Binding of Triazines and Triazinones in the Q<sub>B</sub>-Binding Niche of Photosystem II

Tietjen, Klaus; Draber, W.; Goossens, J. W. S.; Jansen, Johannes R.; Kluth, Joachim F.; Schindler, Michael; Wroblowsky, Heinz‐Jürgen; Hilp, U.; Trebst, Achim

doi:10.1515/znc-1993-3-416

Cited by 8 publications

(4 citation statements)

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“…As PSII electron transport inhibitor and therefore binding with the same binding niche of the D1 protein, benzylamino-substituted cyanoacrylates and benzylaminotriazines have common benzylamino moieties which were assumed to bind to the very same site. 5,6 In our previous research on cyanoacrylates, when benzylamino group was alternated by different heterocyclic methylamino groups, their herbicidal activity changed to a large extent, and some of them exhibited enhanced herbicidal activity. 7 We wonder if a similar effect could be found in the triazine system.…”

Section: ' Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Activities of Arylmethylamine Substituted Chlorotriazine and Methylthiotriazine Compounds

Zhao

Liu

Cui

et al. 2011

J. Agric. Food Chem.

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Heterocyclic rings were introduced into the core structure of s-triazine to design and synthesize a series of novel triazines containing arylmethylamino moieties. These compounds were characterized by using spectroscopic methods and elemental analysis. Their herbicidal, insecticidal, fungicidal, and antitumor activities were evaluated. Most of these compounds exhibited good herbicidal activity, especially against the dicotyledonous weeds, and compound F8 was almost at the same level as the control compound atrazine. Their structure-activity relationships were discussed. At the same time, some triazines had interesting fungicidal and insecticidal activities, of which F4 exhibited 100% efficacy against Puccinia triticina even at 20 ppm, and F5 showed Lepidopteran-specific activity in both leaf-piece and artificial diet assays. Moreover, these compounds showed antitumor activities against leukemia HL-60 cell line and lung adenocarcinoma A-549 cell line.

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Section: ' Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Activities of Arylmethylamine Substituted Chlorotriazine and Methylthiotriazine Compounds

Zhao

Liu

Cui

et al. 2011

J. Agric. Food Chem.

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“…A number of attempts to rationalize the vast body of data relating to the binding of amide-type PSII inhibitors to the herbicide binding site on D1 have been made (1, 25,26,27,28,37,38). The earliest studies (1, 38) made the basic assumption that hydrogen bonds dominated binding affinity and the inhibitors were oriented into models of the binding niche in a way which allowed the most plausible formation of hydrogen bonds.…”

Section: Molecular Modelling Of Inhibitor-binding Site Interactionsmentioning

confidence: 99%

Quantifying the Inhibitor-Target Site Interactions of Photosystem II Herbicides

Huppatz

1996

Weed sci.

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A convergence of research effort in a number of scientific disciplines in the early 1980s resulted in a rapid expansion of knowledge of the structure and function of the photosynthetic reaction center in bacteria and higher plants. The structure of the reaction center from photosynthetic bacteria was determined by X-ray analysis. The herbicide binding protein (the D1 protein) was identified by photoaffinity labelling and found to be an integral part of the photosynthetic reaction center complex in higher plants. Studies using herbicide-resistant mutants enabled the location of the herbicide binding niche on D1 to be determined. Quantitative Structure Activity Relationships (QSAR) of families of inhibitors and their effect on photosynthetic electron transport helped elucidate the nature of the interaction between inhibitors and receptor. Binding appeared to be predominantly hydrophobic with hydrogen bonding also having an important role. Studies with a series of highly potent inhibitors, the 2-cyanoacrylates, identified certain steric constraints in the interaction of these molecules with the binding site. The activity of these inhibitors was particularly sensitive to minor structural change and they proved to be useful probes of receptor topography. The results of structure-activity studies of the 2-cyanoacrylates combined with a refined knowledge of the three-dimensional structure of the inhibitor binding site has enabled computer-based molecular modelling of interactions of these inhibitors with the receptor. The spatial arrangement of the inhibitor functional groups within the binding domain was shown to be a critical factor in determining binding affinity.

