3,4-ジクロロアニリン

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

Pesticide degradation product

log Kow= 2.69

2.69

1.33 at 185 °F (NTP, 1992) - Denser than water; will sink

1.33

1.57 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

NEEDLES FROM PETROLEUM ETHER

LIGHT BROWN CRYSTALS /DICHLOROANILINES/

less than 1 mg/mL at 70.7 °F (NTP, 1992)

Very sol in alcohol, ether; slightly sol in benzene.

Sol in most org solvents

Water solubility of 92 mg/l at 20 °C

Solubility in water: none

331 °F (NTP, 1992)

166 °C

331 °F (166 °C) OPEN CUP

166 °C o.c.

522 °F at 760 mmHg (NTP, 1992)

272 °C

272 °C

WHEN HEATED TO DECOMP ... THEY EVOLVE HIGHLY TOXIC /HYDROGEN/ CHLORIDE FUMES. SOME ORG CHLORIDES DECOMP TO YIELD PHOSGENE. /CHLORIDES/

340 °C. Decomposes on burning. This produces toxic fumes including nitrogen oxides and hydrogen chloride (see ICSC 0163).

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301+H311+H331 (57.4%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Benzenamine, 3,4-dichloro-

Commission Regulation (EC) No 33/2008

Status: Active Update: 19-02-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/1156

3,4-Dichloroaniline: Does not have an individual approval but may be used under an appropriate group standard

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.

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.

An eye irritant; Can induce methemoglobinemia; May cause skin sensitization; [ICSC] High exposures can cause liver and kidney injury; May be toxic after skin absorption; [CAMEO] Toxic by inhalation, ingestion, and skin absorption; May cause serious damage to eyes; [eChemPortal: ESIS] No liver injury detected in study of workers exposed to 3,4-dichloroaniline in the production of diuron; Oral LD50 (rats) = 648 mg/kg; Dermal LD50 (cats) = 700 mg/kg; [HSDB] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May cause skin sensitization; Can be absorbed through skin; Effects in high-dose animal studies include convulsions, cyanosis, lacrimation, and methemoglobinemia; [MSDSonline] Danger of cutaneous absorption; Danger of skin sensitization; [MAK]

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3,4-Dichlorobenzeneamine is included on this list.

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).

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

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.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

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.

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/

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.

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.

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.

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.

LC50 Ophryotrocha diadema (adult) 15 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Ophryotrocha diadema (larvae) 4 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Pimephales promelas (fathead minnow) 34 days old 8.06 mg/l/96 hr (Confidence limit: 7.26-8.95 mg/l) at 25 °C (98% purity) /Conditions of bioassay not specified/

EC50 Pimephales promelas (fathead minnow) 34 days old 6.09 mg/l/96 hr (Confidence limit: 5.71-6.49 mg/l) at 25 °C (98% purity) /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for 3,4-DICHLOROANILINE (11 total), please visit the HSDB record page.

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.

RICE PLANTS AT THE 4-LEAF STAGE WERE SELECTED AND TRANSPLANTED TO SOIL/SAND MIXTURES. AT THE END OF A 16 WEEK PERIOD OF PRETREATMENT WITH A NUTRIENT SOLUTION, THE SOIL OF SELECTED PLANTS WAS TREATED WITH (14)C-LABELED 3,4-DICHLOROANILINE (DCA) AT A FINAL CONCENTRATION OF 16.6 MG/ML. FOR FOLIAR TREATMENT DCA WAS APPLIED AT A FINAL CONCENTRATION OF 138.75 MG/ML. LEAF TREATMENT AND SOIL TREATMENT RESULTED IN ABOUT THE SAME AMOUNT OF RADIOACTIVITY IN THE PLANT. NO SIGNIFICANT RADIOACTIVITY WAS DETECTED IN GRAINS OF THE LEAF-TREATED RICE PLANTS, ALTHOUGH THE SHOOTS OF THESE CONTAINED MORE RADIOACTIVITY THAN DID THE SHOOTS OF THE SOIL-TREATED PLANTS. IT IS SUGGESTED THAT DCA FOUND IN THE RICE GRAIN SAMPLES WAS TEMPORARILY IMMOBILIZED IN SOIL AS HUMIC COMPLEX AND WAS THUS MADE AVAILABLE FOR ROOT UPTAKE DURING THE GRAIN RIPENING PERIOD BY THE MICROBIAL CLEAVAGE OF THESE HUMIC COMPLEXES.

3,4-Dichloroaniline, a metabolite or decomposition product of herbicides such as swep & propanil, has been found in plants.

In a 3 yr study (1968-1970), propanil at 6.7 or 9.0 kg/ha was applied postemergence as single or split applications to rice (Oryza sativa L 'Starbon-T' & 'Nova 66') 15 to 75 days after crop emergence. Residues of DCA in grain & straw from treated rice plants & of propanil & tetrachloroazobenzene in treated soil were determined. Residues of DCA in grain & straw were highest from treatments applied 65 to 75 days after crop emergence; rice straw contained more DCA than did grain.

Hydrolysates of the edible cereal of rice grain were examined using colorimetric & gas liquid chromatography procedures to detect the presence of aniline from incorporated pesticide or pesticide metabolites. Rice grain was collected at maturity from plants grown in Stuttgart, AR, which had been treated with 4 lb/acre of propanil in the 2-leaf stage. Brown head rice samples were purchased commercially. The control sample of Nato rice was reared under glasshouse conditions. The grain samples were ground to a coarse flour for analysis. Colorimetric analysis indicated the presence of aromatic amines in the field rice cereal. Gas liquid chromatography showed no chlorine peaks in the glasshouse grown rice samples, but revealed chlorine peaks in the samples from treated & untreated plants from Stuttgart, as well as commercial brown & white rice samples. DCA equal to 1.7, 1.4, 1.1 & 0.5 mcg propanil/g of grain was found in rough & polished treated samples & rough & polished untreated samples, respectively.

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

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain. Blurred vision.

Abdominal pain. Further see Inhalation.

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).

... 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 mutagenicity of 3,4-dichloroaniline was evaluated in Salmonella tester strains TA98, TA100, TA1535 and TA1537 (Ames test), both in the presence and absence of rat S9 microsomal activation. 3,4-Dichloroaniline, diluted with ETOH, was tested at concentrations up to 30 ug/ plate using the plate incorporation technique. No toxicity was observed in the concentration range selected. 3,4-Dichloroaniline did not cause a positive response in any of the tester strains with or without metabolic activation.

The mutagenicity of 3,4-dichloroaniline was evaluated in Salmonella tester strains TA98, TA100, TA1535 and TA1537 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary toxicity determinations, 3,4-dichloroaniline, diluted in DMSO, was tested at concentrations up to 2 mg/plate using the plate incorporation technique. 3,4-Dichloroaniline did not cause a positive response in any of the tester strains with or without metabolic activation.

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.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3,4-Dichlorobenzeneamine is included on this list.

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.

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.

... 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.

Used to make dyes and pesticides; [Hawley]

Chem intermediate for dyes and pesticides

/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).

(1972) PROBABLY GREATER THAN 9.08X10+5 G

(1975) PROBABLY GREATER THAN 1.36X10+6 G

Nitration of o-dichlorobenzene, followed by reduction.

Catalytic hydrogenation of 3,4-dichloronitrobenzene acid with noble metal catalysts under pressure.

p-Chloroaniline with AlCl3 and HCl.

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/.