3,4-Dichloroaniline

162.02

162.02

636837

202-448-4

20KR9WJ4NS

0144

247

3442|1590

DTXSID7021815

NEEDLES FROM PETROLEUM ETHER|LIGHT BROWN CRYSTALS /DICHLOROANILINES/

29214210

26

2.69

Beige to brown Crystalline Mass and/or Chunks

1.33 g/cm³

71-72 °C

272 °C

166 °C

1.614

H2O: 0.06 g/100 mL

0-6°C

Vapour pressure, Pa at 20°C: 1.3

Relative vapour density (air = 1): 5.6

Oral-rat LD50: 545 mg/kg ;Oral-Mouse LD50: 740 mg/kg

Open flame flammable combustion releases toxic chloride, nitrogen oxide fumes

vol% in air: 2.8.2

Sensitive to prolonged exposure to heat, light and air. Darkens in storage. Insoluble in water.

Aryl Halides

3,4-DICHLOROANILINE is incompatible with oxidizing agents, acids, acid chlorides and acid anhydrides. It can decompose at low pH. Hydrochloric acid accelerates decomposition. Reacts at temperatures above 356° F in the presence of ferric chloride (NTP, 1992).

509 °F (NTP, 1992)|269 °C

6.6908X10+7 J/kmol @ 344.65 K

Critical temperature: 800 K; Critical pressure: 4.11X10+6 Pa

II

6.1

UN 3442 6.1/PG 2

3

23/24/25-41-43-50/53-51/53-33

26-36/37/39-45-60-61-36/37-28

BX2625000

T,N

The warehouse is ventilated, low temperature and dry; stored separately from oxidants, food additives and acids

Stable, but darkens in storage. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides.

P261-P273-P280-P301 + P310-P305 + P351 + P338-P311

H301-H311-H317-H318-H331-H410

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.

This chemical is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Heating will cause rise in pressure with risk of bursting.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 158 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501|H332: Harmful if inhaled [Warning Acute toxicity, inhalation]|P260, P261, P264, P270, P271, P304+P312, P304+P340, P307+P311, P309+P311, P312, P314, P321, P405, and P501|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P309+P311, P311, P312, P314, P321, P322, P330, P333+P313, P337+P313, P361, P363, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P307+P311, P312, P314, P321, P322, P330, P333+P313, P337+P313, P361, P363, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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)|Wear special protective clothing and positive pressure self-contained breathing apparatus. /Dichloroanilines/|POSSIBLE EXPOSURE TO HIGHER CONCN (PIPE BREAKAGE, SPLASHING, CLEANING OR REPAIR OF STORAGE TANKS) NECESSITATES USE OF SAFETY GOGGLES, GAS MASK, APRON, & RUBBER GLOVES. /ANILINE/|RESPIRATOR FOR ORGANIC VAPORS, SPLASHPROOF GOGGLES ... /&/ BOOTS. /ANILINE/|Respiratory protection from aniline is as follows: vapor concentration of 100 ppm or less: a chemical cartridge respirator with a full facepiece and an organic vapor cartridge(s) or a gas mask with a chin-style front or back-mounted organic vapor canister or any supplied-air respirator with a full facepiece, helmet or hood, or any self-contained breathing apparatus with a full facepiece; greater than 100 ppm or entry and escape from unknown concentrations: self-contained breathing apparatus with a full facepiece operated in pressure demand or other positive pressure mode or a combination respirator which includes a type C supplied-air respirator with a full facepiece operated in pressure-demand or other positive pressure or continuous-flow mode and an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode; escape: any gas mask providing protection against organic vapors or any self-contained breathing apparatus. /Aniline/|Butyl rubber protective clothing. ... /Aniline/

