Journal of Agricultural and Food Chemistry,
Год журнала:
2024,
Номер
72(22), С. 12415 - 12424
Опубликована: Май 23, 2024
A
series
of
novel
2-Ar-1,2,3-triazole
derivatives
were
designed
and
synthesized
based
on
our
previously
discovered
active
compound
6d
against
Rhizoctonia
solani.
Most
these
compounds
exhibited
good
antifungal
activity
R.
solani
at
a
concentration
25
μg/mL.
Based
the
results
biological
activity,
we
established
three-dimensional
quantitative
structure–activity
relationship
(3D-QSAR)
model
that
guided
synthesis
7y.
Compound
7y
superior
(EC50
=
0.47
μg/mL)
compared
to
positive
controls
hymexazol
12.80
tebuconazole
0.87
μg/mL).
Furthermore,
demonstrated
better
protective
than
aforementioned
two
commercial
fungicides
in
both
detached
leaf
assays
greenhouse
experiments,
achieving
56.21%
65.75%
efficacy,
respectively,
100
The
ergosterol
content
was
determined
molecular
docking
performed
explore
mechanism
molecules.
DFT
calculation
MEP
analysis
illustrate
this
study.
These
suggest
could
serve
as
lead
for
controlling
Journal of Agricultural and Food Chemistry,
Год журнала:
2024,
Номер
72(11), С. 5636 - 5644
Опубликована: Март 8, 2024
The
evaluation
of
toxicity
and
environmental
behavior
bioactive
lead
molecules
is
helpful
in
providing
theoretical
support
for
the
development
agrochemicals,
line
with
sustainable
ecological
environment.
In
previous
work,
some
acethydrazide
structures
have
been
demonstrated
to
exhibit
excellent
broad-spectrum
fungicidal
activity;
however,
its
compatibility
needs
be
further
elucidated
if
it
identified
as
a
potential
fungicide.
this
project,
compounds
F51,
F58,
F72,
F75
zebrafish
was
determined
at
10
μg
mL–1
1
mL–1.
Subsequently,
toxic
mechanism
compound
F58
preliminarily
explored
by
histologic
section
TEM
observations,
which
revealed
that
gallbladder
volume
common
carp
treated
increased,
accompanied
deepened
bile
color,
damaged
plasma
membrane,
atrophied
mitochondria
cells.
Approximately,
F58-treated
hepatocytes
exhibited
cytoplasmic
heterogeneity,
partial
cellular
vacuolation
mitochondrial
membrane
rupture.
Metabolomics
analysis
indicated
differential
metabolites
were
enriched
formation-associated
steroid
biosynthesis,
primary
acid
taurine
hypotaurine
metabolism
pathways,
well
function-related
glycerophospholipid
metabolism,
linolenic
α-linolenic
arachidonic
suggesting
may
acute
liver
carp.
Finally,
hydrolysis
dynamics
investigated,
obtained
half-life
5.82
days.
above
results
provide
important
guiding
significance
new
green
fungicides.
Molecules,
Год журнала:
2024,
Номер
29(10), С. 2212 - 2212
Опубликована: Май 8, 2024
The
research
on
new
compounds
against
plant
pathogens
is
still
socially
and
economically
important.
It
results
from
the
increasing
resistance
of
pests
to
protection
products
need
maintain
high
yields
crops,
particularly
oilseed
crops
used
manufacture
edible
industrial
oils
biofuels.
We
tested
thirty-five
semi-synthetic
hydrazide–hydrazones
with
aromatic
fragments
natural
origin
phytopathogenic
laccase-producing
fungi
such
as
Botrytis
cinerea,
Sclerotinia
sclerotiorum,
Cerrena
unicolor.
Among
investigated
molecules
previously
identified
potent
laccase
inhibitors
were
also
strong
antifungal
agents
fungal
species
tested.
highest
activity
showed
derivatives
4-hydroxybenzoic
acid
salicylic
aldehydes
3-tert-butyl,
phenyl,
or
isopropyl
substituents.
S.
sclerotiorum
appeared
be
most
susceptible
compounds,
lowest
IC50
values
between
0.5
1.8
µg/mL.
applied
two
variants
phytotoxicity
tests
for
representative
crop
seeds
selected
hydrazide–hydrazones.
Most
show
no
low
phytotoxic
effect
flax
sunflower
seeds.
Moreover,
a
positive
impact
seed
germination
infected
was
observed.
With
potential
application,
cytotoxicity
choice
toward
MCF-10A
BALB/3T3
cell
lines
lower
than
that
azoxystrobin
fungicide
Journal of Agricultural and Food Chemistry,
Год журнала:
2024,
Номер
72(20), С. 11308 - 11320
Опубликована: Май 9, 2024
The
dearomatization
at
the
hydrophobic
tail
of
boscalid
was
carried
out
to
construct
a
series
novel
pyrazole-4-carboxamide
derivatives
containing
an
oxime
ether
fragment.
