Triallat (ISO)

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticides -> Herbicides, Thiocarbamate

Herbicides

Pesticide (Tri Allate) -> USDA PDB

log Kow = 4.6

3.98 (calculated)

4.58

1.273 g/cu cm at 25 °C

Relative density (water = 1): 1.27

Dark brown to yellow solid; (>30 °C clear brown to dark brown liquid)

Oil

In water, 4 mg/L at 25 °C

In water, 4 ppm

Readily soluble in common organic solvents such as acetone, diethyl ether, ethyl acetate, ethanol, benzene and heptane

Soluble in heptane, ethyl alc, acetone, ether, benzene, ethyl acetate

Solubility in water, g/100ml at 25 °C: 0.0002

BP: 117 °C at 0.3 mm Hg

at 0.04kPa: 117 °C

Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx), sulfur oxides, hydrogen chloride gas.

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

34 °C

MP: 29-30 °C

29-30 °C

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P319, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P319, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Commission Regulation (EC) No 1490/2002

Triallate is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2009/77/EC, Reg. (EU) 2018/155, Reg. (EU) 2021/1449, Reg. (EU) 2022/1480, Reg. (EU) 2023/2592, Reg. (EU) No 540/2011

Tri-allate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Triallate, EPA 738-R-00-021 (March 2001). 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 13, 2018: http://www.epa.gov/pesticides/reregistration/status.htm]

Smith EA, Oehme FW; A Review of Selected Herbicides and Their Toxicities. Vet Hum Toxicol 33 (6): 596-608 (1991). A review of selected herbicides and their toxicities.

U389; As stipulated in 40 CFR 261.33, when carbamothioic acid, bis(1-methylethyl)-, S-(2,3,3-trichloro-2-propenyl) ester, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it 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).

Tolerances are established for residues of triallate, S-2,3,4-trichloroallyl diisopropylthiocarbamate and its metabolite 2,3,3-trichloroprop-2-enesulfonic acid (TCPSA) in or on the following food commodity: Bermudagrass, hay.

Tolerances with a regional registration, as defined in 180.1(l),are established for residues of the herbicide (S-2, 3, 4-trichloroallyl diisopropylthiocarbamate) and its metabolite 2, 3, 3-trichloroprop-2-enesulfonic acid (TCPSA) in or on the following food commodities:[Table#3574]

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether or not products containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e., active ingredient-specific) data required to support reregistration of products containing triallate as an active ingredient. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing triallate. Appendix B identifies the generic data requirements that the Agency reviewed as part of its determination of reregistration eligibility of triallate. These data were sufficient to allow the Agency to determine that triallate can be used without resulting in unreasonable adverse effects to humans and the environment. The Agency, therefore, finds that all products containing triallate as the active ingredient are eligible for reregistration, provided specified changes are made to the label. Actions needed to reregister particular products are addressed in Section V of this document. The Agency made its reregistration eligibility determination based on the data required for reregistration, the current guidelines for conducting acceptable studies to generate such data, and published scientific literature. The Agency has found that all currently registered uses of triallate, except canary grass, are eligible for reregistration, provided specified changes are made to the label. Canary grass is not being supported by the registrant for reregistration and tolerances have been revoked. However, the Agency may take appropriate regulatory action if new information comes to the Agency's attention regarding the reregistration of triallate. The Agency may also require the submission of additional data (1) to support the registration of products containing triallate, (2) if the data requirements for registration change, or (3) if the guidelines for generating such data change.

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Triallate is found on List B. Case No: 2695; Pesticide type: Herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): S-(2,3,3-Trichloroallyl) diisopropylthiocarbamate; Data Call-in (DCI) Date(s): 06/04/91,05/03/93, 09/30/94, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

In case of fire in the surroundings, use appropriate extinguishing media.

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Fire extinguishing media: Water spray, foam, dry chemical, carbon dioxide, or other Class B agent.

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide.

Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature 2 - 8 °C.

Store in well-ventilated area, above freezing.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. 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: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U389, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. 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 formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.

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.

For more Preventive Measures (Complete) data for Triallate (8 total), please visit the HSDB record page.

For acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

The triallate tolerance of wheat (Triticum aestivum) cultivars Marius and Mexicali was determined under growth chamber conditions. Mexicali was found to tolerate triallate at levels about fourfold higher than Marius. The susceptible wheat cultivar was protected against triallate by seed treatment with MON 5501. The herbicide concentration in the aerial part of the plants was determined by gas chromatography. Triallate levels were similar in both cultivars treated with 0.5 mg/L of triallate. The safener did not affect the triallate content per plant in the susceptible wheat cultivar treated with 1 mg/L of herbicide.

Greenhouse and field experiments were conducted to determine the effectiveness of dichlormid, R-29148, CGA-92194, flurazole, naphthalic anhydride, and MON-5500 as herbicide antidotes for triallate in wheat and to determine triallate antagonism by seed-applied fungicides and insecticides. Seed treatment of MON-5500 at 0.063% wt/wt was the most effective antidote for triallate in wheat in both greenhouse and field. Dichlormid and R-29148 at 0.5% wt/wt were more effective as antidotes for triallate in wheat than either CGA-92194 or naphthalic anhydride. Flurazole, as a seed treatment, did not reduce triallate injury to wheat. Dichlormid or R-29148 at 2.2 kg ai ha-1 applied broadcast to soil and incorporated reduced injury to wheat from triallate at 1.1 kg ai ha-1 and also reduced injury to oats from 0.3 kg ha-1 triallate. Seed treatments of carboxin at 0.2% wt/wt or imazalil at 0.008% wt/wt antagonized triallate and decreased injury to wheat from triallate at 0.6 kg ha-1. Maneb plus lindane or mancozeb treatment of wheat seed increased injury from triallate.

Triallate is mutagenic. Data concerning the effects of thiocarbamates on man are scarce. However, cases of irritation and sensitization have been observed among agricultural workers. Some thiocarbamates, e.g., molinate, have an effect on sperm morphology and, consequently, on reproduction. However, no teratogenic effects have been observed. The results of mutagenicity studies have shown that thiocarbamates containing dichloroallyl groups are highly mutagenic. Some thiocarbamates are acetylcholine esterase inhibitors. Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved.

LD50; Species: /Lepomis macrochirus/ (Bluegill sunfish); Concentration: 4.9 mg/L for 96 hr /EC (4 lb/gal)/ /Conditions of bioassay not specified in source examined/

LD50; Species: /Oncorhynchus mykiss/ (Rainbow trout); Concentration: 9.6 mg/L for 96 hr /EC (4 lb/gal)/ /Conditions of bioassay not specified in source examined/

LD50; Species: /Colinus virginianus/ (Bobwhite quail) oral >2251 mg/kg

LC50; Species: /Anas platyrhynchos/ (Mallard ducklings) diet >5000 mg/kg for 8 days

For more Ecotoxicity Values (Complete) data for Triallate (8 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 1,659-3,981(2) indicates that triallate is expected to have low to slight mobility in soil(SRC). Volatilization of triallate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 1.2X10-4 mm Hg(3), and water solubility, 4.0 mg/L(3). Triallate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The main loss processes from soil of this compound are volatilization from moist soil, unless it has been incorporated into the soil, and biodegradation(3). Reported losses after 16 weeks of 65 and 75% of added triallate to clay and loam soils, respectively(4), indicate that biodegradation is an important environmental fate process in soil(SRC).

FIELD STUDY: Percentages of triallate recovered in May 1979 from field plots in Saskatchewan, Canada of Regina heavy clay and Weyburn loam after application of triallate in October 1978 were 64% and 62%, respectively. Percentages of triallate recovered in May 1981 from the same field plots of Regina heavy clay and Weyburn loam after application of triallate in October 1980 were 22% and 20%, respectively(1). Annual incorporation of 1.5 kg emulsifiable triallate/ha for 1, 2, and 3 yr, left 0.15, 0.23 and 0.25 kg/ha, as found 1 yr after the last treatment. Residues after applications of granular triallate were 0.44, 1.47 and 0.41 kg/ha(2). Triallate is reported to have a field half-life of 82 days(3).

ECOSYSTEM: Persistence, adsorption and volatility in prairie soils incl Lacombe loam (LL), Weyburn loam (WL), Regina heavy clay (RHC) and Asquith sandy loam (ASL) were studied. Duplicate soils were analyzed after 0, 4, 8 and 12 wk. In 4 wk, 50% of diallate applied at rates equivalent to 2.25 to 2.50 lb/acre was degraded in WL containing moisture at levels in excess of wilting point. Persistence was greater in RHC. Triallate broke down at slower rate than diallate in WL and RHC. Rate was lower in soils containing less moisture. It was almost completely adsorbed by all test soils. Loss through volatilization was dependent on soil type and temp. Recoveries in top 5 cm of test plots after 5 summer months were 15 to 20% of initial application. Next 5 cm of soil contained negligible amt.

