4-아미노-2-클로로톨루엔

less than 1 mg/mL at 72 °F (NTP, 1992)

Soluble in ethanol; slightly soluble in carbon tetrachloride

212 °F (NTP, 1992)

136 °C

~136 °C

468 to 471 °F at 760 mmHg (NTP, 1992)

243 °C

79 °F (NTP, 1992)

26 °C

0.085 mmHg at 77 °F (NTP, 1992)

0.04 [mmHg]

3-chloro-p-toluidine is a brown solid with a mild odor. (NTP, 1992)

CBI; Other Solid

Brown solid; [CAMEO] Low melting solid; mp = 22-25 deg C; [MSDSonline]

Danger

H301 (89.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Benzenamine, 3-chloro-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 3-chloro-4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 11-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/1341

3-chloro-p-toluidine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin and eyes. Other symptoms may include headache, drowsiness, nausea, kidney irritation, dizziness and central nervous system depression. Exposure may can cause cyanosis and methemoglobinemia. It may also cause irritation of the bladder. Symptoms may be delayed. Hypothermia may occur in man. It may also cause loss of coordination, shortness of breath, rapid heartbeat, loss of consciousness, irritation to the respiratory tract, sore throat and nasal discharge. Other symptoms include burning sensation, redness and swelling of the eyes.

A mutagen; Causes weakness and cyanosis in lethal-dose studies of rats; [RTECS] Negative evidence of carcinogenicity in studies of rats and mice; [NTP] Emergency treatment: methemoglobinemia; Toluidine compounds (both o- and p-) may cause methemoglobinemia and hemorrhagic cystitis, but the chlorinated derivatives are more potent in producing these effects; [HSDB] Skin sensitizer from human and guinea pig testing; [EPA Hazard Characterization: Chloroanilines Cluster - 2008] An irritant; Effects in high-dose animal studies include cyanosis; [MSDSonline]

DHEW/NCI; Bioassay of 3-Chloro-p-toluidine for Possible Carcinogenicity CAS No. 95-74-9 (1978) Technical Report Series No. 145 DHEW Pub No. (NIH) 78-1701.[Available from, as of March 5, 2010: http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr145.pdf]

European Commission, ESIS; IUCLID Dataset, 3-Chloro-p-toluidine (95-74-9) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of March 5, 2010: http://esis.jrc.ec.europa.eu/]

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Starlicide (3-chloro-p-toluidine hydrochloride). EPA 738-R-96-003 (September 1995). 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 June 28, 2010:[http://www.epa.gov/pesticides/reregistration/status.htm]

Based on the reviews of the generic data for the active ingredients starlicide, the Agency has sufficient information on the health effects of starlicide and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that starlicide products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing starlicide for all uses are eligible for reregistration. /3-Chloro-p-toluidine hydrochloride/

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. 3-Chloro-p-toluidine hydrochloride is found on List B. Case No: 2610; Pesticide type: insecticide (avicide); Case Status: RED Approved 9/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 3-chloro-p-toluidine hydrochloride; Data Call-in (DCI) Date(s): 2/15/91; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI. /3-Chloro-p-toluidine hydrochloride/

3-CHLORO-P-TOLUIDINE may be sensitive to prolonged exposure to air and light. This chemical may react with oxidizing agents. It is incompatible with acids, acid chlorides, acid anhydrides and chloroformates. It is also incompatible with reducing agents. (NTP, 1992)

/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. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, 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. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, 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. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, 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. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/

For more DOT Emergency Guidelines (Complete) data for 3-Chloro-p-toluidine (8 total), please visit the HSDB record page.

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.

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (material itself does not burn or burns with difficulty). Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Chlorotoluidines, liquid/

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.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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: 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: Contaminated protective clothing should be segregated in a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Chlorotoluidines, liquid/

Personnel protection: Keep upwind. Avoid breathing vapors ... Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing. /Chlorotoluidines, liquid/

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 appropriate chemical protective gloves, boots, and goggles. /Chlorotoluidines, liquid/

LD50 Northern Bobwhite Quail oral 2.9 mg/kg 97.1% a.i. /3-Chloro-p-toluidine hydrochloride/