By
using
fungicide-likeness
analyses
and
virtual
screening,
24
target
compounds
with
theoretical
strong
inhibitory
effects
against
fungal
succinate
dehydrogenase
(SDH)
were
designed
synthesized.
Antifungal
bioassays
showed
that
compound
E1
could
selectively
inhibit
in
vitro
growth
R.
solani,
EC50
value
1.1
μg/mL
superior
agricultural
fungicide
(2.2
μg/mL).
observations
by
scanning
electron
microscopy
(SEM)
transmission
(TEM)
demonstrated
reduce
mycelial
density
significantly
increase
mitochondrial
number
mycelia
cytoplasm,
which
similar
phenomenon
treated
boscalid.
Enzyme
activity
assay
had
significant
effect
SDH
from
IC50
3.3
μM
(7.9
μM).
mode
action
further
analyzed
molecular
docking
dynamics
simulation
studies.
Among
them,
hydrogen
bonds
more
SDH-E1
complex
than
SDH-boscalid
complex.
This
research
on
strategy
benzene
ring
for
constructing
pyrazole-4-carboxamides
fragment
provides
unique
thought
design
new
antifungal
drugs
targeting
SDH.
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.
Journal of Agricultural and Food Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 13, 2025
A
series
of
novel
pyridine-based
compounds
integrating
bioactive
amide
and
hydrazide
groups
were
designed
synthesized
through
an
active
group
splicing
strategy.
The
fungicidal
bioassays
indicated
that
several
showed
remarkable
broad-spectrum
inhibitory
activity.
Notably,
compound
A5
displayed
satisfactory
in
vitro
activity
against
Fusarium
graminearum,
Magnaporthe
oryzae,
Rhizoctonia
solani,
Colletotrichum
gloeosporioides,
Botrytis
cinerea,
Sclerotinia
sclerotiorum,
Alternaria
sp.,
Physalospora
piricola,
with
EC50
values
2.53,
2.84,
1.64,
7.59,
4.67,
5.50,
2.84
μg
mL-1,
respectively.
Additionally,
also
promising
vivo
preventive
efficiency
F.
graminearum
R.
solani
at
100
mL-1.
Preliminary
investigation
the
mechanism
demonstrated
differentially
expressed
genes
differential
metabolites
treated
10
mL-1
exhibited
notable
enrichment
pathways
associated
lipid
metabolism,
potentially
linking
to
plasma
membrane
contraction
observed
by
TEM.
Furthermore,
assess
environmental
compatibility
A5,
its
toxicity
zebrafish,
hydrolysis
rates
different
pH
buffers,
effects
on
growth
wheat
seedlings
evaluated.
These
findings
will
provide
substantial
theoretical
guidance
for
development
new
environmentally
friendly
fungicides.
Journal of Agricultural and Food Chemistry,
Год журнала:
2025,
Номер
73(9), С. 5054 - 5066
Опубликована: Фев. 18, 2025
To
develop
potent
and
safe
antifungal
agents
in
agriculture,
a
total
of
48
novel
quinazolinone-2-carbohydrazide
derivatives
were
designed
synthesized
based
on
the
pharmacophore
hybridization
method.
The
bioassay
results
demonstrated
that
many
compounds
exhibited
powerful
broad-spectrum
inhibition
activities
vitro
against
tested
fungi.
For
instance,
E23
F23
possessed
EC50
(half-maximal
effective
concentration)
values
0.41
0.47
μg/mL
Rhizoctonia
solani,
comparable
to
commercial
fungicide
Boscalid
(EC50
=
0.49
μg/mL).
Additionally,
compound
also
pronounced
effects
Verticillium
dahliae,
Alternaria
Colletotrichum
gloeosporioides
with
0.27,
1.15,
0.27
μg/mL,
respectively.
In
vivo
assays
rice
plants
revealed
this
at
200
nearly
equipotent
curative
protective
R.
as
compared
positive
controls
Carbendazim.
Moreover,
had
an
obvious
activity
fungal
succinate
dehydrogenase
(SDH)
from
solani
half-maximal
concentration
(IC50)
11.76
μM,
interactions
between
SDH
enzyme
further
confirmed
by
molecular
docking
studies.
Furthermore,
presence
triggered
morphological
changes
mycelia
increased
conductivity
permeability
cell
membranes.
Interestingly,
built
three-dimensional
quantitative
structure-activity
relationship
(3D-QSAR)
models
showed
electrostatic
effect
played
more
important
role
maintaining
anti-R.
target
than
other
effects.
Finally,
biosafety
assessment
its
safety
toward
zebrafish.