AQUATIC FATE: Based on a classification scheme(1), a Koc range of 1659 to 3981(2) indicates that triallate 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 1.2X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 1.2X10-4 mm Hg(4), and water solubility, 4.0 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 and 45 days, respectively(SRC). Triallate is relatively stable to hydrolysis; 85%, 85%, 90%, and 85% of added triallate remained after 24 weeks incubation in solutions of pH 4, 6, 7, and 8, respectively(5). According to a classification scheme(6), an estimated BCF of 500(SRC), from its log Kow of 4.60(4) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Estimated aquatic biodegradation half-lives of 680 and 1170 days at pH 6.8 and 7.0, respectively(8), suggest that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triallate, which has a vapor pressure of 1.2X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triallate 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 days(SRC), calculated from its rate constant of 3.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase triallate is degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 340 days(SRC), calculated from its rate constant of 3.3X10-20 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 340 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). Triallate does not contain chromophores that absorb at wavelengths >290 nm(5) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The substance can be absorbed into the body by inhalation and by ingestion.

Inhalation (L793) ; oral (L793); dermal (L793)

IDENTIFICATION AND USE: Triallate is a dark brown to yellow solid (>30 °C clear brown to dark brown liquid). It is a selective herbicide for control of wild oats in wheat. HUMAN STUDIES: Triallate did not induce unscheduled DNA synthesis in human cells. Epidemiological study did not find significant changes in neurological function after high triallate exposure. ANIMAL STUDIES: It was highly irritating to skin, and slightly irritating to eyes in rabbits. Hens fed triallate daily for 10 days had decreased fertility and induced hemorrhaging and degenerative necrotic changes in liver, kidneys, and reproductive organs. Oral administration of 945 mg/kg triallate to mice and 500 mg/kg to rabbits decreased brain acetylcholinesterase activity and the number of erythrocytes in peripheral blood. When given to sheep at 300 mg/kg, it decreased aspartate aminotransferase and increased alanine aminotransferase activities in blood serum. A decrease in peripheral blood RNA was found in pigs given triallate. Brain hemorrhages, focal hepatic cell necrosis and splenic hyperplasia were observed. Triallate inhibited blood cholinesterase and brain cholinesterase slightly in rabbits. When tested for neurotoxicity in Leghorn hens, triallate did not elicit signs of neurotoxicity at 300 mg/kg/day topically or 400 mg/kg/day orally. Sheep may be poisoned by 300 mg/kg of triallate, showing signs of depression, anorexia, salivation, weakness, convulsions and paresis. Triallate produced endocrine changes in ewes and caused a significant increase in severity of oviductal intraepithelial cysts. Long-term studies in mice described hepatocellular carcinoma in both sexes and liver hemangiosarcoma in males. Reduced fetal weight and skeletal variation were noted in developmental studies in rats. When tested for mutagenicity in Salmonella typhimurium, a positive response was present for strains TA-1535 and TA-100 with and without activation and for strain TA 98 with activation. ECOTOXICITY STUDIES: Static acute toxicity tests with Daphnia magna and Chironomus riparius suggested that triallate was very toxic to aquatic invertebrates.

The metabolic products of triallate, diallate and sulfallate appear to be mutagenic or carcinogenic. In particular, the 2-chloro-allyl group is responsible for the mutagenicity of these herbicides. These metabolites likely bind to or disrupt DNA causes base-pair subsitutions. Diallate has been shown to be a carcinogen in mice. Some thiocarbamates (EPTC, Molinate, Pebulate, and Cycloate) share a common mechanism of toxicity, i.e. the inhibition of acetylcholinesterase. An acetylcholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

The Average Daily Intake (AVDI) of triallate in 3 population groups for the period 1988 was determined according to the FDA's monitoring program for chemical contaminants in the U.S. food supply (Total Diet Study or Market Basket Study)(1). For the monitoring period of 1988, the AVDI in 6-11 month old infants, 14-16 yr old males, and 60-65 year old females was 37.6, 73.7, and 107.5 ng/kg body wt/day, respectively(1).

