Agent Green
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Agent Green
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CAS No:
93-79-8
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Formula:
C12H13Cl3O3
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Chemical Name:
Agent Green
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Synonyms:
Acetic acid,2-(2,4,5-trichlorophenoxy)-,butyl ester;Acetic acid,(2,4,5-trichlorophenoxy)-,butyl ester;2,4,5-T Butyl ester;n-Butyl (2,4,5-trichlorophenoxy)acetate;Trioxone;Butyl 2,4,5-T;U 46KW;(2,4,5-Trichlorophenoxy)acetic acid butyl ester;Flomore;2,4,5-T n-Butyl ester;Butyl (2,4,5-trichlorophenoxy)acetate;Arboricid;Krzewotoks;Krzewotox;Tormona;Hi-Ester 2,4,5-T;NSC 190448;Agent Green;53851-79-9
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CAS No:
Description
PHYSICAL DESCRIPTION: Clear colorless liquid or white solid. (NTP, 1992)
2,4,5-t, n-butyl ester appears as clear colorless liquid or white solid. (NTP, 1992)
2,4,5-t, n-butyl ester appears as clear colorless liquid or white solid. (NTP, 1992)
Agent Green Basic Attributes
311.59
311.59
202-277-5
M64EJ224KL
190448
3348
DTXSID7026073
2918990090
Characteristics
35.53000
4.36890
2,4,5-t, n-butyl ester appears as clear colorless liquid or white solid. (NTP, 1992)
1.324g/cm3
28.5 °C
337 °C
142.2ºC
1.528
Insol in water; sol in oils.
1.50e-05 mmHg
Thermal decomposition to emit toxic chloride fumes
AMBER OR DARK AMBER COLORED LIQUID /2,4,5-T ESTERS/|Very weak odor; mixtures with kerosene or diesel oil have odor of the solvent /2,4,5-T esters/
Insoluble in water.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
2,4,5-T, N-BUTYL ESTER is an ester of a chlorinated organic acid. May react exothermically with acids to generate butyl alcohol and 2,4,5-trichlorophenoxyacetic. Strong oxidizing acids may cause a reaction that is sufficiently exothermic to ignite the reaction products. Heat may also be generated with caustic solutions.
May attack some forms of plastics /2,4,5-T esters/|The salts & esters of 2,4,5-T are non-corrosive under normal application conditions /2,4,5-T/
Safety Information
IRRITANT
3348
Warehouse ventilated, low temperature and dry
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number F027, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /2,4,5-T cmpd/|Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/
Nat'l Research Council Canada; Phenoxy Herbicides Their Effects on Environmental Quality (1978) NRCC No. 16075|Vet Admin Rev Lit on Herbicides (1981) VA Contract No. V101(93)p-823|USEPA; Ambient Water Quality Criteria Doc: 2,3,7,8-Tetrachlorodibenzo-p-dioxin (1980) EPA 440/5-80-072|USEPA; Drinking Water Criteria Document: 2(2,4,5-trichlorophenoxy) propionic acid (2,4,5-TP) (1987)
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
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. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures and away from mineral acids and bases. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Wear appropriate chemical protective ... boots and goggles. /2,4,5-T amine, ester, or salt/|... Rubber gloves ... /2,4,5-T esters/
They will burn, though they may take some effort to ignite. /2,4,5-T amine, ester, or salt/
Extinguish fire using agent suitable for type of surrounding fire. /2,4,5-T amine, ester, or salt/|WATER, FOAM, DRY CHEM, CARBON DIOXIDE. ... WATER OR FOAM MAY CAUSE FROTHING. /2,4,5-T ESTERS/
Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. /2,4,5-T amine, ester, or salt/|Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /2,4,5-T amine, ester, or salt/
If material /is not/ involved in a fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. /2,4,5-T amine, ester, or salt/|Keep upwind. ... Avoid breathing vapors or dusts. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /2,4,5-T amine, ester, or salt/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.
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.
