Simplified strigolactams as potent analogues of strigolactones for the seed germination induction of Orobanche cumana Wallr

• Published in: Pest management science Vol. 72; no. 11; pp. 2054 - 2068
• Main Authors: Lumbroso, Alexandre, Villedieu-Percheron, Emmanuelle, Zurwerra, Didier, Screpanti, Claudio, Lachia, Mathilde, Dakas, Pierre-Yves, Castelli, Laure, Paul, Verity, Wolf, Hanno Christian, Sayer, Danielle, Beck, Andreas, Rendine, Stefano, Fonné-Pfister, Raymonde, De Mesmaeker, Alain
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.11.2016; Wiley Subscription Services, Inc
• Subjects: Germination - drug effects; Helianthus; Helianthus - drug effects; Helianthus - growth & development; Lactams - chemical synthesis; Lactams - chemistry; Lactams - pharmacology; Lactones - chemistry; Orobanche; Orobanche - drug effects; Orobanche - growth & development; parasitic weeds; Plant Roots - drug effects; Plant Roots - growth & development; Seeds - drug effects; Seeds - growth & development; soil persistence; strigolactams; strigolactones; suicidal germination; parasitic weeds; strigolactams; soil persistence; strigolactones; suicidal germination
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.4268

BACKGROUND Strigolactones play an important role in the rhizosphere as signalling molecules stimulating the seed germination of parasitic weed seeds and hyphal branching of arbuscular micorrhiza, and also act as hormones in plant roots and shoots. Strigolactone derivatives, e.g. strigolactams, could be used as suicidal germination inducers in the absence of a host crop for the decontamination of land infested with parasitic weed seeds. RESULTS We report the stereoselective synthesis of novel strigolactams, together with some of their critical physicochemical properties, such as water solubility, hydrolytic stability, as well as their short soil persistence. In addition, we show that such strigolactams are potent germination stimulants of O. cumana parasitic weed seeds and do not affect the seed germination and the root growth of sunflower. CONCLUSIONS The novel strigolactam derivatives described here compare favourably with the corresponding GR‐28 strigolactones in terms of biological activity and physicochemical properties. However, we believe strigolactone and strigolactam derivatives require further structural optimisation to improve their soil persistence to demonstrate a potential for agronomical applications. © 2016 Society of Chemical Industry