5915-41-3CCNc1nc(Cl)nc(NC(C)(C)C)n1FZXISNSWEXTPMF-UHFFFAOYSA-NTerbutylazine is a diamino-1,3,5-triazine that is N-tert-butyl-N'-methyl-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6. It has a role as a herbicide, a xenobiotic and an environmental contaminant. It is a chloro-1,3,5-triazine and a diamino-1,3,5-triazine. It is functionally related to a 6-chloro-1,3,5-triazine-2,4-diamine.
5915-41-3DTXSID4027608CHEMBL1888237Herbicides
Active substance -> EU Pesticides database: Approved
Pesticides -> Herbicides, Triazine
Pesticide
Environmental transformation -> Pesticides (parent, predecessor)
Microbiocides, Algicides, Herbicides
log Kow = 3.40
3.06
Colorless powder
White solid
Off-white. Powdery solid, waxy and globular
In water, 5.0 mg/L at 20 °C
In water, 9 mg/L at 25 °C, pH 7.4
In acetone 41, ethanol 14, n-octanol 12, n-hexane 0.36 (all in g/L, 25 °C)
Dimethylformamide, 40 g/liter; ethyl acetate, 10 g/liter; isopropanol, 10 g/liter; tetralin, 10 g/l; xylene, 14.3 g/L
Toluene, 1.04 g/100 ml; ethylene glycol, 0.236 g/100 ml, both at 25 °C
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P270, P273, P301+P317, P319, P330, P391, and P501 (click each P-code to see the statement)
Warning
H302 (93.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P319, P330, P391, and P501 (click each P-code to see the statement)
Chemical: 1,3,5-Triazine-2,4-diamine, 6-chloro-N-(1,1-dimethylethyl)-N'-ethyl-
Regulation (EC) No 1107/2009 (amended)
2008/934/EC, Commission Regulation (EU) 2021/618, Reg. (EU) 2021/824, Reg. (EU) 2024/2781, Reg. (EU) No 2019/291, Reg. (EU) No 820/2011
Terbuthylazine: Does not have an individual approval but may be used under an appropriate group standard
For the triazine herbicides, systemic toxicity unlikely unless large amounts are ingested; May cause irritation; [EPA Pesticides, p. 121] A mild to moderate eye and mild skin irritant; [HSDB] May cause irritation; [MSDSonline]
The major hazards encountered in the use and handling of terbutylethylazine stem from its toxicologic properties. Toxic by inhalation and ingestion, exposure to this colorless to white powder may occur from its use as an herbicide. Effects from exposure may include shortness of breath, muscle spasms, ataxia, and anorexia. In activities and situations where over exposure may occur, wear a self-contained breathing apparatus and personal protective clothing. If contact should occur, immediately flush affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. While terbutylethylazine does not ignite easily, it may burn with the production of irritating and poisonous gases. For fires involving terbutylethylazine, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Terbutylethylazine may be shipped domestically via air, rail, road, and water, in containers bearing the label "Poison". Small dry spills of prometone may be placed into a clean, dry, covered container for later disposal (liquid solutions are first absorbed in sand or other noncombustible absorbent). Large liquid spills should be diked far ahead to prevent terbutylethylazine from entering water sources and sewers. Before implementing land disposal of terbutylethylazine, consult with regulatory agencies for guidance.
Metabolism of terbuthylazine in rats is similar to other chloro-s-triazine herbicides. The major routes of metabolism are hydrolysis of the chlorine moiety and mono- or didealkylation. Hydroxylation of one or both of the dealkylated amine groups may also occur.
Urine and feces contained up to 25 and 15 identified metabolites, respectively, most of which were polar. Degradation of the triazine ring did not occur. Ammeline and ammelide, 2 dechlorinated and dealkylated/hydroxylated metabolites common to all triazines, were identified in low amounts in the feces.
In mammals, following oral administration, ...a de-ethyl metabolite forms rapidly, followed by conjugates of products formed by oxidation of one methyl group of the tert-butyl moiety. All are rapidly excreted.