Irritating to skin and eyes. /2,4,5-T esters/
F027; A hazardous waste from nonspecific sources when a component of a discarded unused formulation. /2,4,5-T/
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). /2,4,5-T Esters/
F027; As stated in 40 CFR 261.31, discarded unused formulations containing tri-, tetra-, or pentachlorophenol or discarded unused formulation containing compounds derived from these chlorophenols. (This listing does not include formulations containing hexachlorophene synthesized from prepurified 2,4,5-trichlorophenol as the sole component.). /2,4,5-T/
During mixing & spraying operations along power line right-of-way, airborne concn of 2,4,5-T esters were < 10-60 ug/cu m. /Chlorophenoxy herbicides/
Toxicity
LD50 Rat female oral 481 mg/kg|LD50 Mouse female oral 940 mg/kg|LD50 Guinea pig female oral 750 mg/kg|LD50 Rabbit male oral 712 mg/kg
The major herbicides sprayed in South Vietnam that contained ester of 2,4,5-T were Orange/Orange II, Purple, and Pink. One gallon of Orange contained approximately 4.6 pounds of the acid equivalent of 2,4,5-T. The specified formulation for Orange was 50% by weight of the n-butyl ester of 2,4,5-T. Assuming one gallon of Orange weighed 10.7 pounds, one gallon of the specified formulation of Orange would contain approximately 5.4 pounds of the n-butyl ester of 2,4,5-T. Therefore, Orange applied at three gallons per acre is estimated to have released a maximum of 13.8 pounds per acre of the acid equivalent of 2,4,5-T and 16.2 pounds per acre of the n-butyl ester of 2,4,5-T per spraying. The actual amount of 2,4,5-T released per acre was probably less than estimated because, actual samples of Orange contained less than 50% by weight of the n-butyl ester of 2,4,5-T. Furthermore, spray drift and volatilization generally reduced the amount deposited per acre. Canopy cover in heavily forested areas would, as in the case of other chemicals, greatly reduce the amount of ester reaching ground level.|The densities of Purple and Pink could not be found in the literature. Assuming the densities of Purple and Pink were similar to Orange, one gallon of Purple or Pink would have weighed approximately 10.7 pounds. The specified formulation of Purple was 30 percent by weight the n-butyl ester of 2,4,5-T and 20% by weight the isobutyl ester of 2,4,5-T, so one gallon of the specified formulation of Purple would contain approximately 3.2 pounds of the n-butyl ester of 2,4,5-T and 2.1 pounds of the isobutyl ester of 2,4,5-T. Therefore, Purple applied at 1.5 gallons per acre is estimated to have released a maximum of 4.8 pounds per acre of the n-butyl ester of 2,4,5-T and 3.2 pounds per acre of the isobutyl ester of 2,4,5-T. the specified formulation of Pink was 60% by weight the n-butyl ester of 2,4,5-T and 40% by weight the isobutyl ester of 2,4,5-T, so one gallon of the specified formulation of Pink would contain approximately 6.4 pounds of the n-butyl ester of 2,4,5-T and 4.3 pounds of the isobutyl ester of 2,4,5-T. Therefore, Pink applied at 1.5 gallons per acre is estimated to have released a maximum of 9.6 pounds per acre of the n-butyl ester of 2,4,5-T, and 6.5 pounds per acre of the isobutyl ester of 2,4,5-T.|Spray from application of the herbicide or in ambient air as a result of spraying(1), spills(2). 2,4,5-T herbicides are no longer used in the US and Canada(4). Both Agent Orange and Agent Purple contained 50% of the n-butyl ester of 2,4,5-T along with other chlorophenoxyacetate esters(3).
