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Home > Encyclopedia > Butylate

Butylate

Butylate structure

Butylate 

structure
  • CAS No:

    2008-41-5

  • Formula:

    C11H23NOS

  • Chemical Name:

    Butylate

  • Synonyms:

    Carbamothioic acid,N,N-bis(2-methylpropyl)-,S-ethyl ester;Carbamic acid,diisobutylthio-,S-ethyl ester;Carbamothioic acid,bis(2-methylpropyl)-,S-ethyl ester;Ethyl N,N-diisobutylthiocarbamate;Ethyl-N,N-diisobutyl thiolcarbamate;Stauffer R 1910;R 1910;Butylate;Sutan;S-Ethyl diisobutylthiocarbamate;S-Ethyl N,N-diisobutylthiolcarbamate;S-Ethyl N,N-diisobutylthiocarbamate;Butilate;Diisocarb;Anelda

  • Categories:

    Agrochemicals  >  Herbicides

Description

Butylate is a clear liquid with an aromatic odor.


Butylate is a tertiary amine.

Butylate Basic Attributes

217.38

217.37

217-916-3

3U78PG73G7

DTXSID7023936

Colorless liquid|Clear amber-to-yellow liquid

29033080

Characteristics

45.6

4.15

Amber Liquid

0.9402 g/cm3 @ Temp: 25 °C

<25 °C

137.5-138 °C @ Press: 21 Torr

110 DEG C (TAG OPEN CUP)

1.4689 (25ºC)

In water, 45 mg/l @ 22 deg C

0-6°C

1.3X10-2 mm Hg @ 25 deg C

Oral-Rat LD50: 4000 mg/kg

Combustion produces toxic nitrogen oxide and sulfur oxide gas

Aromatic odor

Henry's Law constant = 8.45X10-5 atm-cu m/mol at 25 °C (est)

Amber liquid /Technical butylate/|Thermally stable up to 200 °C; hydrolyzed by strong acids and alkalis, in aqueous solution in sunlight|Hydroxyl radical reaction rate constant = 3.08X10-11 cu cm/molec-sec at 25 °C (est)

Non-corrosive

Safety Information

I; II; III

6.1

UN 3082

2

20-51/53

60

EZ7525000

Xn;N,N,Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Thermally stable up to 200 deg C. Hydrolyzed by strong acids and bases.

P273

H332-H411

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Notice of Pesticide Report on FQPA Tolerance Reassessment Progress and Interim Risk Management Decision (TRED) for Butylate (September 2001). EPA issues a TRED for a pesticide that requires tolerance reassessment decisions, but does not require a reregistration eligibility decision at present because: the pesticide was initially registered after November 1, 1984, and by law is not included within the scope of the reregistration program; EPA completed a RED for the pesticide before FQPA was enacted on August 3, 1996; or the pesticide is not registered for use in the U.S. but tolerances are established that allow crops treated with the pesticide to be imported from other countries.[Available from, as of June 15, 2018: http://www.epa.gov/pesticides/reregistration/status.htm]|USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Butylate, EPA 738-F-93-014 (November 1993). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of June 15, 2018: http://www.epa.gov/pesticides/reregistration/status.htm]

|Warning|H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]|P261, P271, P273, P304+P312, P304+P340, P312, P391, and P501|Aggregated GHS information provided by 41 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Chemical-resistant apron when cleaning equipment, mixing, or loading. Chemical-resistant gloves. Protective eyewear.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.|Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.|Evacuate and restrict persons not wearing protective equipment from area of spill of leak until cleanup is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area of spill or leak after cleanup is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Normal measures for preventive fire protection.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