COMBUSTIBLE SOLID /DICHLOROANILINES/

Explosive limits , vol% in air: 2.8-7.2

USE WATER SPRAY, DRY CHEMICAL, FOAM, OR CARBON DIOXIDE. WATER OR FOAM MAY CAUSE FROTHING. USE WATER SPRAY TO KEEP FIRE-EXPOSED CONTAINERS COOL. APPROACH FIRE FROM UPWIND TO AVOID HAZARDOUS VAPORS AND TOXIC DECOMPOSITION PRODUCTS. /DICHLOROANILINES/|If material on fire or involved in fire: Use dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. use water in flooding quantities as fog. /Dichloroaniline/|Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Dichloroaniline/

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.|... ANILINE SHOULD BE REACTED IN CLOSED VESSELS AS FAR AS POSSIBLE. IN FACTORIES VENTILATION SHOULD BE SUFFICIENT TO KEEP ATMOSPHERIC ANILINE CONTENT WELL BELOW PERMITTED LEVEL. /ANILINE/|Eating and smoking should not be allowed in areas where liquid aniline is handled, processed, or stored. /Aniline/|Clothing which becomes soaked with aniline should be promptly removed. /Aniline/|For more Preventive Measures (Complete) data for 3,4-DICHLOROANILINE (8 total), please visit the HSDB record page.

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Dichloroanilines; Dichloroanilines, liquid; Dichloroanilines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Dichloroanilines; Dichloroanilines, liquid; Dichloroanilines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Dichloroanilines; Dichloroanilines, liquid; Dichloroanilines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Dichloroanilines; Dichloroanilines, liquid; Dichloroanilines, solid/|For more DOT Emergency Guidelines (Complete) data for 3,4-DICHLOROANILINE (8 total), please visit the HSDB record page.

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.

A severe eye and skin irritant.

Personal protection: chemical protection suit including self-contained breathing apparatus. Remove all ignition sources. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from strong oxidants and food and feedstuffs. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.

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. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure could cause death. The effects may be delayed. Medical observation is indicated.

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood system. This may result in the formation of methaemoglobin.

NO open flames.

PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or face shield.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 3,4-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

3,4-Dichloroaniline was found to occur only twice in over 4000 samples of waste waters from 46 industrial categories(1). The detections (concentration and source not reported) occurred in a sample from the organics and plastics industry and in a sample from a publicly owned treatment works(1). 3,4-Dichloroaniline has been qualitatively detected in advanced waste treatment water concentrates collected from Pomona, CA on Sep 25, 1974(2).

(14)C-labeled 3,4-dichloroaniline (DCA) was applied to soil under outdoor conditions at 1.43 kg/ha. The following year, potatoes were planted. After the first season, a total of 69.8% of (14)C applied was recovered in soil, plants and leaching water. After the second year, the recovery was still 67.1%. At the end of the first crop season, 69.4% of the total applied radioactivity from (14)C-3,4-dichloroaniline was found in the soil, dispersed down to a depth of 30 cm. Unconverted DCA was about 1% of the residues present after one growing season and <1% after the second year's harvest(1).|3,4-Dichloroaniline was detected at levels ranging from trace (less than 20 ppb) to 16.86 ppm during 1972-1973 monitoring of various stream and estuary sediments in Oahu, Hawaii(1). The monitoring locations were associated with herbicide runoff from sugarcane and pineapple fields(1).

moderately toxic

METHEMOGLOBINEMIA INDUCTION BY 3,4-DICHLOROANILINE ADMIN INTRAPERITONEAL AT DOSE OF 250 MG/KG WAS REDUCED IN BOTH COPPER LOADED & COPPER DEFICIENT RATS.

LD50 Rat oral 648 mg/kg|LD50 Rat ip 280 mg/kg|LD50 Mouse oral 740 mg/kg|LD50 Mouse ip 310 mg/kg|For more Non-Human Toxicity Values (Complete) data for 3,4-DICHLOROANILINE (6 total), please visit the HSDB record page.

