2,6-Dichloro-4-nitroaniline

207.01

207.01

1459581

202-746-4

F0BE9UC5J7

0871

218

DTXSID2020426

Yellow needles from alcohol and acetic acid|Yellow crystals

29214210

71.8

1.80

Dichloran appears as yellow crystals or solid. Slight aniline odor. Used as a fungicide. Insoluble in water, but often formulated as a wettable powder (easily dispersed in water).

0.28 (bulk)

191 °C

130 °C @ Press: 2.0 Torr

130°C/2mm

1.656

H2O: 1 g/L (60 ºC)

0-6°C

Vapour pressure, Pa at 20°C: 0.00016

Oral-rat LD50: 2400 mg/kg; Oral-Mouse LD50: 1500 mg/kg

Thermal decomposition of toxic chloride and nitrogen oxide

Odorless

pKa = 3.31

129.45 Ų [M-H]-

BROWNISH-YELLOW /TECHNICAL PRODUCT, PURITY MORE THAN 90%/|Henry's Law Constant = 8.40X10-8 atm cu m/mol at 25 °C (est)|Hydroxyl radical reaction rate constant = 1.38X10-13 cu cm/molecule-sec at 25 °C (est)

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

DICHLORAN is incompatible with acids, acid chlorides, acid anhydrides, and strong oxidizing agents (NTP, 1992).

Dust explosion possible if in powder or granular form, mixed with air.

NON-CORROSIVE

III

6.1(b)

2811

3

33-36/37/38-20/21/22-51/53-26/27/28

22-26-36-37/39-61-45-36/37-28

BX2975000

Xi,Xn,N,T+

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

STABLE TO HYDROLYSIS & OXIDATION

P260-P264-P273-P280-P284-P301 + P310

H300-H310-H330-H373-H411

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential users/|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Many communities have programs to recycle household waste such as empty bottles and cans. Do not recycle any pesticide containers, however, unless the recycling program specifically accepts pesticide containers and you follow the program's instructions for preparing the empty containers for collection. /Residential users/

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - DCNA (Dicloran), EPA-738-F-05-003 (June 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 16, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]|VETTORAZZI FG; STATE OF THE ART OF THE TOXICOLOGICAL EVALUATION CARRIED OUT BY JOINT FAO/WHO EXPERT COMMITTEE ON PESTICIDE RESIDUES. III. MISCELLANEOUS PESTICIDES USED IN AGRICULTURE & PUBLIC HEALTH; RESIDUE REV 66: 137 (1977)|DICLORAN; WHO TECH REP SER (574): 215 (1975). REVIEW ARTICLE ON THE CHEMICAL AND PHYSICAL PROPERTIES, METABOLISM, AND TOXICITY OF DICLORAN.|Toxicology Review: Critical Review in Toxicology 1 (1): 93 (1971).

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Danger|H300 (94.93%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 142 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|All mixers, loaders, applicators and other handlers must wear: Long-sleeved shirt and long pants; Shoes plus socks; and Chemical-resistant gloves (except for pilots). /Botran 5F Fungicide/

... NON-FLAMMABLE

Appropriate Extinguishing Media: water spray, Class A, B or C extinguisher. /Botran 5F Fungicide/|Fire Fighting Guidance: Wear self-contained breathing apparatus (SCBA). /Botran 5F Fungicide/

Dispersion of fine dust in air may form explosive mixture. /Botran 5F Fungicide/

Do not contaminate /receiving/ water when disposing of equipment, washwaters or rinsate. /Botran 5F Fungicide/|In Case of Spills or Leaks: Keep unnecessary people away and isolate hazard area. Spread absorbent material over spill and sweep up. Sweep up spill carefully. Place material into a clean, dry container and cover for disposal. Wash contaminated areas with water and detergent. Inform authorities if material enters sewer or watercourse. Do not contaminate water, food or animal feed through inappropriate disposal. /Botran 5F Fungicide/|If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /Botran 5F Fungicide/|Do not apply directly to water, to areas where surface water is present or to intertidal areas below the mean high water mark. Drift and runoff may be hazardous to aquatic organisms in water adjacent to treated areas. /Botran 5F Fungicide/|Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application. /Botran 5F Fungicide/|... Do not enter or allow worker entry during the restricted entry interval of 12 hours. Exception: If the product is soil-injected or soil-incorporated, the Worker Protection Standard, under certain circumstances, allows workers to enter the treated area if there will be no contact with anything that has been treated. /Botran 5F Fungicide/|For more Preventive Measures (Complete) data for 2,6-DICHLORO-4-NITROANILINE (14 total), please visit the HSDB record page.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN!