LD50 Mallard duck oral 105 mg/kg 97.1 a.i. /3-Chloro-p-toluidine hydrochloride/

LD50 Ageliaus phoenicens (red-winged blackbird) > 1000 mg/kg bw

LD50 Sturnus vulgaris (European starling) > 1000 mg/kg bw

For more Ecotoxicity Values (Complete) data for 3-Chloro-p-toluidine (38 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 180(SRC), determined from a structure estimation method(2), indicates that 3-chloro-p-toluidine is expected to have moderate mobility in soil(SRC). However, primary aromatic amines can react with humic matter in soil forming an irreversible complex and as a result may be immobilized in soil(3,4). Volatilization of 3-chloro-p-toluidine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 3-Chloro-p-toluidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.04 mm Hg(SRC), determined from a fragment constant method(6). 3-Chloro-p-toluidine applied at 35 ug/g to a sandy loam soil exhibited a half-life of 26 hours and was mineralized(7), suggesting that biodegradation in soil may occur(SRC).

TERRESTRIAL FATE: In a field study, 3-chloro-p-toluidine hydrochloride migration was studied using treated rice baits to Louisiana rice fields exposed for 13 days. The concentration of 2% compound on treated rice baits in the field decreased by approximately 55% in 3 days with several degradation products identified. Under laboratory conditions, multiple degradation products were identified. Degradation products in both instances included acetyl-3-chloro-p-toluidine, 3-hydroxy-p-toluidine, and cis- and trans-azo-3-chloro-p-toluidine(1). /3-Chloro-p-toluidine hydrochloride/

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 180(SRC), determined from a structure estimation method(2), indicates that 3-chloro-p-toluidine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.0X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 22 and 160 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 15(SRC), from an estimated log Kow of 2.27(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 3-Chloro-p-toluidine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 3-Chloro-p-toluidine was biodegraded in Elbe River bed sediment at 20 °C at a rate of 0.47/hr with a calculated half-life of 1.5 hrs(8), suggesting biodegradation may occur in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-chloro-p-toluidine, which has an estimated vapor pressure of 0.04 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-chloro-p-toluidine 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 3.2 hours(SRC), calculated from its rate constant of 1.2X10-10 cu cm/molecule-sec at 25 °C(3). 3-Chloro-p-toluidine does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

/BIRDS and MAMMALS/ Laboratory studies with hawks and American kestrels indicated no adverse effects when they were fed starlings poisoned with 1% starlicide-treated baits. Two kestrels survived eating 11 and 60 poisoned starlings over 24 and 141 days, respectively. Two Cooper's hawks ate 191 and 222 starlings with no observable adverse effects. Three marsh hawks ate 100, 191, and 222 starlings over 75-104 days and survived with no apparent detrimental effects. /3-Chloro-p-toluidine hydrochloride/

/BIRDS and MAMMALS/ The nephrotoxicity of 3-chloro-p-toluidine which induces death through kidney failure is characteristic for many bird species.

/BIRDS and MAMMALS/ Application of the Kenaga "index of chronicity" resulted in the conclusion that DRC-1339 was cumulatively toxic to birds.

/BIRDS and MAMMALS/ Bobwhite quail fed diets containing DRC 1339 suffered some mortality at levels as low as 2.9 ppm, but most survived 10 times this for 120 days. Reproduction in Coturnix was adversely affected by 10 ppm of DRC 1339 and above.

For more Ecotoxicity Excerpts (Complete) data for 3-Chloro-p-toluidine (7 total), please visit the HSDB record page.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=95-74-9]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 3-chloro-p-toluidine can be estimated to be 180(SRC). According to a classification scheme(2), this estimated Koc value suggests that 3-chloro-p-toluidine is expected to have moderate mobility in soil. However, primary aromatic amines can react with humic matter in soil forming an irreversible complex and as a result may be immobilized in soil(3-4). With the increase of humic matter in soil, the tendency towards irreversible complex formation may increase and 3-chloro-p-toluidine may become increasingly immobilized(4). In sandy soil containing marginal amounts of humic matter, 3-chloro-p-toluidine may be mobile(5).

