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.
Keywords: Arabidopsis thaliana; carbonylation; isobenzofuranimines; shoot parameters; root morphology; phytotoxicity
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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.
Araniti F, Mancuso R, Ziccarelli I, Sunseri F, Abenavoli MR, Gabriele B. 3-(Methoxycarbonylmethylene)isobenzofuran-1-imines as a New Class of Potential Herbicides. Molecules. 2014; 19(6):8261-8275.
Araniti, Fabrizio; Mancuso, Raffaella; Ziccarelli, Ida; Sunseri, Francesco; Abenavoli, Maria R.; Gabriele, Bartolo. 2014. "3-(Methoxycarbonylmethylene)isobenzofuran-1-imines as a New Class of Potential Herbicides." Molecules 19, no. 6: 8261-8275.