2,4-D isooctyl ester

333.25

332.09500

246-704-3

M7GLT14C7B

1993

DTXSID0020444

Yellow-brown liquid

35.5

5.13180

White crystals in commerce, a brown or dark brown liquid.

1.14-1.17 g/cm³ @ Temp: 20 °C

12 °C

317 °C

48°C

1.506

H2O: <0.1 g/100 mL at 21 ºC;In water, 0.0324 mg/l @ 25 deg C

Storage temp: Ambient /2,4-D esters/

7.06X10-6 mm Hg @ 25 deg C

Phenolic odor

SRP: 2,4-D ESTERS ARE SOLUBLE IN NON-POLAR ORGANIC SOLVENTS SUCH AS HEXANE, BENZENE, ACETONE, AND ALCOHOLS /2,4-D ESTERS/

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

May attack some forms of plastics. /2,4-D esters/

III

6.1(b)

UN 2810

3

25-36/38-40-50/53-43-22

26-36/37-45-61-60-46-29

AG8575000

T,N,Xn

Shelf life of ester formulations varies, depending on the emulsifying system. Some retain satisfactory emulsifying properties after 3 yr. /2,4-D ester formulations/

P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P405, P501

H301

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U240, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /2,4-D acid, salts & esters/|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/|The following wastewater treatment technologies have been investigated for 2,4-D isooctyl esters: Concentration process: Biological treatment.|For more Disposal Methods (Complete) data for 2,4-D ISOOCTYL ESTERS (7 total), please visit the HSDB record page.

WHO; Environ Health Criteria: 2,4-Dichlorophenoxyacetic acid (2,4-D) (1984)|Nat'l Research Council Canada; Phenoxyherbicides (1978) NRCC No. 16075|Que Hee SS, Sutherland RG; The Phenoxyalkanoic Herbicides (1981)|Vet Admin Rev Lit on Herbicides (1981) VA Contract No. V101(93)p-823|Norris LA; The Movement, Persistance, and Fate of the Phenoxy Herbicides and TCDD in the Forest; Residue Rev 77: 65-135 (1981)

This chemical is combustible. (NTP, 1992)

|Warning|H302 (92.68%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (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)|Protective gloves made of different materials (S/L (supported/lined) nitrile, US/L (unsupported/lined) neoprene, US/UL (unsupported/unlined) neoprene, S/L (supported/lined) neoprene, Tyvek, US/L (unsupported/lined) nitrile, US/UL (unsupported/unlined) nitrile (thin), and US/UL (unsupported/unlined) nitrile (thick)) were tested for permeation by formulation concentrates and aqueous emulsions of Esteron 99 (isooctyl ester of (2,4-dichlorophenoxy) acetic acid) under conditions simulating extremes of field conditions. Tyvek (laminated saranax) and unsupported nitrile gloves gave protection from permeation against formulation concentrates and aqueous emulsions of Esteron 99. The gloves were tested in a 1-PTC 600 ASTM Test Cell with test solution for an 8 hr period. Kinetic studies were also performed at 10 min intervals up to 2 hr to determine the concn of isooctyl ester in the test solution to a detection limit of 115 pg. The supported/lined nitrile glove allowed the greatest mass of the isooctyl ester to cross; unsupported/unlined and unsupported/lined nitrile gloves were at least 200 times better. All of the neoprene gloves performed worse than the unsupported/unlined and unsupported/lined nitrile gloves. Tyvek was more of a barrier to the isooctyl ester than nitrile gloves were. The thinner unsupported/unlined nitrile gloves performed better as a barrier to the ester than the thicker ones. In the 2 hr kinetic experiments all samples demonstrated an initial isooctyl ester penetration. For Tyvek or unsupported/unlined nitrile materials, little subsequent permeation occurred compared with all neoprenes. The lined nitrile and neoprene gloves offered less protection than their unlined counterparts. Nitrile and neoprene were partially degraded or swollen after the 2 hr kinetic studies. Significant changes also occurred in those glove materials (supported and unsupported nitrile and the unsupported/lined and unsupported/unlined nitrile) that were penetrated/permeated by the ester. Tyvek thickness did not change, though one sample did swell as a result of one of the formulation challenges. Swelling was the most pronounced in the neoprene glove material.

