Download PDF
Synthesis 2022; 54(05): 1250-1260
DOI: 10.1055/a-1678-8528
short review

Organic Isocyanates and Isothiocyanates: Versatile Intermediates in Agrochemistry

Clemens Lamberth  ∗
› Further Information
    Permissions and Reprints All articles of this category


Abstract

In recent decades, organic isocyanates and isothiocyanates have been often applied as reactive intermediates in research syntheses or manufacturing routes of many agrochemicals. These heterocumulenes allowed the installation of crucial carboxylic functions, such as carbamates, ureas, and semicarbazones, but have also been used for the construction of five- and six-membered heterocycles, such as tetrazolones, thiazoles, and uracils.

1 Introduction

2 Preparation of Carboxylic Acid Functions

3 Preparation of Heterocyclic Rings

4 Conclusion

Key words

isocyanate - isothiocyanate - herbicide - fungicide - insecticide - agrochemical


Publication History

Received: 27 September 2021

Accepted after revision: 26 October 2021

Accepted Manuscript online:
26 October 2021

Article published online:
07 December 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Six C, Richter F. In Ullmann’s Fine Chemicals, Vol. 2. Elvers B. Wiley-VCH; Weinheim: 2014: 781-800
    Google Scholar
  • 2 Braverman S, Cherkinsky M, Birsa ML. In Science of Synthesis, Vol. 18. Knight JG. Thieme; Stuttgart: 2005: 65-320
    Google Scholar
  • 3 Ulrich H. Chemistry and Technology of Isocyanates. Wiley; Hoboken: 1997
    Google Scholar
  • 4 Ozaki S. Chem. Rev. 1972; 72: 457
    Crossref
  • 5 Engels H.-W, Pirkl H.-G, Albers R, Albach RW, Krause J, Hoffmann A, Casselmann H, Dormish J. Angew. Chem. Int. Ed. 2013; 52: 9422
    CrossrefPubMed
  • 6 Kühle E, Klauke E. Angew. Chem. Int. Ed. 1977; 16: 735
    CrossrefPubMed
  • 7 Serrano E, Martin R. Eur. J. Org. Chem. 2018; 3051
    Crossref
  • 8 Pace V, Monticelli S, de la Vega-Hernandez K, Castoldi L. Org. Biomol. Chem. 2016; 14: 7848
    CrossrefPubMed
  • 9 Mukerjee AK, Ashare R. Chem. Rev. 1991; 91: 1
    Crossref
  • 10 Ghosh AK, Sarkar A, Brindisi M. Org. Biomol. Chem. 2018; 16: 2006
    CrossrefPubMed
  • 11 Pradip D. Curr. Org. Chem. 2019; 23: 2402
  • 12 Thomas M, Alsarraf J, Araji N, Tranoy-Opalinski I, Renoux B, Papot S. Org. Biomol. Chem. 2019; 17: 5420
    CrossrefPubMed
  • 13 Grecian S, Aube J. In Organic Azides . Bräse S, Banert K. Wiley; Hoboken: 2010: 191-237
    Google Scholar
  • 14 Bioactive Carboxylic Compound Classes . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2016
    Google Scholar
  • 15 Dubé P, Nathel NF. F, Vetelino M, Couturier M, Aboussafy CL, Pichette S, Jorgensen ML, Hardink M. Org. Lett. 2009; 11: 5622
    CrossrefPubMed
  • 16 Lamberth C. Chimia 2019; 73: 571
    CrossrefPubMed
  • 17 Sulzer-Mosse S, Cederbaum F, Lamberth C, Berthon G, Umarye J, Grasso V, Schlereth A, Blum M, Waldmeier R. Bioorg. Med. Chem. 2015; 23: 2129
    CrossrefPubMed
  • 18 Broughton E. Environ. Health 2005; 4: 6
    CrossrefPubMed
  • 19 Dietrich H, Cottam Jones J, Laber B. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 387-423
