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Glyphosate: Methods of Synthesis

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Abstract

The review describes the main chemical processes used in the preparation of glyphosate by different methods. Methods for the synthesis of glyphosate are considered, both industrial syntheses (from glycine and by oxidation of N-(phosphonomethyl)-iminodiacetic acid (PhIDAA)) and promising “atom-efficient” methods (dealkylation of N-substituted glyphosates).

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REFERENCES

  1. Szekacs, A. and Darvas, B., Herbic.-Prop. Synth. Control Weeds, 2012, p. 247.

  2. Dill, G.M., Sammons, R.D., Feng, P.C.C., Kohn, F., Kretzmer, K., Mehrsheikh, A., Bleeke, M., Honegger, J.L., Farmer, D., Wright, D., and Haupfear, E.A., Glyphosate Resist. Crops Weeds, 2010, p. 1.

    Google Scholar 

  3. Powles, S.B., Proc. Natl. Acad. Sci., 2010, vol. 107, no. 3, p. 955.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Duke, S.O. and Powles, S.B., Pest Manage. Sci., 2008, vol. 64, no. 4, p. 319.

    Article  CAS  Google Scholar 

  5. Krawczyk, H. and Bartczak, T.J., Phosphorus Sulfur Silicon Relat. Elem., 1993, vol. 82, nos. 1–4, p. 117.

    Article  CAS  Google Scholar 

  6. Peixoto, M.M., Bauerfeldt, G.F., Herbst, M.H., Pereira, M.S., and da Silva, C.O., J. Phys. Chem. A, 2015, vol. 119, no. 21, p. 5241.

    Article  CAS  PubMed  Google Scholar 

  7. Duke, S.O., Pest Manage. Sci., 2018, vol. 74, no. 5, p. 1027.

    Article  CAS  Google Scholar 

  8. Wang, C., Lin, X., Li, L., and Lin, S., PLoS One, 2016, vol. 11, no. 3, p. e0151633.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  9. Maeda, H. and Dudareva, N., Annu. Rev. Plant Biol., 2012, vol. 63, no. 1, p. 73.

    Article  CAS  PubMed  Google Scholar 

  10. Morjan, W.E., Pedigo, L.P., and Lewis, L.C., Environ. Entomol., 2002, vol. 31, no. 6, p. 1206.

    Article  CAS  Google Scholar 

  11. Tanney, J.B. and Hutchison, L.J., Can. J. Microbiol., 2010, vol. 56, no. 2, p. 138.

    Article  CAS  PubMed  Google Scholar 

  12. Roberts, C.W., Roberts, F., Lyons, R.E., Kirisits, M.J., Mui, E.J., Finnerty, J., Johnson, J.J., Ferguson, D.J.P., Coggins, J.R., Krell, T., Coombs, G.H., Milhous, W.K., Kyle, D.E., Tzipori, S., Barnwell, J., Dame, J.B., Carlton, J., and McLeod, R., J. Infect. Dis., 2002, vol. 185, no. s1, p. S25.

    Article  CAS  PubMed  Google Scholar 

  13. Sammons, R.D., Gruys, K.J., Anderson, K.S., Johnson, K.A., and Sikorski, J.A., Biochem., 1995, vol. 34, no. 19, p. 6433.

    Article  CAS  Google Scholar 

  14. Marzabadi, M.R., Gruys, K.J., Pansegrau, P.D., Walker, M.C., Yuen, H.K., and Sikorski, J.A., Biochem., 1996, vol. 35, no. 13, p. 4199.

    Article  CAS  Google Scholar 

  15. Li, J., Peng, Q., Han, H., Nyporko, A., Kulynych, T., Yu, Q., and Powles, S., J. Agric. Food Chem., 2018, vol. 66, no. 30, p. 7880.