EXTINGUISH WITH DRY CHEMICALS, FOAM, OR CARBON DIOXIDE. WATER MAY BE INEFFECTIVE. COOL EXPOSED CONTAINERS WITH WATER. /2,4-D ESTERS/

A TREATMENT SYSTEM BASED ON THE RECIRCULATION OF PESTICIDE-CONTAMINATED WASTEWATER THROUGH A BED OF GRANULAR ACTIVATED CARBON WAS OF PARTICULAR USE TO THE SMALL WASTE GENERATOR. /SRP: UNSPECIFIED ACID OR ESTER OF 2,4-D/

Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/|/When/ cleaning glassware and spray equipment: wash thoroughly with water and detergent soln. Alcohol or ketone type solvents may be used with ester formulations. Preferably, equipment should not be used for application of other pesticides or fertilizers. /SRP: Unspecified ester of 2,4-D/|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.

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Phenoxyacetic acid derivative pesticide, liquid, flammable, poisonous; Phenoxyacetic acid derivative pesticide, liquid, flammable, toxic; Phenoxyacetic acid derivative pesticide, liquid, poisonous, flammable; Phenoxyacetic acid derivative pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Phenoxyacetic acid derivative pesticide, liquid, flammable, poisonous; Phenoxyacetic acid derivative pesticide, liquid, flammable, toxic; Phenoxyacetic acid derivative pesticide, liquid, poisonous, flammable; Phenoxyacetic acid derivative pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Phenoxyacetic acid derivative pesticide, liquid, flammable, poisonous; Phenoxyacetic acid derivative pesticide, liquid, flammable, toxic; Phenoxyacetic acid derivative pesticide, liquid, poisonous, flammable; Phenoxyacetic acid derivative pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ 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. /Phenoxyacetic acid derivative pesticide, liquid, flammable, poisonous; Phenoxyacetic acid derivative pesticide, liquid, flammable, toxic; Phenoxyacetic acid derivative pesticide, liquid, poisonous, flammable; Phenoxyacetic acid derivative pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for 2,4-D ISOOCTYL ESTERS (16 total), please visit the HSDB record page.

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.

Acute eye or skin irritation ... has been reported in agricultural and forestry workers following occupational exposure. /2,4-D herbicides/|Irritating to skin and eyes. /2,4-D esters/

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 10 mg/cu m. /2,4-D/

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 mg/cu m. /2,4-D/

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. 2,4-D Isopropyl esters is included on this list.

D016; A waste containing 2,4-D (such as 2,4-D isooctyl esters) may or may not be characterized as a hazardous waste following testing by the Toxicity Characteristic Leaching Procedure as prescribed by the Resource Conservation and Recovery Act (RCRA) regulations.|U240; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate. /2,4-D, salts and esters/

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 100 lb or 45.4 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-D, salts and esters/

D016; A solid waste containing 2,4-D (such as 2,4-D isooctyl esters) may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste.|U240; As stipulated in 40 CFR 261.33, when 2,4-D acid, salts & esters as commercial chemical products or manufacturing chemical intermediates or off-specification commercial chemical products or manufacturing chemical intermediates, become wastes, they must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). /2,4-D, salts and esters/

DIFFERENTIAL COLLECTION TECHNIQUE ... PROVIDED CIRCUMSTANTIAL EVIDENCE THAT LARGE PERCENTAGE OF ISOOCTYL ESTER OF 2,4-D FOUND IN AIR WAS PRESENT AS AEROSOL.|Analyses of air in breathing zone of pilot and ground crew during a 3 day aerial spray operation with a single engine aircraft, mean of 2,4-D concentrations in air was 0.002 - 0.1 mg/cu m. /2,4-D derived from 2,4-D isooctyl ester in diesel oil/|The herbicide 2,4-D isooctyl ester was not detected in air samples taken from Sept 1987 to March 1988 in the Tala Valley (Natal, South Africa) despite it's widespread use during that time 20-60 km away(1). In agricultural regions of Washington state, the avg concn of 2,4-D isooctyl ester was 0.005 ug/cu m (max concn, 0.53 ug/cu m; 102 24-hr samples) at Kennewick, WA, in 1964; at Pullman, WA in the same year, 2,4-D isooctyl ester was not detected in 99 24-hr samples(2). Residues of 2,4-D were observed in air in central and southern Saskachewan during 1966-68 and 1970-75 spraying seasons. The daily mean concn of 2,4-D isooctyl ester was 0.05-0.59 ug/cu m(3). On application of the ester at a rate of 0.5 kg/ha on a wheat field, the max air concentration of 1,604 ng/cu m was observed on day 1 at a height of 30 cm above the crop canopy. The level had decreased to about 60 ng/cu m on day 5(4).

