Structure–Activity Studies of N-Heterocyclic Benzoyl Arylamine Derivatives Led to a Highly Fungicidal Candidate against Gaeumannomyces graminis var. tritici and Four Fusarium Wheat Pathogens

Abstract

Wheat root diseases can seriously reduce yields and quality of wheat. 1,2,4-Triazole benzoyl arylamine derivatives previously showed good activities against some wheat root fungal pathogens. To further systematically disclose the structure−activity relationship, a series of benzoyl arylamines were designed and prepared. Their structures were characterized and fungicidal activities against Gaeumannomyces graminis var. tritici and Fusarium graminearum were evaluated. The results indicated that the structure of the N-heterocyclic group and the substituted group and their position on the benzamide scaffold had an important influence on the activities, as predicted. Finally, compound 18f was found to show excellent activities against G. graminis var. tritici, F. graminearum, Fusarium culmorum, Fusarium pseudograminearum, and Fusarium moniliforme with half-maximum effective concentrations of 0.002, 0.093, 0.011, 0.881, and 0.287 μg/mL, respectively. These results proposed that compound 18f deserved serious consideration as a novel fungicide candidate for the control of wheat root diseases.

1,2,4‐Triazole benzamide derivative TPB against Gaeumannomyces graminis var. tritici as a novel dual‐target fungicide inhibiting ergosterol synthesis and adenine nucleotide transferase function

“…As expected, 1,2,4-triazole benzoyl arylamine derivatives showed good activities against a variety of pathogens, including Ggt, Fusarium graminearum and Sclerotinia sclerotiorum. [7][8][9] Moreover, TPB showed the greatest antifungal activity among these compounds, with a median effect concentration (EC 50 ) value of only 0.01 ⊘g mL −1 against Ggt, which was superior to the current major commercial fungicides (EC 50 s of tebuconazole and silthiofam against the provided pathogen were 0.13 ⊘g mL −1 and 21.30 ⊘g mL −1 , respectively). 8 TPB was a promising candidate for fungicide, however its antifungal mechanism against Ggt needed to be confirmed.…”

“…1) designed by Henan Agricultural University. [7][8][9] It was a family of 1,2,4-triazole benzoyl arylamine derivatives, containing two key moieties: benzamide and 1,2,4-triazole. Aryl formamide derivatives had a wide range of biological activities, including antifungal, antiviral, insecticidal and herbicidal.…”

“…In addition, the mitochondria of mycelia swelled significantly, mitochondrial membrane dissolved and was destroyed, and cristae were broken and reduced. 7 Therefore, we speculated that TPB exerted its antifungal effect on Ggt by acting on the biomembrane and mitochondria.…”

Antifungal activity of Ligusticum chuanxiong essential oil and its active composition butylidenephthalide against Sclerotium rolfsii

“…[21][22][23][24] It is worth noting that the chemical structures modified on the lead compounds and the functional groups attached to them also can affect the bioactivity. 25,26 Therefore, the exploration of highly active plant-derived compounds is crucial for the discovery of lead compounds and the subsequent development of new pesticides. This process allows for the identification and utilization of potent natural compounds as a foundation for the development of innovative pesticide solutions.…”

“…For example, fungicides Yinguo (2‐allyl phenol) and Yintai (4‐butanoyl phenol), flumorph and Xiangcaoliusuobingmi were created based on ginkgo phenol, cinnamic acid and vanillin as lead compound, respectively 21–24 . It is worth noting that the chemical structures modified on the lead compounds and the functional groups attached to them also can affect the bioactivity 25,26 . Therefore, the exploration of highly active plant‐derived compounds is crucial for the discovery of lead compounds and the subsequent development of new pesticides.…”