatic organisms is low(SRC). 2,3,6-Trichlorobenzoic acid reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum in the Japanese MITI test(6), suggesting that biodegradation is not an important environmental fate process in water(SRC). In an anaerobic freshwater lake sediment grab sample study, 100% of the 2,3,6-trichlorobenzoic acid added to the sediment was transformed in 84-364 days to 2,6-dichlorobenzoate without evidence of mineralization(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3,6-trichlorobenzoic acid, which has a vapor pressure of 5.5X10-4 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,3,6-trichlorobenzoic 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 112 days(SRC), calculated from its rate constant of 1.43X10-13 cu cm/molecule-sec at 25 °C(3). Particulate-phase 2,3,6-trichlorobenzoic acid may be removed from the air by wet or dry deposition(SRC). The photodegradation of 2,3,6-trichlorobenzoic acid observed in water solutions irradiated at wavelengths >290 nm in laboratory tests(4) suggests that the 2,3,6-trichlorobenzoic acid may be susceptible to direct photolysis in the ambient atmosphere(SRC).

2,3,6-Trichlorobenzoic acid was detected in 2 of 216 composite samples of 82 cooked and uncooked common foods collected from 18 markets in 3 different geographical areas of the U.S. (Boston, MA, Kansas City, MO and Los Angeles, CA) between June 1964 and April 1965(1). The concn found in one of the positive samples was 0.02 ppm and in the other the concn was below an unspecified quantitative sensitivity limit(1). The only composite category listed as containing 2,3,6-trichlorobenzoic acid is the oils, fats and shortening composite(1). 2,3,6-Trichlorobenzoic acid was not detected in more than 28,000 U.S. domestic samples and 18,000 imported samples of foods other than fluid milk collected between fiscal year 1970 and 1976 in the FDA Total Diet Program(2).

ENVIRONMENTAL: 2,3,6-Trichlorobenzoic acid was detected not quantified in 3 samples of U.S. domestic fluid milk out of 4,638 total samples collected and tested between fiscal years 1970 and 1976 in the FDA Total Diet Program(1). All of the positive samples were collected in 1971(1).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,3,6-trichlorobenzoic acid can be estimated to be 65(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,3,6-trichlorobenzoic acid is expected to have high mobility in soil(SRC). The estimated pKa of 2,3,6-trichlorobenzoic acid is 1.8(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). 2,3,6-Trichlorobenzoic acid readily leaches through soil; 2,3,6-trichlorobenzoic acid has been found at depths of 11 feet following surface application(5). Approximately 10% of the 2,3,6-trichlorobenzoic acid applied at rates of 0.2 and 0.6 kg/hectare to 8 experimental plots leached an unspecified distance to the tile-drain groundwater in 3 months(6). 2,3,6-Trichlorobenzoic acid was found to be readily leached from soil columns containing 4 different types of soil (Staten Island peaty muck, Stockton adobe clay, Yolo fine sandy loam and Hesperia sandy loam)(7). In a soil column filled with silty clay loam, 2,3,6-trichlorobenzoic acid was leached 20 inches upon the addition of sufficient water to wet the column to 22 inches(8). Most of the residual herbicidal activity of 2,3,6-trichlorobenzoic acid applied to a test field at a rate of 15-30 lb/acre was present in the second, third and fourth foot depth of the 6 foot of depth tested(9).