    Article  CAS  PubMed  Google Scholar 

  16. Funke, T., Han, H., Healy-Fried, M.L., Fischer, M., and Schonbrunn, E., Proc. Natl. Acad. Sci., 2006, vol. 103, no. 35, p. 13010.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Schonbrunn, E., Eschenburg, S., Shuttleworth, W.A., Schloss, J.V., Amrhein, N., Evans, J.N.S., and Kabsch, W., Proc. Natl. Acad. Sci., 2001, vol. 98, no. 4, p. 1376.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Samac, D. and Foster-Hartnett, D., Plant Dis. 2012, vol. 56, no. 2, p. 1104.

    Article  CAS  Google Scholar 

  19. Duke, S.O., Pest Manage. Sci., 2018, vol. 74, no. 5, p. 1025.

    Article  CAS  Google Scholar 

  20. Molin, W.T., Weed Technol., 1998, vol. 12, no. 03, p. 564.

    Article  Google Scholar 

  21. Zhantasov, K.T., Shalataev, S.S., Kadirbayeva, A.A., Zhantasova, D.M., Dzhanmuldaeva, Z.M., Ismailov, B., and Petropavlovsky, I.A., Orient. J. Chem., 2017, vol. 33, no. 3, p. 1381.

    Article  CAS  Google Scholar 

  22. Montchamp, J.-L., Phosphorus Sulfur Silicon Relat. Elem., 2013, vol. 188, nos. 1–3, p. 66.

    Article  CAS  Google Scholar 

  23. Fu, W., Guo, Q., and Wang J., J. Chem. Eng. Data, 2010, vol. 55, no. 9, p. 3915.

    Article  CAS  Google Scholar 

  24. Jia, D., Wang, L., Li, C., and Wang, X., Fluid Phase Equilib., 2012, vol. 327, no. 5, p. 1.

    Article  CAS  Google Scholar 

  25. SU Patent No. 1112760, 1983.

  26. Zhou, J., Li, J., An, R., Yuan, H., and Yu, F., J. Agric. Food Chem., 2012, vol. 60, no. 25, p. 6279.

    Article  CAS  PubMed  Google Scholar 

  27. US Patent No. 4486359, 1984.

  28. CN Patent No. 106543222, 2017.

  29. Mao, J.-G., Wang, Z., and Clearfield, A., New J. Chem., 2002, vol. 26, no. 8, p. 1010.

    Article  CAS  Google Scholar 

  30. Pine, S.H. and Sanchez, B.L., J. Org. Chem., 1971, vol. 36, no. 6, p. 829.

    Article  CAS  Google Scholar 

  31. CN Patent No. 102952159, 2013.

  32. Chen, N., Wang, S., Yao, C.H., Hui, L., and Qu, Y., J. Chem. Eng. Data, 2010, vol. 55, no. 7, p. 2613.

    Article  CAS  Google Scholar 

  33. Jia, D., Zhang, X., Li, J., and Li, C., Fluid Phase Equilib., 2014, vol. 382, p. 54.

    Article  CAS  Google Scholar 

  34. Ogata, Y., Kawasaki, A., and Goto, T., J. Org. Chem., 1968, vol. 33, no. 3, p. 1107.

    Article  CAS  Google Scholar 

  35. Andreev, D.V., Sergeev, E.E., Gribovskii, A.G., Makarshin, L.L., Prikhod’ko, S.A., Adonin, N.Y., Pai, Z.P., and Parmon, V.N., Chem. Eng. J., 2017, vol. 330, no. 3, p. 899.

    Article  CAS  Google Scholar 

  36. Yushchenko, D.Yu., Zhizhina, E.G., and Pai, Z.P., Katal. Prom-sti, 2018, vol. 6, p. 33.

    Google Scholar 

  37. Andreev, D.V., Sergeev, E.E., Gribovskii, A.G., Makarshin, L.L., Prikhod’ko, S.A., Adonin, N.Yu., Pai, Z.P., and Parmon, V.N., Katal. Prom-sti., 2012, no. 5, p. 23.

  38. Pollak, P., Romeder, G., Hagedorn, F., and Gelbke, H.-P., Ullmann’s Encycl. Ind. Chem. (7th Ed.), 2000, vol. 12, no. 4, p. 365.

