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

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

1, 2,* , 2, 1, 1
 and 2,*
Received: 23 April 2014; in revised form: 30 May 2014 / Accepted: 9 June 2014 / Published: 18 June 2014
(This article belongs to the Special Issue Carbonylation Chemistry)
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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 Arabidopsis thaliana; carbonylation; isobenzofuranimines; shoot parameters; root morphology; phytotoxicity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

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.

Chicago/Turabian Style

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.


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