Cutthroat trout (Salmo clarki) were treated with six different paired mixtures of dicamba, picloram, 2,4-D butyl ester, 2,4-D isooctyl ester, and 2,4-D propylene glycol butyl ether ester. Except for 2,4-D isooctyl ester, the LC50's resulting from mixtures of 2,4-D esters and picloram were lower than LC50's of those herbicides tested individually. Dicamba and 2,4-D isooctyl ester were the least toxic individually and mixtures of dicamba or 2,4-D isooctyl ester with the other herbicides tested did not result in increased toxicity. Results reflect the importance of using combination exposures in determining the biological significance of the simultaneous occurrence of more than one herbicide in surface waters.

LD50 Rabbit skin absorption > 4000 mg/kg|LD50 Rat oral 982 mg/kg

2,4-D isooctyl ester's former production and use as a systemic herbicide(1) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 29,000(SRC), calculated from a water solubility of 0.0324 mg/l(2) and a regression-derived equation(3) indicates that 2,4-D isooctyl ester is expected to be immobile in soil(SRC). Volatilization of 2,4-D isooctyl ester from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, volatilization from moist soil surfaces is expected to be attenuated by adsorption to soil(SRC). 2,4-D isooctyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.06X10-6 mm Hg(5). In soil, the hydrolysis of 2,4-D isooctyl ester to 2,4-D and the alcohol was suggested to be microbially mediated(6). 2,4-D isooctyl ester was not detected after 3 years at an initial concentration of 560 ppm and application rate of 1,280 kg/ha(6). 17.8% and 3.6% of 2,4-D isooctyl ester, applied at a rate of 4,480 kg/ha (initial residue concn of 2,640 ppm), was recovered after 3 and 6 years, respectively(6). When the ester was incubated in a silt loam soil for 10 weeks at a concn up to 16 ppm, more than 60% was mineralized (based on carbon content) into CO2(7); less than 2% of the applied ester was found undegraded in soil as 2,4-D(6); over 20% of the carbon was incorporated into the soil probably as new biomass(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 29,000(SRC), calculated from a water solubility of 0.0324 mg/l(2) and a regression-derived equation(3) indicates that 2,4-D isooctyl ester 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 5.7X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 20 hrs and 15 days(2). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 310 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 31,000(SRC), from an estimated log Kow of 6.7(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). However, like 2,4-D butyl ester, 2,4-D isopropyl ester may also be readily metabolized in fish and therefore should not bioconcentrate(8). 2,4-D isooctyl ester could not be degraded by activated sewage acclimated with 2,4-D in a laboratory test(9). However, when the ester was incubated in a silt loam soil for 10 weeks at a concn up to 16 ppm, more than 60% was mineralized (based on carbon content) into CO2(10). Thus, biodegradation of 2,4-D isooctyl ester may occur in water but the rate is unknown(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-D isooctyl ester, which has a vapor pressure of 7.06X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase 2,4-D isooctyl ester 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 33 hrs(SRC), calculated from its rate constant of 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2,4-D isooctyl ester may be removed from the air by wet and dry deposition(SRC). Solutions of 2,4-D isooctyl ester absorb light > 290 nm(2), suggesting 2,4-D isooctyl ester may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 2,4-D isooctyl ester with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 33 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Solutions of the isooctyl ester of 2,4-D absorb light > 290 nm(2), suggesting it may be susceptible to direct photolysis by sunlight(SRC). The ester can hydrolyze to the free acid/anion by photolysis with a half-life of 2-4 days reported for water solutions irradiated at 356 nm(4). A half-life of 50 minutes was reported for 2,4-D in water irradiated at 254 nm; quantitative results using sunlight were essentially identical to the use of artificial light(5). Photodecomposition of 2,4-D leads to the formation of a variety of products but commonly involves reductive dechlorination in aqueous or in organic solutions(6). 2,4-D esters, irradiated with wavelengths longer than 290 nm in organic solvents or at high concentrations in water, yielded 2-, and 4-chlorophenoxyacetic acid esters(7). Ester photolysis rates were also found to be pH independent(7). Hydrolysis of 2,4-D isooctyl ester to free anion in 0.1 N sodium hydroxide (pH 13.0) was almost instantaneous; in 0.1 N sodium carbonate (pH 11.6) hydrolysis was slower(8). In distilled water, over 90% was recovered unchanged after 5 hours(8). When added to soils 2,4-D isooctyl ester underwent hydrolysis to free acid(8). After 24 hours only 20-30% of the ester remained and after 48 hours only 10% remained(8).

