3,5-Dichloroaniline

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

Pesticide degradation product

log Kow= 2.90

2.6

INSOL IN WATER; SOL IN HOT PETROLEUM ETHER

Sol in alcohol, ether, benzene, chloroform

... Water solubility of 759 ppm at 23 °C ... .

Danger

H301 (99.3%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 147 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H371: May cause damage to organs [Warning Specific target organ toxicity, single exposure]

Chemical: Benzenamine, 3,5-dichloro-

Commission Regulation No 844/2012

Status: Active Update: 09-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/14511

Emergency treatment: Methemoglobinemia; The dichloroanilines cause evidence of kidney damage (proteinuria, hematuria, and elevated blood urea nitrogen) at 0.8 mmol/kg given intraperitoneally to rats; [HSDB] An irritant; May induce methemoglobinemia; May be absorbed through skin; [MSDSonline] See 3,4-Dichloroaniline.

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importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3,5-Dichlorobenzeneamine is included on this list.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. 3,5-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

/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 3,5-DICHLOROANILINE (8 total), please visit the HSDB record page.

Acute Tox. 3 (99.3%)

Acute toxicity - category 3

Specific target organ toxicity - Single exposure - Category 2 (blood system)

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.

IMO 6.1; Dichloroanilines

UN 1590; 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: 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.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emmissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

... 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 3,5-DICHLOROANILINE (9 total), please visit the HSDB record page.

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/

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 309(2) indicates that 3,5-dichloroaniline is expected to have moderate mobility in soil(SRC). When released to soil, 3,5-dichloroaniline may undergo covalent chemical bonding with humic materials, which can result in its chemical alteration to a latent form and tight adsorption. When covalently bound in this latent form, leaching in soil systems is not generally expected to occur. This covalent bonding proceeds in two steps; a rapid and reversible bonding followed by a slower and much less reversible reaction(3). Incubation of 3,5-dichloroaniline in covered beakers containing a sandy loam soil for 14 days yielded the azo compound 3,3',5,5'-tetrachloroazobenzene(4). Volatilization of 3,5-dichloroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.58X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 3,5-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.51X10-3 mm Hg(SRC), determined from a fragment constant method(6).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 309(2) indicates that 3,5-dichloroaniline is expected to adsorb to suspended solids and sediment in water(SRC). 3,5-Dichloroaniline may undergo a covalent chemical bonding with sediment resulting in its chemical alteration to a latent form resulting in stronger adsorption. Using the Closed Bottle screening test, a 0% theoretical BOD(Biological Oxygen Demand) was observed over a 30-day inoculation period using a sewage inoculum(3). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.58X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Volatilization half-lives for a model river and model lake are 30 days and 219 days, respectively(SRC), using an estimation method(4). However, the volatilization half-life does not take into account the effects of adsorption. A Koc value of 309(2) and 3,5-dichloroaniline's ability to undergo covalent chemical bonding with sediment, 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, yielding an estimated half-life of 621 days in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 321 days in a model pond 2 m deep(6). According to a classification scheme(7), an estimated BCF of 94(4,SRC), from the log Kow(8), suggests the potential for bioconcentration in aquatic organisms is moderate.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semi-volatile organic compounds in the atmosphere(1), 3,5-dichloroaniline, which has an estimated vapor pressure of 8.51X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,5-dichloroaniline 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 7 hours(SRC) from its estimated rate constant of 5.33X10-11 atm-cu m/mole(3).

The Koc of 3,5-dichloroaniline is 309(1). According to a classification scheme(2), this estimated Koc value suggests that 3,5-dichloroaniline is expected to have moderate mobility in soil. However, chloroanilines have been shown to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC).

