Terbutryn

241.36

241.36

212-950-5

ZXL474TLFP

DTXSID3024318

WHITE, CRYSTALLINE|White powder

2933699012

88

3.74

White Powder

1.115 at 20 deg C

104 °C

154-160 °C @ Press: 0.06 Torr

2 °C

1.55

H2O: 0.0025 g/100 mL

APPROX 4°C

1.69X10-6 mm Hg at 25 deg C

Oral-Rat LD50: 2045 mg/kg; Oral-Mouse LD50: 3884 mg/kg

Combustion produces toxic sulfur oxide and nitrogen oxide gas

Henry's Law constant = 1.15X10-8 atm-cu m/mol at 25 °C (est)

pKa = 4.30 (weak base)

161.23 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|160.48 Ų [M+H]+|160.2 Ų [M+H]+

Hydroxyl radical reaction rate constant = 1.07X10-11 cu cm/molec-sec at 25 °C (est)

Noncorrosive

I; II; III

6.1

UN30779/PG3

2

36-50/53-20/21/22-11

26-60-61-36/37-16

XY4725000

Xi,N,Xn,F

Warehouse ventilated, low temperature and dry

Stable. Incompatible with strong oxidizing agents.

P210-P280-P305 + P351 + P338

H225-H302-H312-H319-H332

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.|Noncombustible containers should be crushed & buried under more than 40 cm of soil. /Herbicides/|Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|Group II Containers: Noncombustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

|Warning|H302 (63.18%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 464 companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

The use of personal protective equipment such as glasses, synthetic gloves & /NIOSH/ approved breathing apparatus/ ... is important. /Herbicides/|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Triazine pesticides, solid NOS/

Nonflammable.

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, carbon dioxide or dry chemical. /Triazine pesticides, solid, NOS/

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, NOS/|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, NOS/

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.|Avoid contact with eyes, contact with skin, inhalation of dust, & contamination of food & feed.|Only clean clothing ... should be worn & clothing should be changed daily ... Adequate sanitary facilites & washing water should be provided for workers to wash before meals. Smoking & consumption of alcoholic drinks before & during the handling of herbicides should be forbidden. Contaminated clothing should be removed immediately & a hot bath taken if possible. Personal hygiene should be encouraged. /Herbicides/|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|For more Preventive Measures (Complete) data for TERBUTRYNE (6 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|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.

Some triazines are mildly irritating to skin, eyes, & upper respiratory tract. /Miscellaneous pesticides of low or moderate toxicity/

The major hazards encountered in the use and handling of terbutryne stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, dermal contact), exposure to this colorless to white, crystalline substance may occur from its manufacture, formulation, and use as an herbicide. Effects from exposure may include skin and eye irritation, nausea, diarrhea, 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 terbutryne does not ignite easily, it may burn with the production of irritating and poisonous gases. For fires involving terbutryne, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Terbutryne may be shipped domestically via air, rail, road, and water, in containers bearing the label "Poison". Small dry spills of terbutryne 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 terbutryne from entering water sources and sewers. Before implementing land disposal of terbutryne, consult with regulatory agencies for guidance.

SEDIMENT: Terbutryne was identified in soil sediment samples from tailwater pits located in Haskell County, Kansaswhich, used to collect irrigation runoff from fields of corn or grain sorghum and sampled in May, June, July, August, and November, 1974(1).

