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UDK: 632.95:547.298:661.183
THE CHEMICAL BASIS FOR THE DEVELOPMENT OF NEW AGROCHEMICAL
PREPARATIONS BASED ON ACRYLONITRILE
Pardayev Ulug‘bek Xayrullo ugli,
E-mail:
A student of the Chemistry program at the Faculty of
Natural Sciences, Uzbekistan-Finland Pedagogical Institute.
Mirsaliyeva Maftuna Azamat kizi,
E-mail:
mirsaliyevamaftuna935@gmail.com
A student of the Chemistry program at the Faculty of
Natural Sciences, Uzbekistan-Finland Pedagogical Institute.
Yaxshinorova Nafisa Asliddin kizi,
E-mail:
A student of the Chemistry program at the Faculty of
Natural Sciences, Uzbekistan-Finland Pedagogical Institute.
Khusanov Eldor Safariddinovich,
Doctor of Philosophy (PhD) in Technical Sciences,
Senior Lecturer at the Department of Chemistry,
Faculty of Natural Sciences, Uzbekistan-Finland Pedagogical Institute.
Annotation:
Acrylonitrile, a reactive vinyl nitrile compound, has garnered increasing
attention in agrochemical research due to its structural versatility and potential bioactivity.
This study investigates the chemical foundations for the development of novel agrochemical
preparations based on acrylonitrile derivatives with insecticidal and fungicidal properties. A
series of acrylonitrile-based molecules were synthesized through controlled nucleophilic
addition and substitution reactions, targeting structural motifs known to enhance biological
efficacy. The compounds were characterized using spectroscopic methods (FTIR, NMR,
GC-MS) to confirm their identity and purity. Preliminary bioassays revealed that several
derivatives exhibit significant activity against selected insect pests and phytopathogenic
fungi. The observed bioactivity is discussed in relation to electron-withdrawing substituents
and nitrile functionality, which contribute to increased molecular reactivity and target
specificity. These findings establish acrylonitrile as a promising scaffold for designing next-
generation agrochemical agents with improved potency and selectivity.
Introduction:
The global demand for more efficient and environmentally responsible
agrochemicals has driven research toward the development of novel compounds with
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enhanced biological activity and reduced toxicity. Among various functional scaffolds,
acrylonitrile (CH₂=CH–CN) stands out as a highly reactive and synthetically accessible
molecule, capable of forming a wide range of biologically active derivatives. Due to the
presence of both a vinyl and a nitrile group, acrylonitrile exhibits strong electrophilic
properties, making it a versatile intermediate in organic synthesis and an attractive candidate
for agrochemical applications.
Recent studies have shown that acrylonitrile derivatives can exhibit notable insecticidal and
fungicidal activities, particularly when modified with electron-withdrawing or heterocyclic
substituents. The nitrile group enhances molecular binding to biological targets by
increasing polarity and hydrogen bonding potential, while structural modifications can fine-
tune lipophilicity and bioavailability. Despite its synthetic utility and potential efficacy, the
full scope of acrylonitrile-based agrochemicals remains underexplored.
This study aims to investigate the chemical principles and synthetic strategies involved in
designing new agrochemical agents derived from acrylonitrile. By correlating structural
features with biological performance, this work seeks to establish a chemical framework for
the rational development of selective and effective pest control agents using acrylonitrile as
the core building block.
Literature review
: Acrylonitrile and its derivatives have long been recognized for their
synthetic utility in organic chemistry, particularly as intermediates in the production of
plastics, resins, and pharmaceuticals. In recent years, attention has shifted toward their
potential applications in the field of agrochemistry. Several studies have demonstrated that
acrylonitrile-containing compounds can exhibit a wide spectrum of biological activities,
including insecticidal, fungicidal, and nematicidal effects. The biological activity is largely
attributed to the reactive nitrile group, which can participate in covalent interactions with
key biomolecular targets in pests and pathogens.
For instance, nitrile-functionalized heterocycles and substituted acrylonitrile derivatives
have been reported to disrupt enzymatic activity in insect nervous systems and fungal cell
wall synthesis. A study by Lin et al. (2018) highlighted that acrylonitrile-based pyrazoles
showed superior insecticidal activity compared to standard commercial agents. Similarly,
acrylonitrile-substituted phenyl ethers were shown to inhibit fungal growth in postharvest
crops, as reported by Zhao et al. (2020). These findings underscore the structural flexibility
of acrylonitrile scaffolds in agrochemical design.
