Journal articles: 'Triazine'

1

Vinogradov, Dmitry B., Alexei N. Izmest’ev, Angelina N. Kravchenko, Yuri A. Strelenko, and Galina A. Gazieva. "Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines." Beilstein Journal of Organic Chemistry 19 (July 28, 2023): 1047–54. http://dx.doi.org/10.3762/bjoc.19.80.

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A series of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-b][1,2,4]triazine to thiazino[2,3-c][1,2,4]triazine.

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Krinochkin, A. P., E. D. Ladin, Ya K. Shtaitz, E. A. Kudryashova, D. S. Kopchuk, E. B. Gorbunov, Yu M. Shafran, G. V. Zyryanov, and V. L. Rusinov. "Interaction of 1,2,4-triazine-5-carbonitriles with 5-hydroxyethylsulfanyl- and 5-hydroxyethoxyethylsulfanyl-3-amino-1,2,4-triazoles." Журнал органической химии 59, no. 11 (December 15, 2023): 1501–6. http://dx.doi.org/10.31857/s0514749223100137.

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The solvent-free interaction of 1,2,4-triazine-5-carbonitriles with first synthesized 5-hydroxyethylsulfanyland 5-hydroxyethoxyethylsulfanyl-3-amino-1,2,4-triazoles at heating has been studied. It was shown that the presence of these substituents at the C5 position of 1,2,4-triazole changes the direction of the reaction, and 5-amino-1,2,4-triazines are formed as the main products, while the products of the ipso -substitution of the C5-cyano group containing the moiety of the substituted 1,2,4-triazole were isolated only as by-products. In the case of using 1,2,4-triazole with a fragment of monoethylene glycol at C5 position of triazine, the formation of a complex mixture of products occurred.

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3

Egorov, Ilya N., Igor S. Kovalev, Vladimir L. Rusinov, and Oleg N. Chupakhin. "Cyclotrimerization of 3-R-1,2,4-Triazin-5(4H)-ones with Cyclic Ketones." Zeitschrift für Naturforschung B 65, no. 11 (November 1, 2010): 1359–62. http://dx.doi.org/10.1515/znb-2010-1111.

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New heterocyclic tetracyclic systems were synthesized. Interaction between 3-R-1,2,4-triazin- 5(4H)-ones and cyclic ketones under acidic conditions leads to the formation of zwitterion derivatives of 5,6,7,8,9,10,11,12-octahydro-[1,2,4]triazino[1,6- ƒ ]phenanthridine and 1,2,3,6,7,8-hexahydro-bicyclopenta[ b,d]pyrido[1,2- ƒ ][1,2,4]triazine.

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4

Collins, David J., Timothy C. Hughes, and Wynona M. Johnson. "Dihydro-1,2,4-triazin-6(1H)-ones. III. Oxidation Products of 1-Methyl-3-phenyl- 4,5-dihydro-1,2,4-triazin-6(1H)-one." Australian Journal of Chemistry 52, no. 10 (1999): 971. http://dx.doi.org/10.1071/ch99047.

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1-Methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one (1) undergoes aerial oxidation to give a mixture of 1- methyl-3-phenyl-1,2,4-triazin-6(1H)-one (2) and 1-methyl-3-phenyl-1,4-dihydro-1,2,4-triazine-5,6-dione (3). The dehydro derivative (2) was cleanly prepared by the oxidation of (1) with 2,3-dichloro-5,6-dicyano-1,4- benzoquinone (ddq). The dehydro derivative (2) underwent a surprising rearrangement to the triazole (12) upon oxidation with OxoneR. Several attempts at unambiguous synthesis of the α-dicarbonyl derivative (3) were unsuccessful; it was obtained, together with the 1,4-dimethyl derivative (13) by methylation of 3-phenyl-1,4- dihydro-1,2,4-triazine-5,6-dione (4) with sodium hydride and methyl iodide.

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5

Zhou, Yifei, and Haixiang Gao. "Energetic salt of guanidinium 3,7-Bis(dinitromethylene)-octahydro-[1,2,4]-triazino-[6,5-e][1,2,4]triazine and its crystal structure." ITM Web of Conferences 47 (2022): 03044. http://dx.doi.org/10.1051/itmconf/20224703044.

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Energetic salt of guanidinium 3,7-Bis(dinitromethylene)-octahydro-[1,2,4]-triazino-[6,5-e][1,2,4]triazine(1) was prepared through the reaction of 3,7-Bis(dinitromethylene)-octahydro-[1,2,4]-triazino-[6,5-e][1,2,4]triazine with guanidinium carbonate. The crystal structure of 1 was characterized. It is the first bicyclic energetic salt based on 3,7-Bis(dinitromethylene)-octahydro-[1,2,4]-triazino-[6,5-e][1,2,4]triazine.

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6

Jain, Sonika, Pankaj Kumar Jain, Shalu Sain, Dharma Kishore, and Jaya Dwivedi. "Anticancer s-Triazine Derivatives: A Synthetic Attribute." Mini-Reviews in Organic Chemistry 17, no. 8 (December 24, 2020): 904–21. http://dx.doi.org/10.2174/1570193x17666200131111851.

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1, 3, 5-Triazine (s-Triazine) is a versatile nucleus to design and develop potent bioactive molecules for drug discovery, particularly in cancer therapy. The aim of this review is to present the most recent trends in the field of synthetic strategies made for functionalized triazine derivatives active against cell proliferation. This review article covers the synthesis of aryl methylamino, morpholino, triamino substituted triazines, antimitotic agents coupled triazines and many more. Many 1,3,5- triazine derivatives, both hetero-fused and uncondensed, have shown remarkable antitumor activities. We have highlighted various derivatives with 1, 3, 5-triazine core targeting different kinases with an aim to help researchers for developing new 1, 3, 5-triazine derived compounds for antitumor activity.

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7

Hurtado, Paola, Ana R. Hortal, Marta Cruz-Guzmán, and Bruno Martínez-Haya. "Fragmentation and Gas Phase Aggregation Processes in the Laser Desorption/Ionization of Chlorodiaminotriazines." European Journal of Mass Spectrometry 13, no. 5 (October 2007): 321–29. http://dx.doi.org/10.1255/ejms.892.

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Fragmentation and supramolecular aggregation induced during the laser desorption/ionization (LDI) of four chlorodiaminotriazines (simazine, atrazine, terbutylazine and propazine) have been investigated. The laser wavelength employed (266 nm) lies within the first absorption band of the four triazines. The main fragmentation channel observed involves the prompt cleavage of the Cl atom, followed by partial or total fragmentation of the side alkyl chains. Breakage of the triazinic ring becomes efficient at moderate laser powers; however, the deamination of the triazine is not observed to take place. In addition, the formation of both covalent and non-covalent triazinic aggregates in the desorption plume is found to be particularly efficient. Aggregates as large as heptamers are neatly detected, with the observation that those with the most intense signal involve the dechlorinated triazinic fragment. Both aggregation and fragmentation are largely suppressed upon dilution of the triazine under matrix-assisted laser desorption/ionization conditions.

