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Your Location：Home>Product Center >> Pesticide API and intermediates >> Metribuzin
  • Metribuzin
Name:Metribuzin
CAS No:21087-64-9

PRODUCT DESCRIPTION

【Name】
Metribuzin
【Iupac name】
4-amino-6-tert-butyl-3-methylsulfanyl-1,2,4-triazin-5-one
【CAS Registry number】
21087-64-9
【Synonyms】
4-Amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazine-5-tetrahydrogenketone
Sencor
Lexone
4-Amino-6-Tert-Butyl-3-(Methylthio)-1,2,4-Triazin-5-One
Sencoral(Bayer)
Lexone(du pont)
4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5-(4H)-one
4-Amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one
1,2,4-triazin-5(4H)-one
PRETILACHLOR
2-Chloro-N-(2,6-diethylphenyl)-N-(2-propoxyethyl)acetamide
4-Amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one
【EINECS(EC#)】
244-209-7
【Molecular Formula】
C8H14N4OS (Products with the same molecular formula)
【Molecular Weight】
214.28
【Inchi】
InChI=1/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3
【InChIKey】
FOXFZRUHNHCZPX-UHFFFAOYSA-N
【Canonical SMILES】
CC(C)(C)C1=NN=C(N(C1=O)N)SC
【MOL File】
21087-64-9.mol

Chemical and Physical Properties

【Appearance】
colorless crystalline solid
【Density】
1.28
【Melting Point】
125℃
【Boiling Point】
312.4 °C at 760 mmHg
【Vapour】
0.000531mmHg at 25°C
【Refractive Index】
1.617
【Flash Point】
142.7 °C
【Water】
Slightly soluble
【Solubilities】
Slightly soluble
【Color/Form】
Colorless crytals
White crystalline solid
【Stability】
Stable at normal temperatures and pressures.
【Storage temp】
APPROX 4°C
【Computed Properties】
Molecular Weight:214.28796 [g/mol]
Molecular Formula:C8H14N4OS
XLogP3:1.7
H-Bond Donor:1
H-Bond Acceptor:5
Rotatable Bond Count:2
Exact Mass:214.088832
MonoIsotopic Mass:214.088832
Topological Polar Surface Area:96.4
Heavy Atom Count:14
Formal Charge:0
Complexity:316
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:1
Effective Rotor Count:2
Conformer Sampling RMSD:0.6
CID Conformer Count:3

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R50/53
【Safety Statements 】
S2;S60;S61
【Safety】

Poison by ingestion and intraperitoneal routes. Low toxicity by skin contact. When heated to decomposition it emits very toxic fumes of NOx and SOx.?
Hazard Codes:?HarmfulXn,DangerousN,FlammableF
Risk Statements: 22-50/53-36-20/21/22-11?
R22:Harmful if swallowed.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36:Irritating to eyes.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R11:Highly flammable. 
Safety Statements: 2-60-61-36-26-16?
S2:Keep out of the reach of children.?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S16:Keep away from sources of ignition. 
RIDADR: UN3077 9/PG 3 
RTECS: XZ2990000

【Transport】
UN3077 9/PG 3
【Fire Potential】
Nonflammable
【Formulations/Preparations】
USEPA/OPP Pesticide Code 101101; Trade Names: Sencor; Bay 94337; Lexone; Canopy.
Wettable powder; water dispersible granules; suspension concentrate
Combinations: saline (with trifluralin); Turbo (with metolachlor).
Liquid suspension, water dispersible granules, dry flowable
【Other Preventative Measures】
Avoid contact with skin, eyes, and clothing. Remove contaminated clothing and wash with soap and hot water before reuse.
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.
【Specification】

?Metribuzin , its cas register number is 21087-64-9. It also can be called?4-Amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one ; 4-Amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one ; Bay 94337 ; Bayer 6159H ; Lexone 4L ; Lexone 75DF ; Preview ; Salute ; Sencor 4L ; Sencor 75DF ; Sencoral . It is a?colorless crystalline solid.And it is?A triazine derivative.

【Octanol/Water Partition Coefficient】
log Kow= 1.7
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Bury empty container or product that cannot be used in a safe place away from water supplies, or dispose of by alternative procedures recommended by federal, state or local authorities. Open dumping is prohibited.