moderately toxic

LD50 Rabbit dermal >2,000 mg/kg|LD50 Rat oral 2450-2500 mg/kg|LD50 Rat oral 2045 mg/kg|LC50 Rat inhalation >8 mg/L/4 hr /80% formulation/|For more Non-Human Toxicity Values (Complete) data for TERBUTRYNE (8 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ Practically nontoxic. Bird: Practically nontoxic to upland game birds.|/BIRDS and MAMMALS/ The effect of terbutryne on the vitamin A content in the liver of pheasants (Phasianus colchicus colchicus L.) was studied. One hundred forty 10-18 week old pheasants were fed grains treated with terbutryne ad libitum for 4 to 20 days. A significant decrease in the vitamin A content of the liver was observed starting from the 20th day, and reaching 56% of the initial level by 2 weeks after treatment. The reduction of the liver vitamin A level is indicative of the harmful effect of terbutryne.|/AQUATIC SPECIES/ Igran in aquatic environment had adverse effect on its population, especially fish. The median lethal effect on carp of exposure for 1-4 days was 8-9 mg/cu m. the toxicity to Leucaspius delineatus was twice that to Carp.|/AQUATIC SPECIES/ The effects of the herbicide terbutryn on a simple lotic food web were investigated during a 72-day exposure period in five artificial indoor streams in a greenhouse. The model compound terbutryn, an s-triazine and an inhibitor of photosynthesis, was applied once in each stream at nominal concentrations of 0.6, 6, 60, or 600 ug/L. Terbutryn concentrations in the water were analyzed by gas chromatography/mass spectrometry, and an overall time to 50% dissipation (DT50) of 28 days was calculated. The development of aufwuchs and the population growth and development of the oligochaete Lumbriculus variegatus were investigated. ... Terbutryn was toxic to L. variegatus at 23.7 mg/L (96-hr median lethal concentration (LC50)) and 16.5 mg/L (96-hr median effective concentration (EC50)) in static acute toxicity tests. Terbutryn decreased aufwuchs production at 0.6 ug/L in the experimental streams. Population growth of L. variegatus was decreased by 50% at 6 ug/L. The effect of terbutryn on the aufwuchs was a direct effect of decreases in the periphyton. However, the effects on L. variegatus were an indirect effect of terbutryn as a consequence of decrease in the aufwuchs food source and occurred at three-orders-of-magnitude-lower concentrations of terbutryn than the acute toxicity effects. Our study demonstrates the utility of indoor lotic microcosm studies for evaluating both direct and indirect effects of contaminants on aquatic ecosystems.|For more Ecotoxicity Excerpts (Complete) data for TERBUTRYNE (10 total), please visit the HSDB record page.

... For patients who suffer from Na+ desequilibrium, the triazine - human serum albumin binding would change ... /as well as/ the toxicological effect of these herbicides. /Triazine herbicides/

Terbutryne's production may result in its release to the environment through various waste streams; its use as a selective herbicide for control of annual broadleaf and grassy weeds(1) will result in its direct release to the environment(SRC).|Residues of terbutryne can enter the environment (soil & water) from runoffs from irrigated fields.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 366 - 41,757(2) indicate that terbutryne is expected to have moderate mobility to immobility in soil(SRC). Terbutryne volatilized 6% and <1% in 50 days from a sandy soil (pH 7.9, 97% sand, 0.3% clay, 1.0% organic matter) at 25 and 15 °C, respectively(3). Terbutryne volatilized 3% and <1% in 50 days from another soil (pH 8.9, 49% sand, 29% clay, 1.3% organic matter) at 25 and 15 °C, respectively(3). Terbutryne is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure, 1.69X10-6 mm Hg(4). Terbutryne may be susceptible to biodegradation based upon half-lives of 2 and 11 weeks in unfumigated and fumigated soil, respectively(5).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 366 - 41,757(2) indicate that terbutryne is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.69X10-6 mm Hg(4), and water solubility, 25 mg/L(5). Sensitized photolysis and photooxidation of terbutryne with photochemically produced hydroxyl radicals may be important removal mechanisms(6-7). According to a classification scheme(8), an estimated BCF of 72(SRC) from its log Kow, 3.74(9) and a regression-derived equation(10) and a reported BCF of 25 in catfish(11) suggest the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Terbutryne had a degradation half-lives of 6.9 - 30 days in river and pond waters under different conditions(12,1).|AQUATIC FATE: HALF-LIFE OF TERBUTRYN IN POND WATER WAS 20-30 DAYS. IN BOTTOM SEDIMENT, CORRESPONDING VALUE WAS 400 DAYS.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), terbutryne, which has a vapor pressure of 1.69X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase terbutryne 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 36 hours(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Terbutryne may be susceptible to sensitized photolysis(4) and photooxidation by photochemically produced hydroxyl radicals(5) based upon data for other methylthio-s-triazine herbicides such as prometryne(5) and ametryne(4).