An estimated BCF of 31,000 was calculated for 2,4-D isooctyl ester(SRC), using an estimated log Kow of 6.7(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC). However, like 2,4-D butyl ester, 2,4-D isopropyl ester may also be readily metabolized in fish and therefore should not bioconcentrate(4).

The Koc of 2,4-D isooctyl ester is estimated as 29,000(SRC), using a water solubility of 0.0324 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,4-D isooctyl ester is expected to be immobile in soil(SRC). 2,4-D isooctyl ester is adsorbed slightly by clay minerals with adsorption to bentonite > illite > kaolinite(4). Large amounts, eg 10.31, 14.16, and 44.63 grams, respectively, would be required to reduce the concentration of 2,4-D isooctyl ester in water from 3 mg/l to 2 mg/l(4). However, the adsorption of 2,4-D isooctyl ester was much greater for soils with high organic carbon than soils with high content of clay(5).

The Henry's Law constant for 2,4-D isooctyl ester is estimated as 5.7X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4-D isooctyl ester is expected to volatilize from water surfaces(2). Estimated volatilization half-lives for a model river and model lake are 20 hrs and 15 days(2). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 310 years if adsorption is considered(3). 2,4-D isooctyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.06X10- 6 mm Hg(4). The total or cumulative vapor losses after 5 days of 2,4-D isooctyl ester applied to a wheat field was 20.8% of the amount applied(5). Ester losses from the soil occurred only when the soil was wet(5). Volatilization of 2,4-D isooctyl ester accounted for only part of the initial rapid rate of loss from the crop canopy(5). The total 2,4-D isooctyl ester and metabolites found in air from a simulated wheat field amounted to 15% in 28 days(6); 2,4-D isooctyl ester predominated through day 5 and then the metabolite 2,5-dichloro-4-hydroxyphenoxyacetic acid became predominant(6). The estimated half-life for vaporization from a surface-water depth of 1 m for the 1-octyl esters of 2,4-D was 11.5 days(7).

2,4-D WAS ELIM IN MILK OF COWS MAINTAINED IN PASTURES TREATED WITH 2,4-D OR ITS BUTYL OR ISOOCTYL ESTER.

2,4-D and its derivatives can be absorbed via the oral, dermal, and inhalation routes. General population exposure is mainly by the oral route, but under occupational and bystander exposure conditions, the dermal route is by far the most important. /2,4-D and its derivatives/|Occupational exposure to 2,4-D isooctyl ester may have occured through inhalation of aerosols containing 2,4-D isooctyl ester during spraying operations and dermal contact with sprayed vegetation. (SRC)

Urinalysis of six volunteer workers (wearing a full line of protective clothing) involved in mixing and loading 2,4-D ester solutions into aircraft and in guiding the spray aircraft in two conifer release programs showed a maximum excretion level of 22.2 ug/kg body weight/day(1). The urinary excretion rate of 2,4-D in 45 commercial lawn care specialists who had been spraying the herbicide for a period of at least 3 weeks ranged from 0.4-6.3 ug/kg body weight/day(2). Thirty nine of 197 children living near and away from possible source of contamination had detectable levels of 2,4-D (detection limit 1 ppb) in their urine at a maximum concentration of 9 ppb(3).

