Novel Naphthyl and Phenyl Maleimide Derivatives: Molecular Design, Systematic Optimization, Antifungal Evaluation, and Action Mechanism
Journal of Agricultural and Food Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 29, 2025
A
systematic
optimization
strategy,
as
an
effective
screening
approach
for
new
antifungal
compounds,
was
implemented
to
rationally
construct
novel
naphthyl
and
phenyl
maleimide
derivatives.
The
structures
of
molecules
A32
B6
were
further
confirmed
by
single-crystal
X-ray
diffraction.
in
vitro
activity
evaluation
showed
that
the
target
compound
obtained
structure
exhibited
excellent
inhibition
(EC50
=
0.59
μg/mL)
against
Rhizoctonia
solani,
which
better
than
control
agent
dimethachlone
(1.21
μg/mL).
Further
vivo
experiments
on
rice
leaves
potted
plants
R.
solani
at
200
μg/mL
possessed
outstanding
protective
efficiency
compared
dimethachlone.
mycelium
morphology
observation
SEM
indicated
(25
severely
damaged
surface
mycelium,
accordance
with
increased
result
cell
membrane
permeability
assay.
MD
simulations
molecular
docking
analysis
revealed
compounds
A1
have
a
similar
binding
mode
active
pocket
plasma
H+-ATPases
(PMA1)
reference
fungicide
fluoroimide.
In
particular,
there
more
hydrogen
bonds
protein
complex
complexes
This
research
constructing
derivatives
strategy
provides
practical
way
find
leads,
thereby
developing
fungicides.
Язык: Английский
Citral‐based amide derivatives improve the antifungal activity of Kresoxim‐methyl against Rhizoctonia solani
Pest Management Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 26, 2025
Abstract
BACKGROUND
Rhizoctonia
solani
,
the
fungal
pathogen
causing
rice
sheath
blight,
threatens
global
food
security.
Prolonged
use
of
Kresoxim‐methyl
(KM),
a
common
fungicide,
has
led
to
resistance
and
reduced
effectiveness.
This
study
investigates
synergistic
effects
citral‐based
amide
derivatives
with
KM
explains
underlying
mechanisms.
RESULT
Among
tested
derivatives,
compound
d25
exhibited
most
pronounced
effect,
achieving
peak
ratio
(SR
=
2.66
±
0.67)
at
molar
25%
in
mixture.
At
10%,
mixture
(Mix)
demonstrated
significant
antifungal
activity
both
vitro
vivo
effectively
reducing
mycelial
dry
weight
enhancing
leaf
protection.
Mechanistic
studies
revealed
that
Mix
disrupted
tricarboxylic
acid
(TCA)
cycle,
thereby
inhibiting
energy
metabolism.
Additionally,
interfered
arachidonic
metabolism,
impairing
cell
membrane
repair
mechanisms
fungicidal
efficacy
KM.
Toxicity
assessments
minimal
cytotoxicity
against
human
lines
low
acute
toxicity
toward
Apis
mellifera
L.
zebrafish.
CONCLUSION
The
findings
elucidate
Mix,
underscoring
their
potential
as
effective
fungicide
synergists.
establishes
robust
theoretical
practical
foundation
for
chemical
control
strategies
R.
providing
new
insights
into
development
safe
efficient
formulations.
©
2025
Society
Chemical
Industry.
Язык: Английский
Structural optimization of SDH‐targeting chalcone derivatives: piperazine‐driven binding stability against Xanthomonas pathogens
Tianyu Deng,
Kaini Meng,
Hong Fu
и другие.
Pest Management Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 29, 2025
Abstract
BACKGROUND
Natural
green
pesticides
have
become
a
global
research
hotspot,
and
identifying
chemical
structural
frameworks
with
excellent
biological
activity
has
the
direction
of
numerous
researchers.
RESULTS
Twenty
chalcone
derivatives
incorporating
1,2,3,4‐tetrahydroquinoline
scaffolds
were
systematically
evaluated
for
their
antibacterial
against
six
plant
pathogenic
bacteria.
Among
tested
compounds,
H1–H10
exhibited
superior
in
vitro
inhibition
Xanthomonas
citri
pv.
mangiferaeindicae
(
Xcm
)
compared
to
Y1–Y10.
Notably,
compound
H6
demonstrated
exceptional
potency,
median
effective
concentration
(EC
50
value
3.25
μg
mL
−1
,
significantly
surpassing
commercial
agent
(TC,
EC
=
75.34
).
In
vivo
efficacy
trials
revealed
that
achieved
65.24%
curative
at
100
outperforming
TC
(42.81%).
Scanning
electron
microscopy
further
confirmed
H6's
disruptive
effects
on
bacterial
membrane
integrity.
Mechanistic
studies
targeting
succinate
dehydrogenase
(SDH),
key
respiratory
enzyme,
energetic
similarities
between
SDH
inhibitor
bixafen
through
molecular
docking
dynamics
simulations.
CONCLUSION
The
moiety
enhanced
binding
affinity,
while
introduced
piperazine
substructure
improved
both
complex
stability
(root
mean
square
deviation
<1.5
Å)
target
engagement.
These
findings
establish
as
promising
lead
developing
next‐generation
inhibitors,
providing
critical
insights
into
structure–activity
relationships
agricultural
antimicrobial
design.
©
2025
Society
Chemical
Industry.
Язык: Английский
Discovery of novel 4‐sulfur‐substituted pyrazol‐5‐yl‐benzamide derivatives containing amide/hydrazide/ester moieties as potential succinate dehydrogenase inhibitors
Pest Management Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Июнь 2, 2025
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
action.
In
this
study,
a
series
novel
4‐sulfur‐substituted
pyrazol‐5‐yl‐benzamide
derivatives
containing
amide,
hydrazide,
or
ester
moieties
were
synthesized
develop
innovative
SDH
inhibitors.
RESULTS
The
bioassay
studies
indicated
that
several
compounds
exhibited
potent
vitro
fungicidal
against
various
fungi.
Particularly,
compound
4d
demonstrated
efficacy,
with
EC
50
values
0.21,
0.95,
0.64,
1.33,
0.66
mg
L
−1
Valsa
mali
,
Botrytis
cinerea
Rhizoctonia
solani
Fusarium
graminearum
Gaeumannomyces
graminis
respectively.
vivo
effectively
prevented
V.
infection
apples
at
showing
superior
protective
curative
effects
(93.4%
85.5%)
compared
lead
A27
(68.7%
57.0%)
commercial
fungicide
fluxapyroxad
(55.4%
43.6%).
Enzymatic
inhibition
assays
molecular
docking
analysis
suggested
could
serve
as
potential
inhibitor.
CONCLUSION
This
study
offers
valuable
insights
for
expanding
spectrum
further
developing
them
©
2025
Society
Chemical
Industry.
Язык: Английский