title: Flupyradifurone: a brief profile of a new butenolide insecticide.
abstract: 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.
  
  
  CONCLUSIONS
  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.
authors.affiliation: Research & Development, Bayer CropScience, 40789, Monheim, Germany.
authors.forename: Ralf
authors.initials: R
authors.lastname: Nauen
authors.forename: Peter
authors.initials: P
authors.lastname: Jeschke
authors.forename: Robert
authors.initials: R
authors.lastname: Velten
authors.forename: Michael E
authors.initials: ME
authors.lastname: Beck
authors.forename: Ulrich
authors.initials: U
authors.lastname: Ebbinghaus-Kintscher
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Thielert
authors.forename: Katharina
authors.initials: K
authors.lastname: Wölfel
authors.forename: Matthias
authors.initials: M
authors.lastname: Haas
authors.forename: Klaus
authors.initials: K
authors.lastname: Kunz
authors.forename: Georg
authors.initials: G
authors.lastname: Raupach
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000633:toxicity; D000818:Animals; D001042:Aphids; D018556:Crops, Agricultural; D006430:Hemiptera; D007305:Insecticide Resistance; D007306:Insecticides / Q000737:chemistry / Q000633:toxicity; D018722:Nicotinic Agonists / Q000737:chemistry / Q000633:toxicity; D011725:Pyridines / Q000737:chemistry / Q000633:toxicity
chemical_list: D007306:Insecticides; D018722:Nicotinic Agonists; D011725:Pyridines; C000606086:flupyradifurone; D015107:4-Butyrolactone
keywords: CYP6CM1; Sivanto®; butenolide; flupyradifurone; metabolic resistance; nicotinic acetylcholine receptor agonist; resistance management; sucking pests