3,4-Dichloroaniline may be found as an impurity in the synthesis of propanil.|3,4-Dichloroaniline is a degradation product of the herbicide diuron and is often found in field soils to which diuron has been applied(1). 3,4-Dichloroaniline is a principal biodegradation intermediate of economically important herbicides such as propanil, diuron, linuron, and swep(2). 3,4-Dichloroaniline's production and use as a chemical intermediate in the production of pesticides and dyes may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: FIELD EXPT WERE CONDUCTED TO DETECT THE RESIDUE LEVELS OF PROPANIL, 3-4-DICHLOROANILINE AND 3,3',4,4'-TETRACHLOROAZOBENZENE IN THE FLOOD WATER BEAUMONT CLAY SOIL UNDER NORMAL RICE (ORYZA SATIVA) CULTIVATION. PROPANIL APPLIED AS A FOLIAR SPRAY AT 3.4 AND 6.8 KG/HA 24 HR BEFORE FLOODING, WAS DISSIPATED FROM THE FLOOD WATER WITHIN 24 HR FOLLOWING THE FLOOD. THE AMOUNT OF PROPANIL DISSIPATED CORRESPONDED TO THE DICHLOROANILINE CONCENTRATION IN THE FLOOD WATER AT 24 HOURS, INDICATIVE OF BIOLOGICAL DEGRADATION OF PROPANIL TO DICHLOROANILINE. NEITHER PROPANIL NOR ITS METABOLITES WERE DETECTED IN SOIL SAMPLES COLLECTED AT 2.5 TO 5.0 CM & 17.5 TO 20.0 CM BELOW THE SURFACE 24 HR FOLLOWING THE APPLICATION OF THE FLOOD WATER.|TERRESTRIAL FATE: THE FATE OF 3,4-DICHLOROANILINE (DCA) IN RICE (ORYZA SATIVA)-PADDY MICROECOSYSTEM WAS DETERMINED. SOIL, TREATED WITH 10 PPM DICHLOROANILINE, WAS PLACED IN GLASS CHAMBERS, PLANTED TO RICE, THEN FLOODED WHEN THE RICE REACHED THE 2-LEAF STAGE. AFTER FLOODING, 4 SPECIES OF AQUATIC ORGANISMS WERE ADDED. THE CONCN OF DCA AND METABOLITES WAS DETERMINED OVER A PERIOD OF TIME. A MAXIMUM OF 2.8% OF THE TOTAL RADIOACTIVITY APPLIED TO SOIL DESORBED OR LEACHED INTO WATER. DCA RECOVERED FROM WATER DECREASED FROM 12 TO 1% OF THE TOTAL RADIOACTIVITY IN WATER BETWEEN 1 AND 30 DAYS AFTER FLOODING. BETWEEN 10.5 AND 18.5% OF THE RADIOACTIVITY REMAINING IN SOIL AT THE END OF THE EXPERIMENTS WAS EXTRACTABLE. OF THE RADIOACTIVITY RECOVERED, BETWEEN 5 AND 11% WAS DCA. RICE ACCUMULATED LESS THAN OR EQUAL TO 0.5% OF THE TOTAL RADIOACTIVITY IN SOIL.|TERRESTRIAL FATE: LABORATORY EXPT ON THE METABOLISM OF ANILINE-BASED HERBICIDES BY SOIL MICROORGANISMS ARE SUMMARIZED. IN THESE EXPT, METABOLISM WAS MEASURED BY THE CARBON DIOXIDE RELEASED BY ALL MICROORGANISMS IN A QUANTITY OF SOIL OVER TIME. IT WAS OBSERVED THAT WHEN ANILINE-BASED HERBICIDES SUCH AS PROPANIL WERE APPLIED TO THE SOIL, THIS SOIL RESPIRATION FIRST INCREASED & THEN DECREASED. IT WAS ANTICIPATED THAT PROPANIL WOULD BE DEGRADED BY SOIL MICROORGANISMS TO PROPIONIC ACID & 3,4-DICHLOROANILINE (DCA). WHEN THESE TWO COMPOUNDS WERE TESTED ON SOIL, IT WAS FOUND THAT DCA DECREASED SOIL RESPIRATION, AN OBSERVATION THAT DEMONSTRATED THE TOXICITY OF DCA TO SOIL MICROORGANISMS. THE DCA CONCENTRATION INCREASED FOR 5 DAYS & THEN SLOWLY DECREASED. DCA, ITSELF UNDERWENT CHANGE, WHICH WAS MANIFESTED BY THE APPEARANCE OF A NEW CHROMATOGRAPHIC PEAK THAT INCREASED IN AMPLITUDE THROUGHOUT A 30-DAY OBSERVATION PERIOD. THIS WAS IDENTIFIED AS THE AZO COMPOUND, 3,3',4,4'-TETRACHLOROAZOBENZENE. AT LEAST 10 OTHER MORE COMPLEX COMPOUNDS ALSO RESULTED FROM THE BREAKDOWN OF DCA.|TERRESTRIAL FATE: THE DECOMPOSITION RATE OF 3,4-DICHLOROANILINE (DCA), ONE OF THE PRINCIPAL METABOLITES OF PHENYLAMIDE PESTICIDES TO CO2 IN 4 DIFFERENT AGRICULTURAL SOILS PRESENT AT 1 PPM CONCENTRATION WAS STUDIED OVER A PERIOD OF 10-16 WEEKS. THE BENZENE RING WAS LABELED WITH (14)C; UPON TERMINATION OF THE DECOMPOSITION TIME (16 WEEKS) THE SOILS WERE EXTRACTED WITH ETHYL ALCOHOL AND THE EXTRACTS ANALYZED BY THIN LAYER CHROMATOGRAPHY. DCA WAS MINERALIZED BY ONLY 3.9 TO 11.9% DEPENDING UPON THE TYPE OF SOIL. FOLLOWING THE COMPLETION OF THE EXPT, 60% OR MORE OF (14)C ACTIVITY REMAINED IN SOIL UNDECOMPOSED (ADSORBED TO SOIL CONSTITUENTS, LINKED COVALENTLY TO ORGANIC SOIL COMPONENTS, OR CONVERTED BY CONDENSATION INTO SECONDARY TRANSFORMATION PRODUCTS) AND COULD NOT BE EXTRACTED BY ANY SOLVENT. THE SLOW DEGRADATION OF THESE CMPD MAY LEAD TO THEIR ACCUM IN AGRICULTURAL SOILS.|For more Environmental Fate (Complete) data for 3,4-DICHLOROANILINE (11 total), please visit the HSDB record page.

