Skip to main content
SpringerLink
Log in
Book cover

Environmentally Friendly Alkylphosphonate Herbicides pp 123–178Cite as

Salts of Alkylphosphonates

  • Chapter
  • First Online:

  • 415 Accesses

Abstract

Based on the bioisosterism, the salts of 1-(substituted phenoxyacetoxy) alkylphosphonic acid were speculated to have more powerful inhibitory effect against plant PDHc E1 and better herbicidal activity than the corresponding alkylphosphonates. Nine series of novel alkali metal salts of O-alkyl 1-(substituted phenoxyacetoxy)alkylphosphonates IIA-IIJ were first designed and synthesized as potential plant PDHc E1 inhibitors.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  1. Baillie AC, Wright K, Wright BJ et al (1988) Inhibitors of pyruvate dehydrogenase as herbicides. Pestic Biochem Physiol 30:103–112

    Article  CAS  Google Scholar 

  2. Kluger R, Pike DC (1977) Active site generated analogues of reactive intermediates in enzymic reactions. Potent inhibition of pyruvate dehydrogenase by a phosphonate analogue of pyruvate. J Am Chem Soc 99:4504–4506

    Article  CAS  Google Scholar 

  3. Kluger R, Gish G, Kauffman G (1984) Interaction of thiamin diphosphate and thiamin thiazolone diphosphate with wheat germ pyruvate decarboxylase. J Biol Chem 259:8960–8965

    CAS  Google Scholar 

  4. He HW, Yuan JL, Peng H et al (2011) Studies of O,O-dimethyl α-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex. J Agric Food Chem 59:4801–4813

    Article  CAS  Google Scholar 

  5. Turhanen PA, Ahlgren MJ, Järvinen T et al (2000) Bisphosphnate prodrugs. Selective synthesis of (1-hydroxyethylidene)-1,1-bisphosphnate partial esters. Synthesis 4:633–637

    Google Scholar 

  6. Krawczyk H (1997) A convenient route for monodealkylation of diethyl phosphonates. Synth Commun 27:3151–3161

    Google Scholar 

  7. Wang T, He HW (2004) Simple and improved perparation of α-oxophosphonate monolithium salts. Phosphorus, Sulfur Silicon Relat Elem 179:2081–2089

    Article  CAS  Google Scholar 

  8. Wang T, Zou P, Peng H et al (2014) Synthesis, crystal structure and biological activity of lithium alkyl (1-(2-(substituted phenoxy)acetoxy)alkyl)phosphonate. Chin J Org Chem 34:215–219

    Article  CAS  Google Scholar 

  9. He HW, Wang T, Yuan JL (2005) Synthesis and herbicidal activities of methyl-1-(2,4-dichlorophenoxyacetoxy)alkylphosphonate monosalts. J Organomet Chem 690:2608–2613

    Article  CAS  Google Scholar 

  10. Peng H, Wang T, Xie P et al (2007) Molecular docking and three-dimensional quantitative structure-activity relationship studies on the binding modes of herbicidal 1-(substituted phenoxyacetoxy)alkylphosphonatesto the E1 component of pyruvate dehydrogenase. J Agric Food Chem 55:1871–1880

    Article  CAS  Google Scholar 

  11. Wang T, He HW (2004) An efficient synthesis of α-(2,4-dichloro-phenoxyacetoxy)aryl methyl phosphonate monosodium salts. Synth Commun 34:1415–1423

    Article  CAS  Google Scholar 

  12. Wang T, Wang W, Peng H et al (2013) Synthesis and herbicidal activities of potassium methyl 1-(substituted phenoxyacetoxy)alkylphosphonate. Chem Res Chin U 29:690–694

    Article  CAS  Google Scholar 

  13. Peng H, Deng XY, Gao L et al (2014) Synthesis and herbicidal activities of 2-methylpropan-2-aminium O-methyl 1-(substituted phenoxyacetoxy)alkylphosphonates. Chem Res Chin U 30:82–86

    Article  Google Scholar 

  14. Gao L, Deng XY, Tan XS et al (2013) Synthesis and herbicidal activities of 2-methylpropan-2-aminium methyl 1-(substituted phenoxyacetoxy)alkylphosphonates. Phosphorus, Sulfur Silicon Relat Elem 188:989–994

    Article  CAS  Google Scholar 

  15. Zygmunt J, Kafarski P, Mastalerz P (1978) Preparation of oxoalkanephosphonic acids. Synthesis 1978(8):609–612

    Article  Google Scholar 

  16. Kafarski P, Soroka M (1982) An improved synthesis of N-(phosphonoacetyl)amino acids. Synthesis 3:219–221

    Article  Google Scholar 

  17. Vepsäläinen J, Nupponen H, Pohjala E (1993) Bisphosphonic compounds V. Selective preparation of (dichloromethylene)bisphosphonate partial esters. Tetrahedron Lett 34:4551–4554

    Article  Google Scholar 

  18. Olah GA, Narang SC (1982) Iodotrimethylsilane—a versatile synthetic reagent. Tetrahedron 38:2225–2277

    Article  CAS  Google Scholar 

  19. Olah GA, Narang SC, Gupta BGB et al (1979) Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent. J Org Chem 44:1247–1251

    Article  CAS  Google Scholar 

  20. Peng H, Long QW, Deng XY et al (2013) Synthesis and herbicidal activities of lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates. Phosphorus, Sulfur Silicon Relat Elem 188:1868–1874

    Article  CAS  Google Scholar 

  21. Long QW, Deng XY, Peng H et al (2013) Synthesis and herbicidal activity of sodium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates. Phosphorus, Sulfur Silicon Relat Elem 188:819–825

    Article  CAS  Google Scholar 

  22. Smith DJH, Ogilvie KK, Gillen MF (1980) The methyl group as phosphate protecting group in nucleotide syntheses. Tetrahedron Lett 21:861–864

    Article  CAS  Google Scholar 

  23. Gangjee A, Zhao Y, Hamel E et al (2011) Synthesis and biological activities of (R)- and (S)-N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride as potent cytotoxic antitubulin agents. J Med Chem 54:6151–6155

    Article  CAS  Google Scholar 

  24. Moonen K, Laureyn I, Stevens CV (2004) Synthetic methods for azaheterocyclic phosphonates and their biological activity. Chem Rev 104:6177–6216

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Institute of Pesticide Chemistry, College of Chemistry, Central China Normal University, Wuhan, People’s Republic of China

    Hong-Wu He, Hao Peng & Xiao-Song Tan

Authors
  1. Hong-Wu He
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hao Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiao-Song Tan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hong-Wu He .

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Chemical Industry Press, Beijing and Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

He, HW., Peng, H., Tan, XS. (2014). Salts of Alkylphosphonates. In: Environmentally Friendly Alkylphosphonate Herbicides. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-44431-3_3

Download citation

Publish with us

Policies and ethics

Search

Navigation