3-アミノ-2,5-ジクロロ安息香酸

Pesticide -> EPA IRIS

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Other

Pesticide

log Kow = 1.11

1.46

less than 0.1 mg/mL at 72 °F (NTP, 1992)

water solubility = 700 mg/l @ 25 °C

SOLUBILITY IN ETHANOL: 172 G/L @ 25 °C

SOL IN ALKALI

SOLUBILITY IN ACETONE: 23.27 G/100 G @ 29 °C

For more Solubility (Complete) data for AMIBEN (9 total), please visit the HSDB record page.

DISASTER HAZARD: WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES SUCH AS /HYDROGEN/ CHLORIDE AND NITROUS OXIDES.

... DANGEROUS; WHEN ... /IN/ CONTACT WITH ACIDS OR ACID FUMES THEY EVOLVE HIGHLY TOXIC /HYDROGEN/ CHLORIDE FUMES. SOME ORG CHLORIDES DECOMP TO YIELD PHOSGENE. /CHLORIDES/

381 to 387 °F (NTP, 1992)

200-201 °C

MP: ABOVE 195 °C /TECHNICAL PRODUCT/

200 °C

0.007 mmHg at 212 °F (NTP, 1992)

0.0000001 [mmHg]

930 mPa @ 100 °C

0.007 [mm Hg] @100 °C

Purplish white powder or light purple solid. (NTP, 1992)

Colorless odorless solid; Technical product is purplish white solid; [HSDB]

This chemical does not meet GHS hazard criteria for 7.1% (3 of 42) of reports.

Danger

H315 (92.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard Traits - Dermatotoxicity

2002/2076

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Chloramben is used as a herbicide on a number of crops. Limited information is available on the health effects of chloramben. Acute (short-term) exposure to high levels of chloramben in humans results in mild to moderate dermal irritation. No information is available on the chronic (long-term) effects of chloramben in humans. Animal studies have reported effects on the liver from chronic oral exposure to chloramben. A National Toxicology Program Study reported that oral exposure to chloramben caused liver tumors in mice, but not in rats. EPA has not classified chloramben for potential carcinogenicity.

Rapidly excreted after ingestion; [EXTOXNET PIP - Chloramben] Little or no sensitization reactions observed in male guinea pigs; Histopathological liver changes observed in 18-month dietary study of mice (LOAEL of 15 mg/kg/day for hepatic effects); [ToxPlanet: EPA - Health Effects Assessments] A mild to moderate skin irritant; [HSDB] A skin and strong eye irritant; Targets the liver; [Sigma-Aldrich MSDS]

USEPA/ODW; Health Advisories for 50 Pesticides (8/88) NTIS No. PB88-245931

DHEW/NCI; Bioassay of Chloramben for Possible Carcinogenicity (1977) Technical Rpt Series No. 25 DHEW Pub No. (NIH) 77-825

Tolerances are established for residues of the herbicide chloramben in or on the following raw agricultural commodities: beans dried; beans, lima; beans, snap; beans, vines; cantaloupes; corn, field, fodder; corn, field, forage; corn, field, grain; cucumbers; peanuts; peanuts, forage; peas, pigeon; peas, pigeon, forage; peppers; pumpkins; soybeans; soybeans, forage; squash, summer; squash, winter; sunflower seed; sweet potatoes; and tomatoes.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Amiben is included on this list.

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.

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 ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 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 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.

Reuse: The use of chemical reagents as a means of disposal is not recommended at the present time. Amiben's shelf life is of sufficient duration to allow for total use of the product in accordance with label directions. On this basis, there should be few instances of small quantities of excess amiben requiring disposal. For the decontamination of amiben containers, the National Agricultural Chemical Association (USA) recommends triple rinse. "Triple rinse" means the flushing of containers three times, each time using a volume of the normal diluent equal to approx ten percent of the container's capacity and adding the rinse liquid to the spray mixture or disposing it by the method prescribed for disposing of the pesticide.

Incinerate in a unit equipped with an effluent gas scrubber at a temperature above 1000 C about 1-2 seconds. Recommendable method: Incineration.

Wet Oxidation: Studies of wet oxidation process applied to amiben herbicide process wastes indicate 88 to 99.5% destruction of the active ingredient.