The photolysis of 3,4-DCA in water & in the form of wet & dry adsorbed layers was studied in artificial light & in sunlight. Laboratory expt revealed that the rate of degradation was a function of the radiation dose. Photolysis was observed even in visible light. Under field conditions, 85-90% was degraded in 3-5 hr in direct sunlight, while 40-70% of propanid degraded in 4 days. Photolysis was also observed under water, but its intensity diminished with increasing thickness of the water layer. The photolysis was considerably more intense in water with pH 7.8 than in distilled water (pH 5.6). Salts of 3,4-DCA are more stable in light than is free 3,4-DCA.|The degradation of 3,4-DCA was studied as a solid, in solution, & in gaseous phase under UV light. A solution in a 1:1 mixture of water & methanol resulted in such metabolites as p-chlorolaniline, aniline, 3,3',4,4'-tetrachloroazoxybenzene, a dechlorination product of the latter, & hydrazobenzene. Irradiation as a solid yielded p-chloroaniline & 3 metabolites; & irradiation in gaseous phase at wavelengths below 290 nm yielded p-chloroaniline & aniline at very small yield rates.|The rate constant for the vapor-phase reaction of 3,4-dichloroaniline with photochemically-produced hydroxyl radicals has been estimated as 2.21X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 3,4-Dichloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). It is expected to directly photolyze due to absorption in the environmental UV spectrum(4,5). Absorption of solar radiation by 3,4-dichloroaniline at midday, midsummer at latitude of 40 deg N was greatest at 317 nm in water(4). The half-life of 3,4-dichloroaniline under these same conditions was 3 hrs(5). A photo irradiation half-life of about 8.7 hr was observed when an aqueous solution of 3,4-dichloroaniline was exposed to UV light of 300-400 nm spectra(6). The major direct photolysis products of 3,4-dichloroaniline in distilled water is 2-chloro-5-aminophenol (>78% conversion) and 3-chloroaniline. Although overall photolysis rates are slower in natural water than in distilled water due to light attenuation, rates are faster in natural water than expected based on the amount of light being received(7).

