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Flupyradifurone: a brief profile of a new butenolide insecticide

BACKGROUND: The development and commercialisation of new chemical classes of insecticides for efficient crop protection measures against destructive invertebrate pests is of utmost importance to overcome resistance issues and to secure sustainable crop yields. Flupyradifurone introduced here is the...

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Autores principales: Nauen, Ralf, Jeschke, Peter, Velten, Robert, Beck, Michael E, Ebbinghaus-Kintscher, Ulrich, Thielert, Wolfgang, Wölfel, Katharina, Haas, Matthias, Kunz, Klaus, Raupach, Georg
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley & Sons, Ltd 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4657471/
https://www.ncbi.nlm.nih.gov/pubmed/25351824
http://dx.doi.org/10.1002/ps.3932
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author Nauen, Ralf
Jeschke, Peter
Velten, Robert
Beck, Michael E
Ebbinghaus-Kintscher, Ulrich
Thielert, Wolfgang
Wölfel, Katharina
Haas, Matthias
Kunz, Klaus
Raupach, Georg
author_facet Nauen, Ralf
Jeschke, Peter
Velten, Robert
Beck, Michael E
Ebbinghaus-Kintscher, Ulrich
Thielert, Wolfgang
Wölfel, Katharina
Haas, Matthias
Kunz, Klaus
Raupach, Georg
author_sort Nauen, Ralf
collection PubMed
description BACKGROUND: The development and commercialisation of new chemical classes of insecticides for efficient crop protection measures against destructive invertebrate pests is of utmost importance to overcome resistance issues and to secure sustainable crop yields. Flupyradifurone introduced here is the first representative of the novel butenolide class of insecticides active against various sucking pests and showing an excellent safety profile. RESULTS: The discovery of flupyradifurone was inspired by the butenolide scaffold in naturally occurring stemofoline. Flupyradifurone acts reversibly as an agonist on insect nicotinic acetylcholine receptors but is structurally different from known agonists, as shown by chemical similarity analysis. It shows a fast action on a broad range of sucking pests, as demonstrated in laboratory bioassays, and exhibits excellent field efficacy on a number of crops with different application methods, including foliar, soil, seed treatment and drip irrigation. It is readily taken up by plants and translocated in the xylem, as demonstrated by phosphor imaging analysis. Flupyradifurone is active on resistant pests, including cotton whiteflies, and is not metabolised by recombinantly expressed CYP6CM1, a cytochrome P450 conferring metabolic resistance to neonicotinoids and pymetrozine. CONCLUSION: The novel butenolide insecticide flupyradifurone shows unique properties and will become a new tool for integrated pest management around the globe, as demonstrated by its insecticidal, ecotoxicological and safety profile. © 2014 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
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spelling pubmed-46574712015-12-02 Flupyradifurone: a brief profile of a new butenolide insecticide Nauen, Ralf Jeschke, Peter Velten, Robert Beck, Michael E Ebbinghaus-Kintscher, Ulrich Thielert, Wolfgang Wölfel, Katharina Haas, Matthias Kunz, Klaus Raupach, Georg Pest Manag Sci Research Articles BACKGROUND: The development and commercialisation of new chemical classes of insecticides for efficient crop protection measures against destructive invertebrate pests is of utmost importance to overcome resistance issues and to secure sustainable crop yields. Flupyradifurone introduced here is the first representative of the novel butenolide class of insecticides active against various sucking pests and showing an excellent safety profile. RESULTS: The discovery of flupyradifurone was inspired by the butenolide scaffold in naturally occurring stemofoline. Flupyradifurone acts reversibly as an agonist on insect nicotinic acetylcholine receptors but is structurally different from known agonists, as shown by chemical similarity analysis. It shows a fast action on a broad range of sucking pests, as demonstrated in laboratory bioassays, and exhibits excellent field efficacy on a number of crops with different application methods, including foliar, soil, seed treatment and drip irrigation. It is readily taken up by plants and translocated in the xylem, as demonstrated by phosphor imaging analysis. Flupyradifurone is active on resistant pests, including cotton whiteflies, and is not metabolised by recombinantly expressed CYP6CM1, a cytochrome P450 conferring metabolic resistance to neonicotinoids and pymetrozine. CONCLUSION: The novel butenolide insecticide flupyradifurone shows unique properties and will become a new tool for integrated pest management around the globe, as demonstrated by its insecticidal, ecotoxicological and safety profile. © 2014 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry. John Wiley & Sons, Ltd 2015-06 2014-11-27 /pmc/articles/PMC4657471/ /pubmed/25351824 http://dx.doi.org/10.1002/ps.3932 Text en © 2015 Society of Chemical Industry http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Nauen, Ralf
Jeschke, Peter
Velten, Robert
Beck, Michael E
Ebbinghaus-Kintscher, Ulrich
Thielert, Wolfgang
Wölfel, Katharina
Haas, Matthias
Kunz, Klaus
Raupach, Georg
Flupyradifurone: a brief profile of a new butenolide insecticide
title Flupyradifurone: a brief profile of a new butenolide insecticide
title_full Flupyradifurone: a brief profile of a new butenolide insecticide
title_fullStr Flupyradifurone: a brief profile of a new butenolide insecticide
title_full_unstemmed Flupyradifurone: a brief profile of a new butenolide insecticide
title_short Flupyradifurone: a brief profile of a new butenolide insecticide
title_sort flupyradifurone: a brief profile of a new butenolide insecticide
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4657471/
https://www.ncbi.nlm.nih.gov/pubmed/25351824
http://dx.doi.org/10.1002/ps.3932
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