Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds

Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds

[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.

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Bibliographic Details
Main Authors: Cala, Antonio, Ghooray, Kala, Fernández-Aparicio, Mónica, Molinillo, José M. G., Galindo, Juan C. G., Rubiales, Diego, Macías, Francisco A.
Other Authors: Ministerio de Economía y Competitividad (España)
Format: artículo biblioteca
Language:English
Published: John Wiley & Sons 2016-11
Subjects:Broomrape, Seed germination, Strigolactone, Phthalimide, Butenolide, GR24,
Online Access:http://hdl.handle.net/10261/158060
http://dx.doi.org/10.13039/501100003329
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/501100006488
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spelling dig-ias-es-10261-1580602018-01-31T14:54:24Z Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds Cala, Antonio Ghooray, Kala Fernández-Aparicio, Mónica Molinillo, José M. G. Galindo, Juan C. G. Rubiales, Diego Macías, Francisco A. Ministerio de Economía y Competitividad (España) European Commission Institut National de la Recherche Agronomique (France) Broomrape Seed germination Strigolactone Phthalimide Butenolide GR24 [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 EC50 values: 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 EC50 values were obtained for structures that were simpler than GR24. © 2016 Society of Chemical Industry This research was supported by the Ministerio de Economía y Competitividad (MINECO), Spain, Project AGL2013-42238-R and COST Programme FA1206. M Fernández-Aparicio received support from the European Union, Marie-Curie FP7 COFUND People Programme, through the award of an AgreenSkills' fellowship (under Grant Agreement No. PCOFUND-GA-2010-267196), with additional support from INRA Division ‘Santé des Plantes et Enviroment, appel à projets scientifiques 2015, Catégorie Biocontrôle’. Peer reviewed 2017-12-11T11:00:22Z 2017-12-11T11:00:22Z 2016-11 artículo http://purl.org/coar/resource_type/c_6501 Pest Management Science 72(11): 2069-2081 (2016) 1526-498X http://hdl.handle.net/10261/158060 10.1002/ps.4323 1526-4998 http://dx.doi.org/10.13039/501100003329 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100006488 en #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/AGL2013-42238-R http://doi.org/10.1002/ps.4323 Sí none John Wiley & Sons
institution IAS ES
collection DSpace
country España
countrycode ES
component Bibliográfico
access En linea
databasecode dig-ias-es
tag biblioteca
region Europa del Sur
libraryname Biblioteca del IAS España
language English
topic Broomrape
Seed germination
Strigolactone
Phthalimide
Butenolide
GR24
Broomrape
Seed germination
Strigolactone
Phthalimide
Butenolide
GR24
spellingShingle Broomrape
Seed germination
Strigolactone
Phthalimide
Butenolide
GR24
Broomrape
Seed germination
Strigolactone
Phthalimide
Butenolide
GR24
Cala, Antonio
Ghooray, Kala
Fernández-Aparicio, Mónica
Molinillo, José M. G.
Galindo, Juan C. G.
Rubiales, Diego
Macías, Francisco A.
Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds
description [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.
author2 Ministerio de Economía y Competitividad (España)
author_facet Ministerio de Economía y Competitividad (España)
Cala, Antonio
Ghooray, Kala
Fernández-Aparicio, Mónica
Molinillo, José M. G.
Galindo, Juan C. G.
Rubiales, Diego
Macías, Francisco A.
format artículo
topic_facet Broomrape
Seed germination
Strigolactone
Phthalimide
Butenolide
GR24
author Cala, Antonio
Ghooray, Kala
Fernández-Aparicio, Mónica
Molinillo, José M. G.
Galindo, Juan C. G.
Rubiales, Diego
Macías, Francisco A.
author_sort Cala, Antonio
title Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds
title_short Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds
title_full Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds
title_fullStr Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds
title_full_unstemmed Phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds
title_sort phthalimide-derived strigolactone mimics as germinating agents for seeds of parasitic weeds
publisher John Wiley & Sons
publishDate 2016-11
url http://hdl.handle.net/10261/158060
http://dx.doi.org/10.13039/501100003329
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/501100006488
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