12.88|Studies on the environmental hazards & fate of herbicides are reviewed. Herbicides do not accumulate by way of the trophic chains, except for diuron & 3,4-dichloroaniline, which accumulate in fish.|A BCF of 30.2 was determined for 3,4-dichloroaniline under static conditions with 60 male zebra fish for 10 hours(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

194.98 L/kg|... UP TO 90% OF 3,4-DICHLORANILINE ... DERIVED FROM BIODEGRADATION OF PHENYLAMIDE HERBICIDES IS ADSORBED SO STRONGLY BY SOIL ORG MATTER THAT IT IS NOT EXTRACTABLE BY SOLVENTS. BOUND DCA IS SUSCEPTIBLE TO ACID & ALKALINE HYDROLYSIS.|3,4-DICHLOROANILINE (DCA) IS MINERALIZED IN SOIL ONLY VERY SLOWLY. THE SLOW MINERALIZATION IS NOT ENTIRELY EXPLAINABLE BY THE INHERENT RECALCITRANCE OF THIS COMPOUND BUT IS ALSO EXPLAINABLE BY THE COMPETING POLYMERIZATION AND BINDING REACTIONS THAT DECREASE ITS AVAILABILITY.|A LINEAR POSITIVE CORRELATION WAS ESTABLISHED BETWEEN THE ADSORPTION OF M,P-DICHLOROANILINE TO 15 SOIL TYPES AND THE ORGANIC MATTER AND EXCHANGEABLE ALUMINUM CONTENTS OF THESE SOILS. A NEGATIVE CORRELATION EXISTED BETWEEN ADSORPTION AND SOIL PH. A MATHEMATICAL MODEL IS GIVEN FOR THE QUANTITATIVE PREDICTION OF THE EQUILIBRIUM DISTRIBUTION OF HERBICIDES IN SOIL, STARTING FROM THE INITIAL HERBICIDE CONCENTRATION IN THE SOIL AND THE SOIL ORGANIC MATTER CONTENT.|BY RADIOCHEMICAL & CONVENTIONAL ANALYSIS, THE EFFECTIVENESS OF THE BLEIDNER DISTILLATION PROCESS FOR RECOVERY OF THE HERBICIDE RESIDUE 3,4-DICHLOROANILINE (DCA) FROM ITS HUMIC COMPLEXES WAS EVALUATED. FROM A FIELD SOIL TREATED WITH DIURON AT THE RATE OF 1.76 KG/HA/YR FOR THE PAST 10 CONSECUTIVE YEARS, BLEIDNER DISTILLATION RECOVERED 1 PPM DCA, ALL FROM HUMIC COMPLEXES. THE MINERALIZATION RATE OF BOUND DCA AND THE DECLINE KINETICS OF DCA RECOVERY BOTH LEAD TO THE CONCLUSION THAT THE TOTAL BOUND DCA ACCUMULATION IN THE ANALYZED SOIL DID NOT EXCEED 2.5 PPM AND THAT IN SOILS OF THE EXAMINED TYPE, THE ACCUMULATION OF BOUND DCA RESIDUES DOES NOT CONSTITUTE A PROBLEM.|A Koc value of 193 (log Koc= 2.29) was measured during a batch adsorption test with a silt loam soil(1). According to a classification scheme(2), this Koc value suggests that 3,4-dichloroaniline is expected to have moderate mobility in soil. Aromatic amines, including 3,4-dichloroaniline, have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution. The initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone(3).

