title: Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds.
abstract: BACKGROUND
  Broomrapes attack important crops, cause severe yield losses and are difficult to eliminate because their seed bank is virtually indestructible. In the absence of a host, the induction of seed germination leads to inevitable death due to nutrient starvation. Synthetic analogues of germination-inducing factors may constitute a cheap and feasible strategy to control the seed bank. These compounds should be easy and cheap to synthesise, as this will allow their mass production. The aim of this work is to obtain new synthethic germinating agents.
  
  
  RESULTS
  Nineteen N-substituted phthalimides containing a butenolide ring and different substituents in the aromatic ring were synthesised. The synthesis started with commercially available phthalimides. The complete collection was assayed against the parasitic weeds Orobanche minor, O. cumana, Phelipanche ramosa and P. aegyptiaca, with the synthetic strigolactone analogue GR24 used as a positive control. These compounds offered low EC50values: O. cumana 38.3 μM, O. minor 3.77 μM, P. aegyptiaca 1.35 μM and P. ramosa 1.49 μM.
  
  
  CONCLUSIONS
  The synthesis was carried out in a few steps and provided the target compounds in good yields. The compounds tested showed great selectivity, and low EC50values were obtained for structures that were simpler than GR24. © 2016 Society of Chemical Industry.
authors.affiliation: Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules, School of Science, University of Cadiz, Puerto Real, Cádiz, Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Cala
authors.affiliation: Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules, School of Science, University of Cadiz, Puerto Real, Cádiz, Spain.
authors.forename: Kala
authors.initials: K
authors.lastname: Ghooray
authors.affiliation: INRA-UMR, 1347, Agroécologie, Dijon, France.
authors.forename: Mónica
authors.initials: M
authors.lastname: Fernández-Aparicio
authors.affiliation: Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules, School of Science, University of Cadiz, Puerto Real, Cádiz, Spain.
authors.forename: José Mg
authors.initials: JM
authors.lastname: Molinillo
authors.affiliation: Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules, School of Science, University of Cadiz, Puerto Real, Cádiz, Spain.
authors.forename: Juan Cg
authors.initials: JC
authors.lastname: Galindo
authors.affiliation: Institute for Sustainable Agriculture, CSIC, Córdoba, Spain.
authors.forename: Diego
authors.initials: D
authors.lastname: Rubiales
authors.affiliation: Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules, School of Science, University of Cadiz, Puerto Real, Cádiz, Spain. famacias@uca.es.
authors.forename: Francisco A
authors.initials: FA
authors.lastname: Macías
mesh_terms: D018525:Germination / Q000187:drug effects; D031672:Orobanche / Q000187:drug effects* / Q000254:growth & development; D010797:Phthalimides / Q000494:pharmacology*; D057685:Plant Weeds / Q000187:drug effects* / Q000254:growth & development; D012639:Seeds / Q000187:drug effects / Q000254:growth & development; D058728:Weed Control
chemical_list: D010797:Phthalimides
keywords: GR24; broomrape; butenolide; phthalimide; seed germination; strigolactone