    CrossrefGoogle Scholar
  • 20 Sharples KR, Hawkes TR, Mitchell G, Edwards LS, Langford MP, Langton DW, Rogers KM, Townson JK, Wang Y. Pestic. Sci. 1998; 54: 368
    Crossref
  • 21 Nauen R, Bretschneider T. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 1085-1102
    Google Scholar
  • 22 Kasahara I, Matsui N, Yamada T, Kaeriyama M, Ishimitsu K. In Synthesis and Chemistry of Agrochemicals II . Baker D, Fenyes JG, Moberg WK. American Chemical Society; Washington DC: 1991: 340-351
    CrossrefGoogle Scholar
  • 23 Griffiths M. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 529-570
    CrossrefGoogle Scholar
  • 24 Quaranta L. In Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012: 105-118
    Google Scholar
  • 25 Jeschke P. In Bioactive Carboxylic Compound Classes . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2016: 439-452
    Google Scholar
  • 26 Sun R, Liu C, Zhang H, Wang Q. J. Agric. Food Chem. 2015; 63: 6847
    CrossrefPubMed
  • 27 Huang D, Yan G. Org. Biomol. Chem. 2017; 15: 1753
    CrossrefPubMed
  • 28 Ort O. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 55-95
    Google Scholar
  • 29 Puri A, Liang PH. In Bioactive Carboxylic Compound Classes . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2016: 303-313
    Google Scholar
  • 30 Hanagan MA, Puri A. In Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012: 39-50
    CrossrefGoogle Scholar
  • 31 Hay JV. Pestic. Sci. 1990; 29: 247
    Crossref
  • 32 Müller K.-H, Gesing E.-RF, Santel H.-J. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 151-172
    Google Scholar
  • 33 Yu Z, Niu C, Ban S, Wen X, Xi Z. Chin. Sci. Bull. 2007; 52: 1929
    Crossref
  • 34 Hamprecht G, Mayer H, Westphalen K.-O, Walter H. Pestic. Sci. 1999; 55: 566-570
    Crossref
  • 35 Murai S, Haga T, Fujikawa K, Sakashita N, Kimura F. In Synthesis and Chemistry of Agrochemicals II . Baker D, Fenyes JG, Moberg WK. American Chemical Society; Washington DC: 1991: 98-106
    CrossrefGoogle Scholar
  • 36 Lamberth C. Heterocycles 2006; 68: 561
    Crossref
  • 37 Okajima N, Aoki I, Kuragano T, Okada Y. Pestic. Sci. 1991; 32: 91
    Crossref
  • 38 Schäfer B. Chem. Unserer Zeit 2008; 42: 408
    Crossref
  • 39 Minamida I, Iwanaga K, Tabuchi T, Uneme H, Dantsuji H, Okauchi T. J. Pestic. Sci. 1993; 18: 31
    Crossref
  • 40 Lamberth C. Heterocycles 2007; 71: 1467
    Crossref
  • 41 Grosscurt AC, van Hes R, Wellinga K. J. Agric. Food Chem. 1979; 27: 406
    Crossref
  • 42 Takasugi JJ, Witucki LA, France DJ, Evans LS, Kohls CL, Neypes MV. In Synthesis and Chemistry of Agrochemicals IV . Baker D, Fenyes JG, Basarab GS. American Chemical Society; Washington DC: 1995: 384-395
    CrossrefGoogle Scholar
  • 43 Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012
    Google Scholar
  • 44 Lamberth C. In Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012: 147-154
    CrossrefGoogle Scholar
  • 45 Lamberth C. In Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012: 155-162
    CrossrefGoogle Scholar
  • 46 Johnson TC, Mann RK, Schmitzer PR, Gast RE. In Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012: 51-60
