Design, synthesis, and characterization of 2,2-bis(2,4-dinitrophenyl)-2-(phosphonatomethylamino)acetate as a herbicidal and biological active agent

Vijay Kumar; Simranjeet Singh; Rohit Singh; Niraj Upadhyay; Joginder Singh

doi:10.1007/s12154-017-0174-z

Design, synthesis, and characterization of 2,2-bis(2,4-dinitrophenyl)-2-(phosphonatomethylamino)acetate as a herbicidal and biological active agent

J Chem Biol. 2017 Jul 9;10(4):179-190. doi: 10.1007/s12154-017-0174-z. eCollection 2017 Oct.

Authors

Vijay Kumar^{1

2}, Simranjeet Singh³, Rohit Singh¹, Niraj Upadhyay⁴, Joginder Singh³

Affiliations

¹ Regional Ayurveda Research Institute for Drug Development, Gwalior, 474009 India.
² Government of India, Ministry of Agriculture, Regional Pesticides Testing Laboratory, Chandigarh, 160030 India.
³ Department of Biotechnology, Lovely Professional University, Phagwara, Punjab Pin-144002 India.
⁴ Department of Chemistry, Dr. Hari Singh Gour University, Sagar, Madhya Pradesh Pin-462007 India.

Abstract

The present study was designed to synthesize the bioactive molecule 2,2-bis(2,4-dinitrophenyl)-2-(phosphonatomethylamino)acetate (1), having excellent applications in the field of plant protection as a herbicide. Structure of newly synthesized molecule 1 was confirmed by using the elemental analysis, mass spectrometric, NMR, UV-visible, and FTIR spectroscopic techniques. To obtain better structural insights of molecule 1, 3D molecular modeling was performed using the GAMESS programme. Microbial activities of 1 were checked against the pathogenic strains Aspergillus fumigatus (NCIM 902) and Salmonella typhimurium (NCIM 2501). Molecule 1 has shown excellent activities against fungal strain A. fumigates (35 μg/l) and bacterial strain S. typhimurium (25 μg/l). To check the medicinal significance of molecule 1, interactions with bovine serum albumin (BSA) protein were checked. The calculated value of binding constant of molecule 1-BSA complex was 1.4 × 10⁶ M^-1, which were similar to most effective drugs like salicylic acid. More significantly, as compared to herbicide glyphosate, molecule 1 has exhibited excellent herbicidal activities, in pre- and post-experiments on three weeds; barnyard grass (Echinochloa Crus), red spranglitop (Leptochloa filiformis), and yellow nuts (Cyperus Esculenfus). Further, effects of molecule 1 on plant growth-promoting rhizobacterial (PGPR) strains were checked. More interestingly, as compared to glyphosate, molecule 1 has shown least adverse effects on soil PGPR strains including the Rhizobium leguminosarum (NCIM 2749), Pseudomonas fluorescens (NCIM 5096), and Pseudomonas putida (NCIM 2847).

Keywords: Biodegradation; Glyphosate; Herbicide; Inhibitory properties; L-fluoro-2,4-dinitrobenzene; PGPR strains.