... ISOOCTYL ESTER OF 2,4-D DISAPPEARED FROM BODIES OF INJECTED MICE MORE RAPIDLY THAN 2,4-D ACID.|Leaves absorb nonpolar (ester) forms most readily. ... The esters of 2,4-D tend to resist washing from plants and are rapidly converted to the acid by the plants. ... Following foliar absorption, 2,4-D translocates within the phloem, probably moving with food material. Following root absorption, it may move upward in the transpiration stream. Translocation is influenced by the growth status of the plant. Accumulation of the herbicide occurs principally at the meristematic regions of shoots and roots. /2,4-D or its esters/|Plasma 2,4-D concn did not exceed 0.2 mg/l in workers exposed to 2,4-D ester at an atmospheric concn of 0.1 to 0.2 mg/l; no accumulation was noted during the work week. ... Workers ... developed 2,4-D urine concentrations of 3 to 14 mg/l after a day of exposure. /2,4-Dichlorophenoxyacetic acid or its esters/|AFTER SC INJECTION OF 2,4-D & ITS BUTYL & ISOOCTYL ESTERS INTO MICE @ 100 MG/KG, ESTERS WERE ELIM RAPIDLY, & ONLY 5-10% OF THE 2,4-D REMAINED AFTER 1 DAY. ... 2,4-D WAS ELIM IN MILK OF COWS MAINTAINED IN PASTURES TREATED WITH 2,4-D OR ITS BUTYL OR ISOOCTYL ESTER.|For more Absorption, Distribution and Excretion (Complete) data for 2,4-D ISOOCTYL ESTERS (7 total), please visit the HSDB record page.

Plants hydrolyze 2,4-D esters to 2,4-D, which is the active herbicide. ... Further metabolism ... occurs through three mechanisms, namely, side chain degradation, hydroxylation of the aromatic ring, and conjugation with plant constituents. /2,4-D esters/|HERBICIDAL ACTIVITY OF ESTERS, NITRILES, AMINES (&, OF COURSE, SALTS) APPEARS SIMILAR IF NOT IDENTICAL TO PARENT ACID. THIS IS APPARENTLY DUE TO PRESENCE OF HYDROLYTIC ENZYMES IN PLANTS & IN SOIL MICROORGANISMS THAT CONVERT THESE DERIVATIVES TO PARENT ACID. /SRP: 2,4-D OR ITS ESTERS/|2,4-D ESTERS ARE HYDROLYZED IN ANIMALS. THE PHENOXY ACIDS ARE EXCRETED PREDOMINANTLY AS SUCH IN THE URINE OF RATS AFTER THEIR ORAL ADMIN, ALTHOUGH MINOR PORTION IS CONJUGATED WITH AMINO ACIDS GLYCINE & TAURINE & WITH GLUCURONIC ACID. /2,4-D AND ESTERS/|Metabolites of 2,4-D other than conjugates have not been detected in human urine.

THESE HERBICIDES 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 COMPOUNDS/|The hydrolysis half-life of the n-butyl ester of 2,4-D was determined to be 100 hours in neutral water and much less in aqueous soil suspensions. Smith (1976) reported that the n-butyl ester of 2,4-D undergoes almost complete hydrolysis to 2,4-D in less than 24 hours in moist soil. Similar results were reported for the hydrolysis of the n-butyl and isooctyl esters of 2,4,5-T to 2,4,5-T. Esters of 2,4-D were completely hydrolyzed to 2,4-D within 9 days in lake water. Therefore, rates of biological hydrolysis appear to be greater than rates of chemical hydrolysis.