    CrossrefGoogle Scholar
  • 47 Shaner D. In Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012: 83-89
    CrossrefGoogle Scholar
  • 48 Wendeborn S, Godineau E, Mondiere R, Smejkal T, Smits H. In Comprehensive Chirality, Vol. 1. Carreira EM, Yamamoto H. Elsevier; Amsterdam: 2012: 120-166
    CrossrefGoogle Scholar
  • 49 Lamberth C. Tetrahedron 2010; 66: 7239
    Crossref
  • 50 Theodoridis G, Baum JS, Hotzman FW, Manfredi MC, Maravetz LL, Lyga JW, Tymonko JM, Wilson KR, Poss KM, Wyle MJ. In Synthesis and Chemistry of Agrochemicals III . Baker D, Fenyes JG, Steffens JJ. American Chemical Society; Washington DC: 1992: 134-146
    CrossrefGoogle Scholar
  • 51 Jeanmart S, Edmunds AJ. F, Lamberth C, Pouliot M, Morris JA. Bioorg. Med. Chem. 2021; 39: 116162
    CrossrefPubMed
  • 52 Matsuzaki Y, Yoshimoto Y, Arimori S, Kiguchi S, Harada T, Iwahashi F. Bioorg. Med. Chem. 2020; 28: 115211
    CrossrefPubMed
  • 53 Stevenson TM, Amoo VE, Chiang GC, Keskeny E, Long JK, Crouse BA, Sharpe P, Hillegass K, Jones L, Yatsko C. In Synthesis and Chemistry of Agrochemicals VI . Baker D, Fenyes JG, Lahm GP, Selby TP, Stevenson TM. American Chemical Society; Washington DC: 2002: 188-198
    Google Scholar
  • 54 Dietz J, Winter C. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 933-947
    CrossrefGoogle Scholar
  • 55 Lamberth C. Pest Manage. Sci. 2013; 69: 1106
    CrossrefPubMed
  • 56 Lamberth C. J. Sulfur Chem. 2004; 25: 39
    Crossref
  • 57 Wang Q, Li H, Li Y, Huang R. J. Agric. Food Chem. 2004; 52: 1918
    CrossrefPubMed
  • 58 Selby TP, Sternberg CG, Bereznak JF, Coats RA, Marshall EA. In Synthesis and Chemistry of Agrochemicals VII . Lyga JW, Theodoridis G. American Chemical Society; Washington DC: 2007: 209-222
    CrossrefGoogle Scholar
  • 59 Zagar C, Liebl R, Theodoridis G, Witschel M. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 173-211
    CrossrefGoogle Scholar
  • 60 Theodoridis G. In Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012: 91-101
    CrossrefGoogle Scholar
  • 61 Theodoridis G. In Fluorine and the Environment, Vol. 2. Tressaud A. Elsevier; Amsterdam: 2006: 121-175
    Google Scholar
  • 62 Hillebrand S, Tietjen K, Zundel J.-L. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 911-932
    CrossrefGoogle Scholar
  • 63 McCann SF, Cordova D, Andaloro JT, Lahm GP. In Modern Crop Protection Compounds, 3rd ed. Jeschke P, Witschel M, Krämer W, Schirmer U. Wiley-VCH; Weinheim: 2019: 1424-1439
    Google Scholar
  • 64 McCann SF, Annis GD, Shapiro R, Piotrowski DW, Lahm GP, Long JK, Lee KC, Hughes MM, Myers BJ, Griswold SM, Reeves BM, March RW, Sharpe PL, Lowder P, Tseng P, Barnette WE, Wing KD. In Synthesis and Chemistry of Agrochemicals VI . Baker D, Fenyes JG, Lahm GP, Selby TP, Stevenson TM. American Chemical Society; Washington DC: 2002: 166-177
    Google Scholar
  • 65 Lahm GP, McCann SF, Harrison CR, Stevenson TM, Shapiro R. In Agrochemical Discovery . Baker DR, Umetsu NK. American Chemical Society; Washington DC: 2001: 20-34
    Google Scholar