  39. Polstorff, K. and Meyer, H., Berichte der Dtsch. Chem. Gesellschaft, 1912, vol. 45, no. 2, p. 1905.

    Article  CAS  Google Scholar 

  40. Duan, P.-G., Wang, X., and Dai, L.-Y., Chem. Eng. Technol., 2007, vol. 30, no. 2, p. 265.

    Article  CAS  Google Scholar 

  41. Liu, Z.-Q., Zhou, M., Zhang, X.-H., Xu, J.-M., Xue, Y.-P., and Zheng, Y.-G., J. Mol. Microbiol. Biotechnol., 2012, vol. 22, no. 1, p. 35.

    PubMed  CAS  Google Scholar 

  42. Tian, J., Shi, H., Li, X., Yin, Y., and Chen, L., Green Chem., 2012, vol. 14, no. 7, p. 1990.

    Article  CAS  Google Scholar 

  43. Cherkasov, R.A. and Galkin, V.I., Russ. Chem. Rev., 1998, vol. 67, no. 10, p. 857.

    Article  Google Scholar 

  44. Riley, D.P. and Fields, D.L., J. Am. Chem. Soc., 1992, vol. 114, no. 5, p. 1881.

    Article  CAS  Google Scholar 

  45. Riley, D.P., Fields, D.L., and Rivers, W., Inorg. Chem., 1991, vol. 30, no. 22, p. 4191.

    Article  CAS  Google Scholar 

  46. Riley, D.P., Fields, D.L., and Rivers, W., J. Am. Chem. Soc., 1991, vol. 113, no. 9, p. 3371.

    Article  CAS  Google Scholar 

  47. Kuil, M.E.W., Beers, A., and Alsters, P.L., Liq. Phase Aerobic Oxid. Catal., 2016, vol. 91, p. 267.

    Google Scholar 

  48. Pinel, C., Landrivon, E., Lini, H., and Gallezot, P., J. Catal., 1999, vol. 182, no. 2, p. 515.

    Article  CAS  Google Scholar 

  49. Besson, M., Gallezot, P., Perrard, A., and Pinel, C., Catal. Today, 2005, vols. 102–103, p. 160.

    Article  CAS  Google Scholar 

  50. Bao, Y., Wu, J., and Hu, X.P., Adv. Mater. Res., 2012, vols. 455–456, p. 872.

    Article  CAS  Google Scholar 

  51. US Patent No. 7067693, 2006.

  52. Liu, Y.B., Liang, E.X., Yi, J.M., Wu, X., and Zhang, P.L., Appl. Mech. Mater., 2014, vols. 556–562, p. 213.

  53. Demin, A.M., Mekhaev, A.V., Esin, A.A., Kuznetsov, D.K., Zelenovskiy, P.S., Shur, V.Y., and Krasnov, V.P., Appl. Surf. Sci., 2018, vol. 440, p. 1196.

    Article  CAS  Google Scholar 

  54. US Patent No. 3954848 (1976).

  55. Franz, J.E., Adv. Pestic. Sci., 1979, p. 139.

    Google Scholar 

  56. Gubarev, Yu.A., Lebedeva, N.S., Andreev, V.P., Nizhnik, Yu.P., and V’yugin, A.I., Russ. J. Gen. Chem., 2007, vol. 77, no. 6, p. 1093.