/Terbutylethylazine/ was rapidly metabolized to water soluble compounds in the leaves of corn, sorghum, and sugar cane and more slowly in susceptible barley, by displacement of the 2-chloro group with glutathione or gamma-glutamylcysteine.
The metabolism of atrazine (and three other triazine herbicides, terbuthylazine, ametryne, and tebutryne) has been investigated in vitro in liver microsomes from rats, pigs, and humans. The principal phase-1 reactions in all three species were N-monodealkylation, hydroxylation of the isopropyl or tert-butyl moiety and sulfoxidation of the substrate. Although all species produced the same type of metabolites, there were spiecies specific differences in the metabolite ratios. Subsequent studies have shown that cytochrome P450 1A2 is the major phase-1 enzyme involved in the metabolism of s-triazine in human liver micrsomes. /Triazine herbicides/
Terbuthylazine has known human metabolites that include 2-[[4-Chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropan-1-ol and 1-[[4-(tert-butylamino)-6-chloro-1,3,5-triazin-2-yl]amino]ethanol.
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
Chemicals used to destroy pests of any sort. The concept includes fungicides (FUNGICIDES, INDUSTRIAL); INSECTICIDES; RODENTICIDES; etc.
현재 필터 조건에 해당하는 반응 기록이 없습니다.
불러오는 중…
CHEBI:30263USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Terbuthylazine. EPA 738-R-95-005 (March 1995). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of October 11, 2012: http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1]
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/29/2006; Reporting date: 11/28/2006.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3,5-Triazine-2,4-diamine, 6-chloro-N-(1,1-dimethylethyl)-N'-ethyl- is included on this list. Effective date: 9/29/2006; Sunset date: 11/28/2006.
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 terbuthylazine 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 terbuthylazine. ... Based on the review of the generic data for the active ingredient terbuthylazine, the Agency has sufficient information on the health effects and its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that terbuthylazine products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing terbuthylazine for all uses are eligible for reregistration.
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 saftey 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. Terbuthylazine is found on List B. Case No: 2645; Pesticide type: herbicide (algaecide); Case Status: RED Approved 12/94; 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): 2-(tert-Butylamino)-4-chloro-6-(ethylamino)-s-triazine; Data Call-in (DCI) Date(s): 06/04/91, 08/01/94, 01/02/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.
Acute Tox. 4 (93.5%)
Acute toxicity - category 4
Acute Tox. 4
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
UN 2763; Triazine pesticide, solid, not otherwise specified
UN 2997; Triazine pesticide, liquid, flammable, toxic, not otherwise specified, flashpoint between 23 °C and 61 °C
UN 2764; Triazine pesticide, liquid, flammable, toxic, not otherwise specified, flashpoint less than 23 °C
UN 2998; Triazine pesticide, liquid, not otherwise specified
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for TERBUTHYLAZINE (6 total), please visit the HSDB record page.
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. /Triazine pesticides, solid, toxic/
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Triazine pesticides, liquid, flammable, toxic; Triazine pesticides, liquid, toxic; Triazine pesticides, liquid, toxic, flammable/
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./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Triazine pesticides, liquid, flammable, toxic; Triazine pesticides, liquid, toxic; Triazine pesticides, liquid, toxic, flammable/
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Triazine pesticides, liquid, flammable, toxic; Triazine pesticides, liquid, toxic; Triazine pesticides, liquid, toxic, flammable/
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Triazine pesticides, liquid, flammable, toxic; Triazine pesticides, liquid, toxic; Triazine pesticides, liquid, toxic, flammable/
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. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. /Triazine pesticides, solid, toxic/
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. Remove trapped material with suction hoses. /Triazine pesticides, solid, toxic/
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Waste resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. /Bellacide 329/
Fiber Drum: Non-refillable container. Do not reuse or refill this container. Offer for recycling, if available. Triple rinse container (or equivalent) promptly after emptying. Triple rinse as follows: Empty the remaining contents into application equipment or a mix tank. Fill the container 1/4 full with water. Replace and tighten closures. Tip container on its side and roll it back and forth, ensuring at least one complete revolution, for 30 seconds. Stand the container on its end and tip it back and forth several times. Turn the container over onto its other end and tip it back and forth several times. Empty the rinsate into application equipment or a mix tank or store rinsate for later use or disposal. Repeat this procedure two more times. /Bellacide 329/
Pail: Non-refillable container. Do not reuse or refill this container. Offer for recycling, if available. Triple rinse container (or equivalent) promptly after emptying. Triple rinse as follows: Empty the remaining contents into application equipment or a mix tank. Fill the container 1/4 full with water and recap. Shake for 10 seconds. Pour rinsate into application equipment or a mix tank or store rinsate for later use or disposal. Drain for 10 seconds after the flow begins to drip. Repeat this procedure two more times. /Bellacide 329/
For more Disposal Methods (Complete) data for TERBUTHYLAZINE (7 total), please visit the HSDB record page.