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“…Studies on herbicidal activity, mode of action, quantitative structure activity relationship and so on have been described in many reviews (van R ensen et al, 1993;Trebst, 1987;Mitsutaka et al, 1986). They inhibit photosynthetic electron trans port (PET) by displacing plastoquinone from the Q B-binding niche of the D1 protein in the photosystem-II reaction center (Oettmeier, 1999;Koike et al, 1989;Tietjen et al, 1993). Although the triazine herbicides have contributed to weed control for many years, they are now phasing out due to occurrence of triazine-resistant weeds, 60 plants were found to be triazine-resistant in 1997 (Kohno et al, 2000).…”

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confidence: 99%

Photosynthetic Electron Transport Inhibition by Pyrimidines and Pyridines Substituted with Benzylamino, Methyl and Trifluoromethyl Groups

Ohki

Takahashi

Kuboyama³

et al. 2001

Zeitschrift Für Naturforschung C

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PET Inhibitory Activity, Atrazine-Resistant Chenopodium album , 4-Benzylamino-2-methyl-6-trifluoromethylpyrimidines The decrease of the num ber of ring nitrogen atoms of 2-benzylamino-4-methyl-6-trifluoromethyl-l,3,5-triazines on herbicidal activity and inhibition of photosynthetic electron trans port (PET) was assayed using thylakoids from Spinacia oleracea or atrazine-resistant Cheno podium album. Three 2-benzylamino-4-methyl-6-trifluoromethyl-l,3,5-triazines, nine pyrimi dines with a benzylamino-, methyl-and trifluoromethyl-group, 2-benzylamino-6-methyl-4-trifluoromethyl-pyridine and N-benzyl-S-methyl-S-trifluoromethylaniline were synthesized and assayed. 2-(4-Bromobenzylamino)-4-methyl-6-trifluoromethylpyrimidine exhibited the highest PET inhibitory activity against Spinacia oleracea thylakoids of all compounds tested. The 2-benzylaminopyrimidines and 2-methylpyrimidines having a 4-halobenzylamino group exhibited higher PET inhibition than atrazine and 2-trifluoromethylpyrimidines against Spi nacia oleracea thylakoids. These PET inhibitory active compounds also exhibited a strong and similar inhibition both against atrazine-resistant Chenopodium album thylakoids as well as against thylakoids from wild-type Chenopodium. The herbicidal activity of 4-(4-bromobenzylamino)-2-methyl-6-trifluoromethylpyrimidine was equivalent to that of known herbicides like simetryne, simazine or atrazine.

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Binding of Triazines and Triazinones in the Q_B-Binding Niche of Photosystem II

Cited by 8 publications

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Design, Synthesis, and Biological Activities of Arylmethylamine Substituted Chlorotriazine and Methylthiotriazine Compounds

Design, Synthesis, and Biological Activities of Arylmethylamine Substituted Chlorotriazine and Methylthiotriazine Compounds

Quantifying the Inhibitor-Target Site Interactions of Photosystem II Herbicides

Photosynthetic Electron Transport Inhibition by Pyrimidines and Pyridines Substituted with Benzylamino, Methyl and Trifluoromethyl Groups

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Binding of Triazines and Triazinones in the QB-Binding Niche of Photosystem II

Cited by 8 publications

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Design, Synthesis, and Biological Activities of Arylmethylamine Substituted Chlorotriazine and Methylthiotriazine Compounds

Design, Synthesis, and Biological Activities of Arylmethylamine Substituted Chlorotriazine and Methylthiotriazine Compounds

Quantifying the Inhibitor-Target Site Interactions of Photosystem II Herbicides

Photosynthetic Electron Transport Inhibition by Pyrimidines and Pyridines Substituted with Benzylamino, Methyl and Trifluoromethyl Groups

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Binding of Triazines and Triazinones in the Q_B-Binding Niche of Photosystem II