A steep hill country area (1.66 ha) of gorse and pasture was sprayed with 2,4,5-T, N-butyl ester (0.72 kg/l solution at an application rate of 300 l/ha) by air. Soil and vegetation samples were collected at regular intervals and a stream at the bottom of the trial area was monitored continuously over 6 mo. Only 0.6% of the applied herbicide entered the stream during the trial, with 0.4% being washed out in the first storm. Measurable traces of the original ester formulation, 2,4,5-T (acid), and the principal breakdown product 2,4,5-trichlorophenol (2,4,5-TCP), with a combined avg of about 0.4 mg/kg, were found in pasture vegetation 6 mo after initial application. The persistence of these residues may be a cause of dietary intake by grazing livestock. Soil residues (expressed as butyl ester) persisted throughout the study, principally as 2,4,5-TCP (12-100 ng/g after 185 days), and were also detected from a treatment 1 yr before the trial began (20-90 ng/g). An estimate of the masses of residues and losses 6 days after spraying accounted for about 20% of the applied mass. A significant part of the balance (80%) is thought to have been lost in spray drift.|TERRESTRIAL FATE: Under field conditions, the n-butyl ester of 2,4,5-T should be hydrolyzed in soil to the parent acid in approximately 1 day or less at moisture levels in excess of the wilting point(1). Massive quantities of the n-butyl ester of 2,4,5-T (up to 4,480 kg/ha, the recommended application rates are 0.56 to 17.9 kg/ha(3)) were applied to field plots in three climatically different areas of the US, namely Northwestern Florida, Western Kansas, and Northwestern Utah(2). The soil type and rainfall in the three areas were: sandy loam (0.5% organic matter (OM), pH 5.6), 150 cm; silt loam (1.7% OM, pH 7), 40 cm; and clay loam (1.4% OM, pH 7.8), 15 cm, respectively. After 2 yrs, the acid of 2,4,5-T compromised most of the total residue at all sites, and 90% of that was confined to the top 15 cm of the soil profile. The application of lime, organic matter, or fertilizer did not increase the rate of disappearance. However the incorporation of activated charcoal impeded degradation, probably by binding the herbicide(2).|TERRESTRIAL FATE: In another experiment involving the fate of massive quantities of 2,4,5-T, n-butyl ester, the herbicide was applied at 560 and 1800 kg/ha to Washington Silt loam (5.0% OM, pH 5.5), Wyoming Clay loam (3.8% OM, pH 7.6) and Mississippi Sandy loam (2.2% OM, pH 4.7) in lysimiters in Pullman, WA(1,2). The analysis did not distinguish between the acid or the ester. Little or no degradation occurred over the first four cool winter months. At the lower application rate, the Washington and Wyoming soils respectively contained 2.4 and 0.5% of the applied ester after 28 months(2). In experiments the following year, residues in Mississippi and Washington soils were reduced to 47.9 and 7.9% after 20 months(2). Most of the residue was found in the top 10 cm; 3.74%, 0.33%, and 2.08% were found in the 10-30 cm depth in the Washington, Wyoming, and Mississippi soils, respectively(2). The experiments indicate that the pesticide is primarily lost by degradation, rather than by leaching or volatilization(SRC). Little or no degradation occurred at the higher level of application(2).|AQUATIC FATE: The 2,4,5-T, n-butyl ester can pollute water from runoff or deposition after spraying operations. It's hydrolysis half-life is 7.5 days at pH 7.5 and 20 °C and considerably longer at lower temperatures(1). The half-life is 1.4 and 12.8 days at pH 8.4 and 5.4, respectively. Hydrolysis is catalyzed by acid or base. The ester will adsorb to humic material in the water column. Humic material not only adsorbs the ester but exerts a pH dependent catalytic effect on the hydrolysis, the result of which would be to retard hydrolysis in basic waters and accelerate it in acid waters. Therefore, the rate of disappearence of the n-butyl ester of 2,4,5-T from natural waters will be dependent on pH and on the amount of humic materials in the water. The half-life is speculative but would probably vary from days to weeks(SRC).|For more Environmental Fate (Complete) data for 2,4,5-T, N-BUTYL ESTER (6 total), please visit the HSDB record page.
