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Home > Encyclopedia > 2,4-D isopropyl ester

2,4-D isopropyl ester

2,4-D isopropyl ester structure

2,4-D isopropyl ester 

structure
  • CAS No:

    94-11-1

  • Formula:

    C11H12Cl2O3

  • Chemical Name:

    2,4-D isopropyl ester

  • Synonyms:

    Acetic acid,2-(2,4-dichlorophenoxy)-,1-methylethyl ester;Acetic acid,(2,4-dichlorophenoxy)-,isopropyl ester;Acetic acid,(2,4-dichlorophenoxy)-,1-methylethyl ester;Isopropyl (2,4-dichlorophenoxy)acetate;Isopropyl 2,4-D ester;2,4-D isopropyl ester;Weedone 128;2,4-Dichlorophenoxyacetic acid isopropyl ester;Esteron 44;NSC 521749

  • Categories:

    Agrochemicals  >  Herbicides

Description

2,4-Dichlorophenoxyacetic acid is a white to yellow crystalline powder with a slight phenolic odor.

2,4-D isopropyl ester Basic Attributes

263.12

263.12

202-305-6

S198602E40

521749

2765

DTXSID5020445

Liquid|Colorless /SRP: dependent on purity/|May be a solid if pure.

2918990090

Characteristics

35.53000

3.32380

Colorless liquid dependent on purity/.

1.255-1.270 g/cm3 @ Temp: 25 °C

5 °C

30 °C @ Press: 1 Torr

Greater than 175 deg F (open cup) /2,4-D esters/

1.5208 (25ºC)

27.36mg/L(temperature not stated)

0-6°C

2.32X10-4 mm Hg @ 25 deg C

Solidifies at 5 °C|Fuel oil-like odor /2,4-D esters/ SRP: Technical product.|May attack some forms of plastics /2,4-D esters/|UV Spectra: ... Three alpha max/molar extinction coefficients are shown by 2,4-D esters: 230 nm (10x4), 285 nm (10x3.4), and 293 nm (10x3.3). /2,4-D esters/

2.39 kcal/mol

Safety Information

III

6.1(b)

3348

22-41-50/53-43

26-39-61-60-46-36/37-29

AG8750000

Xn,N

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

P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, P501

H302

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/|For more Disposal Methods (Complete) data for 2,4-D ISOPROPYL ESTER (6 total), please visit the HSDB record page.

Nat'l Research Council Canada; Phenoxyherbicides (1978) NRCC No. 16075|WHO; Environ Health Criteria: 2,4-Dichlorophenoxyacetic Acid (2,4-D) (1984)|Veterans Administration; Review of Literature on Herbicides, Including Phenoxy Herbicides and Associated Dioxins Vol I p.6-2 (1981) VA Contract No. V101(93)P-823.|Drinking Water Criteria Doc: 2,4-Dichlorophenoxyacetic acid (2,4-D) 1985 (Draft) ECAO-CIN 418.|For more Special Reports (Complete) data for 2,4-D ISOPROPYL ESTER (6 total), please visit the HSDB record page.

|Warning|H302 (100%): 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 44 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

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. /2,4-D herbicides/|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.

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 ester is included on this list.

D016; A waste containing 2,4-D (such as 2,4-D, isopropyl ester) 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 isopropyl ester) 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/

SOURCE DOMINATED: The concn of 2,4-D isopropyl ester ranged from 0-30 ng/cu m (median, 10.6 ng/cu m) in the Spring of 1973(1); in the Spring 1974, the concn of 2,4-D isopropyl ester ranged from 10-130 ng/cu m (median, 38 ng/cu m)(1). Between the period 1970-71 as part of an EPA Air Monitoring Network study (selected sites in 16 states), the mean concn of 2,4-D isopropyl ester was 0.4 ng/cu m (2.55% of samples pos, 13.7 ng/cu m mean of positive samples) with a max concn of 67.3 ng/cu m(2). Residues of 2,4-D isopropyl ester were determined in central and southern Saskatchewan during the 1966-68 and 1970-75 spraying seasons; up to half of the daily samples contained 2,4-D; the daily mean concn of isopropyl ester was 0.01-1.22 mg/cu m(3). Air samples were collected near wheat-growing areas around Pullman and Kennewick highlands, WA, between April and August 1964 after applications of 2,4-D. Although data were given for several products containing 2,4-D, those for 2,4-D isopropyl ester were highest: avg concn of 0.0116 g/cu m and max concn of 1.9 mg/cu m of aerosol form of ester and avg concn of 0.007 mg/cu m and max concn of 0.69 ug/cu m of vaporized ester were found in 24 hr samples(4).