Use local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

2,6-Dichloro-4-nitroaniline was found to occur only once in over 4000 samples of wastewaters from 46 industrial categories(1); the detection (concentration and source not reported) occurred in a sample from the organic and plastics industry(1).

moderately toxic

LD50 Guinea pig oral 1450 mg/kg|LD50 Mouse oral 1500 mg/kg|LD50 Mouse iv 56 mg/kg|LD50 Rat oral 2400 mg/kg

/BIRDS and MAMMALS/ Signs of intoxication /from acute oral administration/: Regurgitation (in mallards), hyporeactivity, ataxia, asthenia, imbalance, slowness, wing-drop, falling when walking, withdrawal, and ataraxia. Regurgitation occurred as soon as 20 min; other signs appeared as soon as 1.5 hr after treatment in mallards. In pheasants, signs appeared the day after treatment, and mortalities occurred between 2 to 4 days after treatment. Remission took up to 5 wk for both species. /Sample purity 97%/

2,6-Dichloro-4-nitroaniline's production and use as a diazo component used for producing disperse dyes(1) may result in its release to the environment through various waste streams(SRC). 2,6-Dichloro-4-nitroaniline's production and use as a fungicide(2) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a measured Koc value range of 660-1100(2), indicates that 2,6-dichloro-4-nitroaniline is expected to have low mobility in soil(SRC). Mobility may increase in coarser soils(3). Volatilization of 2,6-dichloro-4-nitroaniline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.4X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.95X10-6 mm Hg at 25 °C(4), and water solubility, 6.3 mg/L(4). 2,6-Dichloro-4-nitroaniline is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC) and a 6 month-incubation study where only 5% of the compound was lost(5). 2,6-Dichloro-4-nitroaniline is susceptible to direct photolysis in sunlight(4); therefore, photodegradation on surfaces exposed to sunlight may occur(SRC). Field-soil dissipation half-lives of 39-78 days have been observed(2,4). In aerobic mineral soils, the half-life ranged from 6 to 18 months(3); in anaerobic sandy soils, the half-life ranged from 24 to 38 days(3). The persistence of 2,6-dichloro-4-nitroaniline in soil appears to be largely determined by factors favoring certain microbial activities(6). The compound has been shown to degrade more rapidly in soil that has received previous treatments of 2,6-dichloro-4-nitroaniline, apparently as the result of selective microbial buildup and adaptation(6,7). Amending soil with microbial-enhancing substances (such as glucose, alfalfa, and rice straw) has been shown to markedly decrease soil persistence(6,5). Degradation of 2,6-dichloro-4-nitroaniline is faster under anaerobic soil conditions than under aerobic soil conditions(3). Degradation in three CA soils was much faster under flooded laboratory conditions as compared to upland conditions (half-lives of 1-3 weeks versus 13-30 months)(5,8). A half-life of less than 3 days has been reported for a flooded sediment(4). Microbial degradation in soil involves reduction to 4-amino-2,6-dichloroaniline(4).|TERRESTRIAL FATE: A (14)C-labeled sample was incubated in flooded soil that had been amended with d-glucose. After 3 days the amount of dichloran that could be recovered from the soil decreased to 7% & to 3% after 9 days. Evolution of radioactive carbon dioxide could not be detected even after 9-day experimental period. Much of radioactivity (ultimately 65%) could not be removed from the soil sample by extraction with an acetone-water solution. The major extractable soil metabolite was 4-amino-3,5-dichloroacetanilide. Its expected metabolic precursor 2,6-dichloro-p-phenylenediamine was also isolated. A third compound isolated appeared to be formed by dimerization of 2,6-dichloro-p-phenylenediamine.|TERRESTRIAL FATE: Dichloran was strongly fixed in clay soils and was not completely extracted from treated soils. It was slightly water soluble and leached slowly.|AQUATIC FATE: Based on a classification scheme(1), a measured Koc value range of 660-1100(2), indicates that 2,6-dichloro-4-nitroaniline is 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 8.4X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.95X10-6 mm Hg(4), and water solubility, 6.3 mg/L(4). 2,6-Dichloro-4-nitroaniline is not expected to undergo hydrolysis in the environment since it is reported to be stable to hydrolysis over a pH range of 5-9(4). Nitro aromatic compounds absorb light strongly above 290 nm(5); therefore, 2,6-dichloro-4-nitroaniline has been shown to be susceptible to direct photolysis in sunlight(SRC). In aqueous solution at pH 7.1, 2,6-dichloro-4-nitroaniline has a reported half-life of 41 hours when exposed to light greater than 290 nm(4). Biodegradation has been shown to be the major degradation process in soil with the rate of biodegradation increasing significantly in the presence of adapted microbes(6,7); it can therefore be expected that biodegradation in natural water will also occur with the rate dependent on local microbial populations and adaptability.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,6-dichloro-4-nitroaniline, which has a vapor pressure of 1.95X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,6-dichloro-4-nitroaniline 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 116 days, calculated from its rate constant of 1.4X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2,6-dichloro-4-nitroaniline may be removed from the air by wet or dry deposition(SRC). 2,6-Dichloro-4-nitroaniline is susceptible to direct photolysis in sunlight(2).