In long-term degradation studies of massive quantities of 2,4-D and 2,4,5-T in test grids, field plots and herbicide storage areas were carried out. The method of herbicide application had significant impact on the amt applied per unit area and hence on residue persistence: spills > or = soil incorporation > aerial application. 2,4,5-T was more persistent in the soil than 2,4-D. The formulation of the herbicide also had significant impact on its persistence: isooctyl ester > butyl ester > acid. The addition of coconut charcoal increases persistence of the phenoxy herbicide residues, especially residues of 2,4,5-T. The appearance of dichlorophenol and trichlorophenol in soils treated with 2,4-D and 2,4,5-T suggests that they are degradation products of the herbicides. A massive concn of herbicides does not sterilize the soils. Apparently, microbial populations respond both quantitatively and qualitatively to the presence of high concentrations of herbicides and may play an important role in their degradation. The contaminant 2,3,7,8-TCDD had a long persistence time in soils (years) and may be a major consideration in the use of soil biodegradation as a disposal option for unwanted phenoxy herbicides or TCDD-contaminated chemical wastes.|When the n-butyl ester of 2,4,5-T was applied (2.2 kg/ha) to four Saskatchewan soils (pH 5.6-7.3) which were air dried or moistened to their wilting point or field capacity and tested after 1.5 hr, 24-56% of the ester was recovered from soil moistened to field capactiy. After 24 hr all ester had disappeared from the moistened to the wilting point. 70-100% of the ester was recovered after 24 hr from the air dried soil(1). The rapidity of the hydrolysis combined with the fact no detectable hydrolysis was observed after 30 minutes in 0.1 M calcium chloride suggests that the hydrolysis is abiotic and soil-catalyzed(1). The product of hydrolysis is the parent acid, 2,4,5-T(1). Hydrolysis of phenoxyacetic esters is catalyzed by acids and base. However, catalysis by acid is less effective than by base(2). The hydrolytic half-life of the n-butyl ester of 2,4,5-T is 1.4, 7.5 and 12.8 days at 20 °C at pH 8.4, 7.5, and 5.4, respectively(2). At 4 °C the hydrolytic half-life is 10.1, 48.5, 63.0 and 62.0 days at pH 8.4, 7.4, 6.4, and 5.4 respectively(2).|In natural waters containing humic acids another complication arises which has been observed for the 1-octyl ester of 2,4-D but should be a general phenomenon. Hydrolysis in natural waters in the presence of humic material is affected by the adsorption of a fraction of the substrate to the humic material. Under acidic conditions, the humic acid catalyzes the reaction resulting in accelerated hydrolysis while under basic conditions the adsorbed material is simply less available resulting in a decrease of the overall hydrolysis rate(2). A recent theoretical model which has been put forward not only accounts for the decrease of alkaline hydrolysis rate by humic matter but also an increase in the acid hydrolysis rate(3). Vapor phase 2,4,5-T, n-butyl ester will react with photochemically produced hydroxyl radicals in the atmosphere primarily by H-atom abstraction. Assuming a hydroxyl radical concentration of 5X10+5 per cu cm, its half-life is estimated to be 3.7 days(4). The esters of 2,4,5-T should adsorb UV radiation > 290 nm(1); however, photochemical degradation of the 2,4,5-T esters in air or in water has not been demonstrated.|From limited data available, it may be concluded that any phenoxy herbicide, whether applied as ester or as dimethylamine salt formulations, may be chemically transformed to the same phenoxyalkanoic anion in soil and water at rates dependent on pH. These anions would presumably reassociate with a variety of inorganic cations present in the soil to maintain electrical neutrality, and then undergo leaching and biological degradation. /Phenoxy esters/
No data on the bioconcentration of the n-butyl ester of 2,4,5-T could be found in the literature. From the log of its octanol/water partition coefficient, 4.8(1), one would estimate a log BCF of 3.43(2). Because of hydrolysis, this bioconcentration potential must be viewed as an upper limit(SRC).