Toxicity

LD50 Rat oral acute 700 mg/kg|LD50 Mouse (male) oral dose 541 mg/kg|LD50 Guinea Pig (male) oral dose 550 mg/kg|LD50 Chicken (male and female) oral dose 1,420 mg/kg|LD50 Rat oral 375 mg/kg

2,4-D isopropyl ester's production may result in its release to the environment through various waste streams; it's use as a herbicide(1) will result in its direct release to the environment as a result of spraying operations(SRC).

Various amounts of 2,4-D products applied to a target area may be distributed in the general environment, within a few hours or days, by the movements of air, water, or soil, particularly during periods of rain, high winds, or high temperature. Persistence or accumulation of 2,4-D residues from normal use is occasionally possible, mainly under dry or cold conditions where there is little biological activity. /2,4-D products/|TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 600(SRC), determined from a water solubility of 37.3 mg/l(2) and a regression-derived equation(3), indicates that 2,4-D isopropyl ester is expected to have low mobility in soil(SRC). Volatilization of 2,4-D isopropyl ester from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.3X10-4 mm Hg(4), and its water solubility(2). 2,4-D isopropyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). In a study, in which 2,4-D isopropyl ester was incubated with domestic sewage microorganisms, 2,4-D isopropyl ester was hydrolyzed and the acid was later decomposed biologically(5). These results are consistent with microbial hydrolysis after a 7 day acclimation period(5). On prairie soils at moisture contents in excess of the wilting point, the isopropyl ester of 2,4-D undergoes very rapid hydrolysis; the ester is completely converted to the corresponding acid and alcohol in < 1 day(6). The rapid rate of the reaction suggests that it is soil-catalyzed(6). The rate of hydrolysis is probably affected by the organic content of the soil and the degradation rate of the free acid should be dependent upon the presence of acclimated microorganisms(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 600(SRC), determined from a water solubility of 37.3 mg/l(2) and a regression-derived equation(3), indicates that 2,4-D isopropyl 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 2.2X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.3X10-4 mm Hg(4), and water solubility, 37.3 mg/l(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 18 days and 207 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 80(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(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(7). The 2,4-D isopropyl ester is degraded in a laboratory test by activated sewage acclimated to 2,4-D(8). The 2,4-D isopropyl ester is degraded at half the rate of the parent acid which reached a constant rate of oxidation in 11 weeks(8). The hydrolysis half-life of 2,4-D isopropyl ester in water at pH 7.4 and 20 °C is 23.1 days(2). The half-life of 2,4-D isopropyl ester has been calculated to be 17.0 hr at pH 9 and 710 days at pH 6(3). Solutions of 2,4-D isopropyl ester in water absorb light > 290 nm(4). Although the sunlight photolysis of 2,4-D isopropyl ester has not been experimentally determined, several other esters have been studied and found to have half-lives of 2-3 weeks. The products were 2,4-dichlorophenol and compounds resulting from replacement of chlorine by hydroxyl. Photodegradation will be important in surface waters, especially at acid and near neutral pHs where hydrolysis is slow(9,10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-D isopropyl ester, which has a vapor pressure of 2.32X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 2,4-D isopropyl 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 2.3 days(SRC), calculated from its rate constant of 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Solutions of the 2,4-D isopropyl ester in water absorb light > 290 nm(2). Therefore, 2,4-D isopropyl ester may be subject to direct photolysis in the atmosphere(SRC).|ATMOSPHERIC FATE: Sources of the isopropyl ester of 2,4-D in air are the result of spraying or volatilization from plants, soil or water surfaces after spraying. The ester, which may exist in air as the vapor or fine droplets which do not settle in the target area, may be transported long distances. Levels of the less volatile n-butyl ester were appreciable and resulted in damage to grape crops when it was banned in specific counties and the following year when it was banned in the entire state due to its volatility(1). The isopropyl ester will be removed from the air by gravitational settling, rainout and possibly photodegradation. (SRC)