The Henry's Law constant for 3,4-dichloroaniline is estimated as 1.46X10-5 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 6.32X10-3 mm Hg(1), and water solubility, 92 mg/l(2). This Henry's Law constant indicates that 3,4-dichloroaniline is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as approximately 80 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as approximately 28 days(SRC). However, this model underestimates the volatilization half-life of 3,4-dichloroaniline since it does not take into account the effects of adsorption. The Koc value of 195(2) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered (half-life = 56 days in a model pond) and one in which adsorption was ignored (half-life = 36 days in a model pond)(4). 3,4-Dichloroaniline's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). 3,4-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.32X10-3 mm Hg(1).

GROUNDWATER: 3,4-Dichloroaniline was detected in 8 out of 8 wells sampled from an industrialized area in Milan, Italy between Nov 1995 to Nov 1996 at concns ranging from 0.01 ng/l to 0.09 ng/l (1).|DRINKING WATER: 3,4-Dichloroaniline was detected in Dutch tap water using bank filtered Rhine River water as a source(1). A mean concn of less than 50 ng/l was detected in tap water monitored (Sep 1973-Sep 1974) at a location on West German Rhine River using bank filtration(2).|SURFACE WATER: 3,4-Dichloroaniline was detected in 1979 along the Rhine River in 46 of 46 samples at Lobith, Germany(1.2 ppb (max) and 0.39 ppb (mean)), 12 of 12 samples at Boven Merwede, Netherlands (0.47 ppb (max) and 0.33 ppb (mean)) and 13 of 13 samples at Ijssel, Netherlands (0.69 ppb (max) and 0.30 ppb (mean)). 3,4-Dichloroaniline was detected along the Meuse River in 8 of 9 samples at Eijsden, Netherlands(2.1 ppb (max) and 0.29 ppb minimum) and 11 of 12 samples at Lith, Netherlands(0.42 ppb (max) and 0.14 ppb (mean))(1). 3,4-Dichloroaniline was detected in water samples taken along the Rhine River, Germany using an ethanol/cyclohexane distillation process, at 0.043 ug/l at Wekendam on 09/29/89, 0.039 and 0.026 ug/l at Lobith on 09/15/89, and 0.027 ug/l at Lobith on 03/17/89(2).

... ABSORBED THROUGH THE SKIN OR INHALED. /DICHLOROANILINES/|NIOSH (NOES Survey (1981-1983) has statistically estimated that 851 workers (187 of these are female) are potentially exposed to 3,4-dichloroaniline in the US(1). Occupational exposure to 3,4-dichloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 3,4-dichloroaniline is produced or used(SRC). The general population may be exposed to 3,4-dichloroaniline via ingestion of drinking water(2-6) and contact with dyes and pesticide products(7) containing 3,4-dichloroaniline.

