Abstract
Abstract BACKGROUND Succinate dehydrogenase inhibitor (SDHI) fungicides have been widely utilized in the combat of plant pathogenic fungi due to their potent, broad‐spectrum antifungal activity and unique mode of action. In this study, a series of novel 4‐sulfur‐substituted pyrazol‐5‐yl‐benzamide derivatives containing amide, hydrazide, or ester moieties were synthesized to develop innovative SDH inhibitors. RESULTS The bioassay studies indicated that several compounds exhibited potent in vitro fungicidal activity against various fungi. Particularly, compound 4d demonstrated broad‐spectrum fungicidal efficacy, with EC 50 values of 0.21, 0.95, 0.64, 1.33, and 0.66 mg L −1 against Valsa mali , Botrytis cinerea , Rhizoctonia solani , Fusarium graminearum , and Gaeumannomyces graminis , respectively. In vivo studies demonstrated that compound 4d effectively prevented V. mali infection in apples at 50 mg L −1 , showing superior protective and curative effects (93.4% and 85.5%) compared to lead compound A27 (68.7% and 57.0%) and commercial fungicide fluxapyroxad (55.4% and 43.6%). Enzymatic inhibition assays and molecular docking analysis suggested that compound 4d could serve as a potential SDH inhibitor. CONCLUSION This study offers valuable insights for expanding the fungicidal spectrum of pyrazol‐5‐yl‐benzamide derivatives and further developing them as novel SDH inhibitors. © 2025 Society of Chemical Industry.
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Claims 10
Claim · model-written summary
Compound 4d had an in vitro EC50 of 0.21 mg/L against Valsa mali.
- Taxon
- Valsa maliCytospora malie1
- Outcome
- EC 50 valuese0
- Value
- 0.21e0
Verbatim
e0“EC 50 values of 0.21, 0.95, 0.64, 1.33, and 0.66 mg L”
e1“against Valsa mali , Botrytis cinerea , Rhizoctonia solani , Fusarium graminearum , and Gaeumannomyces graminis”
Claim · model-written summary
Compound 4d had an in vitro EC50 of 0.95 mg/L against Botrytis cinerea.
- Taxon
- Botrytis cinerea
Botrytis cinereae1 - Outcome
- EC 50 valuese0
- Value
- 0.95e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“EC 50 values of 0.21, 0.95, 0.64, 1.33, and 0.66 mg L”
e1“against Valsa mali , Botrytis cinerea , Rhizoctonia solani , Fusarium graminearum , and Gaeumannomyces graminis”
Claim · model-written summary
Compound 4d had an in vitro EC50 of 0.64 mg/L against Rhizoctonia solani.
- Taxon
- Rhizoctonia solani
Rhizoctonia solanie1 - Outcome
- EC 50 valuese0
- Value
- 0.64e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“EC 50 values of 0.21, 0.95, 0.64, 1.33, and 0.66 mg L”
e1“against Valsa mali , Botrytis cinerea , Rhizoctonia solani , Fusarium graminearum , and Gaeumannomyces graminis”
Claim · model-written summary
Compound 4d had an in vitro EC50 of 1.33 mg/L against Fusarium graminearum.
- Taxon
- Fusarium graminearum
_on_Corn_(Zea_mays)_at_Waimea%2C_Hawaii.jpg?width=60)
Fusarium graminearume1 - Outcome
- EC 50 valuese0
- Value
- 1.33e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
_on_Corn_(Zea_mays)_at_Waimea%2C_Hawaii.jpg?width=500)
Verbatim
e0“EC 50 values of 0.21, 0.95, 0.64, 1.33, and 0.66 mg L”
e1“against Valsa mali , Botrytis cinerea , Rhizoctonia solani , Fusarium graminearum , and Gaeumannomyces graminis”
Claim · model-written summary
Compound 4d had an in vitro EC50 of 0.66 mg/L against Gaeumannomyces graminis.
- Taxon
- Gaeumannomyces graminis
Gaeumannomyces graminise1 - Outcome
- EC 50 valuese0
- Value
- 0.66e0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“EC 50 values of 0.21, 0.95, 0.64, 1.33, and 0.66 mg L”
e1“against Valsa mali , Botrytis cinerea , Rhizoctonia solani , Fusarium graminearum , and Gaeumannomyces graminis”
Claim · model-written summary
Compound 4d gave a protective effect of 93.4% against V. mali infection in apples, versus 68.7% for lead compound A27.
- Taxon
- apples
Malus domesticae0 - Treatment
- compound 4de0
- Interactor
- V. maliCytospora malie0pathogen
- Outcome
- protectivee1
- Direction
- superiore1
- Value
- 93.4%e1
- Qualifier
- 68.7%e1
- Comparator
- lead compound A27e1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“compound 4d effectively prevented V. mali infection in apples”
e1“showing superior protective and curative effects (93.4% and 85.5%) compared to lead compound A27 (68.7% and 57.0%) and commercial fungicide fluxapyroxad (55.4% and 43.6%)”
Claim · model-written summary
Compound 4d gave a curative effect of 85.5% against V. mali infection in apples, versus 57.0% for lead compound A27.
- Taxon
- applesMalus domesticae0
- Treatment
- compound 4de0
- Interactor
- V. maliCytospora malie0pathogen
- Outcome
- curative effectse1
- Direction
- superiore1
- Value
- 85.5%e1
- Qualifier
- 57.0%e1
- Comparator
- lead compound A27e1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“compound 4d effectively prevented V. mali infection in apples”
e1“showing superior protective and curative effects (93.4% and 85.5%) compared to lead compound A27 (68.7% and 57.0%) and commercial fungicide fluxapyroxad (55.4% and 43.6%)”
Claim · model-written summary
Compound 4d gave a protective effect of 93.4% against V. mali infection in apples, versus 55.4% for fluxapyroxad.
- Taxon
- applesMalus domesticae0
- Treatment
- compound 4de0
- Interactor
- V. maliCytospora malie0pathogen
- Outcome
- protectivee1
- Direction
- superiore1
- Value
- 93.4%e1
- Qualifier
- 55.4%e1
- Comparator
- commercial fungicide fluxapyroxade1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“compound 4d effectively prevented V. mali infection in apples”
e1“showing superior protective and curative effects (93.4% and 85.5%) compared to lead compound A27 (68.7% and 57.0%) and commercial fungicide fluxapyroxad (55.4% and 43.6%)”
Claim · model-written summary
Compound 4d gave a curative effect of 85.5% against V. mali infection in apples, versus 43.6% for fluxapyroxad.
- Taxon
- applesMalus domesticae0
- Treatment
- compound 4de0
- Interactor
- V. maliCytospora malie0pathogen
- Outcome
- curative effectse1
- Direction
- superiore1
- Value
- 85.5%e1
- Qualifier
- 43.6%e1
- Comparator
- commercial fungicide fluxapyroxade1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“compound 4d effectively prevented V. mali infection in apples”
e1“showing superior protective and curative effects (93.4% and 85.5%) compared to lead compound A27 (68.7% and 57.0%) and commercial fungicide fluxapyroxad (55.4% and 43.6%)”
Claim · model-written summary
Enzymatic inhibition assays and molecular docking suggested that compound 4d could serve as a potential SDH inhibitor.
Not reportedTaxon
Verbatim
e0“Enzymatic inhibition assays and molecular docking analysis suggested that compound 4d could serve as a potential SDH inhibitor”