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8

Ducruet, Jean-Marc, Sophie Creuzet, and Josiane Viénot. "Kinetics of Action of Different Photosystem II Herbicides on Thylakoids." Zeitschrift für Naturforschung C 45, no. 5 (May 1, 1990): 348–52. http://dx.doi.org/10.1515/znc-1990-0507.

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The kinctics of inhibition of photosystem II electron transfer by different diuron-like herbicides (ureas, triazines, triazinoncs, biscarbamates. uraciles) were studied, mainly by chlorophyll fluorescence measurements. Uracil derivatives and cyanazine, a particular triazinc. were the slowest acting compounds. The half-times of action were strongly temperature-dependent and were of the order of tens of seconds at 5 °C for urea or triazine inhibitors. The role of different limiting steps in the binding process is discussed.

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9

Lee, Jae Wook, Hyung-Ho Ha, Marc Vendrell, Jacqueline T. Bork, and Young-Tae Chang. "Combinatorial Solid-Phase Synthesis of 6-Aryl-1,3,5-triazines via Suzuki Coupling." Australian Journal of Chemistry 64, no. 5 (2011): 540. http://dx.doi.org/10.1071/ch11034.

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A synthetic methodology to prepare collections of trisubstituted aryl 1,3,5-triazines with broad structural diversity via Suzuki coupling has been developed. We first optimized the combinatorial derivatization of the triazine core using Suzuki cross-coupling. Second, in order to further expand the methodology for the preparation of negatively charged triazines, we adapted this approach to polymer-supported amino acids and prepared aryl triazines with different charge distribution. With a collection of 160 aryl triazine derivatives in good purities and without any purification step, we proved the viability of this orthogonal scheme for the preparation of triazine libraries using amine/amino acid-captured solid supports and Suzuki cross-coupling.

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10

Jacobsen, NW, and AE Philippides. "Heterocyclic Variants of the Purine System. I. Derivatives of Thiazolo[5,4-e]-1,2,4-Triazine." Australian Journal of Chemistry 40, no. 3 (1987): 491. http://dx.doi.org/10.1071/ch9870491.

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Derivatives of the thiazolo [5,4-e]-1,2,4-triazine ring system were prepared from appropriate 6-acylamino-1,2,4-triazin-5(2H)-ones by thiation and cyclization with phosphorus pentasulfide. 5-Methylthio-1,2,4-triazin-6-amines also gave thiazolo [5,4-e]-1,2,4-triazine derivatives when treated with carbon disulfide or phenyl isothiocyanate.

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11

Dai, Qiuzi, Qinsheng Sun, Xiaorong Ouyang, Jinyang Liu, Liye Jin, Ahao Liu, Binsheng He, Tingting Fan, and Yuyang Jiang. "Antitumor Activity of s-Triazine Derivatives: A Systematic Review." Molecules 28, no. 11 (May 23, 2023): 4278. http://dx.doi.org/10.3390/molecules28114278.

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1,3,5-triazine derivatives, also called s-triazines, are a series of containing-nitrogen heterocyclic compounds that play an important role in anticancer drug design and development. To date, three s-triazine derivatives, including altretamine, gedatolisib, and enasidenib, have already been approved for refractory ovarian cancer, metastatic breast cancer, and leukemia therapy, respectively, demonstrating that the s-triazine core is a useful scaffold for the discovery of novel anticancer drugs. In this review, we mainly focus on s-triazines targeting topoisomerases, tyrosine kinases, phosphoinositide 3-kinases, NADP+-dependent isocitrate dehydrogenases, and cyclin-dependent kinases in diverse signaling pathways, which have been extensively studied. The medicinal chemistry of s-triazine derivatives as anticancer agents was summarized, including discovery, structure optimization, and biological applications. This review will provide a reference to inspire new and original discoveries.

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12

Verma, Tarawanti, Manish Sinha, and Nitin Bansal. "Heterocyclic Compounds Bearing Triazine Scaffold and Their Biological Significance: A Review." Anti-Cancer Agents in Medicinal Chemistry 20, no. 1 (April 10, 2020): 4–28. http://dx.doi.org/10.2174/1871520619666191028111351.

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Benzene is a six-membered hydrocarbon ring system and if three carbon-hydrogen units of benzene ring are replaced by nitrogen atoms then triazine is formed. Triazines are present in three isomeric forms 1,2,3- triazine, 1,2,4-triazine, and 1,3,5-triazine according to the position of the nitrogen atom. These are weak bases having weaker resonance energy than benzene, so nucleophilic substitution is preferred than electrophilic substitution. Triazine is an interesting class of heterocyclic compounds in medicinal chemistry. Numerous synthetic derivatives of triazine have been prepared and evaluated for a wide spectrum of biological activities in different models with desired findings such as antibacterial, antifungal, anti-cancer, antiviral, antimalarial, antiinflammatory, antiulcer, anticonvulsant, antimicrobial, insecticidal and herbicidal agents. Triazine analogs have exposed potent pharmacological activity. So, triazine nucleus may be considered as an interesting core moiety for researchers for the development of future drugs.

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13

Jockers, R., and R. D. Schmid. "Synthesis of Long-Chain Triazine Aldehydes - Substrates of Bacterial Luciferase and Photosynthetic Inhibitors." Zeitschrift für Naturforschung C 47, no. 7-8 (August 1, 1992): 573–79. http://dx.doi.org/10.1515/znc-1992-7-814.

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S-triazines are photosynthetic inhibitors. They have been substituted with ω-aminoundecanoic acid. The coupling products have been transformed into triazine aldehydes. These compounds displace radioactive terbutryn and have inhibitory effects on photosynthesis in plants and bacteria. Triazine aldehydes were shown to be effective substrates for bacterial luciferase. A competitive assay between photosystem-II-herbicides and aldehyde-labeled triazines is discussed.

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14

Salhoff, Craig R., and Alex R. Martin. "Kochia scopariaGrowth Response to Triazine Herbicides." Weed Science 34, no. 1 (January 1986): 40–42. http://dx.doi.org/10.1017/s0043174500026412.

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Greenhouse-grown kochia [Kochia scoparia(L.) Schrad. # KCHSC] seedlings from populations having either a 13-yr triazine history or no triazine history were sprayed postemergence with 0, 2, or 20 kg/ha atrazine [6-chloro-N-ethyl-N′-[1-methylethyl)-1,3,5-triazine-2,4-diamine]. Fresh weight was reduced 20% in triazine history kochia treated with 20 kg/ha atrazine. Seedlings with no triazine history were killed by 2 kg/ha atrazine. Biotypes resistant to atrazine were also resistant to five other triazine herbicides. Biotypes susceptible to atrazine were susceptible to the other triazines. Atrazine-resistant biotypes were more susceptible to 2,4-D [(2,4-dichlorophenoxy)acetic acid] than atrazine-susceptible biotypes, but atrazine history had no effect on response to diuron [N′-(3,4-dichlorophenyl)-N,N-dimethylurea].