Avoid contact with eyes, skin, or clothing. Wash thoroughly with soap and water after handling and before eating, drinking, chewing gum, using tobacco, or using the toilet. Remove contaminated clothing and wash clothing before reuse: Put on clean clothing. /Bellacide 329/
Remove personal protective equipment immediately after handling the product. Wash the outside of the gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Bellacide 329/
Follow personal protective equipment manufacturer's instruction for cleaning/maintaining personal protective equipment. If no such instructions for washables exists, use detergent and hot water. Store and wash personal protective equipment separately from other laundry. /Bellacide 329/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
For more Preventive Measures (Complete) data for TERBUTHYLAZINE (13 total), please visit the HSDB record page.
Personal protective equipment includes a long-sleeved shirt, long pants, shoes, socks, and chemical-resistant gloves. A chemical-resistant apron must be immediately available during loading and application and must be worn in case of a leak, spill, or other exposure to the concentrate. /Bellacide 329/
The use of personal protective equipment such as glasses, synthetic gloves, & /NIOSH approved breathing apparatus/ ... is important. /Herbicides/
LD50; Species: Anas platyrhynchos (Mallard duck) 7 months old; oral via capsule >2510 mg/kg for 14 days
LC50; Species: Anas platyrhynchos (Mallard duck) 14 days old; diet >5620 mg/kg for 8 days
LC50; Species: Colinus virginianus (Northern bobwhite) 14 days old; diet >5620 ppm for 8 days
LD50; Species: Apis mellifera (Bee) oral or contact >100 ug/bee
For more Ecotoxicity Values (Complete) data for TERBUTHYLAZINE (25 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 151-514(2,3) indicate that terbuthylazine is expected to have moderate to low mobility in soil(SRC). However, terbuthylazine adsorption in soil can depend upon an electron donor process(4) that results in terbuthylazine residues that are strongly bound to soil(5). Field studies have shown terbuthylazine to be relatively immobile in soil(5,6) and terbuthylazine is reported to have only slight mobility in soil(3). Volatilization of terbuthylazine from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.3X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 6.75X10-7 mm Hg(3), and water solubility, 9.0 mg/L(3). In soil volatilization studies using two soil types, only 0.26-0.65% of applied terbuthylazine volatilized over a 32 to 36 days period(7). Some sensitized photodegradation may occur in moist soils (containing sensitizing agents such humic acid) exposed to sunlight(8). In soil degradation tests using sterile and non-sterile soil, terbuthylazine had a half-life of 82 days in sterilized soil and half-lives of 22-27 days non-sterile soil(9). Microbial degradation proceeds mainly by de-ethylation and hydroxylation, with eventual ring cleavage(3). Terbuthylazine half-lives of 88, 116, and 103 days were observed in loamy clay, calcareous clay, and high clay soils respectively(10). Field studies in biologically activate soil have reported terbuthylazine dissipation half-lives ranging from 6.5 to 149 days(3).
