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Irgarol

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Irgarol Basic information

Product Name:
Irgarol
Synonyms:
  • N'-tert-Butyl-N-cyclopropyl-6-(Methylthio)-1,3,5-t
  • Cybutrin
  • Irgaguard A 2000
  • Irgaguard D 1071
  • Microban Additive IA 1
  • Nuocide 1051
  • 1,3,5-Triazine-2,4-diaMine,N2-cyclopropyl-N4-(1,1-diMethylethyl)-6-(Methylthio)-
  • 2-(tert-Butylamino)-4-(cyclopropylamino)-6-(methylthio)-1,3,5-triazine
CAS:
28159-98-0
MF:
C11H19N5S
MW:
253.37
EINECS:
248-872-3
Product Categories:
  • paint
  • Heterocycles
Mol File:
28159-98-0.mol
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Irgarol Chemical Properties

Melting point:
128-1330C
Boiling point:
428.0±28.0 °C(Predicted)
Density 
1.20±0.1 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
Water Solubility 
Insoluble in water
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
4.13±0.10(Predicted)
color 
White to Almost white
BRN 
792218
EPA Substance Registry System
Cybutryne (28159-98-0)
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Safety Information

Hazard Codes 
Xi;N,N,Xi
Risk Statements 
43-50/53
Safety Statements 
36/37-60-61
RIDADR 
UN 3077
WGK Germany 
2
RTECS 
XY5850675
HazardClass 
9
PackingGroup 
III
HS Code 
29336990
Hazardous Substances Data
28159-98-0(Hazardous Substances Data)
Toxicity
LC50 (96 hr in salt water) in mysid shrimp, inland silverside, sheepshead minnow (ng/l): 400000, 1580000, 3500000; LC50 (96 hr in fresh water) in rainbow trout, bluegill sunfish (ng/l): 790000, 2600000 (Hall)
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Irgarol Usage And Synthesis

Chemical Properties

White Solid

Uses

Irgarol is a highly specific and effective inhibitor of photosynthesis. This makes it ideal, combined with its very low water solubility, for use in long-life antifouling coatings for marine applicati ons to prevent the growth of algae.

Uses

Photosystem-II (PSII) herbicide; inhibits photosynthetic electron transport in chloroplasts

Uses

Booster algicide in antifouling paint.

Definition

ChEBI: A diamino-1,3,5-triazine that is 1,3,5-triazine-2,4-diamine carrying a N-tert-butyl, N'-cyclopropyl and a methylsulfanyl group at position 6.

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.

IrgarolSupplier

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