21087-64-9

Usage

Uses

Used in Agriculture:
Metribuzin is used as a selective herbicide for preemergence broad-leaved weed control in crops such as potatoes, tomatoes, lucerne, raspberry, and sugarcane. It is also used for postemergence weed control in beets and for selective control of annual grasses.
Used in Soybean, Potatoes, Tomatoes, and Sugar Cane:
Metribuzin is used as an herbicide in these crops to inhibit the photosynthesis of susceptible plant species, providing effective weed control.
Used in Asparagus, Peas, Lentils, and Cereals:
Metribuzin is used as a herbicide in these crops for the control of annual grasses and numerous broadleaf weeds, enhancing crop yield and quality.
Used in Fallow Lands:
Metribuzin is applied to fallow lands to control weed growth before planting new crops.
Available in Various Formulations:
Metribuzin is available in liquid suspension, water dispersible granular, and dry flowable formulations, making it suitable for different application methods and agricultural practices.

Reactivity Profile

A triazine derivative. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard

Toxic material. Liver damage and hemato-logic effects. Questionable carcinogen.

Health Hazard

Low to moderate acute toxicity; single highdose may cause depression of central nervoussystem; repeated high doses affect thyroidand stimulate the metabolizing liver enzymes(ACGIH) 1986; excretes out rapidly; noirritant action on skin or eye; no teratogenic,mutagenic or carcinogenic effect observed inanimal studies.LD50 oral (rat): 1100 mg/kgLD50 oral (mouse): 698 mg/kgLD50 oral (guinea pig): 250 mg/kgLD50 skin (rat): 2000 mg/kg.

Trade name

AUTHORITY?; AXIOM? Metribuzin; BAY 61597?; BAY DIC 1468?; BAYER 6159H?; BAYER 6443H?; BAYER 94337?; BOUNDARY?; CANOPY?; CONQUEST?; DIC 1468?; DOMAIN?; LEXONE?; LEXONEEX?; PREVIEW?[C]; PYTHON?; SENCOR?; SENCORAL?; SENCOREX?; SENCORER?; VAPCOR?

Safety Profile

Poison by ingestion and intraperitoneal routes. Low toxicity by skin contact. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Potential Exposure

A potential danger to those involved in manufacture, formulation, and application of this herbicide. A laboratory chemical. Used to make other chemicals.

Environmental Fate

Soil. In soils, metribuzin undergoes deamination and further degradation forming water soluble conjugates (Hartley and Kidd, 1987). Metribuzin degrades rapidly in soil (Kempson- Jones and Hance, 1979; LaFleur, 1980). The half-lives in soil ranged from 4 to 9 weeks at 22°C and 60% moisture content to 9 to 11 weeks at 10°C and 10% moisture content. The highest half-life reported ranged from 15 to 43 weeks in a soil having 60% moisture content maintained at 10°C (Kempson-Jones and Hance, 1979).The dissipation rates (day–1) for metribuzin on Hillsdale silty loam, Cecil silty loam, Regina heavy clay, Melfort clay loam and White City silt loam were 0.013-0.017, 0.055- 0.131, >0.017, >0.0016 and >0.023, respectively.Groundwater. According to the U.S. EPA (1986) metribuzin has a high potential to leach to groundwater.Plant. Metribuzin is metabolized in soybean plants to a deaminated diketo derivative which is nonphytoxic (Duke et al., 1991). Photolytic. The simulated sunlight (l >230 nm) photolysis as a thin film on silica gel or sand yielded 6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5-(4H)-one and two additional photoproducts. In both of the unnamed photoproducts, the methylthio group in the parent compound is replaced by oxygen and one of the compounds also underwent N-deamination (Bartl and Korte, 1975). Chemical/Physical. Emits toxic fumes of nitrogen and sulfur oxides when heated to decomposition (Lewis, 1990).

Shipping

UN2763 Triazine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

Liquid is incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 33509-43-2 4-amino-3-mercapto-6-tert-butyl-1,2,4-triazin-5-one 
• 74-83-9 methyl bromide 
• 74-88-4 methyl iodide 
• 333-27-7 methyl trifluoromethanesulfonate 
• 74-87-3 methylene chloride 
• 33509-43-2 4-amino-6-tert-butyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine 
• 812-01-1 methyl chlorosulfate 
• 35771-42-7 S-methylisothiocarbohydrazide 
• 815-17-8 trimethylpyruvic acid 

