2,6-Dichlorobenzamide

190.023

190.03

217-918-4

E9JWF529EB

53137

DTXSID7022170

Crystals

2924299090

43.1

0.77

Light gray powder.

1.52 g/cm³

198-200 °C

300.7±52.0 °C at 760 mmHg

135.6±30.7 °C

1.600

In water, 2.73X10+3 mg/l @ 23 deg C.

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

4.8X10-6 mm Hg at 25 °C (est)

Henry's Law constant = 1.22X10-9 atm-cu m/mol at 25 °C (est)

log Kow = 1.54|Hydroxyl radical reaction rate constant = 2.88X10-12 cu cm/mole-sec at 25 °C (est)

NONH for all modes of transport

3

S24/25

Xi: Irritant;

Stable under recommended storage conditions.

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document for Dichlobenil EPA 738-R-98-003 (October 1998). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA. /The BAM metabolite of dichlobenil is the major residue detected in plants./[Available from, as of October 26, 2017: http://www.epa.gov/pesticides/reregistration/status.htm]

Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place.|Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains.|Precautions for safe handling: Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|Appropriate engineering controls: General industrial hygiene practice.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

2,6-Dichlorobenzamide was not detected in the biodegradable fraction of household waste collected in 1995, or its 5-month compost; it was detected at trace quantities in all samples of anaerobic mesophilic digestates after 30 days and anaerobic thermophilic digestates after 19 days(1).

IDENTIFICATION AND USE: 2,6-Dichlorobenzamide (BAM) was formerly used as a pesticide. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: BAM was given to rats (35/sex/dose) for 106 weeks at doses 0, 2.2, 3.6, 6.5, or 19 mg/kg/day in males; 0, 2.8, 4.7, 8.5, or 25 mg/kg/day in females. There was a statistically significant decrease in mean body weight gains in both males and females (10% and 20% less than controls, respectively, at week 52), and slightly increased severity of fat deposition in the livers of females. BAM produced an increased incidence of hepatoma in females. The carcinogenic potential of BAM appears to be less than or equal to that of dichlobenil. In a single dose study in which the group of mice was treated at 250 mg/kg, the mice displayed mild neurotoxic effects (lethargy and ataxia), the group treated at 500 mg/kg were severely affected (becoming comatose), and the groups treated at 1000 mg/kg and higher died in extremis. A mouse micronucleus assay using a single dose of BAM (250 mg/kg) was negative. BAM was negative for inducing repair of DNA damage as measured by unscheduled DNA synthesis (UDS), as determined by net nuclear silver grain count in primary rat hepatocytes, exposed up to cytotoxic doses (1000 ug/mL). BAM was negative for inducing reverse gene mutation in TA strains of Salmonella typhimurium with and without metabolic activation. ECOTOXICITY STUDIES: Short term experiments showed that BAM was moderately toxic to guppies Poecilia reticulata, rainbow trout Salmo gairdneri, daphnids Daphnia magna and the algae Chlorella pyrenoidosa and Scenedesmus pannonicus. In long term studies with daphnids concentrations up to 320 mg/L did not significantly alter survival and reproduction. An embryolarval test with rainbow trout, however, showed a significant reduction of survival and growth as well as a delay of yolk resorption at concentrations equal to or exceeding 18 mg/L. The accumulation of unchanged BAM in leaf tips and margins was reported to be the cause of leaf margin chlorosis.

LD50 Mouse (male) oral 1538 mg/kg|LD50 Mouse (female) oral 1144 mg/kg

/AQUATIC SPECIES/ Dichlobenil (2,6-dichlorobenzonitrile) is a broad-spectrum herbicide of which the aquatic toxicological properties are well documented compared to the scarcity of data on the toxicity of its main degradation product BAM (2,6-dichlorobenzamide). Therefore toxicity tests with BAM were carried out with several freshwater species. Short term experiments showed that BAM was moderately toxic to guppies Poecilia reticulata, rainbow trout Salmo gairdneri, daphnids Daphnia magna and the algae Chlorella pyrenoidosa and Scenedesmus pannonicus. In long term studies with daphnids concentrations up to 320 mg/L did not significantly alter survival and reproduction. An embryolarval test with rainbow trout, however, showed a significant reduction of survival and growth as well as a delay of yolk resorption at concentrations equal to or exceeding 18 mg/L. In combination with the data reported in the literature it may be concluded that degradation of dichlobenil into BAM results in a reduction of toxicity and further biodegradability. Normal field applications of this aquatic herbicide are not expected to impose a great risk to aquatic life.|/PLANTS/ The accumulation of unchanged 2,6-dichlorobenzamide in leaf tips and margins was reported to be the cause of leaf margin chlorosis ... .

