Systematic Study on Turpentine-Derived Amides from Natural Plant Monoterpenes as Potential Antifungal Candidates

Abstract

To overcome the high volatility, low aqueous solubility, and few definite action sites of monoterpenoid pesticides and improve their properties and effectiveness in the control of crop pathogenic fungi, herein, a series of natural turpentine-based amide derivatives exhibiting satisfactory antifungal activity were designed and synthesized. A systematic study was conducted on antifungal activity and the physiological and biochemical response of compounds 5o (EC50 = 1.139 μg/mL) and 5j (EC50 = 1.762 μg/mL) against Rhizoctonia solani. The effect of the target compound on the potential target-site succinate dehydrogenase was evaluated. The soluble concentrates of compounds 5o and 5j possessing good performance and control effects were prepared for practical application. To conduct a comprehensive analysis of the relationship between structural descriptors and activity, four representative title compounds were selected for theoretical calculation: 5o, 5j, 5k, and 5j. The binding mode of compound 5o and boscalid with succinate dehydrogenase was analyzed via molecular docking. This study provides a reference for the development of monoterpene pesticides with high efficiency, elucidated target sites, and the appropriate formula.

Design, Synthesis and Antifungal Activity of Nootkatone Derivatives Containing Acylhydrazone and Oxime Ester

“…Antifungal activities assay in vitro: 53 nootkatone derivatives were screened in vitro for their antifungal activities against four phytopathogenic fungi by the mycelial growth inhibitory rate method according to previously reported approaches. [23][24][25][26] Four phytopathogenic fungi such as F. graminearum, P. parasitica, F. oxysporum, P. sp. were used for the assays.…”

Design, synthesis, and mechanism study of novel 1-arylisoquinoline derivatives as antifungal agents

“…N- (2)(3)(4)(5)(6) 4.26 (q, J = 3.0, 2.6 Hz, 2H), 3.82 (s, 1H), 3.81 (d, J = 2.7 Hz, 6H), 3.61 (td, J = 6.0, 2.0 Hz, 1H), 2.81 3(t, J = 5.9 Hz, 1H), 2.75 (t, J = 6.0 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 166.…”

“…The natural-based or -derived compounds have attracted increasing attention as potential candidates to develop "green" agrochemicals due to their extensive biological properties, multiple modes of action and environment friendly [5]. Tetrahydroisoquinoline alkaloids (THIQs) are a kind of natural products with a common tetrahydroisoquinoline motif and widely exist in the Papaveraceae family and some members of the Rutaceae family [6][7].…”

“…Amide is an important classic structural motif in agrochemicals and natural products, often serving as a linking bridge to introduce active pharmacophores for the development of novel pesticides [12]. Valine carbamate fungicides, categorized as amino acid fungicides, feature a double amide bridge chain in their structure, which provides good environmental compatibility [13].…”

Design, Synthesis, Antifungal Evaluation, Structure–Activity Relationship (SAR) Study, and Molecular Docking of Novel Spirotryprostatin A Derivatives

“…Chemical fungicides are traditionally used to control these phytopathogenic fungi. However, the improper use of fungicides can lead to disease resistance and an ecological burden [ 2 ]. Consequently, developing novel antifungal agrochemicals that are harmless to humans or animals and safe for the ecological environment is an urgent demand.…”