3-(Methoxycarbonylmethylene)isobenzofuran-1-imines as a New Class of Potential Herbicides

Molecules

Fabrizio Araniti¹  Raffaella Mancuso²  Ida Ziccarelli²  Francesco Sunseri¹  Maria Rosa Abenavoli¹ 

[1] Dipartimento AGRARIA, Università Mediterranea di Reggio Calabria, Reggio Calabria 89124, Italy;Dipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, Via P. Bucci 12/C, Arcavacata di Rende (Cosenza) 87036, Italy

关键词: Arabidopsis thaliana;    carbonylation;    isobenzofuranimines;    shoot parameters;    root morphology;    phytotoxicity;   

DOI  :  10.3390/molecules19068261

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.