186507-13-1Relevant academic research and scientific papers
Synthesis and fungicidal evaluation of novel chalcone-based strobilurin analogues
Zhao, Pei-Liang,Liu, Chang-Ling,Huang, Wei,Wang, Ya-Zhou,Yang, Guang-Fu
, p. 5697 - 5700 (2007)
Strobilurin derivatives have become one of the most important classes of agricultural fungicide due to a novel action mode, wide fungicidal spectrum, lower toxicity toward mammalian cells, and environmentally benign characteristics. To discover new strobilurin analogues with high activity against resistant pathogens, a series of new chalcone-based strobilurin derivatives are designed and synthesized by integrating a chalcone scaffold with a strobilurin pharmacophore. The preliminary bioassay showed that some of the chalcone analogues exhibited good in vivo fungicidal activities against Pseudoperoniospora cubensis and Sphaerotheca fuliginea at the dosage of 200 μg mL-1. Two compounds, (￡)-methyl 2-[2-({3-[(￡)-3-(2- chlorophenyl)acryloyl]phenoxy}methyl)phenyl]-3-meth-oxyacrylate (1e) and (E)-methyl 2-[2-({3-[(E)-3-(3-bromophenyl)acryloyl]phenoxy}methyl)phenyl]-3- methoxyacrylate (11), were found to display higher fungicidal activities against P. cubensis (EC90 = 118.52 μg ml-1 for 1e and EC 90 = 113.64 μg mL-1 for 11) than Kresoxim-methyl (EC90 = 154.92 μg mL-1) and were identified as the most promising candidates for further study. The present work demonstrated that strobilurin analogues containing chalcone as a side chain could be used as a lead structure for further developing novel fungicides. To our knowledge, this is the first report about the syntheses and fungicidal activities of chalcone-based strobilurin derivatives.
Stereoselective synthesis of highly functionalised pyrrolidines via 1,3-dipolar cycloaddition reactions on a solid support
Hollinshead, Sean P.
, p. 9157 - 9160 (2007/10/03)
Resin bound 3-hydroxyacetophenone 2 was condensed (NaOMe/MeOH/THF) with aryl aldehydes to afford α,β-unsaturated ketones 3a-e. Subsequent reaction with azomethine ylid 5 in the presence of LiBr/DBU provided pyrrolidines 6a-d. These were subsequently acylated and cleaved from the solid support to afford highly functionalised pyrrolidines 8a-d.