The rate constant for the vapor-phase reaction of terbutryne with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 36 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Terbutryne may be susceptible to sensitized photolysis(3) and photooxidation by photochemically produced hydroxyl radicals(2) based upon data for other methylthio-s-triazine herbicides such as prometryne(2) and ametryne(3). Infrared studies of interactions of s-triazines such as terbutryne with mineral surfaces indicate that adsorption is usually accompanied by protonation and hydrolysis(4).

A BCF of 25 was reported in fish for terbutryne(SRC), using catfish (Ictaluris melas), specific conditions not provided(1). According to a classification scheme(2), this BCF suggests that bioconcentration in aquatic organisms is low(SRC). Little potential for bioconcentration of terbutryne was observed in sediment dwelling Chironomus tentans larvae that were living in water-sediment mixtures contaminated with the herbicide(3).

707.95 L/kg|Data from the UK data base as of 1993 gave Koc value ranges from 700 to 11,660 with a mean value of 2863.11(1). Koc values were measured for two Kishon River, Israel sediments; Kfar Yehushua was 389.57 (7.1 pH, 30% sand, 30% silt 40% clay 1.63% TOC) and Haifa industrial area was 729.60 (6.8 pH, 30 % sand, 20% silt, 50% clay, 1.25% TOC)(2). Koc values were analyzed for terbutryne in 5 EUROSOILS (country, %Clay, % organic carbon, pH); EUROSOIL1- 41,757 (Italy, 75, 1.3, 5.1), EUROSOIL2- 372.7 (Greece, 22.6, 3.7, 7.4), EUROSOIL3- 788 (United Kingdom, 17.0, 3.45, 5.2), EUROSOIL4- 366.2 (France, 20.3, 1.55, 6.5), EUROSOIL5- 3539 (Germany, 6.0, 9.25, 3.2)(3). Another measured Koc value of 700 was given for an unspecified soil type(4). According to a classification scheme(5), Koc values of 150 to 500 indicate moderate mobility and >5,000 indicate immobility in soil(SRC).|Terbutryne was classified as immobile in soil thin-layer and thick-layer chromatography and soil-column leaching experiments with sandy loam and silty clay soils in which the Rf range for terbutryne was 0.00-0.10(1). Adsorption of 96-98% and 86-97%, respectively, of the terbutryne applied to an unlimed and limed silt loam soil has been observed(2). Evidence has been reported that indicates that the basicity of s-triazine herbicides, such as terbutryne, is not the main factor governing adsorption to soil humic acids(3). 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(4). Adsorption of terbutryne is favored in soils containing higher concn of clay and organic matter and leaching is limited by adsorption to certain soil constituents(5). Adsorption is reversible and desorption can occur readily depending on conditions including temperature, moisture, and pH(5). Simulated field conditions for a loam soil (pH 7.8, 63.4% sand, 24.6% silt, 12.0% clay, 1.01% organic matter), under saturated field conditions and an application rate of 10 kg/ha of terbutryne gave leaching results of; 5.25, 0.30, 0.03, <0.01, and <0.01 ppm at depths of 0 to 6, 6 to 12, 12 to 18, 18 to 24, and 24 to 30 cm, respectively, after 10 days(6). Terbutryne was found at 0.3% of the applied amount in runoff water and sediment from a rain water simulated sample after 12 hours from unlimed soil(7).

The Henry's Law constant for terbutryne is estimated as 2.1X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 1.69X10-6 mm Hg(1), and water solubility, 25 mg/L(2). This Henry's Law constant indicates that terbutryne is expected to be essentially nonvolatile from water surfaces(3). However, terbutryne volatilized 6% and <1% in 50 days from a sandy soil (pH 7.9, 97% sand, 0.3% clay, 1.0% organic matter) at 25 and 15 °C, respectively(4). Terbutryne volatilized 3% and <1% in 50 days from another soil (pH 8.9, 49% sand, 29% clay, 1.3% organic matter) at 25 and 15 °C, respectively(4).

