1,3,5-Triazines

Quirke, J. Martin E.

doi:10.1016/b978-008096519-2.00042-4

Cited by 48 publications

(34 citation statements)

References 273 publications

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“…Cyanuric chloride and its derivatives have been widely studied in literature [3,4]. Such triazine derivatives are also useful as lubricating oil additives [5,6].…”

Section: Introductionmentioning

confidence: 99%

Friction properties of triazine-containing hybrid composites

et al. 2006

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This paper presents micro and nanofriction studies on thin silica/aminosilica-triazine hybrid composite coatings on silicon substrate. The silica/aminosilica coatings were made on silicon using the dip-coating method and then modified by alkoxy-and aryloxy-triazine derivatives. Formation of hybrid coatings permits a greater flexibility of their resulting properties. Microfriction tests were carried out with a sliding ceramic ball (load range of 10-80 mN) on the composite flat surface, using a tribometer ball-onsample system. Sliding speed was 25 mm/min at room temperature. Nanofriction was measured using the Friction Force Microscopy. It is shown that surface modification of silica/aminosilica layers by triazine derivatives, to form inorganic-organic hybrid coatings, improves friction properties. All tested triazine derivatives, particularly long alkoxy-substituted s-triazines, cause a decrease in the friction coefficients in microfriction tests, in comparison to a non-modified silica/aminosilica thin film. The same effect was also observed for some tested triazine derivatives at nanofriction measurements.

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“…Cyanuric chloride and its derivatives have been widely studied in literature [3,4]. Such triazine derivatives are also useful as lubricating oil additives [5,6].…”

Section: Introductionmentioning

confidence: 99%

Friction properties of triazine-containing hybrid composites

et al. 2006

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“…s-Triazine rings are common scaffolds for the synthesis of industrial chemicals; they are found in pesticides, plastic resins, dyes, and explosives (20). s-Triazine herbicides are widely used in modern agriculture, where they kill susceptible plants by coordinating to the quinone-binding protein in photosystem II, thereby inhibiting photosynthetic electron transfer (19).…”

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confidence: 99%

Arthrobacter aurescens TC1 Metabolizes Diverse s -Triazine Ring Compounds

Strong

Rosendahl

Johnson

et al. 2002

Appl Environ Microbiol

193

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Arthrobacter aurescens strain TC1 was isolated without enrichment by plating atrazine-contaminated soil directly onto atrazine-clearing plates. A. aurescens TC1 grew in liquid medium with atrazine as the sole source of nitrogen, carbon, and energy, consuming up to 3,000 mg of atrazine per liter. A. aurescens TC1 is metabolically diverse and grew on a wider range of s-triazine compounds than any bacterium previously characterized. The 23 s-triazine substrates serving as the sole nitrogen source included the herbicides ametryn, atratone, cyanazine, prometryn, and simazine. Moreover, atrazine substrate analogs containing fluorine, mercaptan, and cyano groups in place of the chlorine substituent were also growth substrates. Analogs containing hydrogen, azido, and amino functionalities in place of chlorine were not growth substrates. A. aurescens TC1 also metabolized compounds containing chlorine plus N-ethyl, N-propyl, N-butyl, N-s-butyl, N-isobutyl, or N-t-butyl substituents on the s-triazine ring. Atrazine was metabolized to alkylamines and cyanuric acid, the latter accumulating stoichiometrically. Ethylamine and isopropylamine each served as the source of carbon and nitrogen for growth. PCR experiments identified genes with high sequence identity to atzB and atzC, but not to atzA, from Pseudomonas sp. strain ADP.s-Triazine rings are common scaffolds for the synthesis of industrial chemicals; they are found in pesticides, plastic resins, dyes, and explosives (20). s-Triazine herbicides are widely used in modern agriculture, where they kill susceptible plants by coordinating to the quinone-binding protein in photosystem II, thereby inhibiting photosynthetic electron transfer (19). Atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-s-triazine) is one of the most widely used herbicides in the United States for the control of broadleaf weeds in corn, sorghum, and sugarcane (1). Other s-triazine herbicides include ametryn, atratone, cyanazine, prometryn, and simazine.The fate of s-triazine compounds in the environment depends on the metabolic activities of soil microorganisms (7,14). Since 1994, a number of laboratories have independently isolated, by enrichment culture, several genera of gram-negative bacteria capable of atrazine dechlorination (4,16,22,31,33,35,36,38). Subsequent to dechlorination, metabolism of hydroxyatrazine liberates nitrogen to sustain bacterial growth. More recently, gram-positive bacteria from the genera Nocardioides (32) and Arthrobacter (22) have been shown to grow on atrazine, the former using atrazine as the sole source of carbon and nitrogen for growth. Streptomyces strain PS1/5 was also shown to metabolize several s-triazine herbicides in the presence of additional carbon and nitrogen in the growth medium (29).It is now established that bacteria metabolize melamine and the triazine herbicides such as atrazine via enzyme-catalyzed hydrolytic reactions (6,11,12,35). The enzymatic basis of atrazine mineralization has been most extensively studied in Pseudomonas sp. strain ADP (3,8,16,17...

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“…The s-triazine compounds have numerous applications throughout industry and agriculture (10,19,25,30). Those containing N-alkyl substituents, like atrazine (2-chloro-4-Nethylamino-6-N-isopropylamino-1,3,5-triazine), have been applied successfully as herbicides (3).…”

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Melamine Deaminase and Atrazine Chlorohydrolase: 98 Percent Identical but Functionally Different

et al. 2001

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The gene encoding melamine deaminase (TriA) from Pseudomonas sp. strain NRRL B-12227 was identified, cloned into Escherichia coli, sequenced, and expressed for in vitro study of enzyme activity. Melamine deaminase displaced two of the three amino groups from melamine, producing ammeline and ammelide as sequential products. The first deamination reaction occurred more than 10 times faster than the second. Ammelide did not inhibit the first or second deamination reaction, suggesting that the lower rate of ammeline hydrolysis was due to differential substrate turnover rather than product inhibition. Remarkably, melamine deaminase is 98% identical to the enzyme atrazine chlorohydrolase (AtzA) from Pseudomonas sp. strain ADP. Each enzyme consists of 475 amino acids and differs by only 9 amino acids. AtzA was shown to exclusively catalyze dehalogenation of halo-substituted triazine ring compounds and had no activity with melamine and ammeline. Similarly, melamine deaminase had no detectable activity with the halo-triazine substrates. Melamine deaminase was active in deamination of a substrate that was structurally identical to atrazine, except for the substitution of an amino group for the chlorine atom. Moreover, melamine deaminase and AtzA are found in bacteria that grow on melamine and atrazine compounds, respectively. These data strongly suggest that the 9 amino acid differences between melamine deaminase and AtzA represent a short evolutionary pathway connecting enzymes catalyzing physiologically relevant deamination and dehalogenation reactions, respectively.

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1,3,5-Triazines

Cited by 48 publications

References 273 publications

Friction properties of triazine-containing hybrid composites

Friction properties of triazine-containing hybrid composites

Arthrobacter aurescens TC1 Metabolizes Diverse s -Triazine Ring Compounds

Melamine Deaminase and Atrazine Chlorohydrolase: 98 Percent Identical but Functionally Different

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