Concentrations of 2,4-D and 2,4,5-T in soils and leachates ... were monitored for up to 28 months to characterize the patterns of herbicide mobility in soils under climatic conditions of the Palouse region of the Pacific Northwest (USA). ... Soils from Washington, Wyoming, or Mississippi ... treated with 1120 or 5600 kg/ha of a 1:1 mixture of 2,4-D and 2,4,5-T n-butyl esters in 1976, 1977, or 1978. The winter of 1976-1977 was mild and relatively dry, and little leachate could be collected. Subsequent winters were wet and the soil columns were saturated by the following springs. 2,4-D (< 1 ppm) was found in leachates from Washington and Wyoming soils receiving the herbicide application in 1976 or 1977 and > 30 ppm was found in leachates from Washington soil treated in 1978. 2,4-D (> 10 ppm) was found in leachates from the acidic Mississippi soil receiving high rate of herbicide application in 1977 or 1978. Concentrations of 2,4,5-T in the same leachates were higher for the Washington and Wyoming soils, but lower (than corresponding concentrations of 2,4-D) for the Mississippi soil. In all cases, 96-99% of the undegraded herbicides ... remained in the 0-10 cm soil layer after 2-3 winters, and only 0.14-1.65% of the 2,4,-D and 0.33-3.7% of the 2,4,5-T remaining ... were present in the 10-30 cm depths. Mobility characterization by soil TLC showed that the ester form of both herbicides was relatively immobile, the acid form was less mobile in the Mississippi soil than in Washington and Wyoming soils and 2,4-D was slightly more mobile than 2,4,5-T under corresponding conditions.|2,4,5-T, n-butyl ester is relatively immobile in soil(4). Soil TLC experiments on three soils resulted in average Rf values of 0.4, 0.5, and 0.6(4). No Koc values for the n-butyl ester of 2,4,5-T could be found in the literature. From the reported log octanol/water partition coefficient, 4.81(1), one would estimate a Koc of 9,900(2). The Freundlich constant and exponent, 1/n, for 2,4,5-T, butyl ester on humic acids at pH 7.65 and 4 °C are 16 mol/l adsorbed per g adsorbent and 1.01, respectively(3).
The n-butyl ester of 2,4,5-T is one of the more volatile esters of 2,4,5-T (vapor pressure 1.5X10-5 torr at 25 degC(1)) and will slowly volatilize from surfaces such as foliage to which it is applied. Using a Henry's Law constant of 5.6X10-6 atm cu-m/mole calculate from the water solubility, 1.1 mg/l(2) and vapor pressure, one estimates a half-life for volatilization 11.8 days from a model river 1 m deep, flowing at m/sec, and with a 3 m/sec wind)(3).
The most probable route of exposure to 2,4,5-T would be inhalation and dermal exposure of workers involved in the manufacture, handling or application of 2,4,5-T, related ester compounds or certain tetradifon formulations which contain 2,4,5-T. The general public could potentially be exposed through inhalation of particulate matter or ingestion of fruit, milk or drinking water contaminated with 2,4,5-T. (SRC)|Exposure to chlorophenoxy herbicides may occur through inhalation, skin contact or ingestion. /Chlorophenoxy herbicides/|Agricultural workers may be exposed to 2,4,5-T, n-butyl ester during spraying operations using herbicides containing this chemical. The general population in areas of the country where this herbicide is used may be exposed from ambient air since there is evidence that such pesticides may be transported moderate distances. (SRC)|... Occupational exposure to chlorophenoxy herbicides ... is known to have occurred during their production, formulation, application & disposal. /Chlorophenoxy herbicides/
Drug Information
THE CHLOROPHENOXY COMPOUNDS ARE ABSORBED ACROSS THE GUT WALL, LUNG, & THE SKIN. THEY ARE NOT SIGNIFICANTLY FAT STORABLE. EXCRETION OCCURS WITHIN HOURS, OR AT MOST DAYS, PRIMARILY IN THE URINE. /CHLOROPHENOXY CMPD/|IN SHEEP GIVEN ORAL DOSE OF 25 MG/KG OF 2,4,5-T ESTER PEAK PLASMA CONCN OF 10 PPM ... FOUND 3-4 HR LATER; 86% OF ADMIN DOSE WAS RECOVERED FROM URINE IN UNALTERED FORM, & 1.4% AS FREE ACID, WITHIN 72 HR. THERE WAS LESS THAN 0.1 PPM OF 2,4,5-T IN TISSUES, BUT IN SHEEP POISONED BY REPEATED DOSES OF 2,4,5-T TISSUE LEVELS WERE 368 PPM. /2,4,5-T ESTERS/
SWEETGUM (LIQUIDAMBAR STYRACIFLUA L) & SOUTHERN RED OAK (QUERCUS FALCATA MICHX) WERE SPRAYED WITH AQUEOUS HOMOGENATE OF 2,4,5-T N-BUTYL ESTER /7 G/L/. AFTER 1 MONTH, LEAVES WERE COLLECTED AND ASSAYED ... TO DETECT RESIDUES. 2,4,5-TRICHLOROPHENOL WAS OBSERVED BUT NO EVIDENCE WAS FOUND TO INDICATE FORMATION OF 2,4,5-TRICHLORANISOLE.