GROUNDWATER: Terbutryne was not detected in groundwater from new wells in the Northern Italy province of Bergamo which were shown to contain simazine and propazine(1). Terbutryne was not detected (detection limit 0.05 ug/L) in 303 well water samples from 12 Midwest states in the summer of 1991 and 66 samples in the summer of 1992(2). Terbutryne was not detected (detection limit 0.05 ug/L) in 106 municipal well water samples from Iowa in the summer of 1995(3), and 88 samples in the summer of 1996(4). Terbutryne has been identified in 1+ Netherlands ground water sample at a concentration of 2.4 ug/L, number of total samples and locations not reported(5). Well water samples taken from Spanish citrus orchards in 1989 and 1999 contained no terbutryne(6).|DRINKING WATER: Terbutryne was not detected in US drinking water samples compiled by the National Pesticide Survey(1).|SURFACE WATER: Terbutryne was detected in 19 of 20 samples with a concn range of 2.0-19 ng/L in samples taken from the River Elbe at Zollenspieker, Germany in 1992-1993(1). Terbutryne was detected in 19 of 20 samples with a concn range of 2.0-12 ng/L in samples taken from the River Elbe at Seemannshoft, Germany in 1992-1993(1). Terbutryne has been identified in Dutch surface water, concentrations and locations not reported(2). Terbutryne was not found in fresh surface water samples in England, Wales and the Anglian region, number of total samples and locations not reported(3). Terbutryne was not found in estuaries and coastal water samples in England and Wales(3). Terbutryne was not found in surface water samples taken at 149 sites in 10 Midwestern states; 55 samples taken before planting (3-4/1989), 132 after planting (5-6/1989) and 145 taken at harvest time (10-11/1989)(4). 53 rivers in the Midwest, covering 9 states were analyzed for terbutryne, none of the 50 samples taken in 1989, 52 samples in 1990, 52 samples in 1994 or 50 samples taken in 1995 contained terbutryne(5). Samples taken in April and June of 1990 from the Adige river in Italy contained no terbutryne(6). Terbutryne was identified in water samples from tailwater pits used to collect irrigation runoff(7).|RAIN/SNOW/FOG: Terbutryne was not detected in rain water samples taken from Mar to Nov 1996 from samples collected in Hannover, Germany(1). Terbutryne was detected in Paris, France rain water samples taken 3/3/1991 at 34 ng/L and 6/20/1991 at 25 ng/L(2). Terbutryne was not detected in Paris rain water samples taken 9/25, 10/30, 11/11 and 12/16-18/1991(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 567 workers (13 of these are female) are potentially exposed to terbutryne in the US(1). The NOES Survey does not include farm workers. Occupational exposure to terbutryne may occur through inhalation of dust particles or spray mists and dermal contact with this herbicide during or after its application or at workplaces where ametryne is produced(SRC). Although specific monitoring data were not located, the general population may be exposed to terbutryne via contact with contaminated water(SRC).

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

They are efficiently absorbed from intestine, and presumably there is some absorption across the skin and lung. /Urea-, uracil- and triazine-based herbicides/|Absorbed through both foliage and roots. It appears to penetrate foliage rapidly, minimizing removal from foliage by rain. /It is/ translocated acropetally through xylem from roots and foliage, accumulating in apical meristems.|In mammals, following oral admin, 73-85% is eliminated in metabolized form in feces within 24 hr.