AQUATIC FATE: Based on a classification scheme(1), a Koc range of 151 to 514(2,3) indicates that terbuthylazine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 2.3X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 6.75X10-7 mm Hg(3), and water solubility, 9.0 mg/liter(3). According to a classification scheme(5), an estimated BCF of 25(SRC), from its log Kow of 3.40(3) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important environmental fate process given half-lives of 73, 205 and 194 days at pH 5, 7 and 9, respectively(3). Terbuthylazine is stable to aqueous photolysis(7). The direct aqueous photolysis half-life is reported to be greater than 40 days in natural sunlight(3). Sensitized photodegradation may have some importance as a fate process in natural waters containing sensitizing agents such as humic acids(8). In river, seawater and groundwater die-away tests, terbuthylazine had half-lives ranging from 44 to 196 days(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), terbuthylazine, which has a vapor pressure of 6.75X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase terbuthylazine 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 35 hours(SRC), calculated from its rate constant of 1.10X10-11 cu cm/molecule-sec at 25 °C(3). Particulate-phase terbuthylazine may be removed from the air by wet and dry deposition(SRC). Due to weak absorption at wavelengths >290 nm(4) and an aqueous photolysis half-life of >40 days in natural sunlight(2), direct photolysis is not expected to be an important fate process(SRC).
/BIRDS and MAMMALS/ On a subacute dietary basis, terbuthylazine is practically non-toxic to birds. Two studies, one on the mallard duck and one on the bobwhite quail produced LC50s greater than 5,620 ppm.
/AQUATIC SPECIES/ Subchronic toxic effects on embryos and larvae of common carp (Cyprinus carpio) were investigated during a 30-day toxicity test. The exposure to terbuthylazin showed no effect on mortality, but significant differences (P<0.0001) were revealed on weight and growth parameters at concentrations of 520 and 820 ug/L. The inhibition of specific growth rate at concentrations of 520 and 820 ug/L was 14% compared to the control group. No significant negative effects on total body length and body weight were observed at lower concentrations (0.9 and 160 ug/L). The concentrations 520 and 820 ug/L were associated with a delay in development compared to other experimental groups and controls. On the basis of weight and growth rate evaluation and determination of developmental stages, the No Observed Effect Concentration (NOEC) of terbuthylazine was estimated at 160 ug/L and the Lowest Observed Effect Concentration (LOEC) was 520 ug/L. According to these results, the reported environmental concentration of terbuthylazine in Czech rivers does not impact growth, development, morphology, or histology of carp embryos and larvae.
/AQUATIC SPECIES/ Terbuthylazine is moderately toxic to freshwater fish: rainbow trout (96-hr LC50 3.4 ppm) and bluegill sunfish (96-hr LC50 7.5 ppm); slightly toxic to freshwater invertebrates (Daphnia magna EC50 50.9 ppm); and highly toxic to estuarine/marine invertebrates (pink shrimp EC50 109.7 ug/L). /From table/
/AQUATIC SPECIES/ Effects of the herbicide formulation Click 500 SC (terbuthylazine 500 ug/L) on common carp Cyprinus carpio were assessed through biometric, biochemical, hematological and antioxidant indices, induction of xenobiotic metabolizing enzymes and histological examination of selected tissues. The fish were exposed to the formulation with terbuthylazine concentrations of 380 ng/L (environmental concentration); 60 ug/L and 550 ug/L for up to 91 days. Hematological indices were assessed using unified methods of hematological examination in fish. Biochemical indices in plasma were measured by biochemical analyzer, ferric reducing ability of plasma (FRAP) and ceruloplasmin activity were determined spectrophotometrically. Concentration of total cytochrome P450, glutathione-S-transferase activity and glutathione content were assessed spectrophotometrically in liver. Activity of liver