Synthesis, Herbicidal Activities, and 3D-QSAR of 2-Cyanoacrylates Containing Aromatic Methylamine Moieties

Abstract

A series of novel 2-cyanoacrylates containing different aromatic rings were synthesized, and their structures were characterized by (1)H NMR, elemental analysis, and single-crystal X-ray diffraction analysis. Their herbicidal activities against four weeds and inhibition of photosynthetic electron transport against isolated chloroplasts (the Hill reaction) were evaluated. Both in vivo and in vitro data showed that the compounds containing benzene, pyridine, and thiazole moieties gave higher activities than those containing pyrimidine, pyridazine, furan, and tetrahedronfuran moieties. To further explore the comprehensive structure-activity relationship on the basis of in vitro data, comparative molecular field analysis (CoMFA) was performed, and the results showed that a bulky and electronegative group around the para-position of the aromatic rings would have the potential for higher activity, which offered important structural insights into designing highly active compounds prior to the next synthesis.

Resistance mechanism of Fusarium fujikuroi to phenamacril in the field

“…), developed by Jiangsu Pesticide Research Institute Co. Ltd (Nanjing, China), is the first identified member of a new chemical group, classified B6 by the Fungicide Resistance Action Committee (FRAC; http://www.frac.info). Many cyanoacrylates exhibit excellent activity against insect pests, weeds, fungal pathogens, viruses and cancer . Moreover, cyanoacrylate not only has a novel mode of action but is also considered to be environmentally safe .…”

“…Many cyanoacrylates exhibit excellent activity against insect pests, weeds, fungal pathogens, viruses and cancer. [8][9][10][11] Moreover, cyanoacrylate not only has a novel mode of action but is also considered to be environmentally safe. 12 In China, phenamacril was temporarily registered in 2007 and formally registered in 2012 for controlling rice bakanae disease by seed dressing and Fusarium head blight (FHB) of wheat by spraying.…”

Synthesis, crystal structure, herbicidal activities and 3D-QSAR study of some novel 1,2,4-triazolo[4,3-a ]pyridine derivatives

“…Pyridine derivatives have also displayed various biological activities . Many commercial herbicides contain a pyridine ring, for example diflufenzopyr, dithiopyr and fluropyr.…”

Synthesis, characterization and targeted cell imaging applications of poly(p-phenylene)s with amino and poly(ethylene glycol) substituents

“…[53][54][55][56][57][58][59][60] To obtain primary alkyl halide, starting material was chosen as 2,5-dibromotoluene as it can readily react with N-bromosuccinimide (NBS) to afford allylic bromination of methyl group of toluene in the presence of peroxide. Suzuki coupling reaction providing more straightforward access to obtain polymer with changeable sequence ratio between amino functional and PEG monomers was used to adjust the higher contribution of amino monomer than PEG macromonomer to PPP structure.…”