The Average Daily Intake (AVDI) of triallate for the period 1986-1991 was determined according to the FDA's monitoring program for chemical contaminants in the U.S. food supply (Total Diet Study or Market Basket Study)(1). For the monitoring period of 1992, the AVDI was <0.0001 ug/kg body wt/day, for all age/sex groups(1).

/AQUATIC SPECIES/ Tandem mass spectrometry (MS) was used to detect herbicide residues in wild populations of amphipods collected from microcosms spiked with a single pulse of either Avadex-BW (triallate) or HoeGrass (diclofop-methyl) at three different concentrations (1.0, 10.0, and 100.0 ug/L). Independent confirmations of both herbicides were obtained by spiking amphipod tissues with 50 pg of authentic standards of triallate or diclofop-acid. The in situ microcosm experiments demonstrated that positive confirmation of triallate could still be made 30 days following an initial single spike of 10 ug/L triallate. ...

/PLANTS/ Oats are susceptible /to phytotoxicity/.

/FIELD STUDIES/ An aquatic, multicomponent microcosm simulating a northern prairie wetland was used to assess the potential effects of six extensively used agricultural pesticides on this important wildlife habitat. Using a nested experimental design, 16 4-liter aquatic microcosms were treated with three concentrations of each of the pesticides carbofuran, fonofos, phorate, atrazine, treflan and triallate. The microcosm units were incubated for 30 days in an environmental chamber, with a 16-hr light:8-hr dark cycle, maintained at 20 °C. Specific limnological, biological and toxicological parameters were monitored over time by observing the interactions of water, animals, sediment and plants with the pesticides. The laboratory protocol was designed as an initial, rapid, economical screening test to determine the effect, but not the fate, of chemical contaminants in terms of toxicity, impaired productivity and community biochemical functions. Static acute toxicity tests with Daphnia magna and Chironomus riparius suggested that carbofuran, fonofos, phorate and triallate were very toxic to aquatic invertebrates. For D. magna the 48-hr EC50 values were 48, 15, 19 and 57 ug/L, respectively. Invertebrate viability tests indicated rapid changes in the toxicological persistence of these pesticides after microcosm interaction. Populations of D. magna were established in the 10 ug/L test concentration of carbofuran, phorate, triallate and fonofos at 1, 1, 14 and 28 days, respectively. Preexposure of the wetland sediments to either triallate or fonofos did not appear to change the relative toxicological persistence of each compound in the water column. Changes in pH, alkalinity, conductivity, dissolved oxygen, total nitrogen and total phosphorus were also observed with different pesticide treatments. Atrazine significantly reduced gross primary productivity and inhibited algal and macrophytic growth. In general, there was no evidence of significant inhibition of microbial functions in the water or hydrosoil of the treated microcosms. The respiratory electron transfer system, phosphatase activity, oxygen consumption and mineralization of dissolved organic carbon were not significantly impacted by any of these pesticides in hydrosoils. However, the impact of atrazine, fonofos and triallate on invertebrates and plants in the microcosm-both key elements in wetland productivity-would suggest that caution be used in application of these pesticides in or near wetland habitats.

U389; As stipulated in 40 CFR 261.33, when carbamothioic acid, bis(1-methylethyl)-, S-(2,3,3-trichloro-2-propenyl) ester, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it 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).

Tolerances are established for residues of triallate, S-2,3,4-trichloroallyl diisopropylthiocarbamate and its metabolite 2,3,3-trichloroprop-2-enesulfonic acid (TCPSA) in or on the following food commodity: Bermudagrass, hay.

Tolerances with a regional registration, as defined in 180.1(l),are established for residues of the herbicide (S-2, 3, 4-trichloroallyl diisopropylthiocarbamate) and its metabolite 2, 3, 3-trichloroprop-2-enesulfonic acid (TCPSA) in or on the following food commodities:[Table#3574]