Photodecomposition of 2,4-D ... leads to the formation of a variety of products but commonly involves reductive dechlorination of the acid, esters, and salts in aqueous or in organic solutions, with 2,4-dichlorophenol acting as a catalyst for the breakdown of 2,4-D, which may involve rupture of the aromatic ring. ... Carbon dioxide is the final oxidation product when aqueous solutions of 2,4-D undergo photodecomposition. /2,4-D/|The rate constant for the vapor-phase reaction of 2,4-D isopropyl ester with photochemically-produced hydroxyl radicals has been estimated as 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The hydrolysis half-life of 2,4-D isopropyl ester in water at pH 7.4 and 20 °C is 23.1 days(2). The half-life of 2,4-D isopropyl ester has been calculated to be 17.0 hr at pH 9 and 710 days at pH 6(3). 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(4). The hydrolysis in soils is much faster with complete degradation occurring in < 1 day(5). The rapid rate of the reaction suggests that it is catalyzed by soil(5). Solutions of 2,4-D isopropyl ester in water absorb light > 290 nm(6). Although the sunlight photolysis of 2,4-D isopropyl ester has not been experimentally determined, several other esters have been studied and found to have half-lives of 2-3 weeks. The products were 2,4-dichlorophenol and compounds resulting from replacement of chlorine by hydroxyl. Photodegradation will be important in surface waters, especially at acid and near neutral pHs where hydrolysis is slow(2,3).

According to a classification scheme(1), an estimated BCF of 80(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(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 isopropyl ester is estimated as 600(SRC), using a water solubility of 37.3 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,4-D isopropyl ester is expected to have low mobility in soil(SRC). 2,4-D isopropyl ester is adsorbed slightly by clay minerals with the adsorption to bentonite > illite > kaolinite(4). Large amounts of bentonite, illite and kaolinite, namely 6.89, 11.79 and 37.59 grams respectively, would be required to reduce the concentration of 2,4-D isopropyl ester in water from 3 mg/l to 2 mg/l(4).

The Henry's Law constant for 2,4-D isopropyl ester is estimated as 2.2X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 2.32X10-4 mm Hg(1), and water solubility, 37.3 mg/l(2). This Henry's Law constant indicates that 2,4-D isopropyl ester is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 18 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 207 days(SRC). 2,4-D isopropyl ester's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 2,4-D isopropyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

SURFACE WATER: During irrigation season, the concentration of 2,4-D isopropyl ester was 1.5 parts/trillion in the Columbia River near Wanatchee, WA(1).|OTHER WATER: During irrigation season, the concentration of 2,4-D isopropyl ester ranged from trace to 0.5 parts/trillion and trace to 18.0 parts/trillion in the irrigation water and return flow, respectively, of the Columbia River near Wanatchee, WA(1).

One pasture was sprayed with 2 lb per acre of 2,4-D isopropyl ester. ... Milk collected from the exposed cows and forage samples from the fields were analyzed for 2,4-D by gas chromatography. The highest levels of 2,4-D were 0.05-0.06 ppm. ... No 2,4-D was detected on the third day after exposure to the isopropyl 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 isopropyl ester may occur through inhalation and dermal contact with this compound at workplaces where 2,4-D isopropyl ester is produced or used. Agricultural workers may be exposed to 2,4-D isopropyl ester during spraying operations using herbicides containing this chemical. The general population may be exposed to 2,4-D isopropyl ester via inhalation of ambient air with this compound in regions where spraying is performed. (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).

Drug Information

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. /SRP: Unspecified ester of 2,4-D/|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. /SRP: Unspecified ester of 2,4-Dichlorophenoxyacetic acid/

TREATMENT OF LEMONS WITH (14)C LABELED 2,4-D ISOPROPYL-ESTER INDICATED THAT THE ESTER WAS HYDROLYZED & PART OF 2,4-D THEN REACTED WITH SOME PLANT CONSTITUENT TO FORM AN ESTER-LIKE COMPLEX. ... SAMPLES OF FRESH CITRUS PEEL WERE PREPARED BY COMPOSITING PEEL SAMPLES OBTAINED FROM ORANGES FROM TREES SPRAYED WITH 2,4-D ISOPROPYL ESTER. IN ADDITION TO FREE ACID & ESTER, CONJUGATE WAS ALSO FOUND. LATTER BECAME AVAILABLE FOR EXTRACTION ONLY AFTER HEAT TREATMENT. ... PRELIMINARY INVESTIGATING INDICATED 2,4-D WAS CONJUGATED WITH PECTIN ...|HYDROLYSIS OF 2,4-D ESTERS HAS BEEN REPORTED IN BARLEY & LEMONS TREATED WITH ISOPROPYL ESTER ... /SRP: DEPENDENT ON EXTRACTION METHOD./ /2,4-D ESTER/|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. /2,4-D/|For more Metabolism/Metabolites (Complete) data for 2,4-D ISOPROPYL ESTER (6 total), please visit the HSDB record page.