The rate constant for the vapor-phase reaction of 2,6-dichloro-4-nitroaniline with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 116 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,6-Dichloro-4-nitroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2,6-Dichloro-4-nitroaniline is reported to be stable to hydrolysis over a pH range of 5-9(3). Nitro aromatic compounds absorb light strongly above 290 nm(4); 2,6-dichloro-4-nitroaniline hace been shown to be susceptible to direct photolysis in sunlight(SRC). In aqueous solution at pH 7.1, 2,6-dichloro-4-nitroaniline has a reported half-life of 41 hours when exposed to light greater than 290 nm(3).

2,6-Dichloro-4-nitroaniline has a moderate potential to bio-accumulate in fish tissue based on a bioconcentration study which indicated a bioconcentration factor (BCF) of 136 in whole fish tissue(1); however, the bioaccumulated residues were almost completely eliminated from fish tissues (86-98%) during a 7-14 day depuration period(1). An estimated BCF of 33 can be calculated in fish for 2,6-dichloro-4-nitroaniline(SRC), using a log Kow of 2.80(2) and a regression-derived equation(3). According to a classification scheme(4), a BCF of 33 suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

1.00e+03 L/kg|Measured Koc values for 2,6-dichloro-4-nitroaniline in a variety of soils are reported to range from 660 to 1100(1). A 2,6-dichloro-4-nitroaniline Koc value of 1000, based on measured data, is recommended for developing QSAR estimation methods(2). According to a classification scheme(3), these Koc values suggests that 2,6-dichloro-4-nitroaniline is expected to have low mobility in soil. Mobility is expected to increase in coarser soils(4).|A soil Rf value of 0.01 was measured for 2,6-dichloro-4-nitroaniline using soil TLC (thin-layer chromatography) which is indicative of soil immobility(1). 2,6-Dichloro-4-nitroaniline was found to have poor soil mobility in laboratory percolation soil columns using a loamy sand soil from a peanut field and a loam soil not used for peanut cultivation(2). 2,6-Dichloro-4-nitroaniline was strongly fixed in clay soils and was not completely extracted from treated soils and it leached slowly(3).

The Henry's Law constant for 2,6-dichloro-4-nitroaniline is estimated as 8.4X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.95X10-6 mm Hg at 25 °C(1), and water solubility, 6.3 mg/L(1). This Henry's Law constant indicates that 2,6-dichloro-4-nitroaniline is expected to be essentially nonvolatile from water surfaces(2). 2,6-Dichloro-4-nitroaniline's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to be an important fate process(SRC). 2,6-Dichloro-4-nitroaniline is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC). 2,6-Dichloro-4-nitroaniline was found to be very resistant to volatilization from solid surfaces (non-soil) as only 5% of the applied compound was lost after 6 months of incubation(3).