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15

Zeng, Ming, Jiaqi Chen, Fengye Li, Haojie Li, Lan Zhao, Dengzhao Jiang, Jun Dai, and Wenbo Liu. "Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation." Molecules 28, no. 9 (April 24, 2023): 3676. http://dx.doi.org/10.3390/molecules28093676.

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1,3,5 triazines, especially indole functionalized triazine derivatives, exhibit excellent activities, such as anti-tumor, antibacterial, and anti-inflammatory activities. Traditional methods for the synthesis of N-(2-triazine) indoles suffer from unstable materials and tedious operations. Transition-metal-catalyzed C-C/C-N coupling provides a powerful protocol for the synthesis of indoles by the C-H activation strategy. Here, we report the efficient ruthenium-catalyzed oxidative synthesis of N-(2-triazine) indoles by C-H activation from alkynes and various substituted triazine derivatives in a moderate to good yield, and all of the N-(2-triazine) indoles were characterized by 1H NMR, 13C NMR, and HRMS. This protocol can apply to the gram-scale synthesis of the N-(2-triazine) indole in a moderate yield. Moreover, the reaction is proposed to be performed via a six-membered ruthenacycle (II) intermediate, which suggests that the triazine ring could offer chelation assistance for the formation of N-(2-triazine) indoles.

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Wippert, Nicolai, Martin Nieger, Claudine Herlan, Nicole Jung, and Stefan Bräse. "Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes." Beilstein Journal of Organic Chemistry 17 (November 22, 2021): 2773–80. http://dx.doi.org/10.3762/bjoc.17.187.

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We describe the synthesis of so far synthetically not accessible 3,6-substituted-4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines as nitrogen-rich heterocycles. The target compounds were obtained in five steps, including an amidation and a cyclative cleavage reaction as key reaction steps. The introduction of two side chains allowed a variation of the pyrazolo[3,4-d][1,2,3]triazine core with commercially available building blocks, enabling the extension of the protocol to gain other derivatives straightforwardly. Attempts to synthesize 3,7-substituted-4,7-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, the regioisomers of the successfully gained 3,6-substituted 4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, were not successful under similar conditions due to the higher stability of the triazene functionality in the regioisomeric precursors and thus, the failure of the removal of the protective group.

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17

Pathak, Suraj Kumar, Yepeng Xiang, Manli Huang, Taian Huang, Xiaosong Cao, He Liu, Guohua Xie, and Chuluo Yang. "Fused tetracyclic tris[1,2,4]triazolo[1,3,5]triazine as a novel rigid electron acceptor for efficient thermally activated delayed fluorescence emitters." RSC Advances 10, no. 26 (2020): 15523–29. http://dx.doi.org/10.1039/d0ra01925a.

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18

Jin, Guo, Hyun Ban, Hiroyuki Nakamura, and Jong-Dae Lee. "o-Carboranylalkoxy-1,3,5-Triazine Derivatives: Synthesis, Characterization, X-ray Structural Studies, and Biological Activity." Molecules 23, no. 9 (August 30, 2018): 2194. http://dx.doi.org/10.3390/molecules23092194.

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Morpholine- and bis(2-methoxyethyl)amine-substituted 1,3,5-triazine derivatives containing an alkoxy-o-carborane in the 6-position of the triazine ring were successfully synthesized. The molecular structures of the methoxy- and ethoxy-o-carboranyl-1,3,5-triazines were established by X-ray crystallography. In vitro studies showed that the methylene bridged morpholine- and bis(2-methoxyethyl)amine-substituted o-carboranyl-1,3,5-triazines accumulated to high levels in B16 melanoma cells and exhibited higher cytotoxicity than p-boronophenylalanine.

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19

Kolesinska, Beata, Agnieszka Mrozek, Justyna Fraczyk, and Zbigniew Kaminski. "P-Triazinylphosphonium chlorides as a new group of coupling reagents." Open Chemistry 11, no. 4 (April 1, 2013): 569–83. http://dx.doi.org/10.2478/s11532-012-0190-3.

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AbstractTertiary phosphines in reaction with 2-chloro-4,6-dialkoxy-1,3,5-triazines gave unstable quaternary P-triazinylphosphonium chlorides, which readily decomposed with a departure of the alkyl group of the triazine ring substituent. Stable quaternary P-triazinylphosphonium chlorides were obtained only in reaction of 2-chloro-4,6-diphenoxy-1,3,5-triazine. Both, stable quaternary P-triazinylphosphonium chlorides as well unstable analogues prepared in situ activated carboxylic acid yielding “superactive” triazine esters, useful as highly efficient reagents in peptide bond synthesis.

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20

Scarponi, Luciano, and Piero Perucci. "Effect of Somes-Triazine Herbicides on Phosphatases from Corn (Zea mays) Roots." Weed Science 34, no. 6 (November 1986): 807–10. http://dx.doi.org/10.1017/s0043174500067928.

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The influence of somes-triazine herbicides on acid phosphatase (acid Pase) and phosphodiesterase (PDase) from corn (Zea maysL. var. ‘Orfeo’) roots was investigated. Terbutryn [N-(1,1-dimethylethyl)-N′-ethyl-6-(methylthio)-1,3,5-triazine-2,4-diamine] stimulated both phosphatases, whereas prometryn [N,N′-bis(1-methylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine] stimulated only the PDase. Atrazine [6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine] and desmetryn [N-methyl-N′-(1-methylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine] inhibited both phosphatases to varying degrees. Atraton [N-ethyl-6-methoxy-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine], prometon [6-methoxy-N,N′-bis(1-methylethyl)-1,3,5-triazine-2,4-diamine], and simazine (6-chloro-N,N′-diethyl-1,3,5-triazine-2,4-diamine) inhibited acid Pase. No effect was exerted by ametryn [N-ethyl-N′-(1-methylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine]. The enzyme assays and the kinetic parameters demonstrated that the interferences observed were due to an action on the synthesis of one or both enzymes rather than on the enzyme reactions. The types of theN-alkyl and the C1-substituent groups in the structures of thes-triazines tested appear important in determining the degree of the interference.

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Pniewska, Alicja, and Urszula Kalinowska-Lis. "A Survey of UV Filters Used in Sunscreen Cosmetics." Applied Sciences 14, no. 8 (April 14, 2024): 3302. http://dx.doi.org/10.3390/app14083302.

