Synthesis of strigolactones analogues by intramolecular [2+2] cycloaddition of ketene-iminium salts to olefins and their activity on Orobanche cumana seeds.
Strigolactones have been the latest identified phytohormones. Among the strigolactones analogues described recently, GR-24 remains the most studied derivative which is used as standard in this field. In order to improve several properties of GR-24 for potential agronomical applications, we investigated the effect of substituents on the B and C-rings on the activity for seed germination induction. We report here the synthesis of 9 GR-24 analogues via a [2+2] intramolecular cycloaddition of ketene-iminium salts and a summary of their activity for the germination of Orobanche cumana (broomrape) seeds.
Syngenta Crop Protection AG, Crop Protection Research, Research Chemistry, Schaffhauserstrasse 101, CH-4332 Stein, Switzerland.
Mathilde
M
Lachia
Syngenta Crop Protection AG, Crop Protection Research, Research Chemistry, Schaffhauserstrasse 101, CH-4332 Stein, Switzerland.
Hanno Christian
HC
Wolf
Syngenta Crop Protection AG, Crop Protection Research, Research Chemistry, Schaffhauserstrasse 101, CH-4332 Stein, Switzerland. Electronic address: alain.de_mesmaeker@syngenta.com.
Alain
A
De Mesmaeker
D000475:Alkenes / Q000737:chemistry; D061565:Cycloaddition Reaction; D005030:Ethylenes / Q000737:chemistry; D018525:Germination / Q000187:drug effects*; D007097:Imines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D031672:Orobanche / Q000187:drug effects* / Q000254:growth & development*; D012492:Salts / Q000737:chemistry; D012639:Seeds / Q000187:drug effects / Q000254:growth & development
D000475:Alkenes; D005030:Ethylenes; D007097:Imines; D007659:Ketones; D007783:Lactones; D012492:Salts; C008223:ketene
Cycloaddition; Germination inducer; Ketene-iminium salts; Orobanche cumana; Strigolactones