THESE HERBICIDES /CHLOROPHENOXY CMPD/ DO NOT ACCUM IN ANIMALS. THEY ARE NOT EXTENSIVELY METAB BUT ARE ACTIVELY EXCRETED INTO THE URINE ... THEIR PLASMA HALF-LIFE IN MAN IS ABOUT 1 DAY. /CHLOROPHENOXY HERBICIDES/
They exert their herbicidal action by acting as a growth hormone in plants. They have no hormonal action in animals, but their mechanism of toxic action is poorly understood. /Chlorophenoxy compounds/
Concentration of ... 2,3,7,8-tetrachlorodibenzo-p-dioxin in samples of herbicide orange /in which 2,4,5-T n-butyl ester is a constituent/ is as follows: Johnson Island inventory 1972: n= 200, range: 0.05-47 ppm, mean 2,3,7,8-tetrachlorodibenzo-p-dioxin concn: 1.91 ppm; Johnson Island inventory 1975: n= 10, range: 0.07-5.3 ppm, mean 2,3,7,8-tetrachlorodibenzo-p-dioxin concn: 1.68 ppm; Naval Construction Battalion Center, Gulfport inventory 1972: n= 42, range: 0.05-13.3 ppm, mean 2,3,7,8-tetrachlorodibenzo-p-dioxin concn: 1.77 ppm; Naval Construction Battalion Center, Gulfport inventory 1975: n= 238, range: < 0.02-15 ppm, mean 2,3,7,8-tetrachlorodibenzo-p-dioxin concn: 2.11 ppm.|2,3,7,8-Tetrachlorodibenzo-1,4-dioxin (I) ... was detected in technical samples of ... 2,4,5-T alkyl esters. ... Thirty-two samples of 50% 2,4,5-T alkyl esters in mineral oil, 8 contained <0.05 ppm 2,3,7,8-tetrachlorodibenzo-1,4-dioxin, and 18 <0.5 ppm 2,3,7,8-tetrachlorodibenzo-1,4-dioxin. The maximum found was 28.3 ppm.|... Dioxins ... still are present /but to lesser extent/ as impurities in commercial preparations of the trichlorophenoxy herbicides. /Trichlorophenoxy herbicides/|IT WAS CONCLUDED @ STOCKHOLM CONF, FEB 7-9, 1977, THAT THE ONLY DIOXIN FOUND IN PHENOXY ACID HERBICIDES WHICH IS OF ENVIRONMENTAL CONCERN IS TCDD /2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN/; IT IS FOUND IN 2,4,5-T & 2,4,5-TP. /PHENOXY ACID HERBICIDES/
SYMPTOMS: Symptoms of exposure to this compound may include skin and eye irritation. ACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. When heated to decomposition it emits toxic fumes. (NTP, 1992)|Carcinogens
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Vietnam veterans' risks for fathering babies with major structural birth defects were assessed using a case-control study. Information regarding military service in Vietnam was obtained from interviews with mothers and fathers of babies in case-control groups and from review of military records. Vietnam veterans, in general, did not have an increased risk of fathering babies with defects (all types combined; relative risk estimate, 0.97). Vietnam veterans who had greater estimated opportunities for agent orange exposure did not seem to be at greater risk for fathering babies with all types of defects combined. However, for a few specific types of defects the estimated risks were higher for subgroups of Vietnam veterans that may have had a greater likelihood of exposure to Agent Orange. These seemingly higher risks could be chance events, the result of some experience in the Vietnam service of the father, or the result of some other unidentified risk factor.