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The aim of this study was to determine the types of UV filters used in adult and children’s sunscreen products sold in Poland (part of the EU market) and their frequency of use. The INCI compositions of sunscreen products were collected and analyzed for the presence of UV filters. The study included 150 randomly selected preparations for adults (from 71 brands) and 50 for children (from 33 brands). The survey concerned the UV filters listed in Annex VI to Regulation (EC) No 1223/2009 of the European Parliament and Council of 30 November 2009 on cosmetic products. The most frequently used UV filters in the child sunscreens were triazine derivatives: bis-ethylhexyloxyphenol methoxyphenyl triazine (60.0%) and ethylhexyl triazone (52.0%), and ethylhexyl salicylate (46.0%), a derivative of salicylic acid. The most common in adult sunscreens were butyl methoxydibenzoylmethane (56.0%), a dibenzoylmethane derivative, followed by the salicylic acid derivative ethylhexyl salicylate (54.7%) and the triazine derivatives bis-ethylhexyloxyphenol methoxyphenyl triazine (54.7%) and ethylhexyl triazone (50.0%). Physical filters, including their nano and non-nano forms, were more popular in sunscreens for children, i.e., 50.0% (TiO2) and 22.0% (ZnO), than for adults: 21.3% (TiO2) and 6.7% (ZnO). For both adults and children, many cosmetic products contained four or five UV filters per preparation; however, the child preparations often used two UV filters. To summarize, the following UV filters dominate in photoprotectors for both adults and children: butyl methoxydibenzoylmethane, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, ethylhexyl salicylate, and diethylamino hydroxybenzoyl hexyl benzoate.

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Zeng, Qun, Yanyang Qu, Jinshan Li, and Hui Huang. "Theoretical studies on the derivatives of tris([1,2,4]triazolo)[4,3-a:4′,3′-c:4′′,3′′-e][1,3,5]triazine as high energetic compounds." RSC Advances 6, no. 7 (2016): 5419–27. http://dx.doi.org/10.1039/c5ra22524h.

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23

Meng, Qi, Gui Yong Wu, Ying Shao, and Xiao Qiang Sun. "Convenient Synthesis and Characterization of Star-Shaped Dendrimers: 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives." Advanced Materials Research 396-398 (November 2011): 2476–84. http://dx.doi.org/10.4028/www.scientific.net/amr.396-398.2476.

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A serial of novel star-shaped 2,4,6-trisubstituted 1,3,5-triazine (s-triazine) dendrimers were synthesized via step-by-step nucleophilic substitution starting from 2,4,6-trichloro-1,3,5-triazine, and were characterized by1H,13C NMR, FT-IR and ESI-MS spectra. The crystal structures for 2b, 2d and 4c have been determined by X-ray diffraction analysis, which indicate that there are hydrogen bonding and short contact interactions existing in intermolecules result in forming three-dimensional network architecture. D NMR experiments demonstrate that symmetrical trialkylamino-s-triazine shows correlated rotations of its N(2-ethoxy-2-oxoethyl) groups, while unsymmetrical 2-R-4,6-bis(dialkylamino)-s-triazines display two non-equivalent N(2-ethoxy-2-oxoethyl) groups, issued from the restricted rotation about the created C(s-triazine)-N bonds, and was conformed by crystallographic data.

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Tan, Ri Hong. "Synthesis and Biological Activities of 1,2,4-Triazine Derivatives." Advanced Materials Research 1033-1034 (October 2014): 283–86. http://dx.doi.org/10.4028/www.scientific.net/amr.1033-1034.283.

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To sdudy the synthesis and biological activities of 1,2,4-triazine derivatives, a series of 1,2,4-triazines were prepared from the reaction of 3-mercapto-5-hydroxyl-6-methyl-1,2,4-triazine with alkyl halide.The structures of prepared compounds were confirmed by IR,1H-NMR and elemental analysis. Biological activities showed the compounds had anti-inflammatory activities.

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Izmest’ev, Alexei N., Dmitry B. Vinogradov, Natalya G. Kolotyrkina, Angelina N. Kravchenko, and Galina A. Gazieva. "Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]triazines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines." Beilstein Journal of Organic Chemistry 17 (May 14, 2021): 1141–48. http://dx.doi.org/10.3762/bjoc.17.87.

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Two series of functionalized imidazothiazolotriazine derivatives were synthesized via the condensation of imidazo[4,5-e]-1,2,4-triazine-3-thiones with acetylenedicarboxylic acid dimethyl and diethyl esters (DMAD and DEAD) and subsequent base-catalyzed rearrangement of the obtained imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazines into regioisomeric imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine derivatives.

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Tsyganova, Anna V., Artem O. Petrov, Alexey V. Shastin, Natalia V. Filatova, Victoria A. Mumyatova, Alexander E. Tarasov, Alina V. Lolaeva, and Georgiy V. Malkov. "Synthesis, Antibacterial Activity, and Cytotoxicity of Azido-Propargyloxy 1,3,5-Triazine Derivatives and Hyperbranched Polymers." Chemistry 6, no. 1 (December 19, 2023): 1–12. http://dx.doi.org/10.3390/chemistry6010001.

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A new method for the synthesis of azido-propargyloxy derivatives of 1,3,5-triazine has been developed utilizing the nitrosation of hydrazyno-1,3,5-triazines. New hydrazines (2-hydrazino-4,6-bis(propargyloxy)-1,3,5-triazine and 2,4-dihydrazino-6-propargyloxy-1,3,5-triazine) were synthesized and characterized via FTIR, NMR spectroscopy and elemental analysis. The hyperbranched polymers with azide (diazide monomer) and propargyloxy terminal groups were obtained via the azide-alkyne polycycloaddition reaction of diazide and monoazide AB2-type monomers. The antibacterial activity against Escherichia coli bacteria of 2,4,6-trispropargyloxy-1,3,5-triazine, 2-azido-4,6-bispropargyloxy-1,3,5-triazine, and 2,4-diazido-6-propargyloxy-1,3,5-triazine and their hyperbranched polymers was studied. Only 2,4-diazido-6-propargyloxy-1,3,5-triazine has weak antibacterial activity in comparison with ampicillin. The cytotoxicity of these compounds against M-HeLa, FetMSC, and Vero cell lines was also studied. 2,4,6-trispropargyloxy-1,3,5-triazine does not show any cytotoxic effect (IC50 ≥ 280 µM). It was shown that the presence of an azide group in the compound directly affects the cytotoxic effect. Hyperbranched polymers have a less cytotoxic effect against M-HeLa (IC50 > 100) in comparison with monomers (IC50 = 90–99 µM). This makes it possible to use these polymers as the basis for biocompatible materials in biomedical applications.

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27

Parker, Ethan T., Micheal D. K. Owen, Mark L. Bernards, William S. Curran, Lawrence E. Steckel, and Thomas C. Mueller. "A Comparison of Symmetrical and Asymmetrical Triazine Herbicides for Enhanced Degradation in Three Midwestern Soils." Weed Science 66, no. 5 (September 2018): 673–79. http://dx.doi.org/10.1017/wsc.2018.41.