/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. /Thiocarbamate pesticide, liquid, flammable, poisonous; Thiocarbamate pesticide, liquid, flammable, toxic; Thiocarbamate pesticide, liquid, poisonous, flammable; Thiocarbamate pesticide, liquid, toxic, flammable/|/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. /Thiocarbamate pesticide, liquid, flammable, poisonous; Thiocarbamate pesticide, liquid, flammable, toxic; Thiocarbamate pesticide, liquid, poisonous, flammable; Thiocarbamate pesticide, liquid, toxic, flammable/|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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, uphill and/or upstream. Ventilate closed spaces before entering. /Thiocarbamate pesticide, liquid, flammable, poisonous; Thiocarbamate pesticide, liquid, flammable, toxic; Thiocarbamate pesticide, liquid, poisonous, flammable; Thiocarbamate 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. /Thiocarbamate pesticide, liquid, flammable, poisonous; Thiocarbamate pesticide, liquid, flammable, toxic; Thiocarbamate pesticide, liquid, poisonous, flammable; Thiocarbamate pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for Butylate (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. Thiocarbamate pesticide, liquid, flammable, toxic, flash point less than 23 degrees C; thiocarbamate pesticide, liquid, toxic; thiocarbamate pesticide, liquid, toxic, flammable, flash point 23 °C or more; and thiocarbamate pesticide, solid, toxic are included on the dangerous goods list. /Thiocarbamate pesticide, liquid, flammable, toxic, flash point less than 23 degrees C; Thiocarbamate pesticide, liquid, toxic; Thiocarbamate pesticide, liquid, toxic, flammable, flash point 23 °C or more; Thiocarbamate pesticide, solid, toxic/|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. Thiocarbamate pesticide, liquid, flammable, toxic, flashpoint less than 23 °C; thiocarbamate pesticide, solid, toxic; thiocarbamate pesticide, liquid, toxic, flammable, flashpoint not less than 23 °C; and thiocarbamate pesticide, liquid, toxic are included on the dangerous goods list. /Thiocarbamate pesticide, liquid, flammable, toxic, flashpoint less than 23 °C; Thiocarbamate pesticide, solid, toxic; Thiocarbamate pesticide, liquid, toxic, flammable, flashpoint not less than 23 °C; Thiocarbamate pesticide, liquid, toxic/

SOIL: The average and range of butylate at agrichemical facilities in Illinois was 639 ug/kg and 40-460,000 ug/kg, respectively(1).

URBAN/SUBURBAN: The maximum concentration of butylate in air over the Mississippi River (from New Orleans, LA to St. Paul, MN) in 1994 was 0.44 ng/cu m(1). However, butylate was only detected in 10% of the samples, which suggests a very poor collection efficiency for butylate in this study(1). Butylate was not detected at four locations on the Mississippi River from urban areas of Minneapolis, MN, Iowa City, IA and Jackson, MS. The compound was not detected in samples from the Eagle Harbor, MI background location. Sampling conducted from early April through mid-September 1995(2).|RURAL/REMOTE: Butylate was tested for but not detected in air samples at St. Damase, Quebec, Canada, an agricultural area in the Yamaska Basin. Sampling was conducted from May to September, 2004(1). Butylate was not detected at three locations on the Mississippi River from rural areas of Cedar Rapids, IA and Rolling Fork, MS. Butylate was present in samples from Princeton, MN. The compound was not detected in samples from the Eagle Harbor, MI background location. Sampling conducted from early April through mid-September 1995(2).

Toxicity

moderately toxic

IDENTIFICATION AND USE: Butylate is a colorless liquid. It is a thiocarbamate compound used as a selective preplant incorporated herbicide. HUMAN STUDIES: Although limited, epidemiologic studies suggest possible associations between butylate use and cancer risk, specifically prostate cancer and non-Hodgkin lymphoma. ANIMAL STUDIES: Butylate was not carcinogenic in rats and dogs. Butylate was not teratogenic in rats and rabbits. Butylate was nonmutagenic in Salmonella typhimurium tester strains TA 1535, 1537, 1538, 98 and 100, with and without metabolic activation. ECOTOXICITY STUDIES: Not dangerous to bees when used as directed.

Commercial and technical grades of 11 herbicides and 13 combinations of commercial grade herbicides were evaluated for their genotoxic properties with Salmonella typhimurium, Saccharomyces cerevisiae directly and following plant and animal activation, or with Zea mays. The herbicides were related by their use in commercial corn (maize) production. Commercial grade formulations of each herbicide and combination of herbicides were also evaluated in situ with the pollen waxy locus assay of Z. mays. Eradicane and bifenox were negative in all assays. Alachlor, propachlor, procyazine and SD50093 (a formulation of cyanazine plus atrazine) were positive in one assay. Cyanazine, dicamba and metolachlor were positive in 2 assays. Atrazine, simazine and butylate were tested only in situ. Atrazine and simazine were positive and butylate was negative. Of the combinations of herbicides evaluated with the 3 genetic assays, alachlor plus bifenox and procyazine plus metolachlor were positive in 1 assay and metolachlor plus atrazine was positive in 2 assays. Of the combinations of herbicides evaluated only in situ, butylate plus atrazine, eradicane plus atrazine, eradicane plus cyanazine and metolachlor plus cyanazine were positive while butylate plus cyanazine was negative.