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/

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

/SRP/: Impurities are carried over from substrates, 2,4-D and isopropyl alcohol, during synthesis.|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/

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.

... A 63-year-old man, inhaled fumes of a solution comprised of 44% 2,4-D isopropyl ester. Within 2-3 hours the subject lost consciousness and within 2 days after return to consciousness cephalea /headache/ and fever appeared, followed by myalgia in the neck and lower limbs, anorexia, muscular hypertonia, tachyarrhythmia, urinary incontinence, and constipation. Sepsis of the urinary tract was identified by urine culture analysis ...|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 SALT/|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 isopropyl ester Use and Manufacturing

Methods of Manufacturing

/2,4-D/ esters are formed by acid-catalyzed esterification with azeotropic distillation of water ... or by a direct synthesis in which the appropriate ester of monochloroacetic acid is reacted with dichlorophenol to form the 2,4-D ester. /2,4-D esters/

Uses

For 2,4-D isopropyl ester (USEPA/OPP Pesticide Code: 030066) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./|For 2,4-D isopropyl ester (USEPA/OPP Pesticide Code: 128879) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./|HERBICIDE FOR PASTURE & RANGELANDS; AGRICULTURAL USE-EG, WHEAT, CORN, GRAIN SORGHUM, RICE AND OTHER GRAINS; INDUSTRIAL/COMMERCIAL USES; LAWNS, TURF, & AQUATIC USE; OTHER FIELD CROPS-EG, NUTS; COMPONENT OF HERBICIDE FOR JUNGLE DEFOLIATION-FORMER USE /2,4-D AND DERIVATIVES/|Plant growth regulator

Production

(1978) 2.19X10+10 G-DEMAND (2,4-D INCL ESTERS & SALTS)|(1982) 2.05X10+10 G-DEMAND (2,4-D INCL ESTERS & SALTS)

USEPA/OPP Pesticide Code 128879; Trade Names: A815, NF-114, triflumidazole, Trifmine, Procure.|USEPA/OPP Pesticide Code 030066; Trade Names: Alco citrus fix.|Amoco 2,4-D Weed Killer No 5 (butyl & isopropyl esters of 2,4-D)|Amoco 2,4-D Weed Killer No 3E (butyl & isopropyl esters of 2,4-D)|For more Formulations/Preparations (Complete) data for 2,4-D ISOPROPYL ESTER (12 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/|Relatively high volatility esters ... /of 2,4-D include/ methyl, ethyl, isopropyl, butyl, amyl. ... These esters ... are liquids which, when properly formulated form emulsions when mixed with water.

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)Ni 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)Ni 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/|Product analysis of 2,4-D, salts, esters and mixed combination products are by acid-base titration, by GLC, or by HPLC. Residues may be determined by gas liquid chromatography of derivatives ... .|For more Analytic Laboratory Methods (Complete) data for 2,4-D ISOPROPYL ESTER (11 total), please visit the HSDB record page.

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)nickel 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)nickel 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.|In General: Renberg's method is simple, but not very quantitative (70 to 82% at 1 to 3 ppm). Homogenize 5 g of tissue in (5 ml of hexane + 10 ml of acetone), eg, with an insertable homogenizer in a dropping funnel with a glass filter disc. Drop the liquid into 1 M hydrochloric acid (5 ml) (use N2 pressure if necessary) in a separatory funnel. Homogenize again with 10 ml of hexane + 5 ml of diethyl ether. Transfer the upper phase to the separatory funnel, shake, and transfer the upper phase to a centrifuge tube. Reextract the aqueous phase with 2 ml/2 ml of diethyl ether/hexane (x2). Combine the extracts in the centrifuge tube. Add sodium sulfate (100 to 300 mg) and centrifuge. Transfer the supernatant to a weighed flask, rinse the sodium sulfate with diethyl ether (3 x 2 ml), combine the washings and supernatant, evaporate the solvent, and calculate the fat content. Dissolve the residue in benzene (1 ml/25 mg fat). Take 3 ml of this and add 3 ml of 0.1 M sodium hydroxide solution. Shake for 5 min and remove the benzene phase. Continue with one of the following methods: 1) 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) an ion exchange clean up in 0.1 M sodium hydroxide.|For more Clinical Laboratory Methods (Complete) data for 2,4-D ISOPROPYL ESTER (6 total), please visit the HSDB record page.

Computed Properties

Molecular Weight:263.11
XLogP3:3.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:262.0163496
Monoisotopic Mass:262.0163496
Topological Polar Surface Area:35.5
Heavy Atom Count:16
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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