2,6-Dichlorobenzamide is the degradation product and major terminal residue in plants of dichlobenil(1,2), and may be indirectly released into the environment after the herbicidal use and transformation of dichlobenil(SRC). Its former use in the manufacture of dichlobenil(3) may have resulted in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a measured Koc value of 30 on activated sludge(2) indicates that 2,6-dichlorobenzamide is expected to have very high mobility in soil(SRC). Volatilization of 2,6-dichlorobenzamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2,6-Dichlorobenzamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Using a soil grab sample, 0.4-6.1% of 2,6-dichlorobenzamide degraded after 4-110 days of incubation(4), indicating that 2,6-dichlorobenzamide does not biodegrade rapidly in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), a measured Koc value of 30 on activated sludge(2) indicates that 2,6-dichlorobenzamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), a measured BCF of 10 in Golden Ide fish(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2,6-Dichlorobenzamide reached 5.6% mineralization after 40 days in pond water(6), indicating that 2,6-dichlorobenzamide does not biodegrade rapidly in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,6-dichlorobenzamide, which has an estimated vapor pressure of 4.8X10-6 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 2,6-dichlorobenzamide 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 5.6 days(SRC), calculated from its rate constant of 2.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2,6-dichlorobenzamide may be removed from the air by wet and dry deposition(SRC). 2,6-Dichlorobenzamide does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 2,6-dichlorobenzamide with photochemically-produced hydroxyl radicals has been estimated as 2.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,6-Dichlorobenzamide is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 2,6-Dichlorobenzamide does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

A BCF of 10 was measured for Golden Ide fish after a 3 day equilibration period(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). The BCF for algae ranges from <10 to 320 after a 1 day equilibration period(1,3).

3.39 L/kg|The Koc of 2,6-dichlorobenzamide measured on activated sludge is reported to be 30(SRC). According to a classification scheme(2), this Koc value suggests that 2,6-dichlorobenzamide is expected to have very high mobility in soil(SRC).|2,6-Dichlorobenzamide, was detected, at a concentration of 28% of applied dichlobenil in the 25-30 cm segment of the column, after aerobic ageing of dichlobenil on a treated silt loam soil column(1). In a field study, an established commercial orchard in the Town of Huron, NY, was treated with dichlobenil at 6 lb ai/acre; the degradate 2,6-dichlorobenzamide was detected to a depth of 72 inches (max sampling depth)(1). More dichlobenil was converted to the water-soluble 2,6-dichlorobenzamide in loam soil than in sandy soil. This water-soluble metabolite was partially leached through the loam soil column with the highest level of irrigation(2). These data suggest 2,6-dichlorobenzamide has the potential to leach into groundwater through soil(1).

The Henry's Law constant for 2,6-dichlorobenzamide is estimated as 1.2X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,6-dichlorobenzamide is expected to be essentially nonvolatile from water surfaces(2). 2,6-Dichlorobenzamide's Henry's Law constant indicates that volatilization from moist soil surfaces will not likely occur(SRC). 2,6-Dichlorobenzamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Using a screening test, 0.5% of applied 2,6-dichlorobenzamide volatilized from sludge(4).