LD50 Rat oral 3878 mg/kg|LD50 Rabbit dermal >4640 mg/kg|LD50 Rat (male) oral 4659 mg/kg|LD50 Rat (female) oral 5431 mg/kg|For more Non-Human Toxicity Values (Complete) data for Butylate (8 total), please visit the HSDB record page.

/OTHER TERRESTRIAL SPECIES/ Not dangerous to bees when used as directed.|/PLANTS/ Molinate and butylate treatments for 4 hr of Vicia faba root tip meristems, showed that both thiocarbamate herbicides increased significantly SCE frequency. Direct treatments of molinate and butylate on human lymphocytes applied 24 hr after the beginning of culture did not induce SCE. When S10 extracts of the Vicia roots, treated for 4 hr with molinate and butylate (in vivo activation) were added to lymphocytes (24 hr after of the beginning of culture), SCE were induced in a concentration-response manner. The in vitro assays, in which molinate and butylate was added at 48 hr lymphocyte cultures for 4 hr, showed a negative response, however, in the treatment where the S10 metabolic mix was added the SCE frequencies were significantly different to the control, and the concentration-response relationship was not observed with molinate, but it was obtained with butylate. The results showed that both herbicides needed the V. faba metabolism to produce SCE in human lymphocyte culture.

Butylate's former production resulted in its release to the environment through various waste streams; and use as a soil-incorporated herbicide(1) resulted in its direct release to the environment(SRC). Between 6 and 15 million lbs of butylate were applied annually in the United States(2). The last butylate product registered for use was cancelled on March 23, 2011(3).

TERRESTRIAL FATE: Based on a classification scheme(1), a reported Koc value of 400(2) indicates that butylate is expected to have moderate mobility in soil(SRC). Volatilization of butylate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.5X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 1.30X10-2 mm Hg(3), and water solubility, 45 mg/L(4). A photodegradation half-life of 280 days on soil has been reported(5). In a microagroecosystem study, delaying soil incorporation of butylate (applied as an emsulifiable concentration) for 24 hrs resulted in a 65% loss by volatilization. When applied in a microencapsulated form, little volatilization occurred(6). Butylate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The decline in butylate soil residues is due primarily to volatilization (47%) with aerobic soil metabolism of secondary importance(5). In soil, microbial degradation involves hydrolysis to ethylmercaptan, diisobutylamine and carbon dioxide; the half-life is 1.5-10 weeks(3) suggesting that biodegradation may be an important environmental fate process in soil(SRC).|FIELD STUDIES: The US Dept of Agric's Pesticide Properties Database lists a soil half-life of 13 days for butylate(1). The soil half-lives under crop growing conditions has been reported to range from 1.5 to 3 weeks(2). Butylate is reportedly lost by vaporization when applied to the surface of wet soils without incorporation(2). Butylate half-lives of approximately 8-28 days were observed in various laboratory and field studies(3); degradation rates were faster in soils previously treated with butylate or other thiocarbamate herbicides(3). In a field study using a soil previously exposed to butylate, the initial soil degradation half-life was approximately 10 days(4). In a 100 day field study (in silt loam and clay loam soils), butylate was found to have a low mobility as only very small quantities were leached to depth of 45-60 cm(5).|AQUATIC FATE: Based on a classification scheme(1), a reported Koc value of 400(2) indicates that butylate 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 8.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 1.30X01-2 mm Hg(4), and water solubility, 45 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 20 hrs and 10 days, respectively(SRC). According to a classification scheme(6), a reported BCF of 410(7) suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data in water were not available(SRC, 2018).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butylate, which has a vapor pressure of 1.30X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase butylate 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 12 hrs(SRC), calculated from its rate constant of 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Butylate's detection in rainwater samples(4) indicates that wet deposition occurs in the environment(SRC). Butylate contains chromophores that absorb at wavelengths >290 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of butylate with photochemically-produced hydroxyl radicals has been estimated as 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Butylate is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(2). Butylate contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Butylate did not degrade when exposed to sunlight for a 16 hr period on TLC plates(4). Butylate has a photodegradation half-life of 280 days on soil(5). Butylate degraded slowly on loam soil that was irradiated outdoors in California at approximately 25 °C; an average of 82% of the butylate remained undegraded after 30 days of irradiation(5). No degradation of butylate occurred in the dark control during the same period(5). Two minor degradates, butylate sulfoxide and butylate sulfone, were identified in the irradiated soil(5). Because butylate is soil-incorporated(5), photodegradation is not likely to be an important route of dissipation in the environment(SRC).

