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