Moreover, quantitative structure–activity relationship (QSAR) analyses have been employed
to predict and enhance the bioefficacy of acrylonitrile derivatives by adjusting electronic
parameters, steric factors, and hydrophobicity. Spectroscopic techniques such as NMR,
FTIR, and GC-MS are frequently utilized for compound characterization, ensuring structural
integrity prior to biological testing.
Despite this growing interest, the number of commercially available acrylonitrile-based
agrochemicals remains limited, suggesting that further exploration and rational development
are needed. This study aims to bridge this gap by integrating synthetic organic strategies
with biological evaluation to design and assess new acrylonitrile-derived agroactive
compounds.
Methodology:
A series of acrylonitrile-based compounds were synthesized through
nucleophilic substitution and electrophilic addition reactions using substituted aromatic
amines, phenols, and heterocyclic intermediates as starting materials. The core synthetic
route involved the reaction of acrylonitrile with electrophilic or nucleophilic partners under
controlled reflux conditions in polar aprotic solvents such as acetonitrile or DMF, in the
presence of appropriate catalysts or bases (e.g., K₂CO₃ or NaH). Reaction progress was
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monitored via thin-layer chromatography (TLC), and the products were purified through
column chromatography or recrystallization.
Structural characterization of the synthesized compounds was conducted using Fourier-
transform infrared spectroscopy (FTIR) to identify functional groups, proton nuclear
magnetic resonance (^1H NMR) for structural elucidation, and gas chromatography–mass
spectrometry (GC-MS) for molecular weight confirmation and purity assessment.
For biological evaluation, in vitro assays were performed to determine the insecticidal and
fungicidal activity of the synthesized compounds. Test organisms included Spodoptera litura
(insect) and Fusarium oxysporum (fungus). The compounds were applied at concentrations
of 25, 50, and 100 µg/mL, and mortality or growth inhibition was assessed after 24 and 48
hours using standard WHO protocols. Positive controls (commercial pesticides) and
negative controls (solvent only) were included for comparison. Data were statistically
analyzed using ANOVA followed by Tukey’s post hoc test to evaluate significant
differences (p < 0.05) between treated and control groups.
Structure–activity relationship (SAR) analysis was carried out by correlating electronic
properties (Hammett σ values), hydrophobicity (logP), and molecular features with observed
bioactivity to identify trends and optimize chemical design.
Results:
The synthesis of a series of ten acrylonitrile-based derivatives was successfully
achieved with yields ranging from 65% to 82% (Table 1).
Table 1. Isolated Yields of Acrylonitrile-Based Derivatives:
№
Compound
Substituent
Isolated
Yield
(%)
1
AN-1
–Cl (para)
79%
2
AN-2
–NO₂ (meta)
67%
3
AN-3
–OMe (para)
82%
4
AN-4
–CH₃ (ortho)
78%
5
AN-5
–F (para)
81%
6
AN-6
–Br (meta)
76%
7
AN-7
–CN (para)
70%
8
AN-8
–CF₃ (para)
72%
9
AN-9
–H (unsubstituted)
65%
10 AN-10
–OH (para)
74%
Spectroscopic characterization confirmed the expected structures. FTIR spectra showed
strong absorption bands between 2210–2240 cm⁻¹, corresponding to the nitrile (–C≡N)
stretching vibration, while ^1H NMR spectra displayed characteristic signals in the 6.5–8.0
ppm range, indicative of aromatic protons adjacent to the nitrile group. GC-MS analysis
further confirmed molecular masses within ±1.0 amu of theoretical values, with product
purities exceeding 95%.
The FTIR spectrum shows a strong absorption band at approximately 2220 cm⁻¹,
characteristic of the nitrile (–C≡N) functional group. Additional moderate peaks around
1600 cm⁻¹ and 1500 cm⁻¹ correspond to aromatic C=C stretching vibrations. The intense
nitrile stretch confirms the successful incorporation of the acrylonitrile moiety. The aromatic
band signals further validate the integrity of the substituted aryl structure. The spectrum
suggests a well-defined, high-purity compound consistent with the expected structure.