... /CHLOROPHENOXY CMPD INCL 2,4-D ESTERS/ EXERT THEIR HERBICIDAL ACTION BY ACTING AS GROWTH HORMONES IN PLANTS. /CHLOROPHENOXY COMPOUNDS/

SIXTEEN SAMPLES OF 2,4-D, AS ESTERS AND AMINE SALTS, WERE ANALYZED FOR CHLORINATED DIBENZO-P-DIOXINS. DI-, TRI-, & TETRA-CHLORODIBENZO-P-DIOXINS WERE IDENTIFIED. ESTER FORMULATIONS SHOWED MUCH HIGHER LEVELS OF CONTAMINATION THAN AMINE /2,4-D ESTERS AND AMINE SALTS/

SYMPTOMS: Symptoms of exposure to this compound may include skin and eye irritation; a burning sensation in the throat and chest; weakness, loss of appetite and weight; and slight albuminuria. ACUTE/CHRONIC HAZARDS: This compound has irritating vapors. When heated to decomposition it emits toxic fumes. (NTP, 1992)

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)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Monitor body temperature and treat if necessary. /Chlorophenoxy herbicides and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with lactated Ringer's /SRP: "To keep open", minimal flow rate/. Titrate to maintain adequate urine flow. Watch for signs of fluid overload. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive without signs of hypovolemia ... . Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Chlorophenoxy herbicides and related compounds/|Alkaline diuresis should be used to treat acute poisoning with chlorophenoxy herbicides or ioxynil in the presence of coma or other poor prognostic indicators, such as acidemia, or if plasma total chlorophenoxy concentrations are 0.5 g/l or more.

IN THREE HUMAN BEINGS, ABSORPTION OF AN UNSPECIFIED ESTER OF DICHLOROPHENOXYACETIC ACID THROUGH SKIN CAUSED POLYNEURITIS, BUT WITH NO DISTURBANCE OF EYES OR VISION. /2,4-D ESTER/|SUBJECTIVE CLINICAL SYMPTOMS REPORTED AMONG WORKERS USING VARIOUS ESTERS & SALTS OF 2,4-D INCL RAPID FATIGUE, HEADACHE, LOSS OF APPETITE & PAIN IN THE REGION OF THE LIVER & STOMACH. SENSITIVITY TO TASTE & SMELL WAS LOWERED. /2,4-D ESTERS AND SALTS/|The chlorophenoxy herbicides have produced contact dermatitis in man ... . /Chlorophenoxy compounds/|IN THE BODY, THE ... ESTERS OF CHLOROPHENOXY COMPOUNDS ARE HYDROLYZED FAIRLY RAPIDLY SO THAT THE MAMMALIAN TOXICITY OF EACH COMPOUND DEPENDS MAINLY ON THE ACID INVOLVED. /CHLOROPHENOXY HERBICIDES/

2,4-D isooctyl

Emulsifiable concentrates|... DED-WEED SULV AMINE ... /CONTAINS/ (2,4-D ISOOCTYL ESTER) ... HEDONAL (ISOOCTYL ESTER) ... FARMCO DLV-400 SPECIAL, 400 G/L ACTIVE INGREDIENT EMULSIFIABLE CONCENTRATION AS ISO-OCTYL ESTER.|Abco W K-DT 133 (isooctyl esters of 2,4-D and 2,4,5-T) /Former/|Abco WKS-65 Brush Killer (isooctyl esters of 2,4-D, 2,4,5-T, and silvex) /Former/|For more Formulations/Preparations (Complete) data for 2,4-D ISOOCTYL ESTERS (63 total), please visit the HSDB record page.

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/|Ester formulations may be used in relatively hard water ... emulsion compatibility test should be made before using with other pesticides or fertilizers. /2,4-D/