ethoxyresorufin-O-deethylase (EROD) activity was measured spectrofluorimetrically. Histopathological examination of liver, skin, gills, spleen, cranial and caudal kidney was performed by light microscopy. An increase (p<0.05) was observed in hepatosomatic index and condition factor in fish from the environmental concentration. A decrease (p<0.05) in hemoglobin and mean corpuscular hemoglobin concentration (MCHC) was found in fish treated with terbuthylazine of 550 ug/L. There was a decline in mean corpuscular volume (MCV) and mean corpuscular hemoglobin (MCH) (p<0.05) in terbuthylazine of 60 ug/L and 550 ug/L. Triglycerides (TAG) (p<0.01) were elevated in all pesticide-treated groups. Alanine aminotransferase (ALT) (p<0.01) and phosphorus (p<0.05) decreased in fish exposed to terbuthylazine of 60 ug/L and 550 ug/L, while albumin (p<0.01) rised in the same groups. An elevation in natrium (p<0.05) in terbuthylazine of 550 ug/L and a rise in protein (p<0.01) in the concentrations of 380 ng/L and 550 ug/L were observed. Correlations between several indices were significant. Ceruloplasmin activity and FRAP were augmented (p<0.01) in the highest concentration tested. Examined xenobiotic detoxification systems were not significantly affected by the exposure. Non-specific histopathological changes were found in the gills and skin of the test fish. The fish treated with terbuthylazine developed a disorder in several haematological and plasma biochemical indices. The levels of markers of oxidative stress increased in response to the exposure. Examined systems involved in detoxification of xenobiotics did not reflect long-term contact with the herbicide. Detected histological lesions were non-specific. The environmental concentration of terbuthylazin affected biometric indices of the test fish.
(14)C-labeled terbuthylazine was applied to the surface of soil columns 100 mm deep and uptake by oat seedlings measured for approx 24 days after germination following 2 contrasting rainfall treatments. Attempts were made to predict measured uptake on the basis of mass flow theory given also measurements of transpiration rates, water, rooting, and herbicide distribution profiles in the soil, and soil adsorption characteristics.
Preliminary medical exam to detect chronic diseases of CNS, liver, heart, kidneys, lung & skin, as well as endocrinological or immunological disturbances, should ... /protect/ susceptible individuals. ... Periodical medical exam of internal organs, skin & eyes is important to avoid chronic occupational intoxications. It should include lab tests & patch tests if necessary. /Herbicides/
Koc values of 259, 260, and 100 in three Swiss soils (Vetroz, pH 7.8, organic matter 2.2%, clay 2.8% silt 10.2%, sand 87.0%; Evouettes, pH 6.1, organic matter 3.6%, clay 12.2% silt 49.4%, sand 38.4%; Collombey, pH 6.7, organic matter 5.6%, clay 22.6% silt 19.6%, sand 57.8%), respectively, have been reported for terbuthylazine(1). Using loamy clay (Typic eutrochrept, pH 8.2, sand 3.6%, silt 64.7%, clay 31.7%, organic carbon 1.11%, CaCO3 1.9%), calcereous clay (Mollic eutrochrept, pH 8.0, sand 29.2%, silt 19.5%, clay 51.3%, organic carbon 1.50%, CaCO3 26.4%), and high clay (Vertic eutrochrept, pH 8.0, sand 24.5%, silt 13.0%, clay 62.5%, organic carbon 1.08%, CaCO3 3.2%) agricultural soils, Kocs of 207, 155, and 174 were measured(2). A Koc of 230 was reported for terbuthylazine(3). Koc values of 267 and 514 were determined in two sediments from the Kishon River in Israel(4). Typical Koc values for light agricultural soils range from 151 to 318 with terbuthylazine being slightly mobile in soil(5). According to a classification scheme(6), a Koc range 151 to 514 suggests that terbuthylazine is expected to have moderate to low mobility in soil. Evidence has been reported that indicates that the basicity of s-triazine herbicides, such as terbuthylazine, is not the main factor governing adsorption to soil humic acids(7). It has been shown that the ability of s-triazines herbicides to act as electron donors to electron acceptor quinone-like units of humic acids also plays an important role in the adsorption(8).