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AbstractThe triazines are one of the most widely used herbicide classes ever developed and are critical for managing weed populations that have developed herbicide resistance. These herbicides are traditionally valued for their residual weed control in more than 50 crops. Scientific literature suggests that atrazine, and perhaps others-triazines, may no longer remain persistent in soils due to enhanced microbial degradation. Experiments examined the rate of degradation of atrazine and two other triazine herbicides, simazine and metribuzin, in both atrazine-adapted and non-history Corn Belt soils, with similar soils being used from each state as a comparison of potential triazine degradation. In three soils with no history of atrazine use, thet1/2of atrazine was at least four times greater than in three soils with a history of atrazine use. Simazine degradation in the same three sets of soils was 2.4 to 15 times more rapid in history soils than non-history soils. Metribuzin in history soils degraded at 0.6, 0.9, and 1.9 times the rate seen in the same three non-history soils. These results indicate enhanced degradation of the symmetrical triazine simazine, but not of the asymmetrical triazine metribuzin.

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28

Ghanizadeh, Hossein, and Kerry C. Harrington. "Ecological Evidence for the Fitness Trade-Off in Triazine Resistant Chenopodium Album L.: Can We Exploit the Cost of Resistance?" Agronomy 9, no. 9 (September 9, 2019): 523. http://dx.doi.org/10.3390/agronomy9090523.

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The alleles responsible for herbicide resistance in weeds can result in a fitness cost within affected plants. Over 200 cases of resistance to triazine herbicides have been confirmed in a wide range of weed species globally. In New Zealand, Chenopodium album L. was the first species reported as resistant to triazines. Several studies have already shown that triazine resistance in weeds is associated with fitness costs. Our current study provides further information about fitness penalties caused by triazine resistance during the vegetative growth phase of C. album. Triazine-resistant phenotypes produced less biomass and were shorter than susceptible ones prior to the onset of flowering. At an early stage of growth, triazine-resistant plants had lower photosynthetic efficacy and growth rates than susceptible plants, indicated by lower net assimilation rate (NAR) and relative growth rate (RGR), respectively. However, at a later stage of growth, the resistant plants had greater RGR values than susceptible phenotypes, though there were no significant differences in NAR between triazine-resistant and susceptible plants at this later stage. The triazine-resistant plants had less capacity for vegetative growth than susceptible plants during competition with wheat, indicating less ability to capture resources by triazine-resistant plants under competition. Overall, this study has revealed that the triazine resistance allele caused a substantial fitness cost to C. album only at the early phase of vegetative growth stage; thus, the use of crop competition to try managing triazine-resistant C. album plants should occur during this early phase.

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29

Bernat, Zofia, Anna Szymanowska, Mateusz Kciuk, Katarzyna Kotwica-Mojzych, and Mariusz Mojzych. "Review of the Synthesis and Anticancer Properties of Pyrazolo[4,3-e][1,2,4]triazine Derivatives." Molecules 25, no. 17 (August 29, 2020): 3948. http://dx.doi.org/10.3390/molecules25173948.

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This review focuses on the cytotoxic effect of new synthetic pyrazolo[4,3-e][1,2,4]triazine derivatives against different tumor cell lines. Some annulated pyrazolotriazines i.e., pyrazolo[4,3-e][1,2,4]triazolo[4,3-b][1,2,4]triazines and pyrazolo[4,3-e]tetrazolo[1,5-b][1,2,4]triazine demonstrated significant broad cytotoxic activity in micromolar range concentration, which could have excellent potential to be new candidate therapeutic agents in cancer chemotherapy.

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30

Li, Yue, Pengzhen Zhong, Junna Zhao, Zexi Pan, Chen Zhang, and Dongmei Cui. "Selective Synthesis of N-[1,3,5]Triazinyl-α-Ketoamides and N-[1,3,5]Triazinyl-Amides from the Reactions of 2-Amine-[1,3,5]Triazines with Ketones." Molecules 28, no. 11 (May 25, 2023): 4338. http://dx.doi.org/10.3390/molecules28114338.

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In this study, we report a selective approach for synthesizing N-([1,3,5]triazine-2-yl) α-ketoamides and N-([1,3,5]triazine-2-yl) amides from ketones with 2-amino[1,3,5]triazines through oxidation and oxidative C−C bond cleavage reaction, respectively. The transformation proceeds under mild conditions, provides good functional group tolerance and chemoselectivity, and will serve as a valuable tool for the synthesis of bioactive products.

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31

Petrov, A. O., Georgiy V. Malkov, Sergei V. Karpov, A. V. Shastin, and A. V. Bakeshko. "Kinetic Study of the Polyaddition of Azide-Alkyne AB₂ Monomers in Nonisotermic Conditions." Key Engineering Materials 816 (August 2019): 151–56. http://dx.doi.org/10.4028/www.scientific.net/kem.816.151.

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Nowadays, hyperbranched polymers (HBP) are obtained by different polycondensation and polyaddition reactions [1]. Almost interest is the reaction of 1,3-dipolar cycloaddition of azides to alkynes (1,3-DCA) [2, 3]. There is a series of papers dedicated to the preparation of triazine-triazole HBPs [4, 5, 6]. These polymers were obtained by the reaction of azido-acetylene AB2 monomers polyaddition: 2-azido-4,6-bis (propyne-2-yloxy) -1,3,5-triazine (ABPOT) and 2,4-diazido-6- (propine-2-yloxy) -1,3,5-triazine (DAPOT) (Fig. 1).

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32

Moreno, Leydi, Jairo Quiroga, Rodrigo Abonia, Jonathan Ramírez-Prada, and Braulio Insuasty. "Synthesis of New 1,3,5-Triazine-Based 2-Pyrazolines as Potential Anticancer Agents." Molecules 23, no. 8 (August 6, 2018): 1956. http://dx.doi.org/10.3390/molecules23081956.

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A new series of 1,3,5-triazine-containing 2-pyrazoline derivatives (8–11)a–g was synthesized by cyclocondensation reactions of [(4,6-bis((2-hydroxyethyl)amino)-1,3,5-triazin-2-yl)amine]chalcones 7a–g with hydrazine hydrate and derivatives. Chalcones 7a–g were obtained by Claisen-Schmidt condensation between aromatic aldehydes and triazinic derivative 5, which was synthesized in high yield by a microwave-assisted reaction. Seventeen of the synthesized compounds were selected and tested by the US National Cancer Institute (NCI) for their anticancer activity against 58 different human tumor cell lines. Compounds 7g and 10d,e,g showed important GI50 values ranging from 0.569 to 16.6 µM and LC50 values ranging from 5.15 to >100 µM.

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33

Liu, Xianxian, and Rebecca E. Parales. "Bacterial Chemotaxis to Atrazine and Related s-Triazines." Applied and Environmental Microbiology 75, no. 17 (July 6, 2009): 5481–88. http://dx.doi.org/10.1128/aem.01030-09.