Using 30 g/g uniformly-labeled 3-chloro-p-toulidine hydrochloride in California loam soil column studies and aged for 24 hrs, it was observed 2% of the initial compound leached through the soil profile. Approximately 90% was sorbed in the upper 6 cm of soil, 1% volatilized, and the major metabolite identified was N-acetyl-3-chloro-p-toluidine(1). /3-Chloro-p-toluidine hydrochloride/

/SIGNS AND SYMPTOMS/ Cyanosis was observed in individuals exposed to 3-chloro-p-toluidine.

/SIGNS AND SYMPTOMS/ Hematuria may be observed in /workers/ handling toluidines and chlorotoluidines. There may be hemorrhagic cystitis with painful and frequent micturition. /Toluidines and chlorotoluidines/

3-Chloro-p-toluidine's production and use in dye manufacturing(1) may result in its release to the environment through various waste streams(SRC). 3-Chloro-p-toluidine hydrochloride's production may result in its release to the environment through various waste streams; its use as an avicide(2) will result in its direct release to the environment(SRC).

AEROBIC: Using samples of River Elbe water taken at Dresden, 55 km downstream from the Czech border between March 1995 and December 1998, 3-chloro-p-toluidine exhibited a biodegradation rate of 0.47/hr, corresponding to a half-life of 1.5 hrs. Experiments were carried out in darkness at 20 °C and circulating raw river water through glass columns filled with pumice. 3-Chloro-4-methylaniline was added to the column at a concentration of 6 ug/L; detection limit was 0.44 ug/L(1).

AEROBIC: 3-Chloro-p-toluidine hydrochloride applied to a sandy loam soil, maintained at 20 °C, at concentrations of 3.5 and 35 ug/g exhibited first order kinetics with a calculated rate constant of 2.74X10-2/hr, corresponding to a half-life of 25 hours. Approximately 13% of the radiolabeled compound applied at 3.5 ug/g was mineralized to carbon dioxide during 99 days of incubation. The primary metabolite was acetyl-3-chloro-p-toluidine, which itself had a half-life of 26 hours. 3-Chloro-p-toluidine hydrochloride applied at 35 ug/g was also mineralized, however at a much slower rate(1). /3-Chloro-p-toluidine hydrochloride/

PURE CULTURE: A partially purified enzyme of the soil fungus Geotrichum candidum converted 3-chloro-p-toluidine to 3,3'-dichloro-4,4'' dimethylazobenzene(2). The same compound was isolated when 3-chloro-p-toluidine was incubated in soil(1). The rate of loss of the parent compound due to this reaction in soil was not given(1).

3-Chloro-p-toluidine

TR-145: Bioassay of 3-Chloro-p-Toluidine for Possible Carcinogenicity (CASRN 95-74-9) (1978 )

06/29/78

No Evidence

No Evidence

No Evidence

An estimated BCF of 15 was calculated in fish for 3-chloro-p-toluidine(SRC), using an estimated log Kow of 2.27(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Bluegill sunfish (Lepomis macrochirus) were continuously exposed to 0.1 um/mL of uniformly -labled 3-chloro-p-toluidine hydrochloride for 28 days, followed by 28 days depuration. Concentrations in the edible, nonedible, and whole-body tissues were 2.9, 12.0, and 7.5 ug/g tissue, respectively. BCF values of 33, 150, and 88, respectively, were calculated. About 64% of the accumulated radiolabeled compound and metabolites were eliminated from the fish by day 28 of depuration. The authors conclude that bioconcentration will be low at sublethal concentrations(1). A log BCF of 1.9445 was reported, corresponding to a BCF of 88(SRC), in bluegill sunfish exposed to 3-chloro-p-toluidine hydrochloride for 28 days in accordance with EPA guideline 165.4 - Laboratory Studies of Pesticide Accumulation in Fish(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration of 3-chloro-p-toluidine hydrochloride in aquatic organisms is low to moderate(SRC). /3-Chloro-p-toluidine hydrochloride/

Based on the reviews of the generic data for the active ingredients starlicide, the Agency has sufficient information on the health effects of starlicide and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that starlicide products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing starlicide for all uses are eligible for reregistration. /3-Chloro-p-toluidine hydrochloride/

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. 3-Chloro-p-toluidine hydrochloride is found on List B. Case No: 2610; Pesticide type: insecticide (avicide); Case Status: RED Approved 9/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 3-chloro-p-toluidine hydrochloride; Data Call-in (DCI) Date(s): 2/15/91; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI. /3-Chloro-p-toluidine hydrochloride/

Ring-labeled (14)C-3-chloro-4-methylaniline hydrochloride (250 ug per bird) was delivered to 21 red-winged blackbirds (Agelaius phoeniceus) and 21 dark-eyed juncos (Junco hyemalis) via oral gavage ... The average half-life of elimination for the initial phase in most tissues examined was 0.16 hr for juncos and 0.62 hr for blackbirds. The average for the slower second phase of elimination was 3.4 hr for juncos and 5.4 hr for blackbirds ...