Most of the terbuthylazine applied to forest soil under field conditions remained in the upper 12 cm even after 108 days; small amounts reached the 12 to 18 cm depth within 10 to 108 days(1). Using field lysimeters, a study based in Udine, Italy, terbuthylazine applied at 1 kg/ha active ingredient, 68%, 12%, and 4% of the applied compound was recovered after 15 days from depths 1-10 cm, 10-20 cm, and 20-30 cm, respectively, indicating that a large majority of terbuthylazine was immobilized in soil as bound residue(2). Terbuthylazine was applied to three Brazilian soils in closed aerated laboratory microcosms; percent of 14C initially applied attributed to leaching was 0.08, 0.01, and 0.00 in sandy soil, clay soil, and organic soil, respectively, under standard climatic conditions (20 °C, 38% relative humidity, 60 mm precipitation/month)(3). Under Brazilian summer conditions (26.8 °C, 60-80% relative humidity, 300 mm precipitation), percent leaching was observed to be 2.99, 0.01, and 0.23, respectively(3).
Terbuthylazine (GS 13529; CAS# 5915-41-3) was evaluated for oral toxicity in juvenile Tif: RAIF (SPF) albino rats (15/sex/group) when administered by gavage at dose rates of 0, 40, 90, or 180 mg/kg/day. Due to early onset of marked toxic effects, on day 4 and continuing through day 14 (termination of treatment) the doses were decreased to 0, 20, 45, or 90 mg/kg/day. Five rats/sex/group were maintained an additional 14 days after cessation of treatment to determine recovery data. Treatment-related mortalities occurred on day 2 (2 females from the 180/90 mg/kg group) and day 4 (2 males from the 180/90 mg/kg group). Clinical signs observed in males and females from groups 3 (90/45 mg/kg) and 4 (180/90 mg/kg group) were hunched posture, rhinorrhea, weakness, and slow movements. These symptoms were observed at the start of treatment, became less frequent and severey when the administered doses were reduced, and were not seen during the recovery period. Mean body weight gain in treated animals (male and female) was reduced in a dose-related manner, with the differences in treated animals from groups 3 (90/45 mg/kg) and 4 (180/90 mg/kg) being statistically significant from controls. During the recovery period, males and females showed comparable body weight gain rates to controls, yet mean body weights remained significantly below controls. Absolute and relative thymus weights were significantly lower than controls in male groups 3 and 4, and female group 4 at the end of the treatment period. At the end of the recovery period, however, no differences in absolute or relative thymus weights were seen between controls and any of the treated animals. Microscopic examination revealed marked necrosis in the thymus of the 2 males and 2 females from group 4 that died before the end of treatment. Examination of the surviving animals at the end of the treatment period revealed slight necrosis of thymic lymph tissue in 1 male and 2 females from group 4, and 1 female from group 3. Three males and 1 female from group 4 also exhibited slight necrosis in mesenteric lymph node. No changes were seen in the thymus in the recovery group.
Terbuthylazine (GS 13529; CAS# 5915-41-3) was evaluated for repeat-dose toxicity in albino rabbits (5-10/sex/group) when administered by gavage for 28 days (5 days/week). The test material was initially administered at dose levels of 0, 5, 50, or 500 mg/kg/day, but due to high mortality in the 500 mg/kg group within the first 3 days of treatment, dose levels were adjusted to 0, 5, 20, or 100 mg/kg for the remaining 25 days. Three males and 2 females from the 500/100 mg/kg group (group 4) were maintained for 13 additional days after the last treatment for recovery data. Six males and 5 females from the 500/100 mg/kg group (group 4) and 1 female from group 3 (50/20 mg/kg) died before scheduled sacrifice. Clinical signs observed included: lethargy, dyspnea, ruffled fur, curved and ventral body position, diarrhea, and tremors. Animals in the recovery group were free of clinical signs only in the second week post-treatment. Body weight gain was depressed in males and females in group 4 (500/100 mg/kg) from the second week on. Animals in the recovery group exhibited more normal body weight gain after cessation of treatment. Body weights for males from group 3 (50/20 mg/kg) at the end of the treatment period were slightly but significantly lower than controls, while animals (1 male, 3 females) from group 4 had terminal body weights markedly lower than controls and other treatment groups. Males and females in the high dose group (group 4) exhibited moderately lower erythrocyte count, lower hemoglobin concentration, a decrease in the hematocrit, and a decrease in the number of leucocytes. There was also a slight decrease in aspartate-aminotransferase (GOT) activity in the high dose animals (males and females). Absolute and relative liver weights in males and females from all treated groups showed significant dose-related changes from controls at the end of treatment. Females from group 4 showed thymus weights that were significantly less than female controls and females from other treatment groups. Necropsy revealed mottled lung and thymus, with congestion and hemorrhage in the respiratory and digestive tracts, thymus and bone marrow, spleen, mediastinum and lymph nodes in most high dose animals. Females in group 4 exhibited atrophy of the thymus, spleen and lymph nodes.