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ABSTRACT Pseudomonas sp. strain ADP utilizes the human-made s-triazine herbicide atrazine as the sole nitrogen source. The results reported here demonstrate that atrazine and the atrazine degradation intermediates N-isopropylammelide and cyanuric acid are chemoattractants for strain ADP. In addition, the nonmetabolized s-triazine ametryn was also an attractant. The chemotactic response to these s-triazines was not specifically induced during growth with atrazine, and atrazine metabolism was not required for the chemotactic response. A cured variant of strain ADP (ADP M13-2) was attracted to s-triazines, indicating that the atrazine catabolic plasmid pADP-1 is not necessary for the chemotactic response and that atrazine degradation and chemotaxis are not genetically linked. These results indicate that atrazine and related s-triazines are detected by one or more chromosomally encoded chemoreceptors in Pseudomonas sp. strain ADP. We demonstrated that Escherichia coli is attracted to the s-triazine compounds N-isopropylammelide and cyanuric acid, and an E. coli mutant lacking Tap (the pyrimidine chemoreceptor) was unable to respond to s-triazines. These data indicate that pyrimidines and triazines are detected by the same chemoreceptor (Tap) in E. coli. We showed that Pseudomonas sp. strain ADP is attracted to pyrimidines, which are the naturally occurring structures closest to triazines, and propose that chemotaxis toward s-triazines may be due to fortuitous recognition by a pyrimidine chemoreceptor in Pseudomonas sp. strain ADP. In competition assays, the presence of atrazine inhibited chemotaxis of Pseudomonas sp. strain ADP to cytosine, and cytosine inhibited chemotaxis to atrazine, suggesting that pyrimidines and s-triazines are detected by the same chemoreceptor.

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34

Fuerst, E. Patrick, Michael Barrett, and Donald Penner. "Control of Triazine-Resistant Common Lambsquarters (Chenopodium album) and Two Pigweed Species (Amaranthusspp.) in Corn (Zea mays)." Weed Science 34, no. 3 (May 1986): 440–43. http://dx.doi.org/10.1017/s0043174500067151.

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Various chemical treatments were evaluated over two growing seasons for control of triazine-resistant common lambsquarters (Chenopodium albumL. # CHEAL) and for control of a triazine-resistant infestation containing both redroot pigweed (Amaranthus retroflexusL. # AMARE) and Powell amaranth (A. powelliiS. Wats. # AMAPO). Atrazine [6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine], cyanazine {2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl] amino]-2-methylpropanenitrile}, and metribuzin [4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one] provided unsatisfactory control of these biotypes. Satisfactory control of common lambsquarters was obtained with preemergence applications of pendimethalin [N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine] or dicamba (3,6-dichloro-2-methoxybenzoic acid), or postemergence applications of dicamba, bromoxynil (3,5-dibromo-4-hydroxybenzonitrile), or bentazon [3-(1-methylethyl)-(1H)-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide]. Satisfactory control of pigweed was obtained with preemergence applications of alachlor [2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide] or postemergence treatments of dicamba, bromoxynil, or 2,4-D [(2,4-dichlorophenoxy) acetic acid].

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35

Okano, Ruiko, Aiko Ohki, Shinpei Ohki, Hitoshi Kohno, Jack J. S. van Rensen, Peter Böger, and Ko Wakabayashi. "Photosynthetic Electron Transport Inhibition by 2-Substituted 4-Alkyl-6-benzylamino-1,3,5-triazines with Thylakoids from Wild-Type and Atrazine-Resistant Chenopodium album." Zeitschrift für Naturforschung C 57, no. 11-12 (December 1, 2002): 1009–15. http://dx.doi.org/10.1515/znc-2002-11-1210.

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The effect of 2-benzylamino-1,3,5-triazines on photosynthetic electron transport (PET) was measured with thylakoids isolated from atrazine-resistant, wild-type Chenopodium album, and spinach to find novel 1,3,5-triazine herbicides bearing a strong PET inhibition. The PET inhibition assay with Chenopodium (wild-type and resistant), yielded a resistance ratio (R/ W = I50 (resistant)/I50 (wild-type)) of 324 for atrazine while for benzylamino-1,3,5-triazine derivatives of diamino-1,3,5-triazines a R/W of 11 to 160 was found. The compounds having a benzylamino group at one of the amino groups in the diamino-1,3,5-triazines have a resistant ratio down to one half to 1/30 of the atrazine value. The average resistance ratio of 21 benzylamino derivatives of monoamino-1,3,5-triazines was found to be about 4.0. The inhibition of 21 benzylamino-1,3,5-triazines assayed with atrazine-resistant Chenopodium thylakoids, indicated by pI50 (R) -values, correlated well with the PET inhibition pI50 (W) of wildtype thylakoids from Chenopodium.

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36

BEVERSDORF, W. D., D. J. HUME, P. GOSTOVIC, G. CHU, W. MONTMINY, and J. MUSCAT. "OAC TRIUMPH SUMMER RAPE." Canadian Journal of Plant Science 70, no. 3 (July 1, 1990): 857–59. http://dx.doi.org/10.4141/cjps90-104.

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OAC Triumph is a canola quality, summer-rape (Brassica napus L.) cultivar resistant to s-triazine herbicides and tolerant to as-triazinone herbicides. In 22 trials over 3 yr in Ontario it has averaged 2% higher in yield and had higher oil content, better lodging resistance and fewer green seeds at harvest than the s-triazine-resistant cultivar OAC Triton. In 12 trials over 3 yr in Western Canada, OAC Triumph exhibited similar advantages over OAC Triton.Key words: Rape (summer), s-triazine-resistant, cultivar description

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37

Epishina, Margarita A., Alexander S. Kulikov, and Leonid L. Fershtat. "Revisiting the Synthesis of Functionally Substituted 1,4-Dihydrobenzo[e][1,2,4]triazines." Molecules 27, no. 8 (April 15, 2022): 2575. http://dx.doi.org/10.3390/molecules27082575.

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A series of novel 1,4-dihydrobenzo[1,2,4][e]triazines bearing an acetyl or ester moiety as a functional group at the C(3) atom of the 1,2,4-triazine ring were synthesized. The synthetic protocol is based on an oxidative cyclization of functionally substituted amidrazones in the presence of DBU and Pd/C. It was found that the developed approach is suitable for the preparation of 1,4-dihydrobenzo[e][1,2,4]triazines, but the corresponding Blatter radicals were isolated only in few cases. In addition, a previously unknown dihydrobenzo[e][1,2,4]triazolo[3,4-c][1,2,4]triazine tricyclic open-shell derivative was prepared. Studies of thermal behavior of the synthesized 1,4-dihydrobenzo[1,2,4][e]triazines revealed their high thermal stability (up to 240–250 °C), which enables their application potential as components of functional organic materials.

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38

Neunhoeffer, Hans, and Heinz Hammann. "Zur Chemie der 1,2,4-Triazine, XI. Synthese von 1,3,5-Triazino[2,1-f][1,2,4]triazinen." Liebigs Annalen der Chemie 1985, no. 4 (April 15, 1985): 857–60. http://dx.doi.org/10.1002/jlac.198519850421.