SURFACE WATER: 2,6-Dichloro-4-nitroaniline was not detected in the raw sewage, lagoon effluents, secondary, tertiary effluents, raw sludge, or treated sludges of 37 Ontario water pollution control plants(1). 2,6-Dichloro-4-nitroaniline concentrations of 5.3-107 ng/L were detected in Elbe River samples collected near Hamburg Germany during 1992-1993(2). 2,6-Dichloro-4-nitroaniline concentrations of <2-474 ng/L were detected in Rhone Rivers samples collected in France in 1994(3).|GROUND WATER: 2,6-Dichloro-4-nitroaniline was detected at unreported concentrations and at unreported locations in a study of 54 private and municipal wells in 7 California communities(1).

As part of the US FDA Total Diet Studies (Market Basket Survey) of the adult diet, analysis of 324 food composites (from 12 different food groups) collected from 27 US cities between Oct 1980 and Mar 1982 found 30 food composites positive for 2,6-dichloro-4-nitroaniline with concentrations ranging from a trace to 0.011 ppm(1); food groups with positive detections included dairy products, potatoes, leafy and root vegetables, fruits, and sugar and adjuncts(1). As part of the US FDA Total Diet Studies (Market Basket Survey) of the toddler and infant diet, analysis of 286 food composites (from 11 different food groups) collected from 13 US cities between Oct 1980 and Mar 1982 found 14 food composites positive for 2,6-dichloro-4-nitroaniline with concentrations ranging from 0.002 to 0.122 ppm(2); food groups with positive detections included meats (fish and poultry), potatoes, vegetables, fruits and fruit juices, and oils and fats(2). As part of the US FDA Total Diet Studies (Market Basket Survey) of the adult diet, analysis of 240 food composites (from 12 different food groups) collected from 20 US cities between Oct 1979 and Sept 1980 found 13 food composites positive for 2,6-dichloro-4-nitroaniline with concentrations ranging from 0.001 to 0.058 ppm(3).|During a 5 year period from Oct 1981 to Sep 1986, the Los Angeles District Lab of the US FDA analyzed 19,851 samples of domestic and imported food and feed commodities for pesticide residues; 2,6-dichloro-4-nitroaniline was detected in 384 samples with levels ranging from 0.05 to greater than 2.0 ppm(1).|As part of the US FDA Total Diet Studies (Market Basket Survey) of the adult diet, analysis of 234 food composites (from 12 different food groups) collected from 24 US cities between April 1982 and April 1984 found 6% of food composites positive for 2,6-dichloro-4-nitroaniline with the total average daily intake for a 25-30 year male equaling 4.56 ug, mainly from fruits and vegetables(1). 2,6-Dichloro-4-nitroaniline was found in 5% of the selected foods in the market basket during the 1986-1991 Total Diet Study(2). During this study it was found that a 25-30 year male would intake 0.0773 ug/kg body wt/day(2). As part of the US FDA Total Diet Studies (Market Basket Survey) of the toddler and infant diet, analysis of 234 identical food items (from 8 different food categories) collected from 13 US cities between 1985 and 1991 found 14 food composites positive for 2,6-dichloro-4-nitroaniline with concns ranging from 0.002 to 0.122 ppm(2); 2,6-dichloro-4-nitroaniline was detected in domestic apples (14 of 2464), domestic oranges (1 of 862), domestic pears (1 of 571), imported apples (8 of 735), bananas (1 of 1097), imported pears (53 of 816)(3). 2,6-Dichloro-4-nitroaniline was detected in celery (24 of 200 samples), grapes (16 of 198), onions (3 of 429), peaches (3 of 84), plums (15 of 53), tomatoes (5 of 207) taken from a pesticide residue screening program on 6970 produce samples(4). 2,6-Dichloro-4-nitroaniline was detected in pesticide residues on blueberries (1 of 74 samples), carrots (1 of 210), peaches (5 of 42), tomatoes (1 of 978), beans (1 of 271), broccoli (2 of 187), celery (40 of 196), grapes (3 of 449), limes (1 of 6), nectarines (6 of 17), plums (1 of 19), and spinach (2 of 167) in agricultural food commodities available in Canada(5).|For the five-year period 1991-1995, 1536 vegetable and 802 fruit samples collected from points of consumer purchase in Ontario Canada were analyzed for pesticide residues(1); dicloran (2,6-dichloro-4-nitroaniline) was detected in 49 samples at concentrations of <0.01 to <10 ug/g(1). For the USDA Total Diet Study July 1986-April 1991, 2,6-dichloro-4-nitroaniline was detected in 237 food samples (5% of total samples)(2).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 2,6-dichloro-4-nitroaniline is 1 to 99; the data may be greatly underestimated(1).|NIOSH (NOHS Survey 1972-1974) has statistically estimated that 3580 workers are potentially exposed to 2,6-dichloro-4-nitroaniline in the USA(1). Occupational exposure may be possible through inhalation of dusts or dermal contact during fungicidal applications of the compound(2). In a study of field workers exposed to 2,6-dichloro-4-nitroaniline during the production of conifer seedlings raised in Forest Service tree nurseries across the country, 2,6-dichloro-4-nitroaniline was used in 2 of 5 nurseries. 10 of 44 were exposed via patch analysis, 13 of 44 were exposed via handrinse analysis. 2,6-Dichloro-4-nitroaniline was not detected in the urine of any these workers(3). The general population is exposed to 2,6-dichloro-4-nitroaniline through consumption of food and drinking water containing residues of the fungicide(2).

