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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 4, pp 791–799 | Cite as

Synthesis of fungicidally active succinate dehydrogenase inhibitors with novel difluoromethylated heterocyclic acid moieties

Original Paper
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Abstract

Novel fungicidally active succinate dehydrogenase inhibitors have been prepared, which either carry a difluoromethyl and methyl-bearing pyrazoline, pyrrole, or thiophene ring in the acid component, mimicking similar-substituted pyrazole carboxamides. As five-membered heterocyclic systems with such a special substitution pattern are barely known, unique synthesis routes had to be developed, which rely, e.g., on the van Leusen pyrrole synthesis and the halogen dance reaction. Synthesis and biological activity against selected Ascomycete pathogens of these difluoromethylated pyrazoline, pyrrole, and thiophene derivatives are reported.

Graphical abstract

Keywords

Fungicide Thiophene Pyrrole Pyrazoline Succinate dehydrogenase inhibitor 

Notes

Acknowledgements

We are grateful to S. Guelfi, D. Haerdi, R. Meisburger, and H.-P. Rothen for excellent technical assistance.

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2017

Authors and Affiliations

  • Harald Walter
    • 1
  • Clemens Lamberth
    • 1
  • Camilla Corsi
    • 1
  1. 1.Chemical ResearchSyngenta Crop Protection AGSteinSwitzerland

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