Bioconcentration factors of 180 for edible tissues, 630 for nonedible tissues, and 410 for whole fish using bluegill sunfish continuously exposed to 14C-butylate at 0.12-0.16 ppm(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). By day 14 of the depuration period, 98-99% of 14C-butylate residues were eliminated from the fish tissues(1).

128.82 L/kg|Based upon experimental adsorption measurements in a silty clay loam soil and a sandy loam soil(1), the Koc of butylate can be calculated to range from 185 to 260(SRC). The US Dept of Agric's Pesticide Properties Database lists a Koc value of 400 for butylate(2). According to a classification scheme(3), these experimental Koc values suggest that butylate is expected to have moderate mobility in soil(SRC). In one soil column leaching study using three different soil types, most of the initially added butylate remained in the upper 4 in of soil with no butylate leaching below 8 in(1). In a 100-day field study (in silt loam and clay loam soils), butylate was found to have a low mobility as only very small quantities were leached to depth of 45-60 cm(4). Adsorption of butylate has been found to increase as the content of organic matter and clay increases, with a corresponding decrease in leaching(1,5). Based on batch equilibrium experiments, butylate was determined to be mobile to moderately mobile in Keeton sandy loam, Columbia loamy sand, Sorrento loam, and Atterberry silt loam soils(6). The adsorption Freundlich values reported for these soils were 1.5, 4.8, 7.3, and 5.5, respectively(6).

The Henry's Law constant for butylate is estimated as 8.5X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 1.30X10-2 mm Hg(1), and water solubility, 45 mg/L(2). This Henry's Law constant indicates that butylate 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 20 hours(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 10 days(SRC). Butylate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Butylate is reportedly lost by vaporization when applied to the surface of wet soils without incorporation(4). In a microagroecosystem study, delaying soil incorporation of butylate (applied as an emsulifiable concentrate) for 24 hrs resulted in a 65% loss by volatilization(5); when applied in a microencapsulated form, little volatilization occurred(5). Butylate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Butylate was not detected in 216 samples of Oregon well water; 20% of wells sampled in Wisconsin tested positive for butylate with a maximum reported concentration of 4.9 ug/L (detection limit 0.2-0.01 ug/L)(1); 21% of 56 wells sampled in the vicinity of an agrochemical dealer facility in Illinois - facility wells - 28 ug/L max, 11.3 ug/L mean; not detected in neighboring wells(1). It has also been detected, not quantified in groundwater and water supplies in Iowa, Texas, and Georgia(1). In the early 1980's, 1174 community wells and 617 private wells were sampled in Wisconsin; butylate was detected, not quantified in one well(2). Of the 73 wells sampled in Nebraska during the mid 1970's through the late 1980's, butylate was not detected (detection limit 0.01-0.05 ppb)(3). Butylate was detected at a concentration between 0.1-1.0 ug/L in 1 of 237 wells, contaminated as a result of a spill, sampled in Ontario, Canada between 1969 and 1978(4); detected (detection limit 1.0 ug/L) in 1 of 359 wells between 1979 and 1984 which were contaminated as a result of a spill(5); detected in wells from 4 of 91 farms (detection limit 1.0 ug/L) in November and December 1984 in Southern Ontario, Canada(6). Butylate was not detected (detection limit <10 ppb) in new drinking water wells sunk in the province of Bergamo, Northern Italy(7). Butylate was detected in ambient groundwater at 11 of 4515 stations at an average concentration of 0.018 ug/L(8). Butylate was present in 5% of ground water samples associated with orchard farming in the Central Columbia Plateau, Washington, sampled 1993-2003. It was not detected in groundwater samples associated with row crops or in public supply wells(9).|DRINKING WATER: Butylate was detected (maximum concentration of 3.12 ng/L) in 5 of 15 surface drinking-water supplies (reservoirs) in the northern Great Plains region, Manitoba, Alberta and Saskatchewan, Canada, sampled from early May to mid-August, 2003(1).|SURFACE WATER: Butylate was reported to be present (not quantified) in the Lake Erie ecosystem - Cuyahoga River, Sandusky River, Maumee River, and the River Raisin(1). Butylate concentration in 7 Lake Erie tributaries draining agricultural watersheds monitored from April 1983 to December 1991 (detection limit 0.05 ug/L) ranged from 0.2-5.7 ug/L(2). Butylate was not detected (detection limit 0.5 parts/trillion) in Adige River water, Northern Italy(3). From 1994 to 1995 in Colorado, butylate was detected in surface waters near agricultural areas at a median concentration of <0.008 ug/L but not at an urban watershed near Denver(4). Butylate was detected in ambient lake/reservoir water at 1 of 79 stations at a concentration of 0.003 ug/L(5). Butylate was detected in other ambient surface water at 88 of 1817 stations at a concentration of 0.05 ug/L(5). A mean concentation of 0.0019 ug/L was reported for Canadian waters and the Great Lakes(6). Butylate was tested for but not detected in sampling conducted in the Yakima River Basin, WA from 1999-2000; detection limit = 0.002 ug/L(6).|RAIN/SNOW: Rainfall in Iowa was sampled from October 1987 through September 1990 from the Big Spring Basin, Iowa City, and the Bluegrass watershed(1). Butylate was detected (detection limit 0.10 ug/L) in 2 of 235 samples at a mean concentration of 0.12 ug/L (sites not specified)(1). Butylate was present at below the detection limit of 1 ng/L in rain samples at St. Damase, Quebec, Canada, an agricultural area in the Yamaska Basin. Sampling was conducted from May to September, 2004(2).