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether or not products containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e., active ingredient-specific) data required to support reregistration of products containing triallate as an active ingredient. The Agency has completed its review of these generic data, and has determined that the data are sufficient to support reregistration of all products containing triallate. Appendix B identifies the generic data requirements that the Agency reviewed as part of its determination of reregistration eligibility of triallate. These data were sufficient to allow the Agency to determine that triallate can be used without resulting in unreasonable adverse effects to humans and the environment. The Agency, therefore, finds that all products containing triallate as the active ingredient are eligible for reregistration, provided specified changes are made to the label. Actions needed to reregister particular products are addressed in Section V of this document. The Agency made its reregistration eligibility determination based on the data required for reregistration, the current guidelines for conducting acceptable studies to generate such data, and published scientific literature. The Agency has found that all currently registered uses of triallate, except canary grass, are eligible for reregistration, provided specified changes are made to the label. Canary grass is not being supported by the registrant for reregistration and tolerances have been revoked. However, the Agency may take appropriate regulatory action if new information comes to the Agency's attention regarding the reregistration of triallate. The Agency may also require the submission of additional data (1) to support the registration of products containing triallate, (2) if the data requirements for registration change, or (3) if the guidelines for generating such data change.

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Triallate is found on List B. Case No: 2695; Pesticide type: Herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): S-(2,3,3-Trichloroallyl) diisopropylthiocarbamate; Data Call-in (DCI) Date(s): 06/04/91,05/03/93, 09/30/94, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

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. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

Triallate isotopically labeled with (14)C and (13)C in the C-1-allylic carbon position was administered orally to male and female Sprague Dawley rats at dose levels of 5 and 500 mg/kg of body wt. ... Kinetics for whole body elimination of radioactivity were consistent with a two compartment open model. The half life of the alpha phase varied from 5.9 to 22.8 hr, and that of the beta phase from 171 to 265 hr.

Rats treated orally with several promutagens and carcinogens containing haloallyl or halopropyl substituents excrete small amount of urinary 2-haloacrylic acids, analyzed as their pentafluorobenzyl esters, such as 2-chloroacrylic acid and trichloroacrylic acid from triallate. Rabbit liver microsomal oxidases also yield 2-chloroacrylic and trichloroacrylic acids from triallate. 2-Haloacroleins as potent mutagens and intermediary metabolites may contribute to adverse toxicological properties of triallate.

The major (57-83% yields) mouse microsomal mixed function oxidase metabolites of (E) and (Z) diallate and triallate are identified by HPLC cochromatography as the corresponding sulfoxides. Other mixed function oxidase metabolites identified by headspace GLC/MS and quantitated by GLC/ECD are 21-chloroacrolein from diallate (9.2% and 1.6% from the Z and E isomers, respectively) and sulfallate (0.3% yield) and 2,3-trichloracrolein from triallate. Addition of glutathione and glutathione S-transferase to the mixed function oxidase system reduces the amounts of sulfoxides and yields new products identified by headspace GLC/ECD and GLC/MS as 2,3-dichlorallylthiol from (E) and (Z) diallate and 2,3,3-trichlorallylthiol from triallate, they also increase by 9 fold the liberation of 2-chloroallythiol from sulfallate. Thus, formation of mutagenic chloroacroleins involves primarily sulfoxidation of (E) and (Z) diallate followed by (2,3) sigmatropic rearrangement-1,2-elimination reactions and S-methylene hydroxylation of triallate and sulfallate and then decomposition of their alpha-hydroxy intermediates. Competing glutathione S-transferase catalyzed conjugations with glutathione divert the sulfoxidized intermediates from activation involving chloroacrolein formation to detoxification on chloroallylthiol liberation.

(13)C, (14)C Triallate was administered orally to Sprague Dawley rats. Twelve excreted metabolites were identified, the most abundant being 2,3,3-trichloro-2-propenesulfinic acid. Five metabolites derived from 2,3,3-trichloro-2-propenethiol were identified in excreta, including a methyl sulfone mercapturate whose structure was confirmed by X-ray crystallography. Three 2-chloroacrylate metabolites were identified, including a 2-chloroacrylate mercapturate whose structure was confirmed by X-ray crystallography. 2,3,3-Trichloro-2-propenol and hydroxytriallate were also identified as metabolites. Dosing of radiolabeled thiol and sulfinic acid to separate animals resulted in excretion of only thiol derived metabolites in the urine of thiol dosed rats, while sulfinic acid and sulfonic acid were excreted by sulfinic acid dosed rats. Triallate metabolism in rats proceeds via three main pathways, ie, S-oxidation leading to sulfur acids, S-oxidation/hydrolysis/reduction leading to thiol derivatives, and C-oxidation of the 2,3,3-trichloropropenethiol moiety. Thus, formation of readily excreted sulfur acids and thiol derivatives is the major route of triallate metabolism in rats.

