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

被引：10

作者：

Araniti, Fabrizio ^{[1
]}

Mancuso, Raffaella ^{[2
]}

Ziccarelli, Ida ^{[2
]}

Sunseri, Francesco ^{[1
]}

Abenavoli, Maria Rosa ^{[1
]}

Gabriele, Bartolo ^{[2
]}

机构：

[1] Univ Mediterranea Reggio Calabria, Dipartimento AGRARIA, I-89124 Reggio Di Calabria, Italy

[2] Univ Calabria, Dipartimento Chim & Tecnol Chim, I-87036 Cosenza, Italy

来源：

MOLECULES | 2014年 / 19卷 / 06期

关键词：

Arabidopsis thaliana; carbonylation; isobenzofuranimines; shoot parameters; root morphology; phytotoxicity; PROTEIN PHOSPHATASE-ACTIVITY; OKADAIC ACID; ARABIDOPSIS-THALIANA; CELL-SHAPE; DERIVATIVES; INTERPHASE; RESISTANCE; INHIBITORS; GROWTH;

D O I：

10.3390/molecules19068261

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

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.

引用

页码：8261 / 8275

页数：15

共 34 条

[21] Ethylene-auxin interactions regulate lateral root initiation and emergence in Arabidopsis thaliana [J].

Ivanchenko, Maria G. ;

Muday, Gloria K. ;

Dubrovsky, Joseph G. .

PLANT JOURNAL, 2008, 55 (02) :335-347

[22] Root System Architecture from Coupling Cell Shape to Auxin Transport [J].

Laskowski, Marta ;

Grieneisen, Veronica A. ;

Hofhuis, Hugo ;

ten Hove, Colette A. ;

Hogeweg, Paulien ;

Maree, Athanasius F. M. ;

Scheres, Ben .

PLOS BIOLOGY, 2008, 6 (12) :2721-2735

[23] Effects of a Coumarin Derivative, 4-Methylumbelliferone, on Seed Germination and Seedling Establishment in Arabidopsis [J].

Li, Xiang ;

Gruber, Margaret Y. ;

Hegedus, Dwayne D. ;

Lydiate, Derek J. ;

Gao, Ming-Jun .

JOURNAL OF CHEMICAL ECOLOGY, 2011, 37 (08) :880-890

[24] Protein degradation and nitrogen remobilization during leaf senescence [J].

Liu, Juan ;

Wu, Yun Hai ;

Yan, Jun Jie ;

Liu, Yu Dong ;

Shen, Fa Fu .

JOURNAL OF PLANT BIOLOGY, 2008, 51 (01) :11-19

[25] Divergent Palladium Iodide Catalyzed Multicomponent Carbonylative Approaches to Functionalized Isoindolinone and Isobenzofuranimine Derivatives [J].

Mancuso, Raffaella ;

Ziccarelli, Ida ;

Armentano, Donatella ;

Marino, Nadia ;

Giofre, Salvatore V. ;

Gabriele, Bartolo .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08) :3506-3518

[26] RESISTANCE OF COMMON GROUNDSEL TO SIMAZINE AND ATRAZINE [J].

RYAN, GF .

WEED SCIENCE, 1970, 18 (05) :614-+

[27] Early senescence induced by 2-3H-benzoxazolinone (BOA) in Arabidopsis thaliana [J].

Sanchez-Moreiras, Adela M. ;

Martinez-Penalver, Ana ;

Reigosa, Manuel J. .

JOURNAL OF PLANT PHYSIOLOGY, 2011, 168 (09) :863-870

[28] PROTEIN-PHOSPHATASE INHIBITORS BLOCK ROOT HAIR-GROWTH AND ALTER CORTICAL CELL-SHAPE OF ARABIDOPSIS ROOTS [J].

SMITH, RD ;

WILSON, JE ;

WALKER, JC ;

BASKIN, TI .

PLANTA, 1994, 194 (04) :516-524

[29]

Streibig JC, 1998, PESTIC SCI, V53, P21, DOI 10.1002/(SICI)1096-9063(199805)53:1<21::AID-PS748>3.0.CO

[30]

2-L

← 1 2 3 4 →