|DERMATOLOGICAL & SYSTEMIC EFFECTS IN WORKERS EMPLOYED IN MANUFACTURING OF SODIUM PENTACHLOROPHENOLATE, SODIUM SALT & BUTYL ESTER OF 2,4,5-T ARE REPORTED. CHLORACNE, PORPHYRIA CUTANEA TARDA, DISORDERS OF FAT, PORPHYRIN, CARBOHYDRATES, & PLASMA PROTEIN METABOLISM, PERIPHERAL NEURONS, NEURASTHENIC SYNDROME, & ORGANIC AFFECTIONS WERE DETERMINED IN 77 PATIENTS. HYPERPIGMENTATION, HYPERTRICHOSIS, & BULLOSIS ACTINICA & MECHANICA WERE DIGANOSED IN 10 OF THE 11 PATIENTS WITH IMPAIRED PORPHYRIN METABOLISM. STEATOSIS & FIBROSIS OF THE LIVER, INCR URINARY EXCRETION OF DELTA-AMINOLEVULINIC ACID, INCR PLASMA PROTEIN LEVELS, INCR ALKALINE PHOSPHATASE ACTIVITY, & WILD HEPATOMEGALLY WERE FOUND. THESE & OTHERS EFFECTS WERE DUE TO 2,3,6,7-TETRACHLORODIBENZODIOXIN, A CONTAMINANT.|The chlorophenoxy herbicides have produced contact dermatitis in man ... . /Chlorophenoxy compounds/|INHALATION OF SPRAY MAY CAUSE BURNING SENSATIONS IN THE NASOPHARYNX & CHEST, & COUGHING MAY RESULT. PROLONGED INHALATION SOMETIMES CAUSES DIZZINESS. /CHLOROPHENOXY COMPOUNDS/|For more Human Toxicity Excerpts (Complete) data for 2,4,5-T, N-BUTYL ESTER (7 total), please visit the HSDB record page.
2,4,5-T butyl ester
Agent Green Use and Manufacturing
REACTION OF 2,4,5-TRICHLOROPHENOXYACETIC ACID WITH N-BUTYL ALCOHOL|Esters of 2,4,5-T are synthesized by esterification of acid with appropriate alkyl alcohol. /2,4,5-T esters/|Chlorophenoxy ester herbicides can ... be produced by direct reaction of chlorophenol with appropriate chloroacetic esters ... /Chlorophenoxy herbicides/
(1977) NOT PRODUCED COMMERCIALLY IN USA|(1982) NOT PRODUCED COMMERCIALLY IN USA
/FORMER USES:/ INDUSTRIAL & COMMERCIAL USES, 63%; RANGELAND, 26%; RICE (EXCLUDING ISOOCTYL ESTER) 8%; LAWNS & TURF, 3% (1983-INCL 2,4,5-TRICHOROPHENOXYACETIC ACID, ESTERS, & SALTS)
Herbicide orange is a reddish-brown to tan colored liquid ... /which contained the following components/: n-butyl ester of 2,4-D: 49.49%, free acid of 2,4-D: 0.13%, n-butyl ester of 2,4,5-T: 48.75%, free acid of 2,4,5-T: 1.00%, inert ingredients (eg, butyl alcohol and ester moieties): 0.63%. /Former/|AS COMPONENT OF 'AGENT ORANGE' (50:50 MIXT OF N-BUTYL ESTERS OF 2,4-D & 2,4,5-T), CONTAINING UP TO 30 MG/KG OR MORE TCDD /2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN/, & OF 'AGENT PURPLE' (50:30:20 MIXT OF N-BUTYL ESTERS OF 2,4-D & N-BUTYL & ISOBUTYL ESTERS OF 2,4,5-T). /Former/|Brulin's Brush Killer (butyl esters of 2,4-D & 2,4,5-T). /Former/|Brush-Rhap B-1.33D-0.67T (butyl esters of 2,4-D & 2,4,5-T). /Former/|For more Formulations/Preparations (Complete) data for 2,4,5-T, N-BUTYL ESTER (20 total), please visit the HSDB record page.