Rat liver enzyme preparations were used to investigate the mechanistic pathways of triallate metabolism. Incubation of (14)C triallate with reduced nicotinamide adenine dinucleotide phosphate fortified microsomes gave rise to metabolites generated via a number of reaction types, including sulfur oxidation/hydrolysis and hydroxylation of the allylic thiol moiety accompanied by rearrangement. Addition of glutathione to microsomal incubations resulted in the formation of glutathione conjugates arising via conjugate addition of glutathione to metabolic intermediates such as trichloroacrolein. Addition of glutathione to microsomal incubations inhibited the binding of triallate derived radioactivity to microsomal proteins. Metabolite identification was accomplished by mass spectrometry and chemical synthesis and by a novel application of heteronuclear multiple quantum coherence NMR spectroscopy.

For more Metabolism/Metabolites (Complete) data for Triallate (6 total), please visit the HSDB record page.

As a general rule, thiocarbamates can be absorbed via the skin, mucous membranes, and the respiratory and gastrointestinal tracts. They are eliminated quite rapidly, mainly via expired air and urine. Two major pathways exist for the metabolism of thiocarbamates in mammals. One is via sulfoxidation and conjugation with glutathione. The conjugation product is then cleaved to a cysteine derivative, which is metabolized to a mercapturic acid compound. The second route is oxidation of the sulfur to a sulfoxide, which is then oxidized to a sulfone, or hydroxylation to compounds that enter the carbon metabolic pool.

Single 500 mg/kg dose administered orally to rabbits was rapidly absorbed from GI tract; present in all organs tested; largest amount accumulated in liver, lungs, kidneys, and spleen; all traces gone by 7th day. No traces of triallate detected in meat, eggs, or internal organs of hens fed 1/240 LD50 dose daily for 100 days. Sheep poisoned with 300 mg/kg had traces detected in meat 84 days later in cold storage.

Absorbed principally by the coleoptiles.

Triallate isotopically labeled with (14)C and (13)C in the C-1-allylic carbon position was administered orally to male and female Sprague Dawley rats at dose levels of 5 and 500 mg/kg of body wt. Most of the dose was rapidly eliminated within 72 hr after administration, and dose recoveries averaged 92% and 96% for the low dose and high dose animals, respectively. Approximately 42-52% of the dose was excreted via the urine and 33-46% via the feces. Expired (14)CO2 accounted for approximately 4% of the dose, while the residual carcass at sacrifice contained approximately 2%. Radioactivity in blood was associated principally with hemoglobin. Kinetics for whole body elimination of radioactivity were consistent with a two compartment open model. The half life of the alpha phase varied from 5.9 to 22.8 hr, and that of the beta phase from 171 to 265 hr.

Used as selective pre-emergence herbicide for control of wild oats and some annual grasses in crops; [HSDB]

Farming (Pesticides) [Category: Industry]

For Triallate (USEPA/OPP Pesticide Code: 078802) 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./

Triallate is a pre-emergent selective herbicide for general use.

Selective herbicide for control of wild oats in wheat.

Thiocarbamates are widely used throughout the world and are produced in great quantities, mainly as herbicides and fungicides.

Triallate is produced by reaction of isopropylamine with phosgene, followed by coupling with 1,1-dichloro-2-chloro-3-mercapto-1-propylene.

Propargyl alcohol + chlorine + carbonyl sulphide + diisopropylamine (chlorination/dehydrochlorination/thiocarbonylation/dehydrochlorination)

Preparation: M.W. Harman, J.J. D'Amico, United States of America patent 3330821 (1967 to Monsanto).

Triallate/Far-Go Herbicide (Gowan Company): Active ingredient: triallate 46.3%.

Avadex Mintill Herbicide (Gowan Company): Active ingredient: triallate 10.0%.

Avadex BW Technical (Gowan Company): Active ingredient: triallate 96.0%.

Buckle Granular Herbicide (Gowan Company): Active ingredient: triallate 10.0% and trifluralin 3.0%.

For more Formulations/Preparations (Complete) data for Triallate (6 total), please visit the HSDB record page.

Herbicides

Pharmaceuticals

HERBICIDES

Registration review posted to Federal Register on 09/24/2014 to insure triallate continues to satisfy the statutory standard and continues intended function without unreasonable adverse effects on human health or the environment.

Use of triallate in Italy was banned in 1977 due to toxicity concerns