Tolerances are established for residues of the herbicide chloramben in or on the following raw agricultural commodities: beans dried: 0.1 ppm; beans, lima: 0.1 ppm; beans, snap: 0.1 ppm; beans, vines: 0.1 ppm; cantaloupes: 0.1 ppm; corn, field, fodder: 0.1 ppm; corn, field, forage: 0.1 ppm; corn, field, grain: 0.1 ppm; cucumbers: 0.1 ppm; peanuts: 0.1 ppm; peanuts, forage: 0.1 ppm; peas, pigeon: 0.1 ppm; peas, pigeon, forage: 0.1 ppm; peppers: 0.1 ppm; pumpkins: 0.1 ppm; soybeans: 0.1 ppm; soybeans, forage: 0.1 ppm; squash, summer: 0.1 ppm; squash, winter: 0.1 ppm; sunflower seed: 0.1 ppm; Sweet potatoes: 0.1 ppm; and tomatoes: 0.1 ppm.

11 [mg/m3]

120 [mg/m3]

690 [mg/m3]

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

LOSS /OF CHLORAMBEN/ BY LEACHING WAS MOST PRONOUNCED FROM A SANDY SOIL & WAS PROGRESSIVELY LESS AS CLAY & ORGANIC COMPONENTS INCREASED.

VOLATILITY & SOIL MOVEMENT ARE MORE DEPENDENT ON FORM OF CHLORAMBEN APPLIED THAN ON SOIL TYPE. ...ALUMINUM & AMMONIUM SALTS... WERE EASILY LEACHED FROM SEVERAL ARKANSAS SOILS. METHYL & BUTOXYETHYL ESTERS RESISTED LEACHING, WHILE AMIDE WAS INTERMEDIATE WITH RESPECT TO LEACHING.

/FROM INVESTIGATIVE STUDIES/ ... ONE MIGHT EXPECT THAT CHLORAMBEN PERSISTENCE ... /MAY/ BE GREATEST AS THE BUTOXYETHYL ESTER IN DRY SOIL OF HIGH ORG CONTENT & LEAST FOR ... SALT IN A MOIST SANDY SOIL WHERE HIGH RAINFALL WOULD ACCELERATE LEACHING.

ABSORPTION OF CHLORAMBEN TO SOIL PARTICLES SIGNIFICANTLY REDUCED HERBICIDAL ACTIVITY. ... IN ONE INSTANCE, UNDER CONTROLLED LAB CONDITIONS, A MUCK SOIL ABSORBED 29% OF APPLIED CHLORAMBEN, WHEREAS A SILTY CLAY LOAM ABSORBED ONLY 9%. ... DESORPTION OF CHLORAMBEN FROM MUCK SOILS IS SLOW.

For more Environmental Fate (Complete) data for AMIBEN (9 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. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=133-90-4]

Chloramben

Hepatic

1.5 x 10 ^-2 mg/kg-day

Amiben is expected to have anionic properties in most soil systems under environmental conditions (pH 5-9). When a column of Ella island soil type (pH 3.8, 1.6% organic matter, 82.7% sand, 12.2% silt, and 5.2% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 1.4 ppm (24.6%) and 5.0 ppm (18.5%) Amiben adsorbed to the soil, respectively. When a column of Kewaunee clay soil type (pH 6.4, 3.8% organic matter, 14% sand, 35.1% silt, and 48.7% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm 14COOH-labelled Amiben, 0.6 ppm (11.1%) and 2.6 ppm (9.8%) Amiben adsorbed to the soil, respectively. When a column of Poygan silty clay soil type (pH 7.2, 10% organic matter, 6% sand, 58.9% silt, and 33.6% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm 14COOH-labelled Amiben, 1.4 ppm (24.6%) and 5.4 ppm (20.1%) Amiben adsorbed to the soil, respectively. Therefore, soil pH and organic matter content are the primary factors controlling Amiben adsorption with higher adsorption to soil occurring either at a low pH with a low organic matter content or at a neutral pH with a high organic matter content(1).