... STUDIES /OF PHENYL (14)C PROPANIL ON PLANTS/ INDICATED THAT A MAJOR PORTION OF 3,4-DICHLOROANILINE ... MOIETY WAS COMPLEXED WITH POLYMERIC CELL CONSTITUENTS, MAINLY LIGNIN.|OATS TOOK UP & TRANSLOCATED WITHIN 6 WEEKS ONLY 0.7% OF THE SOIL-BOUND (14)C-LABELED 3,4-DICHLOROANILINE. UPTAKE FROM SOLUTION WAS 2.2 TO 2.5%. 3,4-DICHLOROANILINE WAS ADDED TO SOIL AT 1 PPM, AND AFTER 16 WEEKS THE NONBOUND FRACTIONS WERE REMOVED WITH WATER & ORGANIC SOLVENTS, FOLLOWED BY PLANTING OF THE OAT. THERE WERE ONLY SLIGHT DIFFERENCES IN RESULTS BETWEEN THE TWO SOIL TYPES (HUMUS-RICH GLEY AND PARABROWN SOILS) STUDIED.|THE CONJUGATION OF PESTICIDES WITH NATURAL MACROMOLECULES IN ANIMALS, PLANTS AND SOIL ORGANIC MATTER WAS REVIEWED. WHEN RICE PLANTS GROWN HYDROPONICALLY WERE TREATED WITH (14)C-3,4-DICHLOROANILINE, GREATER THAN 40% OF THE (14)C WAS FOUND IN THE ROOTS IN ISOLATED LIGNIN FRACTIONS. CHLOROANILINES MAY BE BONDED COVALENTLY TO LIGNIN VIA 1,6 ADDITION TO A QUINONE METHIDE INTERMEDIATE DURING THE LIGNIN SYNTHESIS.|Once ingested into the human body, 3,4-DCA is excreted mainly in the urine.|Using hairless rat skin maintained in a Franz diffusion cell, the percutaneous penetration of four aromatic amines: para-chloroaniline, meta-trifluoromethylaniline, dichloro-3,4-aniline and dichloro-3,5-aniline were studied. The purpose of the studies was to determine the permeation parameters (rate of permeation, permeability rat constant) in order to compare the rate of absorption of the four amines. The results show that the four amines penetrate significantly across the skin, but with different rates. 10 h after in vitro application (2 mg/cm sq), the extent of permeation was para-chloroaniline meta-trifluoromethylaniline > dichloro-3,4-aniline > dichloro-3,5-aniline.

THE HERBICIDE SWEP /(METHYL 3,4-DICHLORO-CARBANILATE) WAS METABOLIZED BY SOIL MICROFLORA/ TO 3,4-DICHLOROANILINE, 3,3',4,4'-TETRACHLOROAZOBENZENE ... AND OTHER UNIDENTIFIED CMPD. ...|CELL FREE EXTRACTS OF RICE, ORYZA SATIVA, CONTAINED A HEAT-LABILE MACROMOLECULE ABLE TO CATALYZE THE TRANSFORMATION OF 3',4'-DICHLOROPROPIONANILIDE TO 3,4-DICHLOROANILINE AND OTHER PRODUCTS.|3,4-DICHLOROANILINE YIELDS 5-AMINO-2,3-DICHLOROPHENOL PROBABLY IN RABBIT ... /FROM TABLE/|3,4-DICHLOROANILINE YIELDS 3,4-DICHLOROANILINE-N-GLUCOSIDE IN RICE ... AND ALSO IN BEAN. /FROM TABLE/|For more Metabolism/Metabolites (Complete) data for 3,4-DICHLOROANILINE (8 total), please visit the HSDB record page.

0.08 Days

/The Velsicol Chemical Corporation/ reported that both 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene are impurities in 3,4-dichloroaniline, and pesticide products that are formulated from 3,4-dichloroaniline (diuron, liuron, and propanil).

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin and severe irritation of the eyes. It reduces the oxygen carrying capacity of the blood and causes shortness of breath by formation of methemoglobin It can cause an allergic skin reaction, rash, chloracne, cyanosis, weakness, tearing, and blurring of vision. Higher exposures can cause abnormal liver an kidney function. Skin permeation can lead to systemic toxicity. ACUTE/CHRONIC HAZARDS: This compound can cause skin irritation and severe eye irritation. When heated to decomposition it emits toxic fumes of chlorine and nitrogen oxides. Thermal decomposition may produce carbon monoxide, carbon dioxide and hydrogen chloride gas. It is highly toxic when absorbed through the skin, swallowed or when vapors from the heated material are inhaled. (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. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

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

Basic treatment: Establish patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline 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 patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation. /Aniline and related compounds/

One yr after a mild chloracne developed in workers involved in production of diuron, & its precursor, 3,4-dichloroaniline, abnormalities were found in the results of serial liver function tests & lipid profiles in some of the same workers. No significant abnormalities of liver function in the DCA-diuron workers were found in an exam of the entire work force. A statistically significant increase in the mean triglyceride values was found & this was greater in those who had chloracne. Mean cholesterol levels were also higher.

