Abstract
Plant fungal diseases severely threaten global crop production. To develop novel antifungal agents, we designed and synthesized a series of novel ternary aromatic (heterocyclic) thione/thioether derivatives and evaluated their antifungal activity. Most of these compounds exhibited excellent antifungal activity in vitro against Sclerotinia sclerotiorum and Rhizoctonia cerealis . In particular, compounds C3, C7, C8, and C11 exhibited remarkable antifungal activity against S. sclerotiorum, with median effective concentration (EC 50 ) values of 0.479, 0.476, 0.240, and 0.390 μg/mL, respectively, which were more potent than that of the positive control carbendazim (0.586 μg/mL). A further in vivo test confirmed that compound C8 possessed better protective efficacy (78.3%) than carbendazim (58.8%) at 200 μg/mL. The 3D-QSAR model highlighted the dominant role of steric effects on the antifungal activity. Further studies revealed that compound C8 is phloem-mobile, rapidly translocates to roots, and strongly inhibits sclerotial formation. In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha. This study demonstrates that compound C8 has potential as an efficient phloem-mobile fungicide.
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Claims 11
Claim · model-written summary
Compound C3 had an EC50 of 0.479 μg/mL against S. sclerotiorum, more potent than carbendazim (0.586 μg/mL).
- Taxon
- rape
_Brassica_napus_-_Habit.jpg?width=60)
Brassica napuse5 - Treatment
- C3e1
- Interactor
- S. sclerotiorum
Sclerotinia sclerotiorume1pathogen - Outcome
- median effective concentration (EC 50 ) valuese1
- Direction
- more potente1
- Value
- 0.479e1
- Qualifier
- 0.586 μg/mLe1
- Comparator
- carbendazime1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
_Brassica_napus_-_Habit.jpg?width=500)
Verbatim
e1“compounds C3, C7, C8, and C11 exhibited remarkable antifungal activity against S. sclerotiorum, with median effective concentration (EC 50 ) values of 0.479, 0.476, 0.240, and 0.390 μg/mL, respectively, which were more potent than that of the positive control carbendazim (0.586 μg/mL)”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
Compound C7 had an EC50 of 0.476 μg/mL against S. sclerotiorum, more potent than carbendazim (0.586 μg/mL).
- Taxon
- rapeBrassica napuse5
- Treatment
- C7e1
- Interactor
- S. sclerotiorumSclerotinia sclerotiorume1pathogen
- Outcome
- median effective concentration (EC 50 ) valuese1
- Direction
- more potente1
- Value
- 0.476e1
- Qualifier
- 0.586 μg/mLe1
- Comparator
- carbendazime1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e1“compounds C3, C7, C8, and C11 exhibited remarkable antifungal activity against S. sclerotiorum, with median effective concentration (EC 50 ) values of 0.479, 0.476, 0.240, and 0.390 μg/mL, respectively, which were more potent than that of the positive control carbendazim (0.586 μg/mL)”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
Compound C8 had an EC50 of 0.240 μg/mL against S. sclerotiorum, more potent than carbendazim (0.586 μg/mL).
- Taxon
- rapeBrassica napuse5
- Treatment
- C8e1
- Interactor
- S. sclerotiorumSclerotinia sclerotiorume1pathogen
- Outcome
- median effective concentration (EC 50 ) valuese1
- Direction
- more potente1
- Value
- 0.240e1
- Qualifier
- 0.586 μg/mLe1
- Comparator
- carbendazime1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e1“compounds C3, C7, C8, and C11 exhibited remarkable antifungal activity against S. sclerotiorum, with median effective concentration (EC 50 ) values of 0.479, 0.476, 0.240, and 0.390 μg/mL, respectively, which were more potent than that of the positive control carbendazim (0.586 μg/mL)”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
Compound C11 had an EC50 of 0.390 μg/mL against S. sclerotiorum, more potent than carbendazim (0.586 μg/mL).