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39

Mykolaichuk, O. V., A. V. Protas, E. A. Popova, M. D. Lutsev, E. Yu Smirnov, V. A. Golotin, V. A. Ostrovsky, I. V. Kornyakov, and K. N. Semenov. "Synthesis and study of some properties of new tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine." Журнал общей химии 93, no. 5 (May 15, 2023): 695–710. http://dx.doi.org/10.31857/s0044460x23050050.

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New tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine were synthesized. Cytotoxic activity of the compounds obtained against human liver tumor cell lines Huh-7 and human lung A549 was studied by the MTT test. It was shown that these substances do not exhibit a pronounced cytotoxic effect. The most significant antitumor activity was shown by 1,3,5-triazine containing 5-phenyltetrazol-2-ylacetohydrazide fragment and 4-methylpiperidine ring as substituents, as well as 1,3,5-triazine containing 5-methyl-1 H -tetrazol-1-ylacetohydrazide fragment and two morpholine rings. For these compounds, the interaction with DNA was studied by UV spectroscopy. For N ’-(4,6-dimorpholino-1,3,5-triazin-2-yl)-2-(5-methyl-1 H -tetrazol-1-yl)acetohydrazide, the DNA binding constant was determined ( K bin 9.02× 104 M.-1) and studied the ability to inhibit the tyrosine kinase domain of surface receptors. It was shown that the studied tetrazole-containing derivatives of 1,3,5-triazine do not exhibit antioxidant properties with respect to NO-radicals and do not cause photoinduced hemolysis.

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40

GAYNOR, J. D., J. A. STONE, and T. J. VYN. "TILLAGE SYSTEMS AND ATRAZINE AND ALACHLOR RESIDUES ON A POORLY DRAINED SOIL." Canadian Journal of Soil Science 67, no. 4 (November 1, 1987): 959–63. http://dx.doi.org/10.4141/cjss87-091.

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Seasonal residues of an acetanilide and triazine herbicide were monitored in ridge, conventional, and zero tillage systems. Alachlor (2-chloro-2′,6′-diethyl-N-(methoxymethyl)acetanilide), and atrazine (2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine) residues were less than 8% of the spring application concentration at the end of the growing season. Moldboard plowing in the fall reduced herbicide residues in spring because of soil dilution by plowing to greater than the sampling depth. Ridge tillage systems had higher spring residues apparently because of reduced herbicide dissipation on the drier ridge tops. The higher residues of the triazines on ridge tops may be injurious to triazine sensitive crops. Key words: Herbicide, till-plant, ridge tillage, des-ethyl atrazine

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41

Krinochkin, A. P., M. R. Guda, A. Rammohan, D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin. "A convenient synthetic approach to 5-(het)arylhydrazine substituted 1,2,4-triazines." Chimica Techno Acta 7, no. 4 (December 20, 2020): 204–8. http://dx.doi.org/10.15826/chimtech.2020.7.4.12.

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42

Le, Thanh, Mohan Bhadbhade, Jiabin Gao, James M. Hook, and Christopher E. Marjo. "Persistence of a self-complementary N–H⋯N tape motif in chloro-s-triazine crystals: crystal structures of simazine and atrazine herbicides and their polymorphic and inclusion behaviour." CrystEngComm 18, no. 6 (2016): 962–70. http://dx.doi.org/10.1039/c5ce02206a.

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43

Hashem, Heba E., and Ahmed M. Abo-Bakr. "Synthesis of Some New 1,2,4-Triazine and 1,2,5-Oxadiazine Derivatives with Antimicrobial Activity." Heteroatom Chemistry 2019 (September 25, 2019): 1–7. http://dx.doi.org/10.1155/2019/2326514.

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1,2,4-Triazine and 1,2,5-oxadiazine derivatives 2–12 were obtained from treated 1,3-oxazolone (1) with phenyl hydrazine or hydroxylamine hydrochloride. Chlorotriazine derivative 3 undergoing condensation reactions with different reagents produced new fused tetrazolo-triazine and triazino-quinazolinone derivatives. 1,2,5-Oxadiazine has been used as a synthon for the fused pyrazolo-oxadiazine derivative. The constitution of the prepared compounds was built up based on microanalytical and spectral data. Some of the new compounds were assessed for their antimicrobial activity.

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44

Gerritse, RG, J. Beltran, and F. Hernandez. "Adsorption of atrazine, simazine, and glyphosate in soils of the Gnangara Mound, Western Australia." Soil Research 34, no. 4 (1996): 599. http://dx.doi.org/10.1071/sr9960599.

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Sandy soils were sampled from second rotation sites of Pinus pinaster Ait. on the Gnangara Mound in Western Australia. Adsorption isotherms were measured for atrazine [6-chloro-N2-ethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine], simazine [6-chloro-N,N'-diethyl-1,3,5-triazine-2,4-diamine], and glyphosate [N-phosphonomethyl-aminoaceticacid]. Adsorption isotherms were also measured for degradation products of atrazine: hydroxyatrazine [6-hydroxy-N2-ethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine] (HA), desethylatrazine [6-chloro-N-isopropyl-1,3,5-triazine-2,4-diamine] (DEA); and of glyphosate: aminomethylphosphonic acid (AMPA). The adsorption of the 2 triazines was proportional to soil organic carbon content and was not affected significantly by other soil parameters. The affinity for soil organic carbon was in the order atrazine = simazine = DEA > HA. Affinity of atrazine for the type of organic matter in the Gnangara Mound soils (expressed as Koc) was significantly greater than is commonly reported for other soils. The adsorption of glyphosate and AMPA increased strongly with iron and aluminium content of soils and decreased with increasing soil organic carbon content. This would indicate that glyphosate and AMPA are mainly adsorbed by clay minerals, while soil organic matter competes for adsorption sites and inhibits adsorption. Contrary to what is usually reported for batch adsorption of pesticides in soils, significant increases in adsorption of the triazines and glyphosate were measured after 1 day of equilibration.

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45

Neunhoeffer, Hans, and Diethart Reichel. "[1,2,4]Triazino[6,5-e]-1,2,4-triazine; II." Synthesis 1988, no. 11 (1988): 877–79. http://dx.doi.org/10.1055/s-1988-27734.

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46

Eberlein, Charlotte V., Kassim Al-Khatib, Mary J. Guttieri, and E. Patrick Fuerst. "Distribution and Characteristics of Triazine-Resistant Powell Amaranth (Amaranthus powellii) in Idaho." Weed Science 40, no. 4 (December 1992): 507–12. http://dx.doi.org/10.1017/s0043174500058045.