Dicloran is well absorbed. ... Rats given (14)C-dicloran at rates of 5 or 10 mg/rat (about 20 or 40 mg/kg) excreted 70 & 77%, respectively, in the urine within 24 hr following intraperitoneal & oral intake; by 48 hr, the corresponding values were 80 & 90%. Only about 1% was excreted in feces, & this was less than 1/5 the amount excreted in the bile.|Oral metabolism studies in rats showed that dicloran is rapidly absorbed and metabolized in rats. Approximately 96 % of the administered dose was excreted in 24 hours. The urine was the major route of excretion (86.3% of the administered dose), and smaller amounts in feces (8.7% of the administered dose). Dicloran does not appear to accumulate in tissues. ... A small amount of dicloran was detected in feces.|In goats intubated with (14)C-dicloran, the administered radiolabel was completely recovered from urine and faeces by 72 hr; 38% was recovered within the first 24 hr from goats treated with 1.5 mg/kg bw and 96% from those given 8 mg/kg bw. More than 10 times more residues were found in goats than in Sprague-Dawley rats 72 hr after treatment, with only trace amounts of residues in other tissues. The liver residues in goats could not be extracted with organic solvents, whereas most of the radiolabelled residues were extractable from rat liver. In contrast, muscle residues from goats treated with a single dose of 8 mg/kg bw were not covalently bound to macromolecules. In a lactating goat given 613 mg (14)C-dicloran in a capsule daily for five days, 0.5% of the administered radiolabel was detected in milk. The parent compound and 4-amino-2,6-dichlorophenol were the major residues.|In groups of five hens dosed with (14)C-dicloran in capsules (0.37 or 6 mg/hen per day) for five days, dicloran was rapidly absorbed, metabolized, and eliminated. More than 80% was excreted, and 50-57% of the administered dose was recovered within 24 hr of dosing.|For more Absorption, Distribution and Excretion (Complete) data for 2,6-DICHLORO-4-NITROANILINE (7 total), please visit the HSDB record page.

