AgroChemical Libraries

The term “agrichemical” (or “agrochemical”) usually refers to a broad range of pesticides, including insecticides, herbicides, fungicides and nematicides. It may also include synthetic fertilizers, hormones and other chemical growth agents.

Several libraries of agrochemical-like compounds were created by assessing physicochemical properties and structural features of the Life Chemicals HTS Compound Collection. At the first stage the following restrictions were applied:

  • 250 < MW < 500
  • 0.3 < ClogP < 4.5
  • HBD ≤ 2
  • HBA < 10
  • RotB < 11

Then, compounds were picked out by similarity search (Tanimoto method with 80 % cut-off) against the reference set of known agrochemical compounds (www.pesticideinfo.org). In addition, a substructure search was also applied. Substructural cores of each class of agrochemical compounds (fungicides, insecticides, herbicides, microbiocides) were selected from the literature [1–18] and on-line databases. Selection of compounds that belong to the corresponding chemical classes was performed with SYBYL-X and MDL ISIS software packages.

Presented below is a list of agrochemical-like compound sets designed by Life Chemicals and as well as corresponding chemical classes they comprise:

Insecticides (1,800 in-stock compounds)

  • Alkyl phthalates
  • Chloronicotinyl compounds
  • Diacylhydrazines
  • N-Methyl carbamates
  • Organochlorine compounds (oligochlorinated)
  • Organophosphorus compounds
  • Pheromones
  • Chlorinated pyrazoles

Microbiocides (1,900 in-stock compounds)

  • Chlorinated phenols
  • Hydantoins
  • Isothiazolones
  • Phenols
  • Quaternary ammonium compounds

Herbicides (7,700 in-stock compounds)

  • 2,6-Dinitroanilines
  • Imidazolinones
  • Dinitrophenols
  • Sulfonylurea
  • Benzoic acids, chlorine substituted
  • Benzoyl urea, chlorine substituted
  • Bipyridilium compounds
  • Chlorophenoxy acids/esters
  • Chloropyridinyls
  • Cyclohexenones
  • Thiocarbamates
  • Triazines
  • Uracils
  • N-phenyl, N'-alkyl substituted ureas
  • N-alkyl, N'-thiadiazole substituted ureas
  • Bis-carbamates

Fungicides (1,000 in-stock compounds)

  • Azoles
  • Benzimidazoles
  • Dicarboxamides
  • Chlorinated benzenes

References

  1. C. Lamberth, S. Jeanmart, T. Luksch, A. Plant, Current challenges and trends in the discovery of agrochemicals, Science, 2013, Vol. 341, pp. 742–746.
  2. O. Ort, in Modern Crop Protection Compounds, W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Eds. (Wiley- VCH, Weinheim, Germany, 2012), pp. 50–88.
  3. M. A. Hanagan, R. J. Pasteris, R. Shapiro, Y. Henry, B. Klyashchitsky, paper presented at the 242nd American Chemical Society (ACS) National Meeting, Denver, CO, 28 August to 1 September 2011, abstr. no. AGRO-79.
  4. T. Pitterna et al., Bioorg. Med. Chem. 17, 4085–4095 (2009).
  5. A. Plant, Agrow Silver Jubilee Issue, XI–XV (2010).
  6. R. M. Hollingworth, in Agrochemical Discovery, D. R. Baker, N. K. Umetsu, Eds. (American Chemical Society, Washington, DC, 2001), pp. 238–255.
  7. C. L. Cantrell, F. E. Dayan, S. O. Duke, J. Nat. Prod. 75, 1231–1242 (2012).
  8. F. E. Dayan, C. L. Cantrell, S. O. Duke, Bioorg. Med. Chem. 17, 4022–4034 (2009). 
  9. C. Lamberth, Nachr. Chem. 55, 130–134 (2007).
  10. S. D. Lindell, L. C. Pattenden, J. Shannon, Bioorg. Med. Chem. 17, 4035–4046 (2009).
  11. L. Zirngibl, Antifungal Azoles (Wiley-VCH, Weinheim, Germany, 1998).
  12. K.-J. Schleifer, in Pesticide Chemistry, H. Ohkawa, H. Miyagawa, P. W. Lee, Eds. (Wiley-VCH, Weinheim, Germany, 2007), pp. 77–88.
  13. C. M. Tice, Pest Manag. Sci. 57, 3–16 (2001). 
  14. C. M. Tice, Pest Manag. Sci. 58, 219–233 (2002).
  15. C. Lamberth, J. Dinges, in Bioactive Heterocyclic Compound Classes - Agrochemicals, C. Lamberth, J. Dinges, Eds. (Wiley-VCH, Weinheim, Germany, 2012), pp. 3–20.
  16. P. Jeschke, in Modern Methods in Crop Protection Research, P. Jeschke, W. Krämer, U. Schirmer, M. Witschel, Eds. (Wiley-VCH, Weinheim, Germany, 2012), pp. 73–128.G.
  17. Theodoridis, in Fluorine and the Environment – Agrochemicals, Archaeology, Green Chemistry and Water, A. Tressaud, Ed. (Elsevier, Amsterdam, 2006), pp. 121–175.
  18. M. López-Ramos, F. Perruccio, J. Chem. Inf. Model. 50, 801–814 (2010).