3,5-Dichloroaniline is an intermediate in the production of certain fungicides. This study characterized the capacity of 3,5-dichloroaniline and two putative metabolites to induce methemoglobin formation. In vivo intraperitoneal (i.p.) administration of 0.8 mmol/kg 3,5-dichloroaniline resulted in elevated (P < 0.05) methemoglobin levels at 2 and 4 h after injection and returned to control values within 8 h. In vitro methemoglobin generation was monitored in washed erythrocytes incubated for 60 min at 37~ C with 4 and 8 mM 3,5-dichloroaniline. Methemoglobin generation in vitro was higher (P < 0.05) than control values in erythrocytes incubated for 30 min with 0.2-0.6 mM 4-amino-2,6-dichlorophenol or 5-100 muM 3,5-dichlorophenylhydroxylamine. The in vitro methemoglobin generating capacity in decreasing order was: 3,5-dichlorophenylhydroxylamine > 4-amino-2,6-dichlorophenolults of the in vitro studies further indicated that none of the compounds tested induced lipid peroxidation. Erythrocytes incubated with 5-100 muM 3,5-dichlorophenylhydroxylamine in vitro were associated with depletion of glutathione. These results indicated that: (a) 3,5-dichloroaniline and its metabolites can induce methemoglobin formation; (b) the N-hydroxy metabolite was the most potent inducer of hemoglobin oxidation and (c) glutathione depletion was associated with methemoglobin formation by 3,5-dichlorophenylhydroxylamine.

IN CLOSED-BOTTLE TEST, 3,5-DICHLOROANILINE IS HIGHLY RESISTANT TO BIODEGRADATION AFTER 10 DAYS OF INCUBATION TIME. IN SIMULATED ACTIVATED-SLUDGE PROCESS, APPROX 97% IS BIOELIMINATED AFTER 10-16 DAYS ADAPTATION TIME & APPROXIMATELY 15-20% DICHLOROANILINE IS REMOVED BY VAPORIZATION, BIOELIMINATION, & SORPTION BY APPARATUS.

The effects of dichlorine-substituted anilines on Guelph loam were studied. 3,5-Dichloroaniline at concentrations of 5 to 100 ug/g soil was inhibitory against the oxidation of the nitrogen of ammonia to nitrite nitrogen, but not nitrite nitrogen to nitrate nitrogen. It showed an initially faster rate up to 4 weeks, followed by a reduced rate of disappearance. The dichloroanilines were more persistent than aniline or the monochloroanilines.

AEROBIC: Incubation of 3,5-dichloroaniline in covered beakers containing a sandy loam soil for 14 days yielded the azo compound 3,3',5,5'-tetrachloroazobenzene(1). Using the Closed Bottle screening test, a 0% theoretical BOD(Biological Oxygen Demand) was observed over a 30-day inoculation period using a sewage inoculum(2). In a simulated biological treatment system using an activated sludge inocula, elimination of 3,5-dichloroaniline over 29-41 days of operation was approximately 15-16% with bio-elimination (biodegradation plus adsorption to sludge) accounting for 5%, adsorption to the apparatus accounting for about 6-7%, and volatilization accounting for less than 4%(2). ANAEROBIC: Reductive dehalogenation of 3,5-dichloroaniline was examined in an anaerobic estuarine sediment which had been pre-exposed to various industrial organic chemicals. The first-order rate constant for 3,5-dichloroaniline was 0.005 day-1 with a half life of 149 days(3). This half-life was 3 times longer than other dichloroanilines studied. No degradation of 3,5-dichloroaniline (based on theoretical methane evolution) was observed in an anaerobic-water screening test over a 28 day incubation period using a digester sludge inocula(4).

An estimated BCF of 94 was calculated for 3,5-dichloroaniline(SRC), using a log Kow of 2.90(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.

The Henry's Law constant for 3,5-dichloroaniline is estimated as 1.58X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 3,5-dichloroaniline is expected to volatilize from water surfaces(2). 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)(2) is estimated as approximately 30 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 219 days(SRC). However, the volatilization half life does not take into account the effects of adsorption. A Koc value of 309(3), 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, yielding an estimated half-life of 621 days in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 321 days in a model pond 2 m deep(4). 3,5-Dichloroaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 3,5-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.51X10-3 mm Hg(SRC), determined from a fragment constant method(5).

IN GUELPH LOAM, 3,5-DICHLOROANILINE, AT CONCN OF 5-100 UG/G SOIL, WAS INHIBITORY AGAINST THE OXIDN OF THE NITROGEN OF AMMONIA TO NITRITE NITROGEN BY NITROSOMONAS, BUT NOT NITRITE NITROGEN TO NITRATE. THE DICHLOROANILINES SHOWED INCREASED TOXICITY AGAINST NITROSOMONAS.