Downstream Products

• 52236-30-3 6-t-butyl-1,2,4-triazin-3,5(2H,4H)-dione 
• 56507-37-0 4-amino-6-tert-butyl-1,2,4-triazine-3,5(2H,4H)-dione 
• 35045-02-4 6-t-butyl-3-methylthio-1,2,4-triazine-5(4H)-one 
• 90269-30-0 4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one 
• 35045-02-4 6-tert-butyl-3-methylsulfanyl-2(4)H-[1,2,4]triazin-5-one 
• 33509-43-2 4-amino-6-tert-butyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine 
• 64529-56-2 Ethiozin 
• 102363-02-0 4-Amino-6-tert-butyl-3-m-tolylsulfanyl-4H-[1,2,4]triazin-5-one 

Relevant academic research and scientific papers

Preparation method of metribuzin

The invention discloses a preparation method of metribuzin. The preparation method is characterized in that methanol-water is used as a solvent; under the conditions that a pH value is 11.5-12.5, andlithium ions exist, triazinone reacts with halomethane at a temperature of 5-20 DEG C till the triazinone completely disappears. The preparation method disclosed by the invention has the beneficial effects that when the metribuzin is prepared, the lithium ions are added in a reaction system, so that the selectivity to the generation of the metribuzin by reaction is improved; by the addition of thelithium ions, the ability of the triazinone to exist in the form of mercaptan is improved, so that the concentration and the reactivity of sulfur anions in the reaction system are increased; a generated product mainly is an S-methylation product, so that the production possibility of an N-methylation product is reduced, therefore, no impurity is basically generated in the product, and the purityof the metribuzin is above 99 percent.

Synthesis method of metribuzin

The invention relates to a synthesis method of metribuzin. The metribuzin is prepared from methylmercapto-carbazide and 3,3-dimethyl ketobutyric acid through reaction under the effect of catalysts, wherein the structure formula of methylmercapto-carbazide is shown in description. Compared with the prior art, the synthesis method has the advantages that the cyclization reaction conditions are mild;the reaction time is short; the yield is high; the product quality is high; the discharging quantity of three wastes (waste water, waste gas and waste solid) is reduced; the yield and the economic benefits are improved.

A metribuzin preparation method and method of treating waste (by machine translation)

The invention relates to a method for the preparation of ketone [...] and waste liquid processing method, will be triazones and dimethyl sulfate in paraxylene and concentrated presence of sulfuric acid, in the 75 - 80 °C lower heat insulating reaction, after the reaction, lowering the temperature to 60 °C and below, water quenching reaction, para-xylene layer by washing, reduced pressure distillation, drying to obtain the metribuzin. The invention uses the market to facilitate purchase of triazones as raw materials, in order to para-xylene as the solvent, concentrated sulfuric acid as the catalyst, through the dropping dimethyl sulphate preparation method of metribuzin, the few by-products in the reaction process, the processing method is simple. Waste water treatment in the links, paraxylene and [...] can be recycled, unreacted triazones easy to recycle. The method of the invention has high recovery rate, low cost, production cycle is short, the prepared metribuzin has high purity, comply with the safety requirements of environmental protection. (by machine translation)

Preparation method of metribuzin

The invention relates to a preparation method of metribuzin, which is characterized in that 4-amino-6-tert-butyl-3-sulfydryl-1,2,4-triazine-5(4H)-one and methyl trifluoromethanesulfonate react in thepresence of toluene and trifluoromethanesulfonic acid to prepare the metribuzin. The method is low in raw material cost, simple, high in metribuzin purity and yield, low in wastewater treatment difficulty and low in cost, meanwhile, the generated low-COD wastewater can be recycled, no toxic or side effect exists in the production process, and the method is suitable for industrial production.

Synthetic method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-ketone

The invention discloses a synthetic method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-ketone. The synthetic method comprises the following steps: sequentially adding process water, caustic soda flakes, triazone and a catalyst into a dissolving kettle till complete dissolution under stirring conditions; transferring a material into a synthetic kettle, introducing methyl bromide into the synthetic kettle under stirring conditions, preparing to obtain metribuzin and performing heat preservation for 0.5-1 hour after the end of reaction; introducing nitrogen gas into a reaction kettle to blow out redundant methyl bromide, meanwhile raising the temperature in the synthetic kettle to 48-55 DEG C and performing heat preservation for 0.5-1.5 hours; cooling, washing and filtering the material to obtain metribuzin. The synthetic method disclosed by the invention has the benefits that the adding quantity of the catalyst is small, and no toxic or side effect exists; on one hand, the raw material input cost and the post-processing process cost of a recycled product solvent are reduced; on the other hand, the consumption of the catalyst is less, and compared with methanol, the risk of easy explosion is avoided, so that the safety coefficients in the production process are improved.

