| Identification | Back Directory | [Name]
Irgarol | [CAS]
28159-98-0 | [Synonyms]
IRGAROL
Cybutrin
CYBUTRYNE
IRGAROL(R)
IRGAROL 1051
Nuocide 1051
Irgarol (Ciba)
N2-(tert-Butyl)
Cybutryne [iso]
Einecs 248-872-3
Irgaguard A 2000
Irgaguard D 1071
IRGAROL 1051/1071
Microban Additive IA 1
IRGAROL PESTANAL, 250 MG
-N4-cyclopropyl-6-(methylthio)
N'-tert-Butyl-N-cyclopropyl-6-(Methylthio)-1,3,5-t
N-cyclopropyl-N'-substituted-1,3,5-triazine-2,4-diamine
2-METHYLTHIO-4-TERT-BUTYLAMINO-6-CYCLOPROPYLAMINO-S-TRIAZINE
2-METHYLTHIO-4-TERTIARYBUTYLAMINO-6-CYCLOPROPYLAMINO-S-TRIAZINE
2-TERT-BUTYLAMINO-4-CYCLOPROPYLAMINO-6-METHYLTHIO-1,3,5-TRIAZINE
2-(tert-Butylamino)-4-(cyclopropylamino)-6-(methylthio)-s-triazin
2-(TERT-BUTYLAMINO)-4-(CYCLOPROPYLAMINO)-6-(METHYLTHIO)-S-TRIAZINE
N′-tert.-Butyl-N-cyclopropyl-6-(methylthio)-1,3,5-triazin-2,4-diamin
2-(Methylthio)-4-(tert-butylamino)-6-cyclopropylamino-1,3,5-triazine
N-Cyclopropyl-N'-tert-butyl-6-(methylthio)-1,3,5-triazine-2,4-diamine
N'-tert-butyl-N-cyclopropyl-6-(methylthio)-1,3,5-triazine-2,4-diamine
Irgarol,2-(tert-Butylamino)-4-(cyclopropylamino)-6-(methylthio)-s-triazine
3,5-Triazine-2,4-diamine,N-cyclopropyl-N’-(1,1-dimethylethyl)-6-methylthio-1
2-(tert-Butylamino)-4-(cyclopropylamino)-6-(methylthio)-1,3,5-triazine
N-CYCLOPROPYL-N'-(1,1-DIMETHYLETHYL)-6-(METHYLTHIO)-1,3,5-TRIAZINE-2,4-DIAMINE
1,3,5-Triazine-2,4-diamine, N-cyclopropyl-N-(1,1-dimethylethyl)-6-(methylthio)-
1,3,5-Triazine-2,4-diaMine,N2-cyclopropyl-N4-(1,1-diMethylethyl)-6-(Methylthio)- | [EINECS(EC#)]
248-872-3 | [Molecular Formula]
C11H19N5S | [MDL Number]
MFCD01863779 | [MOL File]
28159-98-0.mol | [Molecular Weight]
253.37 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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 | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [Water Solubility ]
Insoluble in water | [form ]
neat | [pka]
4.13±0.10(Predicted) | [color ]
White to Almost white | [BRN ]
792218 | [Major Application]
agriculture
environmental | [InChI]
1S/C11H19N5S/c1-11(2,3)16-9-13-8(12-7-5-6-7)14-10(15-9)17-4/h7H,5-6H2,1-4H3,(H2,12,13,14,15,16) | [InChIKey]
HDHLIWCXDDZUFH-UHFFFAOYSA-N | [SMILES]
CSc1nc(NC2CC2)nc(NC(C)(C)C)n1 | [EPA Substance Registry System]
1,3,5-Triazine-2, 4-diamine, N-cyclopropyl-N'-(1,1- dimethylethyl)-6-(methylthio)- (28159-98-0) |
| Hazard Information | Back Directory | [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 | [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. | [Uses]
Booster algicide in antifouling paint. | [Description]
Cybutyrn is a phytotoxic biocide. It has a low aqueous solubility and is non-volatile. It is moderately toxic to fish, aquatic invertebrates and plant. It is highly toxic to algae. No information is available on its impact on human health. | [Production Methods]
Cybutryne was manufactured using the same industrial chemical processes applied to other substituted 1,3,5 triazine biocides. Commercial production began with cyanuric chloride, the universal starting material for triazine pesticides, which was reacted stepwise with the required tert butylamine and cyclopropylamine under controlled, low temperature conditions to ensure selective mono and di substitution on the triazine ring. A final substitution introduced the methylthio group, completing the N substituted triazine structure. Each substitution step required careful pH control, staged addition, and cooling because cyanuric chloride reacts exothermically and becomes progressively less reactive after each substitution. | [Mechanism of action]
Reduces plant photosynthetic ability; Highly phytotoxic | [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. | [Pesticide Type]
Algistat; Herbicide |
| Safety Data | Back Directory | [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 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Skin Sens. 1 | [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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