30125-65-6

Usage

Uses

Used in Environmental Applications:
N-tert-butyl-6-(methylsulfanyl)-1,3,5-triazine-2,4-diamine is used as a pollutant in environmental studies for understanding the degradation process of herbicides and their impact on the environment. This knowledge can help in developing strategies to mitigate the environmental effects of such pollutants.

Upstream product

• 28159-98-0 2-methylthio-4-t-butylamino-6-cyclopropyl-amino-s-triazine 

Relevant academic research and scientific papers

Fate and ecotoxicity of the new antifouling compound Irgarol 1051 in the aquatic environment

Residue analyses and ecotoxicity assessment were conducted on the new antifouling compound Irgarol 1051 (2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine) and its degradation product M1 (2-methylthio-4-tert-butylamino-6-amino-s-triazine) in order to delineate the environmental fate and impact of Irgarol 1051 on the aquatic ecosystem. For the first time, the Irgarol degradation product (M1) was positively identified in environmental samples. During the 1998 Irgarol survey, concentrations of M1 (up to 1870 ng/l) were generally higher than those of Irgarol in the coastal waters of the Seto Inland Sea in Japan, suggesting a greater environmental persistence for M1 than for the parent compound Irgarol 1051 in the aquatic ecosystem. Ecotoxicity testing revealed that Irgarol 1051 and M1 were moderately toxic to a marine bacterium and the four crustaceans tested, but were highly toxic to some algae and higher plants. In the root elongation inhibition bioassay, M1 showed a phytotoxicity at least 10 times greater than that of Irgarol and six other triazine herbicides (terbutryn, terbutylazine, terbumeton, simetryn, atrazine and simazine). These results strongly suggest that both Irgarol 1051 and its persistent degradation product M1 may potentially affect and/or damage the primary producer community in aquatic ecosystems. To safeguard the aquatic ecosystem from the damaging impact of micro contaminants, it is recommended that, besides monitoring for the target parent compound, major degradation products should also be included in environmental surveys. Otherwise, there is a risk of underestimating the ultimate impact of a particular toxicant on the environment. Copyright (C) 2000 Elsevier Science Ltd. Residue analyses and ecotoxicity assessment were conducted on the new antifouling compound Irgarol 1051 (2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine) and its degradation product M1 (2-methylthio-4-tert-butylamino-6-amino-s-triazine) in order to delineate the environmental fate and impact of Irgarol 1051 on the aquatic ecosystem. For the first time, the Irgarol degradation product (M1) was positively identified in environmental samples. During the 1998 Irgarol survey, concentrations of M1 (up to 1870 ng/l) were generally higher than those of Irgarol in the coastal waters of the Seto Inland Sea in Japan, suggesting a greater environmental persistence for M1 than for the parent compound Irgarol 1051 in the aquatic ecosystem. Ecotoxicity testing revealed that Irgarol 1051 and M1 were moderately toxic to a marine bacterium and the four crustaceans tested, but were highly toxic to some algae and higher plants. In the root elongation inhibition bioassay, M1 showed a phytotoxicity at least 10 times greater than that of Irgarol and six other triazine herbicides (terbutryn, terbutylazine, terbumeton, simetryn, atrazine and simazine). These results strongly suggest that both Irgarol 1051 and its persistent degradation product M1 may potentially affect and/or damage the primary producer community in aquatic ecosystems. To safeguard the aquatic ecosystem from the damaging impact of micro contaminants, it is recommended that, besides monitoring for the target parent compound, major degradation products should also be included in environmental surveys. Otherwise, there is a risk of underestimating the ultimate impact of a particular toxicant on the environment.

Mercuric chloride-catalyzed hydrolysis of the new antifouling compound Irgarol 1051

Irgarol 1051, 2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine is a newly developed herbicidal additive for use in copper-based antifouling paints. It is intended to replace the antifouling agent tributyltin, which has been regulated internationally due to its severe impact on the aquatic ecosystem. However, there is no information in the open literature on the abiotic degradation of Irgarol, a fact that hinders the assessment of its ultimate impact on the environment. This study showed that mercuric chloride was capable of rapidly catalyzing the hydrolysis of Irgarol 1051 in distilled water and buffer solutions. The degradation appeared to follow the reaction of a catalyzed hydrolysis and was not significantly affected by the pH tested (5 to 9). All other 5 heavy metal salts tested (AgNO3, CdCl2, CuSO4, PbCl2 and ZnCl2) had practically no catalytic property on Irgarol hydrolysis, implying the involvement of a specific activity for Hg2+ in this reaction. The mechanism for the catalyzed hydrolysis may be the formation of bidentate chelation through nitrogen (No. 5) on the ring and the nitrogen on the cyclopropylamino side chain in Irgarol 1051 with the Hg2+ ion. The resulting four-member chelate complex would weaken the cyclopropyl-amino bond considerably, thus facilitating the hydrolysis reaction. Ultraviolet spectroscopy of the reaction mixtures and the identification of Irgarol hydrolysis product M1 (2-methylthio-4-tert-butylamino-6-amino-s-triazine) by GC-MS and LC-MS provided the basis for the proposed mechanism on the HgCl2-catalyzed hydrolysis of Irgarol 1051. M1 appeared to be more stable than the parent compound Irgarol 1051, thus implying its possible accumulation in the environment. One practical aspect of this work is that HgCl2 should not be used in preserving water samples in Irgarol 1051 monitoring programs.

Integrated photocatalytic-biological treatment of triazine-containing pollutants

The degradation of triazine-containing pollutants including simazine, Irgarol 1051 and Reactive Brilliant Red K-2G (K-2G) by photocatalytic treatment was investigated. The effects of titanium dioxide (TiO2) concentration, initial pH of reaction mixture, irradiation time and ultraviolet (UV) intensity on photocatalytic treatment efficiency were examined. Complete decolorization of K-2G was observed at 60 min photodegradation while only 15 min were required to completely degrade simazine and Irgarol 1051 under respective optimized conditions. High-performance liquid chromatography (HPLC), gas chromatography/mass spectrometry (GC/MS) and ion chromatography (IC) were employed to identify the photocatalytic degradation intermediates and products. Dealkylated intermediates of simazine, deisopropylatrazine and deethyldeisopropylatrazine, and Irgarol 1051 were detected by GC/MS in the initial phase of degradation. Complete mineralization could not be achieved for all triazine-containing pollutants even after prolonged (>72 h) UV irradiation due to the presence of a photocatalysis-resistant end product, cyanuric acid (CA). The toxicities of different compounds before and after photocatalytic treatment were also monitored by three bioassays. To further treat the photocatalysis-resistant end product, a CA-degrading bacterium was isolated from polluted marine sediment and further identified as Klebsiella pneumoniae by comparing the substrate utilization pattern (Biolog microplate), fatty acid composition and 16S rRNA gene sequencing. K. pneumoniae efficiently utilized CA from 1 to 2000 mg/L as a good nitrogen source and complete mineralization of CA was observed within 24 h of incubation. This study demonstrates that the biodegradability of triazine-containing pollutants was significantly improved by the photocatalytic pre-treatment, and this proposed photocatalytic-biological integrated system can effectively treat various classes of triazine-containing pollutants.

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.