886-50-0

Basic information

• Product Name: Terbutryn
• Synonyms: 1,3,5-Triazine-2,4-diamine, N-(1,1-dimethylethyl)-N'-ethyl-6-(methylthio)-;2-(tert-butylamino)-4-(ethylamino)-6-(methylthio)-s-triazin;2-Methylthio-4-ethylamino-6-tert-butylamino-s-triazine;2-tert.Butylamino-4-aethylamino-6-methylthio-1,3,5-triazin;2-Tert.-butylamino-4-ethylamino-6-methylthio-[1,3,5]triazin;2-tert-Butylamino-4-ethylamino-6-methylmercapto-s-triazine;4-Aethylamino-2-tert-butylamino-6-methylthio-s-triazin;5-triazine-2,4-diamine,n-(1,1-dimethylethyl)-n’-ethyl-6-(methylthio)-3
• CAS NO: 886-50-0
• Molecular Formula: C₁₀H₁₉N₅S
• Molecular Weight: 241.36
• EINECS: 212-950-5
• Product Categories: HERBICIDE;TA - TEPesticides&Metabolites;Alpha sort;Herbicides;Pesticides&Metabolites;Q-ZAlphabetic;Triazines;Alphabetic;Agro-Products;Amines;Bases & Related Reagents;Heterocycles;Isotope Labelled Compounds;Nucleotides;Sulfur & Selenium Compounds;NULL;Pyridazines
• Mol File: 886-50-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 104-105°C
• Boiling Point: 154-160°C
• Flash Point: 2 °C
• Appearance: White/Powder
• Density: 1.45
• Vapor Pressure: 1.21E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: APPROX 4°C
• PKA: 4.03±0.10(Predicted)
• Water Solubility: 0.0025 g/100 mL
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 611817
• CAS DataBase Reference: Terbutryn(CAS DataBase Reference)
• NIST Chemistry Reference: Terbutryn(886-50-0)
• EPA Substance Registry System: Terbutryn(886-50-0)

Safety Data

• Hazard Codes: Xi,N,Xn,F
• Statements: 36-50/53-20/21/22-11
• Safety Statements: 26-60-61-36/37-16
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: XY4725000
• Hazardous Substances Data: 886-50-0(Hazardous Substances Data)

Usage

Description

Terbutin is a systemic and conductive herbicide, which can be used for pre-emergence and post-emergence weeding, and the effective period in the soil is 3-10 weeks. It is mainly used in winter wheat, barley, sorghum, sunflower, potatoes, peas, soybeans, peanuts and other crop fields to control perennial ryegrass, ryegrass and autumn germinating chickweed, marigolds, poppies, kangaroo, crabgrass, foxtail Wait.

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 886-50-0 differently. You can refer to the following data:
1. A labelled triazine herbicide.
2. Selective herbicide for control of annual broad-leaved and grass weeds in wheat.

Definition

ChEBI: A methylthio-1,3,5-triazine that is 2-(methylsulfanyl)-1,3,5-triazine substituted by a tert-butylamino and an ethylamino group at positions 2 and 4 respectively.

Synthesis

Cyanuric chloride reacts with ter-butylamine to generate 2,4-dichloro-6-tert-butylamino-1,3,5-triazine; then reacts with ethylamine to generate 2-chloro-4-ethylamino-6-tertiary Butylamino-1,3,5-triazine, and finally reacts with methyl mercaptan to generate Terbutryn.

Environmental Fate

Plant. In plants, the methylthio group is oxidized to hydroxy derivatives and by dealkylation of the side chains. Residual activity in soil is limited to approximately 3–10 weeks (Hartley and Kidd, 1987).

InChI:InChI=1/C10H19N5S/c1-6-11-7-12-8(15-10(2,3)4)14-9(13-7)16-5/h6H2,1-5H3,(H2,11,12,13,14,15)

Synthetic route

terbuthylazine (5915-41-3) + carbonic acid dimethyl ester (616-38-6) → terbutryn (886-50-0)

Conditions	Yield
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Inert atmosphere;	99%
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Schlenk technique; Inert atmosphere;	99%

terbutryn (886-50-0) → N-nirosoterbutryn

Conditions	Yield
With pyridine; nitrosonium tetrafluoroborate In acetonitrile for 1h;	43%

MCPA (94-74-6) + terbutryn (886-50-0) → 2-methyl,4-chlorophenoxyacetic acid terbutryn

Conditions	Yield
In n-heptane at 5℃;

3,6-dichloro-O-anisic acid (1918-00-9) + terbutryn (886-50-0) → 3,6-dichloro-2-methoxybenzoic acid : 2-N-tert-butyl-4-N-ethyl-6-methylsulfanyl-1,3,5-triazine-2,4-diamine (1:1)

Conditions	Yield
In ethanol at 5 - 50℃;

Upstream product

• 5915-41-3 terbuthylazine 
• 616-38-6 carbonic acid dimethyl ester 

Relevant articles and documents

Palladium-Catalyzed Thiomethylation via a Three-Component Cross-Coupling Strategy

In this report, the combination of masked inorganic sulfur and dimethyl carbonate was designed to achieve thiomethylated cross coupling of aryl chlorides. Remarkably, this powerful strategy realized thiomethylation of nucleosides bearing unprotected ribose, chloride-containing pharmaceuticals with late-stage coupling, and herbicides possessing multiple heteroatoms and steric hindrance. Moreover, this protocol is practically amenable to multigram-scale synthesis with a lower catalysis loading and a higher yield.

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.

Pesticide-polymer systems prepared from vinyl monomers

Controlled release pesticide-polymer systems are prepared by the polymerization of vinyl monomers containing pendant pesticides. The vinyl monomers are prepared by reacting an acrylic acid derivative with a pesticide or a pesticide derivative having an active hydrogen. The pesticide-polymer systems prepared from the pesticide vinyl monomers release the active pesticide material by hydrolysis or chemical depolymerization under conditions of use.