Occupational exposure and general population exposure should be low or non-existent since butylate is no longer produced or used in the US (March, 2011). (SRC)

Drug Information

Absorbed by the roots and coleoptiles, with translocation acropetally.|The metabolism of the thiocarbamate herbicide SUTAN (butylate) was studied after administration of single oral doses of [isobutyl-1-(14)C]SUTAN to male and female rats. The radiolabelled dose was rapidly absorbed and excreted, with 79% of the dose excreted in the urine in 72 hr. The small percentages of radioactivity excreted in the feces and as (14)CO2 were significantly higher (P less than or equal to 0.05) in males than in females. SUTAN was extensively metabolized, and no unmetabolized SUTAN was found in the urine. A total of 18 of the 29 urinary metabolites were identified, and identified metabolites represented 83-88% of the urinary radioactivity. Diisobutylamine was the major urinary metabolite in both males and females, averaging 51% of the urinary radioactivity. Other significant urinary metabolites included primary hydroxylated and tertiary hydroxylated diisobutylamines and a series of mercapturic acid pathway metabolites, including an S-glucuronide and several hydroxylated and unhydroxylated mercapturates. Oxidations at the three alkyl groups produced a variety of minor urinary metabolites, and hydroxylation of the primary or tertiary carbon on the isobutyl groups, followed by an intramolecular reaction, generated a series of minor cyclized metabolites.

