N,N-ジイソブチルチオカルバミド酸S-エチル

Pesticide -> EPA IRIS

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Thiocarbamate

Pesticide (Butylate) -> USDA PDB

Pesticide

log Kow = 4.15

3.45

Colorless liquid

Clear amber-to-yellow liquid

In water, 45 mg/L at 22 °C

In water, 36 mg/L at 20 °C

Miscible with common organic solvents, e.g. acetone, ethanol, xylene, methyl isobutyl ketone, kerosene

Miscible with 4-methylpentan-2-one

137.5-138 °C at 21 mm Hg

BP: 138 °C at 21 mm Hg

BP: 310 °C at 10 mm Hg. Hydrolysis rate: 1.1X10-3/day at 25 °C, pH 5-9

When heated to decomposition it emits very toxic fumes of /nitrogen oxides and sulfur oxides/.

The time required to destroy 3 concentrations (10, 100, and 1000 ppm) of 9 formulated herbicides (alachlor, atrazine, bentazon, butylate, cyanazine, 2,4-D, metolachlor, metribuzin, and trifluralin) and two formulated insecticides (arbofuran and malathion) by ultraviolet (UV)-ozonation (O3) was measured in a 66 UV lamp unit. The time required for 90% destruction was dependent on the concentration and increased as the concentration of pesticide increased. UV irradiation in the presence of ozone rapidly photooxidized all pesticides at 10 and 100 ppm and averaged 22 and 61 min, respectively. Longer times were required for pesticides at 1000 ppm.

0.0013 [mmHg]

1.29X10-2 mm Hg (1.73X10+3 mPa) at 25 °C

This chemical does not meet GHS hazard criteria for 2.4% (1 of 42) of reports.

Warning

H332 (97.6%): Harmful if inhaled [Warning Acute toxicity, inhalation]

P261, P271, P273, P304+P340, P317, P391, and P501 (click each P-code to see the statement)

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

Warning

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]

The Agency does not expect the current risks associated with butylate use to differ from those identified during the butylate reregistration process. In order to mitigate the risks identified in the RED, the Agency specified mitigation measures, which are already in effect on butylate product labels. The existing stocks sales and distribution deadlines included in the July 14, 2010 and the March 23, 2011 cancellation orders ensure that butylate sale, distribution, and use will decline and then cease entirely in the United States in the future. During this period, given the mitigation measures that are specified in the RED and are currently in place, the Agency believes that existing stocks of butylate products may be used until depleted without causing unreasonable risk to human health and the environment. Pursuant to 40 CFR section 155.57 and 155.58, the Agency is issuing the registration review final decision for butylate, thus concluding the butylate registration review, for the reasons discussed above. The affected product registrations are subject to the terms and conditions of the July 14, 2010 and March 23, 2011 cancellation orders.

Based on the reviews of the generic data for the active ingredient butylate, the Agency has sufficient information on the health effects of butylate and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency concludes that products containing butylate and registered for use on field corn, sweet corn and popcorn are eligible for reregistration. The Agency has determined that butylate products, labeled and used as specified in this Reregistration Eligibility Document, will not pose unreasonable risks or adverse effects to humans or the environment.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Butylate is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0071; Pesticide type: herbicide; Registration Standard Date: 09/30/83; Case Status: RED Approved 09/93; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Butylate; Data Call-in (DCI) Date(s): 09/30/90, 11/26/93; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

/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.

(FL) FLORIDA 350 ug/L

(ME) MAINE 350 ug/l

(WI) WISCONSIN 400 ug/L

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/

UN 2771; Thiocarbamate pesticides, solid, toxic

UN 2772; Thiocarbamate pesticide, liquid, flammable, toxic, flash point less than 23 degrees C

UN 3005; Thiocarbamate pesticide, liquid, toxic, flammable, flash point not less than 23 degrees C

UN 3006; Thiocarbamate pesticide, liquid, toxic

For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for Butylate (6 total), please visit the HSDB record page.

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.

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

General storage may be used. Prior to working with this chemical you should be trained on its proper handling and storage. Store in tightly closed containers in a cool, dry place.

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.

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.

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.

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.

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.

LC50; Species: Gammarus fasciatus, mature; Conditions: static bioassay without aeration, 15 °C, pH 7.2-7.5, water hardness 4-50 mg/L as CaCO3 and alkalinity 30-35 mg/L; Concentration: 11 mg/L for 96 hr (95% confidence limit: 8-16 mg/L)

LC50; Species: /Colinus virginianus/ (Bobwhite quail) diet 40000 mg/kg diet for 7 days

LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout); Concentration: 4.2 mg/L for 96 hr /Conditions of bioassay not specified/

LC50; Species: /Lepomis macrochirus/ (Bluegill sunfish); Concentration: 6.9 mg/L for 96 hr /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for Butylate (6 total), please visit the HSDB record page.

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).

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.

/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.

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of August 9, 2018: http://actor.epa.gov/dashboard/]

Butylate

Hepatic

5 x 10 ^-2 mg/kg-day

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).

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).

/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.

The Agency does not expect the current risks associated with butylate use to differ from those identified during the butylate reregistration process. In order to mitigate the risks identified in the RED, the Agency specified mitigation measures, which are already in effect on butylate product labels. The existing stocks sales and distribution deadlines included in the July 14, 2010 and the March 23, 2011 cancellation orders ensure that butylate sale, distribution, and use will decline and then cease entirely in the United States in the future. During this period, given the mitigation measures that are specified in the RED and are currently in place, the Agency believes that existing stocks of butylate products may be used until depleted without causing unreasonable risk to human health and the environment. Pursuant to 40 CFR section 155.57 and 155.58, the Agency is issuing the registration review final decision for butylate, thus concluding the butylate registration review, for the reasons discussed above. The affected product registrations are subject to the terms and conditions of the July 14, 2010 and March 23, 2011 cancellation orders.

Based on the reviews of the generic data for the active ingredient butylate, the Agency has sufficient information on the health effects of butylate and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency concludes that products containing butylate and registered for use on field corn, sweet corn and popcorn are eligible for reregistration. The Agency has determined that butylate products, labeled and used as specified in this Reregistration Eligibility Document, will not pose unreasonable risks or adverse effects to humans or the environment.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Butylate is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0071; Pesticide type: herbicide; Registration Standard Date: 09/30/83; Case Status: RED Approved 09/93; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Butylate; Data Call-in (DCI) Date(s): 09/30/90, 11/26/93; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

(FL) FLORIDA 350 ug/L

(ME) MAINE 350 ug/l

(WI) WISCONSIN 400 ug/L

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.

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.

Used as a selective pre-planting herbicide; [Merck Index]

Farming (Pesticides) [Category: Industry]

For butylate (USEPA/OPP Pesticide Code: 041405) there are 0 labels match. /SRP: Not registered for current 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./

A thiocarbamate compound used as a selective preplant incorporated herbicide. Because of its volatility, it must be incorporated immediately after application. Controls most grassy weeds, including nutgrass, in corn. Do not apply on milo or sorghum.

A selective herbicide ... well tolerated by corn. ... Effective against annual grass weed species such as barnyard grass ... crabgrass ... foxtails ... and goosegrass ... it is also effective against nutsedges ... bermudagrass seedlings ... and johnsongrass seedlings ... .

Herbicide

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)

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.