Discovery of New Benzohydrazide Derivatives Containing 4-Aminoquinazoline as Effective Agricultural Fungicides, the Related Mechanistic Study, and Safety Assessment
Journal of Agricultural and Food Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 23, 2025
A
total
of
38
new
benzohydrazide
derivatives
bearing
the
4-aminoquinazoline
moiety
were
designed
and
synthesized
based
on
active
subunit
combination
approach
tested
in
detail
for
their
inhibition
activities
against
eight
agricultural
phytopathogenic
fungi.
The
bioassay
results
indicated
that
many
compounds
exhibited
extraordinary
fungicidal
vitro
For
example,
A5,
A6,
A11,
A17
had
EC50
(half-maximal
effective
concentration)
values
0.66,
0.71,
0.40,
0.42
μg/mL
Colletotrichum
gloeosporioides,
respectively,
comparable
to
boscalid
(0.36
μg/mL)
much
superior
carbendazim
(6.96
μg/mL).
Of
particular
importance
was
compound
A6
with
a
3,4-difluorophenyl
group
found
possess
good
broad-spectrum
antifungal
effects,
ranging
from
0.63
3.82
In
vivo
assays
also
revealed
curative
protective
efficacies
72.6%
78.9%
at
200
Rhizoctonia
solani-caused
rice
sheath
blight,
higher
than
those
(70.7
65.2%,
respectively).
Moreover,
mechanism-of-action
studies
disrupted
cell
membrane
integrity
R.
solani,
as
proved
by
relative
conductivity
measurements,
leakage
cellular
contents,
fluorescence
microscopy,
scanning
electron
microscopy
observations.
Significantly,
this
an
succinate
dehydrogenase
(SDH)
solani
inhibitory
concentration/IC50
=
11.02
μM),
slightly
weaker
SDH
inhibitor
(5.17
μM).
Further
molecular
docking
analysis
could
form
strong
interactions
key
residues
enzyme
via
hydrogen
bond,
electrostatic,
π-cation
interactions,
holding
promise
acting
fungicide
leads
targeting
SDH.
Finally,
safety
assessments
safe
honeybees.
Язык: Английский
Design, synthesis, crystal structure, fungicidal activity, and mechanism of action of novel thiazole-based hydrazide derivatives containing the 4-aminoquinazoline moiety
Bioorganic Chemistry,
Год журнала:
2025,
Номер
156, С. 108237 - 108237
Опубликована: Фев. 2, 2025
Язык: Английский
Design, Synthesis, Antifungal Evaluation, and Action Mechanism of Novel l-Carvone-Based Derivatives as Potential Succinate Dehydrogenase Inhibitors
Journal of Agricultural and Food Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 16, 2025
Natural
products
serve
as
a
crucial
source
of
compounds
for
developing
novel
agricultural
antifungals.
In
this
work,
we
utilized
the
natural
product
l-carvone
molecular
scaffold
to
design
and
synthesize
three
series
l-carvone-based
derivatives.
The
in
vitro
bioassay
results
indicated
that
most
target
exhibited
remarkable
antifungal
activity.
Notably,
compound
C3
demonstrated
broad-spectrum
activity
against
Rhizoctonia
solani,
Botrytis
cinerea,
Sclerotinia
sclerotiorum,
Gibberella
zeae,
Valsa
mali,
with
EC50
values
0.274,
0.985,
4.17,
5.71,
2.29
μg/mL,
respectively.
vivo
preventative
efficacies
C11
R.
solani
C13
B.
cinerea
revealed
they
had
potential
mechanism
study,
cell
membrane
permeability
experiment
showed
significantly
increased
membrane,
microscopic
observations
could
destroy
structural
integrity
cells
reduce
number
mitochondria,
thus
affecting
normal
growth
mycelia.
Furthermore,
mitochondrial
detection,
succinate
dehydrogenase
(SDH)
enzyme
assay,
dynamics
(MD)
simulations,
docking
experiments
further
action
binding
mode
SDH
may
be
similar
those
thifluzamide.
abovementioned
provided
valuable
reference
discovery
inhibitor
fungicides.
Язык: Английский
Development and Biological Evaluation of New Diphenyl Ether Formylhydrazide Compounds as Potent Inhibitors of Succinate Dehydrogenase
Journal of Agricultural and Food Chemistry,
Год журнала:
2024,
Номер
72(47), С. 26133 - 26141
Опубликована: Ноя. 14, 2024
Succinate
dehydrogenase
(SDH),
also
recognized
as
succinate
ubiquinone
oxidoreductase
(SQR),
is
considered
one
of
the
most
promising
targets
for
fungicide
development,
garnering
significant
international
interest.
We
have
focused
on
development
highly
effective,
broad-spectrum-targeted
SDH
inhibitors.
Using
an
active
scaffold
combining
strategy,
we
designed
and
synthesized
a
series
novel
diphenyl
ether
formylhydrazine
derivatives,
compounds
demonstrated
broad-spectrum
antifungal
activity.
Notably,
compound
Язык: Английский