Metabolic pathway of butylate in rats proceeds as follows: thiocarbamate, thiocarbamate sulfoxide, S-(N,N-dialkylcarbamoyl)glutathione, D-(N,N-dialkylcarbamoyl)cysteine, S-(N,N-dialkylcarbamoyl)mercapturic acid, S-(N,N-dialkylcarbamoyl)mercaptoacetic acid, and N-(S-(N,N-dialkylcarbamoyl)mercaptoacetyl)glycine. S-(N-isobutylcarbamoyl)mercapturic acid is also formed. About 40% of the (14)CO-butylate administered is metabolized by ester cleavage and (14)CO2 liberation without going through the thiocarbamate sulfoxide as an intermediate.|When administered to rats, butylate yielded a glycine conjugate of the mercaptoacetic acid product that was not detected with EPTC; but the cysteine conjugate was not detected with butylate. An N-de-isobutylmercapturic acid was formed from butylate but the corresponding EPTC product was not seen.|In mammals, following oral administration, the major metabolite is the N,N-dialkylcarbamoyl conjugate.|The metabolism of the thiocarbamate herbicide SUTAN (butylate) was studied after administration of single oral doses of [isobutyl-1-(14)C]SUTAN to male and female rats. The radiolabelled dose was rapidly absorbed and excreted, with 79% of the dose excreted in the urine in 72 hr. The small percentages of radioactivity excreted in the feces and as (14)CO2 were significantly higher (P less than or equal to 0.05) in males than in females. SUTAN was extensively metabolized, and no unmetabolized SUTAN was found in the urine. A total of 18 of the 29 urinary metabolites were identified, and identified metabolites represented 83-88% of the urinary radioactivity. Diisobutylamine was the major urinary metabolite in both males and females, averaging 51% of the urinary radioactivity. Other significant urinary metabolites included primary hydroxylated and tertiary hydroxylated diisobutylamines and a series of mercapturic acid pathway metabolites, including an S-glucuronide and several hydroxylated and unhydroxylated mercapturates. Oxidations at the three alkyl groups produced a variety of minor urinary metabolites, and hydroxylation of the primary or tertiary carbon on the isobutyl groups, followed by an intramolecular reaction, generated a series of minor cyclized metabolites.

Inhibition of lipid synthesis- not ACCase inhibition.

/SRP:/ Immediate first aid: Remove patient from contact with the material. Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Dithiocarbamates and Related Compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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 ... . /Dithiocarbamates and Related Compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or is in severe respiratory distress. Use moderate hyperventilation (rate of 20 respirations per minute) if signs of cerebral edema are present. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Dithiocarbamates and Related Compounds/|Decontaminate skin promptly by washing with soap and water. Treat contamination of the eyes immediately by prolonged flushing with copious amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other herbicides/|For more Antidote and Emergency Treatment (Complete) data for Butylate (9 total), please visit the HSDB record page.

/EPIDEMIOLOGY STUDIES/ Recent epidemiological studies have suggested an increased risk of non-Hodgkin lymphoma (NHL) from carbamate insecticide use among farmers. To further explore the possible relationships, we conducted a pooled analysis of three population-based case-control studies conducted in four midwestern states in the United States. A total of 985 white male subjects and 2895 control subjects were included in this analysis. Unconditional logistic regression was used to estimate the association and control for confounding. Compared with nonfarmers, farmers who had ever used carbamate pesticides had a 30% to 50% increased risk of NHL, whereas farmers without carbamate pesticide use showed no increased risk. Analyses for individual carbamate pesticides found a more consistent association with Sevin but not carbofuran, butylate, or S-ethyl dipropylthiocarbamate plus protectant. Among farmers using Sevin, the risk of NHL was limited to those who personally handled the product, those who first used the product for > or = 20 years before their disease diagnosis, and those who used the product for a longer period. These associations persisted after adjusting for other major classes of pesticides. These results suggest an increased risk of NHL associated with carbamate pesticide use, particularly Sevin. Further investigation of the association is warranted.|/EPIDEMIOLOGY STUDIES/ Although limited, epidemiologic studies suggest possible associations between butylate use and cancer risk, specifically prostate cancer and non-Hodgkin lymphoma (NHL). We examined butylate use and cancer risk more broadly in the Agricultural Health Study (AHS), a cohort of licensed pesticide applicators in Iowa and North Carolina. Pesticide use information was collected using self-administered questionnaires. Poisson regression was used to calculate rate ratios (RR) and 95% confidence intervals (CI). Two exposure metrics were used: lifetime exposure days (LD) and intensity-weighted lifetime exposure days (IWLD). We used two referent groups: unexposed to butylate and the lowest butylate usage category. This analysis included 19,655 applicators with complete butylate use information; 5297 applicators were exposed to butylate, making this the largest study of butylate to date. The mean follow-up time since enrollment was 9 years. Prostate cancer risk was significantly elevated among applicators in the highest LD category in both referent groups (low-exposed referent: RR(LD)=2.09, 95% CI=1.27-3.44). We observed a significantly elevated joint effect of prostate cancer family history and high butylate usage across both exposure metrics and both referent groups (low-exposed referent: RR(LD)=2.00, 95% CI=1.07-3.74), and a non-significant, elevated interaction between butylate use and prostate cancer family history, similar to a previous AHS finding. Statistically significant increased risks and exposure-response trends were seen for all lymphohematopoietic cancers (AL) and NHL for both exposure metrics and referent groups (low-exposed referent: AL:RR(LD)=2.27, 95% CI=1.18-4.37; NHL: RR(LD)=3.44, 95% CI=1.29-9.21). Our analysis did not find meaningful associations for other cancers analyzed. Further study is warranted for AL, NHL and prostate cancers.|/GENOTOXICITY/ Molinate and butylate treatments for 4 hr of Vicia faba root tip meristems, showed that both thiocarbamate herbicides increased significantly SCE frequency. Direct treatments of molinate and butylate on human lymphocytes applied 24 hr after the beginning of culture did not induce SCE. When S10 extracts of the Vicia roots, treated for 4 hr with molinate and butylate (in vivo activation) were added to lymphocytes (24 hr after of the beginning of culture), SCE were induced in a concentration-response manner. The in vitro assays, in which molinate and butylate was added at 48 hr lymphocyte cultures for 4 hr, showed a negative response, however, in the treatment where the S10 metabolic mix was added the SCE frequencies were significantly different to the control, and the concentration-response relationship was not observed with molinate, but it was obtained with butylate. The results showed that both herbicides needed the V. faba metabolism to produce SCE in human lymphocyte culture.