Bluegill sunfish (Lepomis macrochirus) were continuously exposed to 0.1 ug/mL of uniformly radiolabeled (14)C-3-chloro-p-toluidine hydrochloride (CPTH) for 28 days, after which the fish were transferred to flowing untreated water for a 28-day depuration period ... The steady-state concentrations in the bluegill tissues were reached by day 7 of exposure to the radiolabeled compound, with mean concentrations in the edible, nonedible, and whole-body tissues determined to be 2.9, 12.0, and 7.5 ug/g of tissue, respectively. Bioconcentration factors of 33x, 150x, and 88x were calculated for the three types of tissues. About 64% of the accumulated radiolabeled CPTH and metabolites were eliminated from the fish on day 28 of depuration. The distribution of radioactivity was found to be similar in all tissue groups. One metabolite was confirmed as N-acetyl-3-chloro-p-toluidine, with two metabolites suggested to be 4-acetamido-2-chlorobenzoic acid and 4-amino-2-chlorobenzoic acid. The N-acetylated breakdown product has been previously reported to occur in both mammals and birds; thus, the metabolism of CPTH in fish may parallel that observed in these other species. /3-Chloro-p-toluidine hydrochloride/

Single oral doses of approx 500 mg/kg bw of 3-chloro-p-toluidine were administered to rats (strain and sex not given), and the urine was examined for the unchanged substance and for three possible metabolites, namely: 4-amino-2-chlorobenzoic acid (oxidation of the methyl group of the carboxyl group); 3-chloro-p-acettoluidide (acetylation of the amino group); and 4-acetamino-2-chlorobenzoic acid (oxidation of the methyl group to the carboxyl group and actylation of the amino group). The following percentages of the administered substance were found within 98 hr: unchanged substance 6%, 4-acetamino-2-chlorobenzoic acid 8%, 4-amino-2-chlorobenzoic acid 2.5%, and 3-chloro-p-acettoluidide 1%. Although the whereabouts of the rest was unknown, the formation of conjugated derivatives, such as glucuronides or mercaptourides, is very probably. With regard to the methemoglobin formation, the formation of the hydroxylamine derivative (4-hydroxyamino-2-chlorotoluene) was also to be expected. The excretion of the examined compounds was completed practically 50 hr after the application. /3-Chloro-p-toluidine hydrochloride/

(14)C-3-Chloro-p-toluidine HCL was injected iv to starlings. A hydroxylamine metabolite of the parent compound possibly binds to liver protein and may be responsible for hepatic necrosis.

Study of the tissue distribution and the binding behavior of (14)C-labeled 3-chloro-p-toluidine (the hydrochloride was administered iv at a dose of 5.9 mg/kg bw) in male mice (strain not given): the radioactivity associated with the compound was unevenly distributed in different parts of the body. With the exception of the spleen, brain, and liver, a two-phased elimination was differentiated whereby the first phase was fast and the second one was slow. The half lives of the fast phase were equal for all tissues except muscle (6.85 hr) and ranged between 1.52 and 3.96 hr. The half-lives of the slower phase showed a different pattern, being shortest (14.55 hr) in the intestine and longest (326 hr) in the adipose tissue. Covalent binding of 3-chloro-p-toluidine or its metabolites to proteins was ascertained in the liver, kidney, lung, and erythrocytes. The subcellular distribution of the radioactivity corresponded to the protein composition of the individual fractions. Of these fractions, the soluble liver and kidney cell fraction exhibited the highest absolute and specific activity (activity per mg protein). The extent of the covalent binding does not correlate with the tissue half-life nor with the pathological tissue findings. The covalent binding in erythrocytes could be an indication of a reactive methemoglobin-forming metabolite. /3-Chloro-p-toluidine hydrochloride/