A process for preparing 4-amino-6-tert-butyl-3-methylthio -1, 2, 4-triazin -5 (4H)-one

The invention discloses a method for preparing 4-amino-6-tertiary butyl-3-methylmercapto-1,2,4-triazine-5(4H)-ketone, which comprises the following steps of: keeping the temperature and reacting 4-amino-6-tertiary butyl-3-sulfydryl-1,2,4-triazine-5(4H)-ketone, dimethyl sulphate with anhydrous sodium carbonate in the mol ratio of 1:(1.2-1.5):(1.6-2.1) by taking acetone as the solvent and potassium iodide as the catalyst below 20-30 DEG C for 4-5 hours, and finally, recycling acetone, adding water to separate materials, and separating and drying to obtain 4-amino-6-tertiary butyl-3-methylmercapto-1,2,4-triazine-5(4H)-ketone. Raw materials used in the method disclosed by the invention are easy to obtain and low in cost; the method disclosed by the invention is moderate for a reaction and easy for controlling reaction parameters and is capable of ensuring the safety in the production process; potassium iodide is used as the catalyst, therefore, reaction is rapidly completed at normal temperature; the production period is greatly reduced; the production cost is effectively reduced; the product yield is high and can be above 90%; products with the content of above 96% can be directly obtained; the method disclosed by the invention meets industrial production requirements and has better application prospect.

A 4-amino-6-tert-butyl-3-methylthio -1, 2, 4-triazin -5 (4H)-one synthesis method

The invention discloses a synthesis method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one, which comprises the following steps: by using acetone as solvent and potassium iodide as a catalyst, reacting 4-amino-6-tert-butyl-3-thio-1,2,4-triazine-5(4H)-one, dimethyl sulfate and anhydrous sodium carbonate according to a mol ratio of 1:(1.05-1.5):(1.5-2) while keeping the temperature at 15-45 DEG C for 2-5 hours; and finally, recovering the acetone, adding water to perform precipitation, separating, and drying to obtain the 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one. The raw materials used in the method disclosed by the invention are accessible and low in cost; the method disclosed by the invention is mild in reaction, and the reaction parameters are easy to control, thus ensuring the safety of the production process; the potassium iodide is used as the catalyst, so that the reaction can be quickly and completely performed at normal temperature, thus greatly shortening the production cycle and effectively lowering the production cost; the yield of the product is high and is up to 90% or above; and the product with a content of 96% or above can be directly obtained. Thus, the invention conforms to requirements of industrial production, and has better application prospects.

4-amino-6-tert-butyl-3-methylthio -1, 2, 4-triazin -5 (4H)-ketone preparation method

The invention discloses a preparation method of 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine 5 (4H)-ketone. The method comprises steps of: reacting 4-amino-6-tert-butyl-3-sulfydryl-1,2,4-triazine-5 (4H)-ketone, dimethyl sulfate and anhydrous sodium carbonate in a molar ratio of 1:1.1-1.4:1.5-2 in a solvent acetone and in the presence of a catalyst potassium iodide at 15-45 DEG C for 2-4 h; and finally recovering acetone, adding water to dilute the material, separating and drying to obtain the 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine 5 (4H)-ketone. The raw materials used in the method are easily available, and cheap; and the method provided by the invention has advantages of moderate reaction and easily controlled reaction parameters, and can guarantee the safety of the production process. Potassium iodide is used as a catalyst, so as to realize rapid complete reaction at room temperature, reduce the production cycle and effectively reduce production cost; the product yield reaches more than 90%, and products with content of more than 96% can be directly obtained. The preparation method satisfies requirements of industrial production, and has a good application prospect.

Variable Release Water Dispersible Granule Composition

A water dispersible granule composition comprising microcapsules comprising at least one agrochemical active ingredient encapsulated within a urea formaldehyde polymeric shell wall, at least one inert filler and at least one agrochemical excipients.

Method of preparing substituted 4-amino-3-alkylthio-1,2,4-triazine-5-ones

The present invention provides a method of preparing 4-amino-3-alkylthio-1,2,4-triazine-5-ones of the formula (I) wherein R, R1, R2 and R3 are as defined herein, the method comprising reacting in the presence of a base and under at least one condition selected from the presence of at least one inorganic compound selected from inorganic sulfites and inorganic bisulfites, an inert gas purge, and an alternating inert gas blanket and vacuum, a 4-amino-3-mercapto-1,2,4-triazin-5-one of the formula (II) wherein R, R1 and R2 are as defined herein, with an alkylating agent of the formula R3-X, wherein R3 and X are as defined herein and collecting the reaction product.