Triazolyl phenyl disulfides: 8-Amino-7-oxononanoate synthase inhibitors as potential herbicides

• Published in: Pesticide biochemistry and physiology Vol. 125; pp. 78 - 83
• Main Authors: Hahn, Hoh-Gyu, Choi, Jung-Sup, Lim, Hee Kyung, Lee, Kee-In, Hwang, In Taek
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01.11.2015
• Subjects: 8-Amino-7-oxononanoate synthase (AONS); Acyltransferases - antagonists & inhibitors; Acyltransferases - metabolism; Arabidopsis - drug effects; Arabidopsis - enzymology; Arabidopsis Proteins - antagonists & inhibitors; Arabidopsis Proteins - metabolism; Disulfides - chemical synthesis; Disulfides - chemistry; Disulfides - pharmacology; Herbicide; Herbicides - chemical synthesis; Herbicides - chemistry; Herbicides - pharmacology; l-Alanine; Molecular Structure; Recover; Target enzyme; Triazoles - chemical synthesis; Triazoles - chemistry; Triazoles - pharmacology; Triazolyl phenyl disulfide; 8-Amino-7-oxononanoate synthase (AONS); Triazolyl phenyl disulfide; l-Alanine; Recover; Target enzyme; Herbicide
• ISSN: 0048-3575; 1095-9939
• DOI: 10.1016/j.pestbp.2015.05.006

The chemical validation of a potential herbicide target was investigated with 8-amino-7-oxononanoate synthase (AONS, also known as 7-keto-8-aminopelargonate synthase, KAPAS) and triazolyl phenyl disulfide derivatives in vitro and in vivo. AONS activity was completely inhibited by these synthesized compounds, with an IC50 of 48 to 592μM in vitro. Forty five-day old Arabidopsis thaliana plants were completely killed by representative compound KHG23844 {N-(2-fluorophenyl)-3-(phenyldisulphanyl)-1H-1,2,4-triazole-1-carboxamide} at the application rate of 250gha−1 of foliar treatment in greenhouse conditions. Foliar application of 1000gha−1 KHG23844 induced 2.3-fold higher l-alanine accumulation in the treated A. thaliana plants. Foliar supplement of 1mM biotin at 1 and 2days before KHG23844 application effectively recovered the growth inhibition of A. thaliana plant treated with KHG23844. The results strongly suggested that representative compound KHG23844 and its derivatives are potential AONS inhibitors. [Display omitted] •We synthesized new 468 triazolyl phenyl disulfide compounds.•Chemical validation was investigated with 8-amino-7-oxononanoate synthase.•Target inhibition in vitro and herbicidal activity in vivo was confirmed.•l-Alanine accumulation and recovery effect by biotin supplement was identified.