AFTER ORAL ADMIN OF (14)C-LABELED DICHLORAN TO MALE RATS, DICHLORAN WAS ... METABOLIZED, & EXCRETED WITH 89% OF THE LABEL IN THE URINE. ... 24 HR URINE POOLS CONTAINED ONLY FREE & CONJUGATED 2,6-DICHLORO-4-HYDROXYANILINE (DCHA); 1 DICHLORAN: 1 DICHLORAN GLUCURONIDE; 6 DICHLORAN SULFATE. HYDROLYSIS OF THE URINE SHOWED TWO COMPOUNDS IN ADDITION TO TRACES OF STARTING MATERIAL. 4-AMINO-3,5-DICHLOROPHENOL ACCOUNTED FOR 70% OF THE URINARY RADIOACTIVITY; 4-AMINO-2,6-DICHLOROANILINE FOR ABOUT 2.4%. SMALL AMOUNTS OF AN ARYLDIAMINE WAS INDICATED. IN VITRO STUDIES SHOWED THAT MOUSE LIVER MICROSOMES CONVERTED DICHLORAN TO THE AMINOPHENOL AND THE PHENYLENEDIAMINE. TLC SHOWED THAT THIS CONVERSION WAS SMALL. ABOUT 91% OF THE BOTRAN WAS RECOVERED UNCHANGED.|The in-vitro metabolism of 2,6-dichloro-4-nitroaniline was studied in efforts to characterize the isozymes of cytochrome-P-450 by which it is metabolized and to determine the origin of the oxygen in the phenol metabolite. Female Sprague-Dawley-rats were given 500 mg/kg or 1000 mg/kg of 2,6-dichloro-4-nitroaniline by gavage or 80 mg/kg phenobarbital (PB) intraperitoneally (ip) for 4 days. On day five the animals were injected with 35 mg/mg pentobarbital ip, and sleeping times were recorded. Liver microsomes were prepared from immature female Sprague-Dawley-rats treated with 75mg/kg PB, 40 mg/kg 3-methylcholanthrene (MC), or 1000 mg/kg 2,6-dichloro-4-nitroaniline. The parent compound appeared to induce its own metabolism. In-vitro microsomal aerobic production of 3,5-dichloro-p-aminophenol (DCAP) was increased 4 to 6.5 fold with respect to controls after treatment with 2,6-dichloro-4-nitroaniline. The addition of specific antibodies to cytochrome-P-450d inhibited the microsomal production of DCAP, indicating that the removal of the nitro group and subsequent replacement with a hydroxyl group was initiated by cytochrome-P-450d in the mixed function oxidase system. This hydroxyl group came from water and not molecular oxygen. The findings showed that cytochrome-P-450d was induced by 2,6-dichloro-4-nitroaniline and this cytochrome initiated the hepatic metabolism of 2,6-dichloro-4-nitroaniline to an N-hydroxylamine, followed by a non P-450 mediated attack of water causing the removal of nitrous-acid and the formation of the phenol.|RATS FED DICLORAN EXCRETE A TRACE OF THE UNCHANGED CMPD PLUS 3,5-DICHLORO-4-AMINOPHENOL & 2,6-DICHLORO-P-PHENYLENEDIAMINE. THIS APPARENTLY REPRESENTS 2 ROUTES OF METABOLISM, AS INTERCONVERSION OF THE 2 METABOLITES COULD NOT BE DEMONSTRATED. IN RATS GIVEN (14)C DICLORAN, 70% OF THE ACTIVITY IN THE FIRST 24 HR URINE REPRESENTED THE OTHER METABOLITE, & THE REMAINDER WAS IN THE FORM OF UNIDENTIFIED MATERIALS.|Oral metabolism studies in rats showed that dicloran is rapidly absorbed and metabolized ... The major urine metabolites were DCHA- sulfate and DCHA-glucuronide which accounted for 45.5% to 79% of the total dose. Other metabolites detected were DCHA (3.3 to 22.8%), DCAP (0.3% to 8.5%), and DCNAP (<0.1% to 1.0%).|For more Metabolism/Metabolites (Complete) data for 2,6-DICHLORO-4-NITROANILINE (7 total), please visit the HSDB record page.

AFTER ORAL ADMIN OF 14(C) LABELED DICHLORAN TO MALE RATS, DICHLORAN WAS RAPIDLY ABSORBED, METABOLIZED, & EXCRETED WITH 89% OF LABEL IN URINE. URINARY EXCRETION WAS FIRST ORDER, K= 0.199/HR & HALF-LIFE= 3.5 HR. ... EXCRETION OF URINARY RADIOACTIVITY IN HUMAN SUBJECTS COULD BE DESCRIBED BY TWO SIMULTANEOUS PSEUDO FIRST-ORDER PROCESSES WITH MEAN RATE CONSTANTS OF 0.0749 & 0.0260/HR, WHICH ARE EQUIV TO EXCRETION HALF-TIMES OF 9.26 & 27.4 HR, RESPECTIVELY.