Terbutryn ... was metabolized by both rats and goats after a single oral dose by one or more of the following pathways: S-demethylation, conversion of thiomethyl into hydroxyl, N-de-ethylation, oxidation of the terminal carbon of the ethyl group to a carboxylic acid, oxidation of a terminal carbon of the t-butyl group to an alcohol or a carboxylic acid, or conjugation with glucuronic acid.|Carbon-labeled terbutryn was admin as single oral doses to rats and goats. Urine was collected at intervals up to 72 hr and then analyzed ... after isolation of glucuronides by chromatographic procedures. Five conjugates isolated and identified were: 2-amino-4-(t-butylamino)-6-(S-glucuronyl)-s-triazine; 2-(t-butylamino)-4-ethylamino-6-(S-glucuronyl)-s-triazine; 2-ethyl-amino-(2-methyl)glucuronylpropyl)amino-6-(S-methylthio)-s-triazine; 2-amino-4-(2-(1-glucuronyl-2-methylpropyl)amino)-6-methylthio-s-triazine; 2-ethylamino-4-(2-(2-methyl propan-1-olyl)amino)-6-(S-glucuronyl)-s-triazine.|After administration of terbutryne to rats, urinary metabolites observed ... included: 2-hydroxy terbutryne; 2-amino-4-hydroxy-6-t-butylamino-s-triazine; 2-amino-4-t-butylamino-6-mercapto-s-triazine; two S-glucuronides and two t-butyl-O-glucuronides. Other metabolites were formed by one or a combination of the following reactions: N-alkyl oxidation to alcohols or acids: S-demethylation; N-deethylation; and disulfide formation.|Microsomes prepared from livers from 30 to 70 year old patients undergoing liver resection were incubated with 6.3 to 1,000 uM atrazine, terbuthylazine, terbutryne, or ametryne , and the incubation mixtures were analyzed for metabolites. The compounds produced a variety of metabolites indicative of S-oxidation, N-dealkylation, and side chain C-oxidation. The metabolites were formed by processes showing biphasic kinetics, Michaelis constants for the first and second phases varying from 1.4 to 20 uM and from 54 to 530 uM, respectively. Atrazine, terbuthylazine, ametryne, or terbutryne at 25 uM was incubated with human liver microsomes containing substrates for cytochrome-P4501A2 (CYP1A2), cytochrome-P4502A6, cytochrome-P4502D6, cytochrome-P4502C9, cytochrome-P4502C19, cytochrome-P4502E1, or cytochrome-P4503A4 (CYP3A4) isozymes. Other microsomal preparations were incubated with 25 or 600 uM of the S-triazines in the presence or absence of alpha-naphthoflavone (aNF), furafylline, quinidine, sulfaphenazole, diethyl-dithiocarbamate, gestodene, or ketoconazole, inhibitors of various specific cytochrome-P450 (P450) isozymes, at concentrations 5 to 10 times greater than their inhibition constants. Microsomal preparations containing substrates for CYP1A2 and CYP3A4 showed the best correlation with the rates of metabolism of the S-triazines. Only aNF and furafylline, inhibitors of CYP1A2, inhibited metabolism of the S-triazines. A human liver microsomal preparation with demonstrated high levels of flavin containing monooxygenase (FMO) activity and purified recombinant human FMO-3 were incubated with ametryne and terbutryne. The extent of sulfoxidation of the two compounds was determined. No significant formation of sulfoxide metabolites was detected, indicating that the FMO system was not involved in the metabolism of S- triazines by human liver microsomes. The authors conclude that these results clearly identify CYP1A2 as the major phase-I P450 isozyme that is involved in the metabolism of S-triazines by human liver microsomes.|For more Metabolism/Metabolites (Complete) data for TERBUTRYNE (7 total), please visit the HSDB record page.|Terbutryn has known human metabolites that include 1-[[4-(tert-butylamino)-6-methylsulfanyl-1,3,5-triazin-2-yl]amino]ethanol, 2-[[4-(Ethylamino)-6-methylsulfanyl-1,3,5-triazin-2-yl]amino]-2-methylpropan-1-ol, and Terbutrynsulfoxide.