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A triazine-resistant (TR) biotype of Powell amaranth was discovered in 1989 in a potato field treated with metribuzin. A survey of all agricultural counties in Idaho showed that the TR Powell amaranth infestation was localized in the southeastern corner of Gooding county in southern Idaho. To determine the mechanism of triazine resistance, I50values for inhibition of photosystem II were determined for atrazine, metribuzin, and diuron using thylakoids isolated from TR and triazine-susceptible (TS) biotypes. TR/TS ratios based on I50values were 134 for atrazine, 62 for metribuzin, and 1.9 for diuron. Results of binding studies with atrazine and metribuzin were consistent with the I50studies, indicating that resistance was due to reduced binding of triazines to the thylakoid membrane D1 protein. Sequencing the chloroplastpsbA gene from TR and TS biotypes revealed a serine 264 to glycine change in the TR biotype. The mutation presumably resulted in reduced hydrogen bonding between triazine herbicides and the Dl protein.

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Morita, E., A. B. Sullivan, and A. Y. Coran. "Vulcanization Chemistry." Rubber Chemistry and Technology 58, no. 2 (May 1, 1985): 284–94. http://dx.doi.org/10.5254/1.3536066.

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Abstract Prevulcanization inhibitors based on triazines can be prepared. In each case the triazine ring is amino-substituted such that one or two of the amino hydrogen atoms per amino-group are alkylthio- or arylthio-substituted. The new triazine-derived prevulcanization inhibitors are extremely active in accelerated sulfur vulcanization of diene rubbers (e.g., NR or SBR). Differing accelerators or accelerator systems may require different triazine-derived prevulcanization inhibitors for best results. Provided that the reactivity of the inhibitor is sufficiently near the ideal, its weight-basis activity is greatest when its equivalent weight per S—N bond is least. Overall, hexakis(cyclohexylthio)melamine and especially hexakis(isopropylthio)melamine are the most effective premature vulcanization inhibitors tested, on an equal-weight basis.

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48

Zaki, Remon M., Adel M. Kamal El-Dean, Shaban M. Radwan, and Ahmed F. Saber. "Efficient synthesis, reactions and spectral characterization of pyrazolo[4’,3’:4,5]thieno[3,2-d] pyrimidines and related heterocycles." Heterocyclic Communications 25, no. 1 (April 3, 2019): 39–46. http://dx.doi.org/10.1515/hc-2019-0004.

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AbstractNew pyrazolothienopyrimidines were synthesized. The key intermediate 4-aminothieno[2,3-c]pyrazole-5-carbonitrile 1 was converted to the chloroacetyl amino derivative 2 followed by nucleophilic substitution and Dimorth rearrangement upon treatment with nitrogen nucleophiles to give the pyrimidinones 3a-c. Treatment of 3a with formaldehyde and with triethyl orthoformate afforded the respective tetracyclic derivatives 4 and 5. Condensation of the amino group in the o-aminocarbonitrile 1 with triethyl orthoformate followed by cycloaddition reaction with hydrazine led to the formation of pyrazolothienopyrimidine 8. Compound 8 was used as a synthetic precursor to heterocyclic compounds comprised of pyrazole, triazole, triazine, and triazepine derivatives.

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Fuerst, E. Patrick, Charles J. Arntzen, Klaus Pfister, and Donald Penner. "Herbicide Cross-Resistance in Triazine-Resistant Biotypes of Four Species." Weed Science 34, no. 3 (May 1986): 344–53. http://dx.doi.org/10.1017/s0043174500066960.

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The cross-resistance of triazine-resistant biotypes of smooth pigweed (Amaranthus hybridusL. # AMACH), common lambsquarters (Chenopodium albumL. # CHEAL), common groundsel (Senecio vulgarisL. # SENVU), and the crop canola (Brassica napusL. var. Atratower) to a selection of herbicides was evaluated at both the whole plant and chloroplast level. The triazine-resistant biotypes of all four species showed a similar pattern of cross-resistance, suggesting that a similar mutation had occurred in each species. The four triazine-resistant biotypes were resistant to injury from atrazine [6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine], bromacil [5-bromo-6-methyl-3-(1-methylpropyl)-2,4-(1H,3H)pyrimidinedione], and pyrazon [5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone] and were slightly resistant to buthidazole {3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone}. The triazine-resistant biotypes were more sensitive to dinoseb [2-(1-methylpropyl)-4,6-dinitrophenol]. Triazine-resistant smooth pigweed showed resistance to cyanazine {2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl] amino]-2-methylpropanenitrile} and metribuzin [4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one] with slight resistance to linuron [N′-(3,4-dichlorophenyl)-N-methoxy-N-methylurea] and desmedipham {ethyl [3-[[(phenylamino)carbony] oxy] phenyl] carbamate}. There was little or no resistance to diuron [N′-(3,4-dichlorophenyl)-N,N-dimethylurea], bromoxynil (3,5-dibromo-4-hydroxybenzonitrile), bentazon [3-(1-methylethyl)-(1H)-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide], or dicamba (3,6-dichloro-2-methoxybenzoic acid). Parallel studies at the chloroplast level indicated that the degree of resistance to inhibition of photosynthetic electron transport was highly correlated with the degree of resistance to herbicidal injury. This correlation indicates that atrazine, cyanazine, metribuzin, pyrazon, bromacil, linuron, desmedipham, and buthidazole cause plant injury by inhibition of photosynthesis. This correlation also indicates that triazine resistance and cross-resistance at the whole plant level is due to decreased sensitivity at the level of photosynthetic electron transport. Cross-resistance to numerous additional herbicides was evaluated on isolated chloroplast thylakoid membranes and these results are discussed.14C-atrazine was displaced from thylakoid membranes by several herbicides, indicating that these herbicides compete for a common binding site.

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Deohate, Pradip P., and Roshani S. Mulani. "Microwave Irradiative Synthesis of Triazine Substituted Pyrazoles and Study of Antitubercular and Antimicrobial Activities." Asian Journal of Chemistry 31, no. 5 (March 28, 2019): 1087–90. http://dx.doi.org/10.14233/ajchem.2019.21826.

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Abstract:

Microwave irradiative synthesis of triazine substituted pyrazoles i.e. (4-benzylideneamino-6-methyl-[1,3,5]-triazin-2-yl)-(5-methyl-2-substituted benzoyl/isonicotinoyl/cinnamoyl-pyrazol-3-yl)-amines have been achieved by the cyclocondensation of N-(4-benzylideneamino-6-methyl-[1,3,5]-triazin-2-yl)-3-oxo butyramide with substituted acid hydrazides. Synthesis of required butyramide was done by reacting 2,4-diamino-6-methyl-[1,3,5]-triazine with benzaldehyde and then condensing the product with ethyl acetoacetate. Structural investigation of synthesized compounds has been done by chemical transformation, elemental analysis and IR, 1H NMR, mass spectral studies. Study of antitubercular and antimicrobial activity of title compounds against some selected Gram-positive and Gram-negative microorganisms was performed to establish the relationship between structure and activity of compound.

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Journal articles on the topic 'Triazine'

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