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Enhancement of in vitro fungicidal activity of fuberidazole to Botrytis cinerea by cucurbiturils

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Abstract

The host–guest interaction of fuberidazole (FBZ) fungicide with cucurbituril (CB) macromolecules was characterized in pure water using UV–vis spectrophotometric and NMR techniques. The in vitro applications (at pH 5.5 in pure water) of host–guest complexes were conducted against Botrytis cinerea. While addition of CB5 to FBZ had no significant effect in vitro, mixing CB7 or CB8 with FBZ in a 1:2 ratio improved fungal growth inhibition at least threefold, when compared to the corresponding concentration of the unbound fungicide molecules. Empty CB hosts were completely inactive. Furthermore, the inhibitory activity to B. cinerea was relatively maintained down to a concentration of 5:10 μM of the CB7/8@FBZ complexes, relative to any of controls. Complexation by CB7/8 further improved the photostability of the fungicides with photostabilization factors of 7 and 3, respectively. CB7/8 bound the protonated forms of these guests very strongly but their neutral forms were significantly weaker, which reflects a complexation-induced increase of their pK a values by 3.8 units with CB7 and 1.4 units with CB8. The present investigation constitutes an innovative, nonclassical, approach to enhance fungicides efficacy utilizing macromolecules with a potential application in crop protection technology.

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Acknowledgments

The authors would like to acknowledge the Office of Research Support and Sponsored Projects at UAEU for their support under the grant numbers 31S075 to S.AQ. and 31S074 to N.S., within the framework of National Research Foundation (NRF) funding program, the Interdisciplinary fund number 31S035 to S.AQ. We would also like to thank Prof. Dr. Werner Nau and his research group for their significant contributions in previous joint accomplishments on the recognitions of benzimidazole fungicides by CB in aqueous solutions. We thank Ms. Zeinab A. Abdalla for her contribution in the initiation of this study.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, United Arab Emirates University, P.O. Box 15551, Al-Ain, United Arab Emirates

    Na’il Saleh

  2. Department of Biology, College of Science, United Arab Emirates University, P.O. Box 15551, Al-Ain, United Arab Emirates

    Suad M. Ajeb, Arjun Sham & Synan F. AbuQamar

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  1. Na’il Saleh
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  2. Suad M. Ajeb
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Correspondence to Na’il Saleh or Synan F. AbuQamar.

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Saleh, N., Ajeb, S.M., Sham, A. et al. Enhancement of in vitro fungicidal activity of fuberidazole to Botrytis cinerea by cucurbiturils. J Incl Phenom Macrocycl Chem 79, 301–309 (2014). https://doi.org/10.1007/s10847-013-0352-8

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