GROUNDWATER: 2,6-Dichlorobenzamide was detected, not quantified, in an untreated groundwater sample from a well at an industrialized area near Limibiate, Italy in 1996(1). The concentration of 2,6-dichlorobenzamide in 2 groundwater supplies used for public drinking water in Sweden ranged from trace to <0.1 ug/L(2). 2,6-Dichlorobenzamide has been detected at concentrations up to 0.30 ppb at groundwater pumping stations in 1991 and at concentrations up to 180 ppb in shallow groundwater between the years, 1988-90, in the Netherlands(3). In 3 studies published between 2005 and 2008, 2,6-dichlorobenzamide was detected in ground water samples from Italy, Slovenia, Sweden and the Netherlands at concentration ranging from 10-5400 ng/L(4).|GROUNDWATER: Water quality data compiled from the Retrieval (STORET) Data Warehouse and the USGS National Water Information System (NWIS) reports water monitoring data for 2,6-dichlorobenzamide. The State of Oregon Dept. of Environmental Quality reports data for 2,6-dichlorobenzamide. Data from the 2015-2017 monitoring years follows(1).[Table#4162]|DRINKING WATER: In 1992, the concentration of 2,6-dichlorobenzamide in Swedish public drinking water ranged from trace to 0.6 ug/L(1); these samples were derived from groundwater wells(1).|SURFACE WATER: The concentration of 2,6-dichlorobenzamide in Shinano (Japan) river water ranged from <0.02 ug/L to 0.17 ug/L in samples collected once a month from May to September 1996(1). In studies published in 2007 and 2001, 2,6-dichlorobenzamide was detected in surface and river water samples from Sweden and Japan at concentration ranges of 50-110 ng-L and 12-240 ng/L, respectively(2).|For more Environmental Water Concentrations (Complete) data for 2,6-Dichlorobenzamide (6 total), please visit the HSDB record page.

Occupational exposure to 2,6-dichlorobenzamide may occur through dermal contact with soils and waters contaminated with this compound at workplaces where its parent compound, dichlobenil, is produced or used. Limited monitoring data indicate that the general population may be exposed to 2,6-dichlorobenzamide via ingestion of plants and drinking water contaminated with this compound and dermal contact with surface waters containing this compound, especially in areas where its parent compound, dichlobenil, has been applied. (SRC)

/In foliar and roots/ ... 2,6-dichlorobenzamide is readily absorbed and translocated in xylem with the transpiration stream /and/ ... accumulates ... in foliar tissues. Autoradiograms of apple leaves from seedlings and young trees show that translocated [(14)C]2,6-dichlorobenzamide is distributed throughout the leaf and tends to accumulate at the leaf margins after prolonged periods of root uptake.

... Both free and conjugated 3-hydroxy-2,6-dichlorobenzamide were ... isolated as metabolites from apple ... leaves treated directly with 2,6-dichlorobenzamide. Free and conjugated 3-hydroxy-2,6-dichlorobenzamide have been detected chromatographically in wheat seedlings and kale (Brassica oleracea) plants after short-term (1-5 days) root and soil uptake studies with [(14)C]2,6-dichlorobenzamide.|Long-term soil uptake studies (14 weeks) with [(14)C]2,6-dichlorobenzamide showed that the major metabolites in leaves of young apple trees were 3- and 4-hydroxy-2,6-dichlorobenzamide in a ratio of 6:1. Approx 85% of the hydroxylated metabolites were conjugated as glycosides. ... It appears that plants are able to hydroxylate and conjugate ... 2,6-dichlorobenzamide and that hydroxylation at the 3 position ... is favored. A comparison of dichlobenil and 2,6-dichlorobenzamide metabolism after 5 days in root treated bean seedlings showed that 2,6-dichlorobenzamide was hydroxylated and conjugated much slower than dichlobenil.|2,6-Dichlorobenzamide is metabolized to 2,6-dichlorobenzoic acid probably in phaseolus. /From table/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

2,6-dichlorobenzamide

FDA Method 212.1. Organochlorine Residues (Nonionic) General Method for Nonfatty Foods Including Acetonitrile Extraction, Water/Acetonitrile Extraction, Aqueous Acetonitrile to Petroleum Ether Transfer, and Florisil Column Cleanup. Detection limit not specified.|FDA Method 212.2. Organochlorine Residues (Nonionic) General Method for Nonfatty Foods Including Acetone Extraction, Isolation in Organic Phase, and Optional Florisil Column Cleanup. Detection limit not specified.|FDA Method 242.1. Organonitrogen Residues General Method for Nonfatty Foods Including Acetone Extraction and Isolation in Organic Phase. Detection limit not specified.

Transformation products|Pesticides -> Herbicides -> Nitrile herbicides -> Transformation products|Environmental transformation -> Pesticide transformation products (metabolite, successor)

2,6-Dichlorobenzamide is a known environmental transformation product of Dichlobenil.|AE C653711 is a known environmental transformation product of Fluopicolide.