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Molecules 2014, 19(6), 8261-8275; doi:10.3390/molecules19068261

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

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
Authors to whom correspondence should be addressed.
Received: 23 April 2014 / Revised: 30 May 2014 / Accepted: 9 June 2014 / Published: 18 June 2014
(This article belongs to the Special Issue Carbonylation Chemistry)
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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. View Full-Text
Keywords: Arabidopsis thaliana; carbonylation; isobenzofuranimines; shoot parameters; root morphology; phytotoxicity Arabidopsis thaliana; carbonylation; isobenzofuranimines; shoot parameters; root morphology; phytotoxicity

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Araniti, F.; Mancuso, R.; Ziccarelli, I.; Sunseri, F.; Abenavoli, M.R.; Gabriele, B. 3-(Methoxycarbonylmethylene)isobenzofuran-1-imines as a New Class of Potential Herbicides. Molecules 2014, 19, 8261-8275.

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