The nephrotoxic potential of 3,5-dichloroaniline was examined in male Sprague Dawley rats. Rats were admin 0.4, 0.8 or 1.0 mmol/kg, ip, or 0.9% saline (1.0 ml/kg, ip), & renal function was monitored at 24 & 48 hr. 3,5-Dichloroaniline at 0.4 mmol/kg did not produce evidence of nephrotoxicity. However, 0.8 mmol/kg decreased urine volume & osmolality, increased proteinuria, elevated the blood urea nitrogen concn & decreased basal & lactate-stimulated p-aminohippurate accumulation. Three of 4 rats receiving 1.0 mmol/kg died prior to 48 hr postinjection. In vitro incubation of renal cortical slices with 3,5-dichloroaniline resulted in decreased p-aminohippurate & tetraethylammonium uptake when 3,5-dichloroaniline concn of 1X10-6 M or greater were used. These results indicate that 3,5-dichloroaniline is nephrotoxic to Sprague Dawley rats when admin in a dose of 0.8 mmol/kg or higher & is capable of altering organic ion transport in vitro.

Dichloroaniline produces methemoglobinemia in rats & mice. /Dichloroaniline/

3,5-Dichloroaniline (3,5-DCA), a derivative needed in the manufacture of dyes, pesticides and industrial compounds has been reported to induce renal damage. This study investigated whether pretreatment with inducers or inhibitors of P450 altered 3,5-DCA toxicity. P450 levels were induced in male Fischer 344 rats (4-12/group) by pretreatment (i.p.) with phenobarbital (PB, 75 mg/kg/day for 3 days), beta-naphthoflavone (BNF, 100 mg/kg/day for 4 days) or pyridine (PYR, 100 mg/kg/day for 4 days). P450 activity was inhibited by pretreatment with piperonyl butoxide (PiBx) 30 min prior to injection of 3,5-DCA. Upon completion of a designated pretreatment regimen, 0.4 or 0.8 mmol/kg 3,5-DCA was injected into F344 rats. Pair-fed controls were injected with 25% ethanol solution or physiological saline (2.5 ml/kg). The renal changes monitored at 24 and 48 h following treatment with 0.8 mmol/kg 3,5-DCA were characterized by increased blood urea nitrogen (BUN) level and decreased renal cortical slice accumulation of p-aminohippurate (PAH). Plasma alanine transaminase activity (ALT/GPT) was increased 24 h after injection of 0.8 mmol/kg 3,5-DCA while liver wt. was unchanged. PB or PYR pretreatment did not alter the renal or hepatic effects of 3,5-DCA while BNF pretreatment slightly reduced toxicity. In contrast, PiBx pretreatment increased the renal and hepatic changes associated with 3,5-DCA. The results with PiBx suggest that either the parent compound possesses some direct cytotoxicity or that a toxic metabolite was generated through a biotransformation pathway not inhibited by PiBx.

Chlorinated anilines are widely used as chemical intermediates in the manufacture of numerous dyes, pesticides, drugs and industrial compounds. The purpose of this study was to examine the nephrotoxic potential of the six dichloroaniline isomers in vivo and in vitro. In the in vivo studies, male Fischer 344 rats (4-8 rats/group) were administered a single, intraperitoneal injection of a dichloroaniline isomer (0.4, 0.8 or 1.0 mmol/kg) as the hydrochloride salt or given vehicle (0.9% saline, 2.5 ml/kg), and renal function monitored at 24 and 48 hr. Renal effects induced by dichloroaniline were characterized by decreased urine volume, increased proteinuria, hematuria, modest elevations in blood urea nitrogen concentrations, decreased accumulation of p-aminohippurate by renal cortical slices, and no change or a slight decrease in kidney weight. Renal morphological changes were observed as proximal tubular necrosis with lesser effects on distal tubular cells and collecting ducts. Based on the overall effects on renal function and morphology, the decreasing order of nephrotoxic potential was found to be 3,5-dichloroaniline greater than 2,5-dichloroaniline greater than 2,4-, 2,6- and 3,4-dichloroaniline greater than 2,3-dichloroaniline. The ability for the dichloroaniline to induce nephrotoxicity correlated well with the lipophilic properties of the dichloroaniline isomers and Hammett constants (sigma) for the various chloro substitutions. In the in vitro studies, renal cortical slices from naive male Fischer 344 rats were co-incubated with a DCA isomer (0-10(-3) M) and p-aminohippurate or tetraethylammonium. All dichloroaniline isomers decreased PAH and tetraethylammonium accumulation at 10(-3) M dichloroaniline concentration in the media with 3,5-dichloroaniline inducing the largest decrease at this concentration. These results indicate that dichloroaniline are capable of altering renal function in vivo and in vitro and that 3,5-dichloroaniline possesses the greatest nephrotoxic potential in vivo and in vitro.

