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.
Molecules. 2014 Jun 18;19(6):8261-75. doi: 10.3390/molecules19068261.
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.
一类新型潜在除草剂——3-(甲氧羰基亚甲基)异苯并呋喃-1-亚胺已被发现。两种特定分子(E)-甲基 2-[3-(丁基亚氨基)异苯并呋喃-1(3H)-亚基]乙酸酯(1)和(E)-甲基 2-苯基-2-[3-(苯基亚氨基)异苯并呋喃-1(3H)-亚基]乙酸酯(2)的除草活性已经过测试，这两种分子是通过钯催化的 2-炔基苯甲酰胺氧化羰基化反应制备的。化合物 1 和 2 均对拟南芥的茎叶系统表现出强烈的植物毒性效应。两种分子对茎叶的影响相似，但化合物 1 对根系参数（如主根长度、根毛和密度）表现出更强的影响（表现出较低的 ED50 值），而化合物 2 则导致根系形态的重要畸形。我们的结果表明，这些分子是非常有前途的合成除草剂。