In a study of the adsorption of organic herbicides by montmorillonite, Amiben at an initial concentration of 500 umol/L exhibited no adsorption or negative adsorption to Na-montmorillonite soil (pH 6.8 and 87.0 cation exchange capacity) and H-montmorillonite soil (pH 3.35 and 73.5 cation exchange capacity)(3). Amiben was more strongly adsorbed to soil with high organic matter content; furthermore, adsorption of Amiben to soil particles significantly reduced herbicidal activity(5). Based on adsorption studies of 12 soils, a mean Koc value of 190 was determined for amiben(1). In another adsorption study, an experimental Koc value of 21 was determined for Amiben(2). These Koc values indicate that Amiben will have high to very high mobility in soil and will leach(4). However, protonated Amiben may exhibit higher adsorption at lower pHs than its Koc values indicate(SRC).

STUDIES WITH SOIL MICROFLORA INDICATED THAT BREAKDOWN OF AMIBEN OCCURRED...& THAT THE CARBOXYL WAS CLEAVED SLOWLY BUT STEADILY.

MOVES READILY IN SANDY SOILS OR FOLLOWING HEAVY RAINS. ... BROKEN DOWN BY MICROORGANISMS. ... SOME PHOTOCHEMICAL LOSS IN AQUEOUS SOLN. ON MOIST SOIL LOSS REPORTED BUT SOIL MUST REMAIN MOIST FOR LOSS TO OCCUR ... AVG PERSISTENCE @ RECOMMENDED RATES: APPROXIMATELY 6 TO 8 WEEKS.

When a column of Ella island soil type (pH 3.8, 1.6% organic matter, 82.7% sand, 12.2% silt, and 5.2% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 56.2 and 39.1% biodegradation was observed for Amiben, respectively. When a column of Kewaunee clay soil type (pH 6.4, 3.8% organic matter, 14% sand, 35.1% silt, and 48.7% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 42.7 and 27.7% biodegradation was observed for Amiben, respectively. When a column of Poygan silty clay soil type (pH 7.2, 10% organic matter, 6% sand, 58.9% silt, and 33.6% clay) was perfused for 160 days with a microbial medium containing 5.7 and 26.9 ppm (14)-COOH-labelled Amiben, 40.3 and 22.6 % biodegradation was observed for Amiben, respectively(1).

In an aerobic biodegradation study in a Honeoye silt loam at 25 °C and pH 6.5, amiben biodegraded slowly at rate of 4,500, 6,500, 11,500, and 74,000 cpm (cumulative (14)-CO2 evolution) after 7, 14, 28, and 112 days, respectively(1). According to a bioassay using the soybean plant and 50 ppm Amiben in soil, there was no breakdown of Amiben over an 11-month incubation period in moist soil at 15 °C; at incubation temperatures of 25 and 35 °C, Amiben breakdown over an 11-month period was 42 and 46 percent, respectively(2). Amiben showed the greatest loss of activity in Staten Island peaty muck (42% dissolved organic carbon and pH 5.8) which suggests that the rate of degradation depends on the organic content(3).

Tolerances are established for residues of the herbicide chloramben in or on the following raw agricultural commodities: beans dried; beans, lima; beans, snap; beans, vines; cantaloupes; corn, field, fodder; corn, field, forage; corn, field, grain; cucumbers; peanuts; peanuts, forage; peas, pigeon; peas, pigeon, forage; peppers; pumpkins; soybeans; soybeans, forage; squash, summer; squash, winter; sunflower seed; sweet potatoes; and tomatoes.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Amiben is included on this list.

(FL) FLORIDA 110 ug/L

(MN) MINNESOTA 100 ug/l

(WI) WISCONSIN 150 ug/l

THE MAJOR PATHWAY OF CHLORAMBEN METABOLISM IN BOTH TOLERANT & SUSCEPTIBLE PLANT SPECIES APPEARS TO BE A RAPID FORMATION OF METHANOL-SOLUBLE CONJUGATES & "BOUND" INSOLUBLE RESIDUES.

IN PLANTS, AMIBEN IS CONVERTED TO N-GLUCOSYLAMINE. THE ENZYME, ISOLATED FROM SOYBEANS ... FOUND TO BE SPECIFIC FOR URIDINE DIPHOSPHATE-5'-GLUCOSE & CORRESPONDING THYMIDINE ANALOG.