AEROBIC: The percent losses of herbicidal effectiveness of 0.1-32 ppm of 2,3,6,-trichlorobenzoic acid in an aerobic grab sample test with 4 different soils were 15.9%, 3.2%, 6.2%, and 9.0% after 120 days in incubation in Staten Island peaty muck, Stockton adobe clay, Yolo fine sandy loam and Hesperia sandy loam, respectively(1). Leaching of the 2,3,6-trichlorobenzoic acid was ruled out as a mechanism of effectiveness reduction(1). Incubation for 80 days of test concentrations of 100 ppm using a soil perfusion system with Celeryville muck with high microbial activity resulted in only 2% degradation (as measured by chloride ion acclimation in the perfusate)(2). 2,3,6-Trichlorobenzoic acid, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(3). No degradation of 100 ppm 2,3,6,-trichlorobenzoic acid was observed in 36 days incubation in aqueous laboratory aerobic sewage die-away screening tests using raw sewage inoculum(4). Addition of glucose or benzoate and m-chlorobenzoate to the sewage did not promote degradation of the 2,3,6-trichlorobenzoic acid(4).

ANAEROBIC: In an anaerobic freshwater lake sediment grab sample study, 100% of the 2,3,6-trichlorobenzoic acid added to the sediment was transformed in 84-364 days to 2,6-dichlorobenzoate without evidence of mineralization(1).

The BCF of 2,3,6-trichlorobenzoic acid was <0.4 at a concentration of 293 ppb and <3.5 at a concentration of 29.3 ppb using carp (Cypinus carpio) which were exposed over a 6-week period(1). According to a classification scheme(2), these BCF values suggest bioconcentration in aquatic organisms is low(SRC).

An estimated pKa of 1.8(1) indicates 2,3,6-trichlorobenzoic 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). 2,3,6-Trichlorobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.5X10-4 mm Hg(3).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Subchronic toxicological effects of 2,4,6-trichlorobenzyl chloride and its oxidative derivative trichlorobenzoic acid were investigated. 2,4,6-Trichlorobenzyl chloride was dissolved in ethanol and added to rat chow on a weekly basis at concentrations of 0, 0.15, and 0.30 percent. Trichlorobenzoic acid was fed in dietary levels of 0, 10, 30, or 100 ppm for 90 days Sprague-Dawley albino rats and beagle dogs. Acute 50% lethal dose in male and female rats was determined to be 3075 mg/kg. In subchronic studies, a marked reduction in weight gain was apparent throughout the study in male and female rats given 3000 ppm 2,4,6-trichlorobenzyl chloride and male rats given 1500 ppm 2,4,6-trichlorobenzyl chloride for 3 weeks. The only microscopic changes noted were hepatic degenerative alterations, prominent in all male and female rats receiving 3000 ppm 2,4,6-trichlorobenzyl chloride. No blood or urine chemistry changes were seen. Rats and dogs receiving 100 ppm 2,4,6-trichlorobenzoic acid for 90 days showed no treatment related effects on survival, growth, food consumption, or behavior. No significant differences were noted in blood or urine parameters in these animals, and no histologic changes were seen. /It was/ concluded that 2,4,6-trichlorobenzyl chloride has lower acute oral toxicity than benzyl halides. 2,4,6-Trichlorobenzyl chloride also appears to be less acutely toxic than its acid derivative, trichlorobenzoic acid. Repeated exposures to 2,4,6-trichlorobenzyl chloride resulted in chemically induced liver injury with marked degenerative/regenerative processes and no excessive accumulation of lipids. /It was suggested/ that 2,4,6-trichlorobenzyl chloride may be metabolized differently from other benzyl halides, perhaps because of its aromatic constituents or differences in solubility which affect uptake or retention.

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Trichlorobenzoic acid is found on List D. Case No: 4088; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI):Trichlorobenzoic acid; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled.".

Used in herbicide formulations; [HSDB]

Cancelled--active ingredient no longer contained in any registered products; [HSDB]

Farming (Pesticides) [Category: Industry]

For 2,3,6-Trichlorobenzoic acid (USEPA/OPP Pesticide Code: 017302) there are 0 labels match. /SRP: Not registered for current 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./

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

... In herbicide formulations /Former use/

Benzac

Fen-all

Benzabar

Tryben

For more Formulations/Preparations (Complete) data for 2,3,6-TRICHLOROBENZOIC ACID (7 total), please visit the HSDB record page.