... Their chief mode of action appears to involve carbohydrate metabolism. The chlorinated s-triazines inhibit starch accumulation by blocking the prodn of sugars. Similar behavior has been shown for the methoxy & methylthio-s-triazines. It has been reported that the s-triazines affect the tricarboxylic acid cycle with activation of phospho-phenyl pyruvate-carboxylase causing the disappearance of sucrose & glyceric acid with the formation of aspartic & malic acids. /S-triazines/|Inhibition of photosynthesis by disruption of light reactions and blockade of electron transport is the mechanism of action of the 1,3,5-triazine herbicides. /1,3,5-Triazines, from table/|The influence of some s-triazine herbicides on acid phosphatase and phosphodiesterase from corn (Zea mays) roots were investigated. Terbutryn stimulated both phosphatases, whereas prometryn stimulated only the phosphodiesterase. Atrazine desmetryn, prometon, and simazine inhibited acid phosphatase. No effect was exerted by ametryn. The enzyme assays and the kinetic parameters demonstrated that the interferences observed were due to an action on the synthesis of one or both enzymes rather than on the enzyme reactions. The types of the N-alkyl and the chlorine-subsitutuent groups in the structures of the s-triazines tested appear important in determing the degree of the interference.

/SRP:/ Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Irritating materials/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation at the first sign of upper airway obstruction may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/

/SIGNS AND SYMPTOMS/ Adverse effects have occurred only rarely as result of ... contact with these herbicides. Most injuries reported have been skin irritation after prolonged contact. In varying degrees these herbicides are likely to produce irritation of gut if ingested in substantial quantity. ... Some compounds of these classes cause irritation of eyes and mucous membranes, particularly if direct contact is protracted. Nausea, vomiting, and diarrhea can be expected to result from ingestion of large quantities. /Urea-, uracil- and triazine-based herbicides/|/GENOTOXICITY/ ... In this study, the DNA-damaging ability of the herbicide was evaluated in the alkaline single-cell microgel-electrophoresis ("comet") assay by testing terbutryn in the presence of S9 mix (rat liver homogenate containing microsomal enzymes plus cofactors) prepared with liver homogenate from both uninduced (basal) and Aroclor 1254-induced rats. DNA damage was recorded in freshly isolated human peripheral blood leukocytes. A statistically significant increase in the extent of primary DNA damage, more pronounced in the absence of S9 mix, took place only when terbutryn concentrations were high (100 and 150 ug/mL), in the presence of a concomitant mild cytotoxic effect.

2-(tert-butylamino)-4-(ethylamino)-6-(methylthio)-s-triazine

'Igran' 50wp & 80wp, wettable powder (500 or 800 g active ingredient /kg); 'igram' 500fw, 'clarosan 500fw, prebane 500 fw, soluble concentrate (500 g/L) ...|Mixed formulations: (terbutryn +) linuron; ... metobromuron; ... neburon; MCPA + simazine: mecoprop + simazine.|MIXTURES INCLUDE: DICURAN EXTRA, TERBUTRYNE + CHLORTOLURON (1:6); GESAPRIM COMBI (REG NUMBER 8063-10-2), (TERBUTRYNE + ATRAZINE (1:1)); IGRATER (REG NUMBER 52080-96-3), (TERBUTRYNE + METOBROMURON (1:1)); LEXTRA (PAN BRITANNICA IND), (TERBUTRYN + TRIFLURALIN); OPOGARD, SORGOPRIM (1:1), TOPOGARD (7:3) (REG NO 8066-11-3), (TERBUTRYN + TERBUTHYLAZINE); PEAWEED (PAN BRITANNICA IND), (TERBUTRYN + PROMETRYN); PIOTAL, (TERBUTRYN + CHLOROTOLURON + TERBUTHYLAZINE (1:5:4); TEMPO (FARM PROTECTION), SC (150 G TERBUTRYN + 150 G LINURON/L).