butylate

Butylate Use and Manufacturing

Methods of Manufacturing

Butylate is made by the reaction of di-isobutylamine with phosgene to give the carbamoyl chloride which is reacted with ethanethiol to give butylate.|Preparation: ... H. Tilles, J. Antognini, United States of America patent 2913327 (1959 to Stauffer)

Uses

Herbicide.

Between 6 and 15 million lbs of butylate are applied annually to crops in the United States.

USEPA/OPP Pesticide Code 041405; Trade Names: R-1910; Sutan+; Genate plus; Sutazine+, component of (with 080803).|Emulsifiable concentrate, granules.|Emulsifiable concentrate- 6 lb active ingredient/US gal; granules- 10% active ingredient; emulsifiable concentrates- containing 3 lb butylate/US gal and 1 lb 2,4-D/US gal. Same combination available in granules in mixtures of 6% and 2% & 12% and 4% (butylate and 2,4-D).|Mixtures (butylate +) atrazine|For more Formulations/Preparations (Complete) data for Butylate (8 total), please visit the HSDB record page.

Carbamothioic acid, N,N-bis(2-methylpropyl)-, S-ethyl ester: ACTIVE|Do not apply on milo or sorghum.|The rates recommended are: for the control of annual grasses and nut grass 3 kg ai/ha; for the control of dicotyledonous weeds in addition to grasses 4 kg/ha, or 3 kg/ha butylate + either atrazine or cyanazine.|Usual carrier: Emulsifiable liquid formulations are diluted in water and applied at a volume of 20 to 100 gallons per acre of total liquid.

Method: ASTM D5475; Procedure: gas chromatography with a nitrogen-phosphorus detector; Analyte: butylate; Matrix: ground water and finished drinking water; Detection Limit: 0.15 ug/L.|Method: EPA-NERL 525.2; Procedure: gas chromatography/mass spectrometry; Analyte: butylate; Matrix: finished drinking water, source water, or drinking water in any treatment stage; Detection Limit: 0.064 ug/L.|Method: EPA-TSC/NERL 507; Procedure: gas chromatography with a nitrogen-phosphorus detector; Analyte: butylate; Matrix: ground water and finished drinking water; Detection Limit: 0.053 ug/L.|Method: USGS-NWQL O-1121-91; Procedure: gas chromatography-mass spectrometry; Analyte: butylate; Matrix: natural water; Detection Limit: 0.052 ug/L.|For more Analytic Laboratory Methods (Complete) data for Butylate (10 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|HERBICIDES

Computed Properties

Molecular Weight:217.37
XLogP3:4.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:217.15003553
Monoisotopic Mass:217.15003553
Topological Polar Surface Area:45.6
Heavy Atom Count:14
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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