    Article  CAS  Google Scholar 

  57. US Patent No. 5948938, 1999.

  58. US Patent No. 5072033, 1999.

  59. US Patent No. 5061820, 1991.

  60. US Patent No. 5023369, 1991.

  61. Bur, S.K., Compr. Org. Synth. (2nd Ed.), 2014, vol. 6, p. 755.

    Google Scholar 

  62. Thavaneswaran, S. and Scammells, P.J., Bioorg. Med. Chem. Lett., 2006, vol. 16, no. 11, p. 2868.

    Article  CAS  PubMed  Google Scholar 

  63. US Patent No. 5043475, 1991.

  64. EP Patent No.0439445, 1991.

  65. US Patent No. 6528680, 2003.

  66. US Patent No. 6696602, 2004.

  67. WO Patent No. 2004014925, 2004.

  68. CN Patent No. 1482130, 2004.

  69. CN Patent No. 1557820, 2004.

  70. RF Patent No. 2618629, 2016.

  71. Pai, Z.P., Yushchenko, D.Y., Khlebnikova, T.B., and Parmon, V.N., Catal. Commun., 2015, vol. 71, p. 102.

    Article  CAS  Google Scholar 

  72. Pai, Z.P., Chesalov, Y.A., Berdnikova, P. V, Uslamin, E.A., Yushchenko, D.Y., Uchenova, Y. V, Khlebnikova, T.B., Baltakhinov, V.P., Kochubey, D.I., and Bukhtiyarov, V.I., Appl. Catal., A, 2020, vol. 604, p. 117786.

  73. Manassero, A., Passalia, C., Negro, A.C., Cassano, A.E., and Zalazar, C.S., Water Res., 2010, vol. 44, no. 13, p. 3875.

    Article  CAS  PubMed  Google Scholar 

  74. Morgenstern, D.A., Fobian, Y.M., and Oburn, D.S., Catal. Org. React., 2000, p. 349.

    Google Scholar 

  75. Stern, M.K., Environ. Challenges Chem. Sci. 21st Century, 2003, p. 140.

  76. US Patent No. 3956370, 1976.

  77. US Patent No. 3927080, 1975.

  78. EP Patent No. 0055695, 1982.

  79. US Patent No. 5068404, 1991.

  80. Murzin, D.Yu., Kinet. Catal., 2020, vol. 61, no. 1, p. 80.

    Article  CAS  Google Scholar 

  81. WO Patent No. 9941260A1, 1999.

  82. RF Patent No. 2641897, 2018.

  83. Pyrjaev, P.A., Yushchenko, D.Y., Moroz, B.L., Pai, Z.P., and Bukhtiyarov, V.I., Chem. Sel., 2019, vol. 4, no. 36, p. 10756.

    CAS  Google Scholar 

  84. Pyryaev, P.A., Moroz, B.L., Zyuzin, D.A., Nartavo, A.V., and Bukhtiyarov, V.I., Kinet. Catal., 2010, vol. 51, no. 9, p. 885.

    Article  CAS  Google Scholar 

  85. Bulushev, D.A., Yuranov, I., Suvorova, E.I., Buffat, P.A., and Kiwi-Minsker, L., J. Catal. 2004, vol. 224, no. 1, p. 8.

    Article  CAS  Google Scholar 

  86. RF Patent No. 2663905, 2018.

  87. Yushchenko, D.Y., Simonov, P.A., Khlebnikova, T.B., Pai, Z.P., and Bukhtiyarov, V.I., Catal. Commun., 2019, vol. 121, p. 57.

    Article  CAS  Google Scholar 

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Funding

This work was supported by the Ministry of Science and Higher Education of the Russian Federation within the governmental order for Boreskov lnstitute of Catalysis (project AAAA-A21-121011390007-7).

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Authors and Affiliations

  1. Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    D. Yu. Yushchenko, T. B. Khlebnikova, Z. P. Pai & V. I. Bukhtiyarov

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  1. D. Yu. Yushchenko
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  2. T. B. Khlebnikova
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  3. Z. P. Pai
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  4. V. I. Bukhtiyarov
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Correspondence to D. Yu. Yushchenko.

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Translated by L. Smolina

Abbreviations and notation: EPSP, 5-enoylpyruvyl-shikimate-3-phosphate synthase; IDA, iminodiacetic acid; PhIDAA, N‑(phosphonomethyl)-iminodiacetic acid; Ox, oxidant; Cat, catalyst.

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Yushchenko, D.Y., Khlebnikova, T.B., Pai, Z.P. et al. Glyphosate: Methods of Synthesis. Kinet Catal 62, 331–341 (2021). https://doi.org/10.1134/S0023158421030113

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