The WHO Recommended Classification of Pesticides by Hazard identifies Terbutryne (technical grade) as unlikely to present an acute hazard in normal use; Main Use: herbicide.|Applications may be made preemergence or post-emergence in fall or early spring in winter wheat & postemergence in fall or early spring in winter barley. It may be applied preemergence, alone or with aatrex or milogard in grain sorghum. Applications can be made with ground & aerial equipment. ... /It is/ compatible with most other pesticides & fertilizers when used at normal rates.|Registration notes: Discontinued in USA.|/In 1995/ Terbutryn /was/ a General Use Pesticide (GUP). The U.S. Environmental Protection Agency had proposed the revocation of all tolerances for residues of terbutryn in or on barley, sorghum, and wheat. They /did/ not plan to recommend action levels to replace the tolerances (Federal Register 59(138):37019). Many terbutryn product registrations had been cancelled. The EPA has classified it as Toxicity Class III-slightly toxic. Products containing terbutryn bear the Signal Word "Caution".|For more General Manufacturing Information (Complete) data for TERBUTRYNE (6 total), please visit the HSDB record page.

Five classes of triazine herbicides were analyzed by high-performance liq chromatography-mass spectrometry. Separations were performed on a reversed-C8 column, using acetonitrile-water as mobile phase, followed by in-line UV & mass spectral analysis. Positive & negative ion spectra were recorded. Most of herbicides were more sensitive in the positive ion mode. Terbutryne was one the herbicides included in this study.|RESULTS OF THIN LAYER CHROMATOGRAPHIC SEPARATION (NON-REVERSED PHASE) FOR 2 CHROMATOGRAPHIC SYSTEMS FOR S-TRIAZINE HERBICIDES, ONE OF WHICH WAS TERBUTRYNE, ARE PRESENTED. IN 1 CHROMATOGRAPHIC SYSTEM, THE TLC GLASS PLATES WERE PRECOATED & COVERED WITH SILANIZED SILICA GEL 60-F-254 & IMPREGNATED WITH 20% DIETHYLENE GLYCOL SOLN IN ACETONE. IN THE 2ND SYSTEM, THE SAME PRECOATED GLASS PLATES WERE IMPREGNATED WITH 20% FORMAMIDE SOLN IN ACETONE. MOBILE PHASES ARE GIVEN FOR BOTH.|A GAS-LIQUID CHROMATOGRAPHIC METHOD FOR THE DETERMINATION OF TERBUTRYN IN WETTABLE POWDER FORMULATIONS IS DESCRIBED. THE SAMPLES WERE EXTRACTED OR DISSOLVED IN CHLOROFORM & CHROMATOGRAPHED ON CARBOWAX 20M. DIELDRIN WAS USED AS INTERNAL STANDARD.|BASIC PROPERTIES OF S-TRIAZINES, EG, TERBUTRYNE, PROPAZINE, SIMAZINE, & PROMETONE, WERE STUDIED BY GAS CHROMATOGRAPHIC, SPECTROPHOTOMETRIC, AND ELECTROCHEMICAL METHODS. INDIVIDUALS S-TRIAZINES CAN BE DIFFERENTIATED BY THEIR RETENTION INDICES.|For more Analytic Laboratory Methods (Complete) data for TERBUTRYNE (11 total), please visit the HSDB record page.

Analytical methodology for the separation and characterization of s-triazine residues in urine was developed. In the sample preparation procedure developed, a urine sample at pH 12 was extracted with hexane 3 times, using sodium chloride as an emulsion inhibitor. The combined hexane extract was dried by passing it through a sodium sulfate column and concentrated by rotary evaporation. The sample was transferred to a graduated centrifuge tube and further concentrated to 0.5 ml under a stream of dry nitrogen. The sample was analyzed by gas chromatography using the Hall electrolytic conductivity detector in the nitrogen-specific mode. Terbutryne was one the triazines.|Procedure for determining s-triazine herbicides /including/ terbutryne in urine & biological tissues by gas chromatography/flame ionization detection is described. Urine samples are extracted with ether & biological tissues with chloroform. Residues obtained after evaporation of solvent are dissolved in dimethylformamide. Most of the lipids can be removed by n-pentane partitioning.

Agrochemicals -> Herbicides|Pharmaceuticals|Herbicides, Transformation products|Pesticides -> Herbicides -> Triazine herbicides -> Methylthiotriazine herbicides|HERBICIDES

Terbutryn has known environmental transformation products that include Irgarol-descyclopropyl and Terbutylazine-2-hydroxy.