The concentration of 3-chloro-p-toluidine and diazotizable metabolites was determined in whole blood of female mice (strain not given) following ip administration of 3-chloro-p-toluidine hydrochloride at a dose of 2 mmol/kg bw (= 356 mg/kg bw). The concentration dropped almost linearly within the first 12 hr (half-life 6.6 hr) and attained zero after 24 hr. /3-Chloro-p-toluidine hydrochloride/

Ring-labeled (14)C-3-chloro-4-methylaniline hydrochloride (250 ug per bird) was delivered to 21 red-winged blackbirds (Agelaius phoeniceus) and 21 dark-eyed juncos (Junco hyemalis) via oral gavage, and the distribution and excretion of radioactivity were determined at 15 and 30 min and 1, 4, 8, 12, and 24 hr (n = 3 per time point). Direct measurement of radioactivity as well as measurement following combustion was accomplished using a liquid scintillation counter. Elimination from most tissues followed a two-compartment model, with very rapid elimination occurring between time 0 and 4 hr and a much slower elimination phase occurring after that. The average half-life of elimination for the initial phase in most tissues examined was 0.16 hr for juncos and 0.62 hr for blackbirds. The average for the slower second phase of elimination was 3.4 hr for juncos and 5.4 hr for blackbirds. The radioactivity in blackbird kidney tissues did not change significantly for the duration of the test, pointing toward the kidney as a possible site of action ...

Radioactivity was unevenly distributed in the body and the extent of covalent binding to kidney protein exceeded binding to liver protein after iv admin of (14)C-3-chloro-p-toluidine in the starling.

The maximal covalent binding occurred at 18 hr to kidney protein, and at 12-18 hr to liver and lung protein after iv admin of (14)C-3-chloro-p-toluidine in mice.

Used as a bird control agent and in the production of the acid dye palatine fast yellow; [HSDB]

Farming (Pesticides) [Category: Industry]

For 3-chloro-p-toluidine hydrochloride (USEPA/OPP Pesticide Code: 009901) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./ /3-Chloro-p-toluidine hydrochloride/

Currently, all starlicide products are classified for restricted use with the exception of one. The restricted use classification is necessary to address the potential for harm to applicators and because products are applied to various baits and placed in a variety of areas where exposure to endangered or other non-target species could occur. A ready-to-use 0.1% formulation, which is used in unoccupied cattle and poultry feeding structures, is the only remaining end-use product currently classified for general use. Because of the potential for adverse effects to non-target organisms which could result from the use of this product, the Agency is reclassifying it as restricted use. /3-Chloro-p-toluidine hydrochloride/

... Intermediate in the manufacture of the herbicide chlortoluron and the red pigment intermediate "2B-Acid."

... Used as an intermediate in the production of other intermediates for the manufacture of organic pigments and agricultural chemicals.

2023: 500,000 - <1,000,000 lb

(1972) Probably > 4.54X10+5 g

(1975) Probably > 4.54X10+5 g

Benzenamine, 3-chloro-4-methyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzenamine, 3-chloro-4-methyl-. Aggreated National Production Volume: <500,000 lbs.

A complete list of currently registered active pesticide products can be found in the National Pesticide Information Retrieval System's USEPA/OPP Registered and Cancelled Pesticide Product Database. These pesticide products are registered for use in the U.S. but approved products may change periodically and so federal, state and local authorities must be consulted for currently approved products.

Compound DRC-1339 Concentrate (USDA): Starlicide 97% /3-Chloro-p-toluidine hydrochloride/

Starlicide Complete (PM Resources): Starlicide 0.1% /3-Chloro-p-toluidine hydrochloride/

Starlicide Technical (PM Resources): Starlicide 97% /3-Chloro-p-toluidine hydrochloride/

All Other Chemical Product and Preparation Manufacturing

Benzenamine, 3-chloro-4-methyl-: ACTIVE

Slow-acting drug to kill bird pests, particularly starlings, by mixing 1 part of medicated feed with 10 parts of other pelleted feed near perimeter of feedlots, under feedbanks, in aisles, or along fence rows. Dosage: available as a 1% concentration in treated pellets.

An avicide that has been used to control starlings in CA. /3-Chloro-p-toluidine hydrochloride/