As a fungicide, it delays germination and causes a severe check to hyphal growth. It is suggested that dicloran is a structurally non-specific toxicant exerting its effect by disorganizing cell growth and division in particular plant pathogens. The mode of action in test animals is not clear.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the nose, eyes, skin and throat, coughing, chest discomfort, nausea and vomiting. Absorption into the body leads to the formation of methemoglobin which in sufficient concentrations causes cyanosis. Exposure to this compound may also cause sensitization and bladder irritation. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Gastrointestinal decontamination. If a large amount of the fungicide has been ingested in the last few hours, and if copious vomiting has not already occurred, it may be reasonable to consider GI decontamination. Activated charcoal can be used along with the addition of the cathartic sorbitol to the charcoal slurry. If sorbitol is given separately, it should be diluted with an equal volume of water before administration. No more than one dose of sorbitol is recommended and it should be used with caution in children and the elderly. If contact with the toxicant has been minimal (for example, oral contamination only, promptly flushed out of the mouth), administration of charcoal without a cathartic, followed by careful observation of the patient, probably represents optimal management. /Substituted benzenes/|Skin decontamination. Dermal contamination should be washed off with soap and water. Flush contamination from the eyes with copious amounts of water. If irritation persists, specialized medical care should be obtained. /Substituted benzenes/|Porphyria. Persons affected by porphyria should avoid sunlight, which exacerbates the dermal injury by porphyrins. /Substituted benzenes/|/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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/|For more Antidote and Emergency Treatment (Complete) data for 2,6-DICHLORO-4-NITROANILINE (6 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ In a double-blind clinical study, 20 male volunteers were given 10 mg of dicloran (purity unspecified), equivalent to 0.14 mg/kg bw per day, and 10 received a placebo, once daily, for 90 days. The dose and duration were based on the estimated maximum residues obtained from consumption of fruits and vegetables over one year. Hematological examinations and tests for liver and kidney function were performed at various intervals over the course of the study; the results were found to be normal.

2,6-dichlor-4-nitroaniline

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Cough. Sore throat.

Redness.

Redness. Pain.

Dust, wettable powder, and flowable.|4% DUST & 50% WETTABLE POWDER IN UNITED KINGDOM; 8% DUST & 50% WETTABLE POWDER IN NETHERLANDS; 4 & 8% DUSTS & 50% WETTABLE POWDER IN USA. BOTRAN 35-35 (ORTHO) 35% DICHLORAN, 35% CAPTAN.|Botran 75-W Fungicide (Gowan Company), Dicloran 75%.|Botran Technical (Gowan Company), Dicloran 95%.|Botran 5F Fungicide (Gowan Company), Dicloran 46.7%.

Pesticide, fertilizer, and other agricultural chemical manufacturing|Benzenamine, 2,6-dichloro-4-nitro-: ACTIVE|Over 200,000 pounds of 2,6-dichloro-4-nitroaniline (dichloran) is applied annually throughout the United States; it's primary uses as a fungicide are on celery, lettuce, and grapes; it is primarily used in California and the Pacific Northwest.|The WHO Recommended Classification of Pesticides by Hazard identifies dicloran (technical grade) as Class III: slightly hazardous; Main Use: fungicide, other than for seed treatment.

Method: EPA-EAD 1625; Procedure: gas chromatography/mass spectrometry; Analyte: dichloran; Matrix: water; Detection Limit: not provided.|Product analysis by gas liquid chromatography. Residues determined by gas liquid chromatography with electron capture detector.|TO IDENTIFY DICHLORAN ON THIN-LAYER CHROMATOGRAMS DIAZOTIZE & COUPLE DICHLORAN TO N-(1-NAPHTHYL)ETHYLENE-DIAMINE FORMING PURPLISH RED COLOR DETERMINED @ 515 NM.|A COMPARISON OF TWO GAS-LIQUID CHROMATOGRAPHY METHODS AND UV ABSORPTION FOR THE ANALYSIS OF HERBICIDES IN FOODS. GAS-LIQUID CHROMATOGRAPY WITH ELECTRON CAPTURE DETECTION WAS MOST APPROPRIATE METHOD FOR DETECTING DICHLORAN.|For more Analytic Laboratory Methods (Complete) data for 2,6-DICHLORO-4-NITROANILINE (8 total), please visit the HSDB record page.

Agrochemicals -> Fungicides|Pharmaceuticals