Pest management science · 2026
Inspired by norbornylene: design, synthesis, antifungal activity, and mechanism of action of novel stereoisomeric dicarboximide fungicides.
СтатьяНазвание и аннотация: Перевод в очереди
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Chen Yao, Ren Zili, Liu Jun, Yao Mengyuan, Zhao Rui, Li Haoran, Gao Quan, Cao Haiqun, Wang Jiawang
Аннотация
BACKGROUND: Bridged bicyclic systems, characterized by their distinctive three-dimensional topology and inherent ring strain, confer unique spatial configurations and chemical reactivity. Increasing the molecular three-dimensionality and the fraction of sp3-hybridized carbon atoms (Csp3) in lead compounds enhances drug-like behavior. In particular, the norbornene scaffold-an archetypal bridged bicyclic framework-offers significant potential for pesticide optimization by enhancing bioactivity.
RESULTS: We designed and synthesized 54 novel stereoisomeric derivatives containing norbornene and evaluated their antifungal activity. The bioassay results showed that most of the target compounds possessed great in vitro antifungal activity against a wide range of plant pathogenic fungi. For example, half-maximal effective concentration (EC50) = 0.31 mg/L of compound Y15 against Botrytis cinerea was comparable with that of the commercially available drug dimethachlon (EC50 = 0.37 mg/L), and 150.8-fold higher than norbornene (EC50 = 46.74 mg/L). In addition Y15 showed great aquatic biosafety, with an acute toxicity half-maximal lethal concentration (LC50) > 80.0 mg/L to zebrafish 48 h (superior to dimethachlon (LC50 = 11.90 mg/L)). RNA sequencing and quantitative reverse transcription polymerase chain reaction experiments showed that compound Y15 affected a large number of differentially expressed genes related to carbohydrate metabolism, oxidoreductase activity and membrane composition, and had a relatively large number of genes involved in microbial metabolic activity and the biosynthesis of secondary metabolites.
CONCLUSION: We reported a series of novel dicarboximide fungicides containing a bridging ring structure that provided a new basis for the molecular design and mechanistic study of stereoisomeric fungicides. © 2026 Society of Chemical Industry.
RESULTS: We designed and synthesized 54 novel stereoisomeric derivatives containing norbornene and evaluated their antifungal activity. The bioassay results showed that most of the target compounds possessed great in vitro antifungal activity against a wide range of plant pathogenic fungi. For example, half-maximal effective concentration (EC50) = 0.31 mg/L of compound Y15 against Botrytis cinerea was comparable with that of the commercially available drug dimethachlon (EC50 = 0.37 mg/L), and 150.8-fold higher than norbornene (EC50 = 46.74 mg/L). In addition Y15 showed great aquatic biosafety, with an acute toxicity half-maximal lethal concentration (LC50) > 80.0 mg/L to zebrafish 48 h (superior to dimethachlon (LC50 = 11.90 mg/L)). RNA sequencing and quantitative reverse transcription polymerase chain reaction experiments showed that compound Y15 affected a large number of differentially expressed genes related to carbohydrate metabolism, oxidoreductase activity and membrane composition, and had a relatively large number of genes involved in microbial metabolic activity and the biosynthesis of secondary metabolites.
CONCLUSION: We reported a series of novel dicarboximide fungicides containing a bridging ring structure that provided a new basis for the molecular design and mechanistic study of stereoisomeric fungicides. © 2026 Society of Chemical Industry.