RESIDUES OF 2,4-D ISOOCTYL ESTER WERE DETERMINED IN DERMAL EXPOSURE PADS & HAND RINSES OBTAINED FROM WORKERS INVOLVED IN THE APPLICATION OF THE HERBICIDE. THE 2,4-D ESTER RESIDUES WERE EXTRACTED FROM DERMAL EXPOSURE PADS WITH METHANOL AND DIRECTLY CONVERTED TO THE METHYL ESTER WITH BORON TRIFLUORIDE. RESIDUES OF 2,4-D ISOOCTYL ESTER IN HAND RINSES WERE TREATED WITH POTASSIUM HYDROXIDE, PURIFIED WITH REVERSE-PHASE LIQUID CHROMATOGRAPHY, AND CONVERTED TO THE METHYL ESTER. THE DERIVATIZED RESIDUES WERE QUANTITATED BY ELECTRON CAPTURE GAS CHROMATOGRAPHY AND SATISFACTORY RECOVERIES WERE OBTAINED AT A DETECTION LIMIT OF 0.02 UG OF 2,4-D/SQ CM FOR DERMAL EXPOSURE PADS, & 0.03 UG/ML FOR HAND-RINSE SAMPLES.|Whole Plants: Macerate plant tissue with water. Add 0.6 M sodium hydroxide. Reflux or heat on a steam bath. Filter and wash the filter cake with water. Combine the filtrates. Suspend the filter cake in 2 M hydrochloric acid. Reflux or heat on a steam bath. Extract with equal volumes of ether (x3). Combine these with the filtrate. The above acid hydrolysis is done in case there are conjugates resistant to alkaline hydrolysis. The recovery of the above using only the alkaline hydrolysis was greater than 89 to 92% with (14)C-labeled material. ... Continue with a liquid /liquid cleanup, followed by electron capture/gas chromatography quantitiation ... 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)nickel electron capture detector temperatures are 220, 195, and 220 °C, respectively. The flow rate of nitrogen carrier is 80 ml/min. /2,4-D and esters or salts of 2,4-D/|Water: Filter out any particulate matter. Take a 1-l or smaller volume sample. Saturate with sodium chloride. Adjust the pH to < 2 with hydrochloric acid. Extract with acetonitrile (5 x 500 ml). Adjust the saline solution to > pH 13 and extract with diethyl ether (3 x 500 ml). Reacidify to < pH 2 with hydrochloric acid and extract with acetonitrile (5 x 500 ml). Extraction is approximately 99% efficient. ... Continue with a liquid/liquid cleanup, followed by electron capture/gas chromatography quantitation ... 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)nickel electron capture detector temperatures are 220, 195, and 220 °C; respectively. The flow rate of nitrogen carrier is 80 ml/min. /2,4-D and esters or salts of 2,4-D/|Mass spectra: intense parent ion (P)= 162; intense P-glyoxal= 220. /SRP: Either can be used for specific ion monitoring/|For more Analytic Laboratory Methods (Complete) data for 2,4-D ISOOCTYL ESTERS (10 total), please visit the HSDB record page.

RESIDUES OF 2,4-D ISOOCTYL ESTER WERE DETERMINED IN URINE OBTAINED FROM WORKERS INVOLVED IN THE APPLICATION OF THE HERBICIDE. RESIDUES OF 2,4-D ISOOCTYL ESTER IN URINE WERE TREATED WITH POTASSIUM HYDROXIDE, PURIFIED WITH REVERSE-PHASE LIQUID CHROMATOGRAPHY, AND CONVERTED TO THE METHYL ESTER. THE DERIVATIZED RESIDUES WERE QUANTITATED BY ELECTRON CAPTURE GAS CHROMATOGRAPHY AND SATISFACTORY RECOVERIES WERE OBTAINED AT A DETECTION LIMIT OF 0.07 UG/ML OF URINE.|Fat Samples: Dissolve sample in hot ethanol; reflux for 1 hr, and chill. Add 0.1 N sodium hydroxide. Extract with diethyl ether. ... Continue with a liquid/liquid cleanup, followed by electron capture/gas chromatography quantitation ... 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.|Plasma: This is based on the method for the drug Clofibrate. Add enough hydrochloric acid to the sample for pH < 2. Extract with equal volumes of ether (x3). To measure the 2,4-D in complex form, add aqueous sodium hydroxide to the aqueous layer and ... continue with a liquid/liquid cleanup, followed by electron capture/gas chromatography quantitation ... 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.|Metabolites: This is a general method recommended by McLeod and Wales. Reflux 5 g of tissue for 1 hr with 19 ml of benzene and separate the supernatant from particulates by filtration through a medium-porosity fritted glass funnel via negative pressure. Re-extract the particulate matter again with fresh 10 ml (19:1) acetone/benzene. Combine the filtrates and concentrate to 25 ml. Use the low-temperature bath apparatus as laid out by McLeod and Wales. Further characterization of the actual metabolites has not been accomplished. There is much room for further separation technology.|For more Clinical Laboratory Methods (Complete) data for 2,4-D ISOOCTYL ESTERS (7 total), please visit the HSDB record page.

HERBICIDES