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Mode of action of herbicidal derivatives of aminomethylenebisphosphonic acid. I. Physiologic activity and inhibition of anthocyanin biosynthesis

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Abstract

N-Pyridylaminomethylenebisphosphonic acids constitute a class of promising herbicides. Since their mode of action at the cellular level is still poorly understood, we studied the influence of N-pyridylaminomethylenebisphosphonic acids on plant growth, at the whole plant and undifferentiated tissue levels, using seedlings and cell suspension cultures of mono- and dicotyledonous species. These compounds exhibited strong herbicidal properties, being equipotent with the popular herbicide glyphosate. Since they also depressed buckweed anthocyanin biosynthesis, the shikimate pathway could represent a site of action of N-pyridylaminomethylenebisphosphonic acids.

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Abbreviations

EPSP:

5-enol-pyruvylshikimate-3-phosphate

2,4-D:

2,4-dichlorophenoxyacetic acid.

References

  • Amrhein N, Deus B, Gehrke P, Steinrucken HC (1980) The site of inhibition of the shikimate pathway by glyphosate. Plant Physiol 66:830–834

    Article  PubMed  CAS  Google Scholar 

  • Anderson KS, Sikorski JA, Johnson KA (1988) Evaluation of 5-enol-pyruvylshikimate-3-phosphate synthase substrate and inhibitor binding by stopped-flow and equilibrium fluorescence measurements. Biochemistry 27:7395–7406

    Article  PubMed  CAS  Google Scholar 

  • Bondinell WE, Vnek J, Knowles PF, Sporecher M, Sprinson M, Sprinson DB (1971) Mechanism of 5-enol-pyruvylshikimate-3-phosphate synthase. J Biol Chem 246:6191–6196

    PubMed  CAS  Google Scholar 

  • Czerwiński W, Gancarz R, Przybylka E, Wieczorek JS (1982) Preliminary evaluation of physiological activity of 9-amino-9-fluorenephosphonic acid derivatives. Acta Agrobot 34:253–260

    Google Scholar 

  • Forlani G, Suardi M, Parisi B, Nielsen E (1994) Regulatory effect of exogenous branched-chain amino acids in Nicotiana plumbaginifolia cell suspension culture. Plant Growth Regul 14:203–209

    Article  CAS  Google Scholar 

  • Gancarz R, Weilkopolski W, Jaskulska E, Kafarski P, Lejczak B, Mastalerz P, Wieczorek JS (1985) Phosphonic analogues of morphactins. IV. 9-Aminofluoren-9-ylphosphine oxides. Pestic Sci 16:234–238

    Article  CAS  Google Scholar 

  • Grossbard E, Atkinson D (eds) (1985) The herbicide glyphosate. Butterworth, London

    Google Scholar 

  • Knapp S, Dong Y, Rupitz K, Withers SG (1995) β-Glucosidase inhibitors incorporating pyridinium as a glucosyl mimic. BioMed Chem Lett 5:763–766

    Article  CAS  Google Scholar 

  • Lange H, Shropshire W Jr, Mohr H (1971) Analysis of phytochromemediated anthocyanin synthesis. Plant Physiol 47:649–655

    PubMed  Google Scholar 

  • Langeluddeke P, Krausse D, Rose E, Wallmuller F, Walther KH (1981) Unkratbekampfung mit Hoe 39866 in Obst- und Weinbau. Bundestalt Land Forst Wirtsch 203:256

    Google Scholar 

  • Leo GC, Castellino S, Sammons RD, Sikorski JA (1992) EPSP synthase inhibitor design. I. Conformations of enzyme-bound shikimate-3-phosphate and 5-enol-pyruvylshikimate-3-phosphate using TRNOE. BioMed Chem Lett 2:151–154

    Article  CAS  Google Scholar 

  • Maier L (1981) Organische Phosphoeverbindungen. 75. Herstellung und Eigenschaften von Aminomethylendiphosphinaten und-diphosphopnaten RR1CH[P(O)R2(OR3)] und Derivaten. Phosphorus Sulfur 11:311–322

    Article  CAS  Google Scholar 

  • Mancinelli AL, Schwartz OM (1984) The photoregulation of anthocyanin synthesis. IX. The photosensitivity of the response in dark- and light-grown tomato seedlings. Bot Rev 51:93–105

    Google Scholar 

  • Miller JC, Miller JN (1984) Statistics for analytical chemistry. Ellis Harwood Ltd, Chichester

    Google Scholar 

  • Moedritzer K, Irani RR (1966) The direct synthesis of α-aminomethylphosphonic acids: Mannich-type reactions with orthophosphorous acid. J Org Chem 31:1603–1607

    Article  CAS  Google Scholar 

  • Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassay with tobacco tissue cultures. Physiol Plant 15:473–497

    Article  CAS  Google Scholar 

  • Rengel Z, Kordan HA (1987) Effects of the growth regulators on light-dependent anthocyanin production in Zea mays seedlings. Physiol Plant 69:511–516

    Article  CAS  Google Scholar 

  • Steinrucken HC, Amrheim N (1984) 5-Enol-pyruvylshikimate-3-phosphate synthase of Klebsiella pneumoniae. 2. Inhibition by glyphosate [N-(phosphonomethyl)glycine]. Eur J Biochem 143: 352–357

    Google Scholar 

  • Suzuki F, Yoshihiro F, Yamamoto S, Mizutani H, Funabashi C, Ohya T, Ikai T, Oguchi T (1979) N-Pyridylaminomethylenediphosphonsaureverbindungen. Ger Offen. 2.831.578

  • Tachibana K, Watanabe T, Sekizawa Y (1986) Inhibition of glutamine synthetase and quantitative changes of free amino acids in shoots of bioalaphos-treated Japanese barnyard millet. Nihon Noyaku Gakkaishi (J Pestic Sci) 11:27–32

    CAS  Google Scholar 

  • Wojtasek H, Wieczorek P, Lejczak B, Boduszek B, Gancarz R, Kafarski P (1990) Herbicidal activity of derivatives of 9-amino-fluoren-9-ylphosphonic acid. Pestic Sci 32:245–252

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry, Biochemistry, and Biotechnology, Technical University of Wroclaw, Wroclaw, Poland

    B. Lejczak, B. Boduszek & P. Kafarski

  2. Department of Genetics and Microbiology, University of Pavia, Pavia, Italy

    G. Forlani

  3. Institute of Chemistry, University of Opole, Opole, Poland

    H. Wojtasek & P. Wieczorek

Authors
  1. B. Lejczak
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  2. B. Boduszek
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  3. P. Kafarski
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  4. G. Forlani
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  5. H. Wojtasek
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  6. P. Wieczorek
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Lejczak, B., Boduszek, B., Kafarski, P. et al. Mode of action of herbicidal derivatives of aminomethylenebisphosphonic acid. I. Physiologic activity and inhibition of anthocyanin biosynthesis. J Plant Growth Regul 15, 109–113 (1996). https://doi.org/10.1007/BF00198924

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  • DOI: https://doi.org/10.1007/BF00198924

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