- Taxon
- rapeBrassica napuse5
- Treatment
- C11e1
- Interactor
- S. sclerotiorumSclerotinia sclerotiorume1pathogen
- Outcome
- median effective concentration (EC 50 ) valuese1
- Direction
- more potente1
- Value
- 0.390e1
- Qualifier
- 0.586 μg/mLe1
- Comparator
- carbendazime1
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e1“compounds C3, C7, C8, and C11 exhibited remarkable antifungal activity against S. sclerotiorum, with median effective concentration (EC 50 ) values of 0.479, 0.476, 0.240, and 0.390 μg/mL, respectively, which were more potent than that of the positive control carbendazim (0.586 μg/mL)”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
In vivo, compound C8 gave better protective efficacy (78.3%) than carbendazim at 200 μg/mL.
- Taxon
- rapeBrassica napuse5
- Treatment
- compound C8e2
- Outcome
- protective efficacye2
- Direction
- bettere2
- Value
- 78.3%e2
- Qualifier
- 200 μg/mLe2
- Comparator
- carbendazime2
- Setting
- in vivo teste2
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e2“A further in vivo test confirmed that compound C8 possessed better protective efficacy (78.3%) than carbendazim (58.8%) at 200 μg/mL”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
Most of the ternary thione/thioether derivatives showed excellent in vitro antifungal activity against Sclerotinia sclerotiorum and Rhizoctonia cerealis.
- Taxon
- rapeBrassica napuse5
- Interactor
- Sclerotinia sclerotiorumSclerotinia sclerotiorume0pathogen
- Second interactor
- Rhizoctonia cerealis
Ceratobasidium cerealee0pathogen - Outcome
- antifungal activity in vitroe0
- Qualifier
- excellente0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Most of these compounds exhibited excellent antifungal activity in vitro against Sclerotinia sclerotiorum and Rhizoctonia cerealis”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
The 3D-QSAR model indicates that steric effects play a dominant role in the antifungal activity.
- Taxon
- rapeBrassica napuse5
- Outcome
- antifungal activitye3
- Qualifier
- dominant role of steric effectse3
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e3“The 3D-QSAR model highlighted the dominant role of steric effects on the antifungal activity”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
Compound C8 is phloem-mobile.
- Taxon
- rapeBrassica napuse5
- Outcome
- phloem-mobilee4
Not reportedDirection
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e4“compound C8 is phloem-mobile, rapidly translocates to roots, and strongly inhibits sclerotial formation”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
Compound C8 rapidly translocates to roots.
- Taxon
- rapeBrassica napuse5
- Outcome
- translocates to rootse4
- Qualifier
- rapidlye4
Not reportedDirection
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e4“compound C8 is phloem-mobile, rapidly translocates to roots, and strongly inhibits sclerotial formation”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
Claim · model-written summary
Compound C8 strongly inhibits sclerotial formation of Sclerotinia sclerotiorum.
- Taxon
- rapeBrassica napuse5
- Interactor
- Sclerotinia sclerotiorumSclerotinia sclerotiorume0pathogen
- Outcome
- sclerotial formatione4
- Qualifier
- strongly inhibitse4
Not reportedDirection
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e4“compound C8 is phloem-mobile, rapidly translocates to roots, and strongly inhibits sclerotial formation”
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”
e0“Most of these compounds exhibited excellent antifungal activity in vitro against Sclerotinia sclerotiorum and Rhizoctonia cerealis”
Claim · model-written summary
In field trials, compound C8 gave significantly better control efficacy (64.9%) against rape sclerotinia stem rot than carbendazim (45.5%) at 750 g a.i./ha.
- Taxon
- rapeBrassica napuse5
- Treatment
- compound C8e5
- Interactor
- sclerotinia
Sclerotiniae5pathogen - Outcome
- control efficacye5
- Direction
- significantly bettere5
- Value
- 64.9%e5
- Qualifier
- 750 g a.i./hae5
- Comparator
- carbendazime5
- Setting
- field trialse5
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e5“In field trials, compound C8 provided significantly better control efficacy against rape sclerotinia stem rot (64.9%) than carbendazim (45.5%) at 750 g a.i./ha”