3,4-dichloroaniline

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Blue lips, fingernails and skin. Dizziness. Headache. Nausea. Shortness of breath. Confusion. Convulsions. Unconsciousness.

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain. Blurred vision.

Benzenamine, 3,4-dichloro-: ACTIVE|The concn of 3,3'4,4'-tetrachloroazobenzene in 3,4-dichloroaniline and in different herbicides from a variety of manfacturers ranged from 9 to 1400 ug/g (ppm).|Workers in a propanil plant have experienced chloracne ... /this effect is/ apparently due to contaminants in one of the starting materials for the synthesis, namely 3,4-dichloroaniline. The contaminants are 3,4,3',4'-tetrachloroazobenzene & its oxy derivative, both strongly chloracnegenic.|/Some/ humans may have sustained long term systemic effects, particularly photosensitization and hyperpigmentation /from exposure to 3,3',4,4'-tetrachloroazobenzene and its azoxy derivative which are impurities in 3,4-dichloroaniline/.

FOUR 3,4-DICHLOROANILINE PRODUCTS WERE ANALYZED BY A PROCEDURE BASED ON GAS CHROMATOGRAPHY & MASS SPECTROMETRY. THE FORMULATIONS WERE EXTRACTED WITH ACETONE & THE RESIDUE PARTITIONED BETWEEN METHANOL, 1M HCL & HEXANE. HEXANE EXTRACTS WERE PURIFIED BY COLUMN CHROMATOGRAPHY ON SILICA GEL & ANALYZED BY GAS CHROMATOGRAPHY WITH ELECTRON CAPTURE DETECTION. DETECTION LIMITS WERE 0.1 UG/G USING 1 G SAMPLES.|METHODS FOR ANALYZING LINURON & ITS METABOLITES (INCL 3,4-DCA) EITHER BY GAS LIQ CHROMATOGRAPHY AFTER ETHYLATION OR DIRECTLY BY HIGH PRESSURE LIQUID CHROMATOGRAPHY, USING NORMAL & REVERSE PHASE RESPECTIVELY, WERE DEVELOPED. A COMPARISON WAS MADE BETWEEN HIGH PERFORMANCE LIQUID CHROMATOGRAPHY EQUIPPED WITH ELECTRON CAPTURE & FLAME-IONIZATION DETECTION & UV-ADSORPTION DETECTION METHODS. MASS SPECTRA OF THE COMPOUNDS & THE DERIVATIVES ARE ALSO PRESENTED.|USE OF UV SPECTROPHOTOMETRY FOR DETERMINING DIURON & 3,4-DICHLOROANILINE IN WATER.|APPLICATION OF THE HALL ELECTROLYTIC CONDUCTIVITY DETECTOR FOR THE ANALYSIS OF CHLOROANILINES & CHLORONITROANILINES IN POTW (WATER TREATMENT) SLUDGES. /CHLOROANILINES AND CHLORONITROANILINES/|For more Analytic Laboratory Methods (Complete) data for 3,4-DICHLOROANILINE (8 total), please visit the HSDB record page.

Studies were carried out to establish a method for determination of 3,4-dichloroaniline in urine by gas chromatography with electron capture detection. A 50 ml urine specimen was acidified to a pH less than 1 by adding 1-2 ml of concn hydrochloric acid; then hydrolysis was conducted at 60 °C for 20 min, & the pH of the hydrolysate was made weakly alkaline. The 3,4-dichloroaniline formed was extracted with 10 ml of benzene. The emulsion containing benzene & 3,4-dichloroaniline was centrifuged & the solvent layer was injected onto the gas chromatograph. The limit of detection was 0.1 ug of 3,4-dichloroaniline in 1 ml of urine, & an average recovery of 91% was achieved when 3,4-dichloroaniline was present at 5 ug/ml of urine. The values obtained coincided well with the ultraviolet method.

Environmental transformation -> Pesticide transformation products (metabolite, successor)

3,4-dichloroaniline is a known environmental transformation product of diuron.|3,4-dichloroaniline is a known environmental transformation product of Linuron.