... THE PROLONGED IN VIVO STABILITY, IMMOBILITY, & ACCUM OF ... /THE N-GLUCOSIDE CONJUGATE/ IN BOTH SUSCEPTIBLE & TOLERANT PLANTS STRONGLY ... /SUGGESTS/ THAT N-GLUCOSIDE BIOSYNTHESIS IS A MAJOR DETOXICATION MECHANISM.

YIELDS 3-AMINO-2,5-DICHLOROBENZOIC ACID-N-GLUCOSIDE IN SOYBEAN, BARLEY, BEET, TOMATO, CUCUMBER. /FROM TABLE/

CHLORAMBEN METAB IN PLANTS. A REPORTED CHLORAMBEN-X CONJUGATE IDENTIFIED AS METHYL 3-AMINO-2,5-DICHLOROBENZOATE (CHLORAMBEN METHYL ESTER) WAS AN ARTIFACT FORMED BY TRANSESTERIFICATION OF AN UNKNOWN ESTER METABOLITE DURING CLEAN UP OF METHANOL EXTRACTS OF FLORISIL COLUMNS.

... /STUDIES IN A LACTATING COW SHOWED THAT OVER/ A PERIOD OF 4 DAYS, DIETARY CHLORAMBEN (5 PPM IN DAILY RATION) WAS RAPIDLY EXCRETED IN URINE (88%) & FECES (5%). NO RESIDUES WERE DETECTED IN THE MILK. APPROX 18% OF CHLORAMBEN IN URINE WAS PRESENT AS UNKNOWN CONJUGATED MATERIAL.

... UNPUBLISHED FEEDING STUDIES WITH DOGS ... SHOWED ... THAT DIETARY CHLORAMBEN (5 PPM) WAS RAPIDLY EXCRETED IN URINE & FECES, & NO ... RESIDUES WERE DETECTED IN TISSUE SAMPLES TAKEN ... .

ACIDIC COMPOUNDS SUCH AS 3-AMINO-2,5-DICHLOROBENZOIC ACID ARE BOUND TO BOVINE SERUM ALBUMIN. BLOOD/TISSUE RATIOS OF (14)C FROM RATS DOSED WITH LABELED ACID WERE HIGHLY CORRELATED WITH THE LOGARITHM OF BINDING AFFINITY CONSTANTS.

Chloramben is used as a herbicide to control grasses and broadleaf weeds on soybeans, dry beans, lima beans, asparagus, pumpkins, squash, corn, tomatoes, peppers, and sweet potatoes.

Used as a selective pre-emergence herbicide to control annual grasses and broad-leaf weeds in various food crops (mainly soybeans), trees, and shrubs; [EXTOXNET PIP - Chloramben]

Farming (Pesticides) [Category: Industry]

HERBICIDE FOR GRASSES & BROADLEAF WEEDS ON SOYBEANS, DRY BEANS, LIMA BEANS, ASPARAGUS, PUMPKINS, SQUASH, CORN, TOMATOES, PEPPERS, SWEET POTATOES

PREPLANT INCORPORATED OR PRE-EMERGENCE WEED CONTROL. APPLIED AT PLANTING OF CORN, DRY BEANS, LIMA BEANS, PEANUTS, PUMPKINS, SEEDLING ASPARAGUS, SOYBEANS, SQUASH, SUNFLOWERS, ESTABLISHED TOMATOES AND PEPPERS, CUCUMBERS, CANTALOUPES, SNAPBEANS, AND SWEET POTATOES. POST EMERGENCE IN SOYBEANS.

/IT IS MADE BY/ CHLORINATION OF BENZOIC ACID, FOLLOWED BY NITRATION & REDUCTION.

CHLORAMBEN IS SYNTHESIZED FROM PURIFIED DINOBEN BY REDUCTION OF NITRO GROUP.

THESE INCLUDE; 'AMIBEN', AQUEOUS SOLN (240 G AE/L) & 'AMIBEN GRANULAR 10%', GRANULES (100 G AE/KG).

THE TECHNICAL PRODUCT IS ... ABOUT 90% PURE ...

Benzoic acid, 3-amino-2,5-dichloro-: ACTIVE

INHIBITS ROOT DEVELOPMENT OF SEEDLING WEEDS.

/AMIBEN IS SUGGESTED FOR USE/ ... AT 2-4 KG AE/HA.

Used at 2 ug ai/kg