The rate constant for the vapor-phase reaction of 3,5-dichloroaniline with photochemically-produced hydroxyl radicals has been estimated as 5.33X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 3,5-Dichloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2).

Occupational exposure to 3,5-dichloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 3,5-dichloroaniline is produced or used(SRC). The general population may be exposed to 3,5-dichloroaniline via drinking water(1,2) and pesticide, dye, and pharmaceutical products containing 3,5-dichloroaniline(2).

GROUNDWATER: 3,5-Dichloroaniline was detected in 7 out of 8 wells sampled from an industrialized area in Milan, Italy between Nov 1995 to Nov 1996 at concentrations ranging from 0.01 ng/l to 0.055 ng/l(1).

SURFACE WATER: In 1979, 3,5-Dichloroaniline was detected in the Rhine River in 11 of 46 samples at Lobith, Germany (0.19 ppb (max), 0.02 ppb (mean)), 2 of 12 samples at Boven Merwede, Netherlands (0.08 ppb (max), 0.01 ppb (mean)), and 2 of 13 samples at Ijssel, Netherlands (0.18 ppb (max), 0.02 ppb (mean))(1).

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. 3,5-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. 3,5-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

Three bacterial strains were isolated from soils adapted to iprodione and identified as Pseudomonas fluorescens, Pseudomonas sp. and Pseudomonas paucimobilis. The first two strains transformed iprodione to N-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine and under restrictive conditions to 3,5-dichlorophenylurea acetic acid; the latter subsequently degraded N-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine to 3,5-dichlorophenylurea acetic acid and 3,5-dichlorophenylurea acetic acid to 3,5-dichloroaniline. We constructed bacterial combinations consisting of Pseudomonas paucimobilis plus one of the iprodione degraders and showed that these combinations transformed iprodione into 3,5-dichloroaniline. It is known that 3,5-dichloroaniline was the major metabolite found in adapted soils, suggesting that such a bacterial combination might be responsible for degrading iprodione into 3,5-dichloroaniline in adapted soils.

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 in the production of fungicides (vinclozolin and iprodione), dyes, and pharmaceuticals; [HSDB]

CHEM INTERMED FOR VINCLOZOLIN FUNGICIDE (EG, FOR GRAPES) & IPRODIONE FUNGICIDE (EG, FOR USE ON TURF); CHEM INTERMED FOR ORGANIC SYNTHESIS

Sumilex, a fungicide very effective against gray mold in many crops, is developed from derivatives of 3,5-dichloroaniline.

3,5-Dichloroaniline is used in the production of pesticides, dyes and pharmaceuticals.

(1979) 2.00X10+4 G (PRINCIPAL CUSTOMS DISTRICTS)

(1982) 1.38X10+6 G (PRINCIPAL CUSTOMS DISTRICTS)

BY CHLORINATION OF P-NITROANILINE WITH HYDROCHLORIC ACID & SODIUM HYPOCHLORITE FOLLOWED BY DIAZOTIZATION & SUBSEQUENT REDUCTIVE DECOMPOSITION IN ACID TO YIELD 3,5-DICHLORONITROBENZENE WHICH IS REDUCED WITH IRON & HYDROCHLORIC ACID; AMINATION OF TRICHLOROBENZENE

Addition of m-dichlorobenzene to ammonia (ring bromination /isomerization/ ammoniation).