28159-98-0

Basic information

• Product Name: Irgarol
• Synonyms: IRGAROL;IRGAROL 1051;IRGAROL 1051/1071;IRGAROL(R);CYBUTRYNE;2-(TERT-BUTYLAMINO)-4-(CYCLOPROPYLAMINO)-6-(METHYLTHIO)-S-TRIAZINE;N-CYCLOPROPYL-N'-(1,1-DIMETHYLETHYL)-6-(METHYLTHIO)-1,3,5-TRIAZINE-2,4-DIAMINE;3,5-Triazine-2,4-diamine,N-cyclopropyl-N’-(1,1-dimethylethyl)-6-methylthio-1
• CAS NO: 28159-98-0
• Molecular Formula: C₁₁H₁₉N₅S
• Molecular Weight: 253.37
• EINECS: 248-872-3
• Product Categories: Heterocycles;paint
• Mol File: 28159-98-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 128-1330C
• Boiling Point: 427.971 °C at 760 mmHg
• Flash Point: 212.629 °C
• Appearance: White solid
• Density: 1.202 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.13±0.10(Predicted)
• Water Solubility: Insoluble in water
• BRN: 792218
• CAS DataBase Reference: Irgarol(CAS DataBase Reference)
• NIST Chemistry Reference: Irgarol(28159-98-0)
• EPA Substance Registry System: Irgarol(28159-98-0)

Safety Data

• Hazard Codes: Xi;N,N,Xi
• Statements: 43-50/53
• Safety Statements: 36/37-60-61
• RIDADR: UN 3077
• WGK Germany: 2
• RTECS: XY5850675
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 28159-98-0(Hazardous Substances Data)

Usage

Description

Irgarol is a white solid chemical compound, specifically a diamino-1,3,5-triazine derivative with a N-tert-butyl, N'-cyclopropyl, and a methylsulfanyl group at position 6. It is highly specific and effective as an inhibitor of photosynthesis, which makes it suitable for various applications in different industries.

Uses

Used in Marine Applications:
Irgarol is used as a long-life antifouling agent for marine applications to prevent the growth of algae. Its low water solubility and effectiveness in inhibiting photosynthesis contribute to its long-lasting performance in these coatings.
Used in Antifouling Paint:
Irgarol is used as a booster algicide in antifouling paint, enhancing the paint's ability to prevent the growth of algae and other aquatic organisms on submerged surfaces.
Used in Agriculture:
Irgarol is used as a photosystem-II (PSII) herbicide, inhibiting photosynthetic electron transport in chloroplasts. This application helps control the growth of unwanted plants in agricultural settings.

Metabolic pathway

Metabolism of irgarol 1051 by the fungus Phanerochaete chrysosporium proceeds mainly via partial N-dealkylation at the cyclopropylamino group, resulting in a tentatively identified 2-methylthio-4-tert- butylamino-6-amino-1,3,5-triazine.

Synthetic route

N2-tert-butyl-6-chloro-N4-cyclopropyl-1,3,5-triazine-2,4-diamine (26737-71-3) + carbonic acid dimethyl ester (616-38-6) → 2-methylthio-4-t-butylamino-6-cyclopropyl-amino-s-triazine (28159-98-0)

Conditions	Yield
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Inert atmosphere;	93%
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Schlenk technique; Inert atmosphere;	93%

tert-butyl-(4-chloro-6-methylsulfanyl-[1,3,5]triazin-2-yl)-amine (4622-80-4) + Cyclopropylamine (765-30-0) → 2-methylthio-4-t-butylamino-6-cyclopropyl-amino-s-triazine (28159-98-0)

Conditions	Yield
With sodium hydroxide In toluene

2-methylthio-4-t-butylamino-6-cyclopropyl-amino-s-triazine (28159-98-0) → Deethylterbutryne (30125-65-6)

Conditions	Yield
mercury dichloride In acetate buffer at 21℃; for 2h; pH=5; Kinetics; Further Variations:; pH-values; Reagents; Hydrolysis;
With mercury dichloride In water; acetonitrile at 21℃; for 2h;	14.5 mg
With dihydrogen peroxide; titanium(IV) oxide In water UV-irradiation;

ethylene glycol (107-21-1) + 2-methylthio-4-t-butylamino-6-cyclopropyl-amino-s-triazine (28159-98-0) → Reaxys ID: 11367229

Conditions	Yield
With Uniqema (HLB 6); silica gel; dibutyltin dilaurate In paraffin oil (nujol) at 25 - 40℃; for 19.4167 - 19.6667h; Product distribution / selectivity;
With poly(lauryl methacrylate)-g-poly(ethylene oxide); silica gel; dibutyltin dilaurate In paraffin oil (nujol) at 25 - 40℃; for 19.4167 - 19.6667h; Product distribution / selectivity;

Upstream product

• 4622-80-4 tert-butyl-(4-chloro-6-methylsulfanyl-[1,3,5]triazin-2-yl)-amine 
• 765-30-0 Cyclopropylamine 
• 26737-71-3 N²-tert-butyl-6-chloro-N⁴-cyclopropyl-1,3,5-triazine-2,4-diamine 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 30125-65-6 2-methylthio-4-tert-butylamino-6-amino-s-triazine 

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.

Process for the preparation of 2,4-di(alkylamino)-6-alkylthio-s-triazines

An improved process for the preparation of 2,4-di(alkylamino)-6-alkylthio-s-triazines wherein cyanuric chloride is reacted in successive steps with two appropriate alkylamines and an alkyl mercaptan is described where the improvement involves use of a single water-immiscible solvent and a phase transfer catalyst in the mercaptan addition step.