Approx 11.3 million gallons of Agent Orange were sprayed in Vietnam ... of this only 950,000 gallons were Orange II (isooctyl ester) as compared to n-butyl ester.|Chlorophenoxy herbicides are applied alone or as mixtures with other herbicides, in solutions, dispersions, or emulsions in water &/or oil, using equipment that produces large droplets to avoid spray drift. /Chlorophenoxy herbicides/|Relatively high volatility esters ... /of 2,4,5-T incl/ methyl, ethyl, isopropyl, butyl, amyl & others known to possess relatively high vapor activity. These esters ... are liquids which, when properly formulated form emulsions when mixed with water. Because they are highly volatile, they should not be used under high temp conditions for weed control in areas adjacent to susceptible plants, such as cotton, tomatoes, grapes, flowers, & ornamentals.|New Zealand: The spraying of phenoxyherbicides is restricted within prescribed distances of vineyards. /Phenoxyherbicides/|THE ACTION ... OF /2,4,5-T SALTS & ESTERS/ ARE SIMILAR TO 2,4-D PREPARATIONS, ALTHOUGH ESTER FORMULATIONS ARE SOMEWHAT LESS VOLATILE. /2,4,5-T/
EPA Method 515: The Determination of Chlorinated Herbicides in Drinking Water. This method is applicable to the determination of certain chlorinated herbicides in drinking water. It is applicable, but not limited to, the analysis of the following parent acid and salts and esters of the acid. The chemical form is not distinguished. Results are calculated and reported as total free acid. (The sample is acidified to convert any salts present to the parent acid. The acids and esters are extracted with ethyl ether. The esters are hydrolyzed and converted to acid salts with potassium hydroxide solution. ... The acids are extracted into organic phase and then convertedto their methyl esters by the use of a micro-diazomethane generator). Samples are analyzed by either packed or capillary column gas chromatography using and electron capture detector. Using this method, 2,4,5-T, N-butyl ester has an estimated detection limit (student t factor times the standard deviation of at least 7 replicate analyses) of 0.20 ug/l. Using a packed column, mean recovery is 88% with a standard deviation of 5% in reagent water. /2,4,5-T/|Chlorinated phenoxy acids and their esters are determined by gas chromatography. Organic acids, especially chlorinated acids are interferrant. Phenols and chlorophenols also may interfere. The practical detection limit of this method depends on the sample size and instrumentation used. A concentrated extract of 0.05 ml permits detection limit of approximately 2 ng 2,4,5-T/l. Single laboratory precision and the recovery average for 2,4,5-trichloroacetic acid is respectively 8.0 and 100 for the concentration range of 90-290 ng/l. /2,4,5-T/|Product analysis is by ... GLC of a suitable ester ... . Residues may be determined by GLC of a suitable ester. /2,4,5-T/|Samples of phenoxyalkanoic herbicides in whole plants are acidified, hydrolyzed, and extracted into ether, and analyzed by electron capture gas chromatography (EC/GC) ... using a pyrex column ... packed with 1:1 10% DC 200/15% QF-1 on 80/100 mesh Chromosorb W (AW-DMCS). The injector, column, and (63)Ni electron capture detector temperatures are 220, 195, and 220 °C, respectively. The flow rate of nitrogen carrier is 80 ml/min. /Phenoxyalkanoic Herbicides/|For more Analytic Laboratory Methods (Complete) data for 2,4,5-T, N-BUTYL ESTER (8 total), please visit the HSDB record page.
Health Hazards -> Carcinogens
Computed Properties
Molecular Weight:311.6
XLogP3:4.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:309.993027
Monoisotopic Mass:309.993027
Topological Polar Surface Area:35.5
Heavy Atom Count:18
Complexity:263
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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