/GENOTOXICITY/ Terbuthylazine and carbofuran are suspected to cause non-Hodgkin's lymphoma and lung cancer. /The researchers/ evaluated the effects of prolonged exposure to low concentrations on primary DNA damage by comet assay, and on the structural integrity of c-Myc and TP 53 genes by FISH-comet. Another novelty in studying these pesticides' genotoxicity is the use of 14-day extended-term human lymphocyte cultures. Concentrations corresponded to values of ADI and OEL: for terbuthylazine 0.58 ng/mL and 8 ng/mL; for carbofuran 8 ng/mL and 21.6 ng/mL, respectively. A possible effect of metabolic activation (S9) was also considered. Carbofuran treatment induced a significant migration of DNA into the tail in a concentration-dependent manner, while for terbuthylazine the effect was significant only at the higher concentration. Terbuthylazine caused migration of both c-Myc signals into the comet tail. A significant occurrence of TP 53 signals in the tail was observed at 8 ng/ml. Prolonged carbofuran treatment significantly elevated the migration of a single c-Myc signal into the tail in a concentration-dependent manner. With S9, distribution of signals shifted toward increased presence of both signals in tail. Our results showed impaired structural integrity of c-Myc and TP 53 due to prolonged exposure to terbuthylazine and carbofuran.
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/29/2006; Reporting date: 11/28/2006.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3,5-Triazine-2,4-diamine, 6-chloro-N-(1,1-dimethylethyl)-N'-ethyl- is included on this list. Effective date: 9/29/2006; Sunset date: 11/28/2006.
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 terbuthylazine 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 terbuthylazine. ... Based on the review of the generic data for the active ingredient terbuthylazine, the Agency has sufficient information on the health effects and its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that terbuthylazine products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that products containing terbuthylazine for all uses are eligible for reregistration.
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 saftey 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. Terbuthylazine is found on List B. Case No: 2645; Pesticide type: herbicide (algaecide); Case Status: RED Approved 12/94; 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): 2-(tert-Butylamino)-4-chloro-6-(ethylamino)-s-triazine; Data Call-in (DCI) Date(s): 06/04/91, 08/01/94, 01/02/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.
In a rat metabolism study, (14)C-terbuthylazine (3.6 mg) was administered orally to Wistar rats. Terbuthylazine was rapidly (50% excreted by 16-17 hrs) and completely metabolized and did not accumulate in tissues. Radioactivity was excreted equally in urine and feces in males, but in females about 66% of the radiolabel was excreted in the urine.
In mammals, following oral administration, 72-84% is eliminated in the urine and feces within 24 hr, and almost all within 48 hr.
Terbuthylazine (TBA) is an herbicide widely used in corn cultivation. Herein we evaluate the measurement of hair TBA as biomarkers of exposure. Five Sprague Dawley rats were gavaged with TBA for 3 days, and then the back hair was shaved and analyzed for TBA. In addition, head hair samples from 10 corn farmers, 9 rural residents, and 6 urban residents were collected at the end of the application season. Hair TBA was detected by liquid chromatography triple quadrupole mass spectrometry after solvent extraction. TBA was quantifiable in all rat samples with a mean concentration of 0.92 (+ or - 0.26)ng/mg, which corresponds to a 0.12% incorporation rate. TBA was quantifiable in all farmer samples (median: 0.67 ng/mg), in 75% of rural resident samples (0.01ng/mg) and in none of the urban resident samples (<0.01 ng/mg), with a statistical difference among groups (P<0.01). Our results suggest that TBA is incorporated in hair and prompt further investigation on the use of hair TBA as a potential biomarker of cumulative exposure.