Use and Manufacturing

【Use and Manufacturing】
Consumption Patterns

Use of metribuzin in the United States was 4.8 million lbs in the year 1987.
【Usage】

Herbicide.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
【Biomedical Effects and Toxicity】
Absorbed through the leaves from surface treatment, but the major significant route for uptake is via root system. ... Uptake through the roots is best described as osmotic diffusion. Metribuzin is translocated upward in the xylem and moves distally when applied at the base of leaves.
After absorption, it is rapidly distributed and rapidly excreted unchangd or metabolized (oxidized) and excreted via the urine.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: In soil, metribuzin was degraded to carbon dioxide. Autoclaving of soil decreased metribuzin metabolism. Those metabolites observed in plants (metribuzin, 3,5-diketo and deaminated diketo) were also observed in the soil. Deaminated diketo was the primary metabolite in soil. Metribuzin, applied in June to a fine sandy loam soil, degraded during the growing season to the extent that less than 10% of applied herbicide was present by October 25, freeze-up time. Metribuzin, 3,5-diketo and deaminated diketo were observed in soil samples and metabolite residue levels were at their maximum near the middle of July. In a study with Guelp loam, the half-life of metribuzin was about 3 months. Under greenhouse conditions with soils from the lower alluvial floodplain of the Mississippi River, metribuzin half-life varied from 17 to 28 days and followed first-order kinetics. In four Manitoba soils under dry conditions at 15 C, some nonbiological degradation of metribuzin occurred. The rate law was somewhat less than first-order and half-lives varied from 90 to 115 days. Field soil samples awaiting analysis underwent degradation. At -37C, about 50% of the herbicide could be lost in 282 days. 3,5-Diketo and deaminated diketo also degraded under storage conditions. In laboratory studies with a sandy loam soil, metribuzin calculated half-life was about 329, 44 and 16 days at 5, 20 and 35C, respectively. Metribuzin and deaminated diketo were observed.
TERRESTRIAL FATE: Based on a classification scheme(1), an average Koc value of 60(2) suggests that metribuzin is expected to have high mobility(SRC). Little leaching occurs on soils with high organic content, but metribuzin is readily leached in sandy soils(2,4). Adsorption of metribuzin decreases as soil pH increases(2). Loss from soil surfaces via volatilization is not an important fate process(2,3). Volatilization of metribuzin from moist soil surfaces is not expected to be an important fate process given an estimated Henry's Law constant of 1.2X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 4.4X10-7 mm Hg(5), and water solubility, 1050 mg/l(5). Metribuzin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). Metribuzin had a half-life of 2.5 days on sandy loam soil irradiated outdoors in Kansas City, MO at temperatures up to 31 deg C(6). The major photolytic products of metribuzin were pentylidene and hexylidene metribuzin in soil(6). Biodegradation is the primary means of metribuzin dissipation from soils(2). The activity of soil microorganisms, higher temperatures, and aerobic conditions increase the rate of metribuzin biodegradation(2). Half-lives are 172 and 439 days for sandy loam under aerobic and anaerobic conditions, respectively(2). Primary metabolites are the deaminated, diketo, and deamined diketo metabolites(2). The calculated field dissipation half-lives of metribuzin in sandy loam soils in California were 128 and 40 days at Watsonville and Fresno, respectively(6).
AQUATIC FATE: Based on a classification scheme(1), an average experimental Koc value of 60(2), indicates that metribuzin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected based upon an estimated Henry's Law constant of 1.2X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 4.35X10-7 mm Hg(3), and water solubility, 1100 mg/l(3). Photodecomposition is an important process for the degradation of metribuzin in aqueous solution(3). Metribuzin was found to have a half-life of 4.3 hours in surface water from Kansas City, MO (pH 6.6) irradiated with natural sunlight at 25 deg C(4). The identified degradate was deaminated metribuzin(4). A BCF of 10 was measured for Golden ide fish (Leuciscus idus melanotus)(5). According to a classification scheme(6), this whole body BCF suggests the potential for bioconcentration of metribuzin in aquatic organisms is low(SRC). No data were located on the biodegradation of metribuzin in water; however, microbial degradation is the primary fate process of metribuzin in soil(2,3), which suggests that biodegradation may be an important fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), metribuzin, which has a vapor pressure of 4.35X10-7 mm Hg at 20 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase metribuzin 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 21 hrs(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 deg C(SRC) determined using a structure estimation method(3). Particulate-phase metribuzin may be removed from the air by wet and dry deposition(SRC).

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