title: 3-(Methoxycarbonylmethylene)isobenzofuran-1-imines as a new class of potential herbicides.
abstract: A novel class of potential herbicides, the 3-(methoxycarbonylmethylene) isobenzofuran-1-imines, has been discovered. The herbicidal activity has been tested on two particular molecules, (E)-methyl 2-[3-(butylimino)isobenzofuran-1(3H)-ylidene]acetate (1) and (E)-methyl 2-phenyl-2-[3-(phenylimino)isobenzofuran-1(3H)-ylidene]acetate (2), prepared by palladium-catalyzed oxidative carbonylation of 2-alkynylbenzamides. Both compounds 1 and 2 showed a strong phytotoxic effect on both shoot and root systems of Arabidopsis thaliana. The effects observed on the shoot were similar for both molecules, but while compound 1 showed a stronger effect on root parameters (such as primary root length, root hair and density, showing lower ED50 values), compound 2 caused important malformations in root morphology. Our results indicate that these molecules are very promising synthetic herbicides.
authors.affiliation: Dipartimento AGRARIA, Università Mediterranea di Reggio Calabria, Reggio Calabria 89124, Italy.
authors.forename: Fabrizio
authors.initials: F
authors.lastname: Araniti
authors.affiliation: Dipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, Via P. Bucci 12/C, Arcavacata di Rende (Cosenza) 87036, Italy. raffaella.mancuso@unical.it.
authors.forename: Raffaella
authors.initials: R
authors.lastname: Mancuso
authors.affiliation: Dipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, Via P. Bucci 12/C, Arcavacata di Rende (Cosenza) 87036, Italy.
authors.forename: Ida
authors.initials: I
authors.lastname: Ziccarelli
authors.affiliation: Dipartimento AGRARIA, Università Mediterranea di Reggio Calabria, Reggio Calabria 89124, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Sunseri
authors.affiliation: Dipartimento AGRARIA, Università Mediterranea di Reggio Calabria, Reggio Calabria 89124, Italy. mrabenavoli@unirc.it.
authors.forename: Maria Rosa
authors.initials: MR
authors.lastname: Abenavoli
authors.affiliation: Dipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, Via P. Bucci 12/C, Arcavacata di Rende (Cosenza) 87036, Italy. bartolo.gabriele@unical.it.
authors.forename: Bartolo
authors.initials: B
authors.lastname: Gabriele
mesh_terms: D017360:Arabidopsis / Q000187:drug effects; D006540:Herbicides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D018517:Plant Roots / Q000187:drug effects; D018520:Plant Shoots / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D006540:Herbicides; D007097:Imines