Used to control algae, fungi, and bacteria in ornamental aquaria and commercial and industrial circulating water systems; Also used as broad-spectrum herbicide for maize, cereals, vines, fruits, coffee, potatoes, sugar cane, rubber, forestry, and other crops; [HSDB]
Registered strictly for aquatic non-food uses in the US; [EPA REDs]
Farming (Pesticides) [Category: Industry]
For terbutylethylazine (USEPA/OPP Pesticide Code: 080814) 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./
Terbuthylazine was registered in the United States in 1975. Tolerances were established for terbuthylazine in or on corn fodder and forage, corn grain (including popcorn grain), and sorghum forage and grain (40 CFR 180.333). However, since no end-use products were registered for use of terbuthylazine as a herbicide these tolerances were revoked in 1992 ... Products formulated for end-use were registered as algicide and microbicides/microbistats starting in 1986.
Terbuthylazine is an algicide, a microbicide and microbistat used to control algae and slime-forming algae, fungi, and bacteria. ... It is labeled for aquatic non-food industrial, commercial, and residential uses. Industrial and commercial uses are for ornamental fountains, ponds, and for water cooling systems, including evaporative condensers, heat-exchange systems, and commercial and industrial cooling towers. Residential uses are for ornamental ponds/aquaria.
1,3,5-Triazine-2,4-diamine, 6-chloro-N-(1,1-dimethylethyl)-N'-ethyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5727]
Terbuthylazine is produced by reaction of cyanuric chloride with tert-butylamine, followed by treatment with ethylamine in the presence of sodium hydroxide.
Produced by reacting trichloro-1,3,5-triazine in a first step with 1 equivalent of tert-butylamine and, in second step, with 1 equivalent of ethylamine in the presence of sodium hydroxide ...
Premix Partners: Acetochlor; Alachlor; amitrole; Atrazine; Bromoxynil; Glyphosate; Isoxaben; Mesotrione; S-Metolachlor; Oxyfluorfen; Pendimethalin; Propachlor; Tembotrione; Terbutryn.
Suspension concentrate, emulsifiable concentrate.
Technical product is greater than or equal to 96% pure.
AMA-204 (Kemira Chemicals, Inc.), Terbuthylazine 4%.
For more Formulations/Preparations (Complete) data for TERBUTHYLAZINE (7 total), please visit the HSDB record page.
Microbiocides, Algicides, Herbicides
Pesticides -> Herbicides -> Triazine herbicides -> Chlorotriazine herbicides
Pharmaceuticals
Environmental transformation -> Pesticides (parent, predecessor)
1,3,5-Triazine-2,4-diamine, 6-chloro-N2-(1,1-dimethylethyl)-N4-ethyl-: ACTIVE
The WHO Recommended Classification of Pesticides by Hazard identifies terbuthylazine (technical grade) as Class III: slightly hazardous; Main Use: herbicide.
Slightly longer duration in its action than simazine and atrazine ... .
USA: Not marketed.
용도A triazine herbicide.
정의ChEBI: A diamino-1,3,5-triazine that is N-tert-butyl-N'-methyl-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6.
Terbuthylazine (GS 13529; CAS# 5915-41-3) was evaluated for chronic toxicity and carcinogenicity in albino rats (strain, numbers, and sex not reported). The test material was administered in the diet at concentrations of 0, 30, 150, or 750 ppm for 24 months. Increased incidence of mammary gland carcinomas, foam cells in the lungs, nodular thyroid hyperplasia, and biliary cysts were reported for high-dose females. High dose males exhibited foam cells in the lungs, benign interstitial cell tumors, and nodular hyperplasia of Leydig cells in the testis. This document is a letter containing a brief summary of the results and no further information was reported.