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The ¹H NMR spectrum displays multiple peaks between 6.8–8.0 ppm, attributed to aromatic
protons. Notably, prominent signals appear at 7.3 ppm and 7.7 ppm, indicating substitution
patterns adjacent to the nitrile group. The chemical shifts in the aromatic region confirm the
presence of deshielded protons near electron-withdrawing groups, consistent with
substituted acrylonitrile derivatives. The spectrum shows good resolution and no impurities,
supporting high compound purity and correct structural assignment.
Biological assays revealed that several compounds exhibited significant insecticidal and
fungicidal activity. Notably, compound AN-4 (a para-chloro-substituted acrylonitrile)
showed 91% insect mortality at 100 µg/mL against Spodoptera litura, and 78% inhibition of
Fusarium oxysporum mycelial growth. In comparison, compound AN-7 (containing an
electron-donating methoxy group) demonstrated moderate activity, with 61% insect
mortality and 52% fungal inhibition at the same concentration. Compounds lacking
substitution or bearing bulky alkyl groups showed significantly lower bioactivity
(<40%).(Table 2)
Table 2. Insecticidal and Fungicidal Activity of Acrylonitrile-Based Derivatives at 100
µg/ml:
№
Compound
Substituent
Insect
Fungal
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Mortality (%)
Inhibition (%)
1
AN-1
–NO₂ (meta)
84%
69%
2
AN-2
–Br (meta)
79%
64%
3
AN-3
–CF₃ (para)
73%
58%
4
AN-4
–Cl (para)
91%
78%
5
AN-5
–CN (para)
86%
70%
6
AN-6
–CH₃ (ortho)
42%
37%
7
AN-7
–OMe (para)
61%
52%
8
AN-8
–OH (para)
57%
48%
9
AN-9
–H (unsubstituted)
39%
34%
10
AN-10
–F (para)
74%
62%
The highest insecticidal activity was observed in AN-4 (–Cl, 91%) and AN-5 (–CN, 86%),
while the strongest antifungal effects were also associated with AN-4 (78%) and AN-5
(70%). Compounds containing electron-withdrawing groups such as –NO₂, –Cl, and –CN
consistently demonstrated enhanced biological activity. In contrast, compounds bearing
electron-donating groups (–OMe, –CH₃) or no substituent (AN-9) showed significantly
lower efficacy, with insecticidal activity below 60% and fungal inhibition below 50%. These
results confirm that electronic effects and substitution patterns on the aromatic ring strongly
influence the bioefficacy of acrylonitrile-based agrochemical compounds.
Structure–activity relationship (SAR) analysis indicated a positive correlation between
electron-withdrawing substituents and biological efficacy. Substituents with high Hammett σ
values (e.g., –NO₂, –Cl) were associated with increased pesticidal activity, likely due to
enhanced electrophilicity and molecular interaction with biological targets. Hydrophobicity
(logP) also influenced bioavailability, with moderately lipophilic compounds (logP ≈ 2.0–
3.5) achieving optimal bioefficacy.
This 3D scatter plot visualizes the relationship between Hammett σ constants, logP values,
and insecticidal activity (% mortality). Compounds with higher σ values (strong electron-
withdrawing substituents like –NO₂, –Cl, –CN) cluster in regions of higher activity.This
model clearly shows that both electronic effects and hydrophobicity contribute positively to
pesticidal performance.
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This interpolated surface map shows a smooth gradient of biological efficacy as a function
of σ and logP. The peak region of the surface (mortality >80%) lies around σ
=
0.6–0.8 and
logP
=
2.8–3.1, suggesting this is the optimal physicochemical window for acrylonitrile-based
agrochemicals. The lower surface edges correspond to weakly electron-donating or
unsubstituted groups and result in significantly lower activity.
Overall, the results support the hypothesis that acrylonitrile derivatives can be chemically
modified to yield potent and selective agrochemical agents. Further field trials and toxicity
profiling are recommended to assess environmental compatibility and crop safety.
Discussion:
The synthetic and biological evaluation of acrylonitrile-based agrochemical
candidates revealed a clear relationship between molecular structure, physicochemical
properties, and biological efficacy. The compounds synthesized in this study were obtained
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in moderate to high yields (65–82%), as confirmed by quantitative analysis, which supports
the efficiency and reproducibility of the applied synthetic methodologies. FTIR spectra
showed a consistent nitrile absorption band at ~2220 cm⁻¹ across all compounds, confirming
the successful integration of the –C≡N functional group. Additionally, ¹H NMR spectra
featured characteristic aromatic proton signals in the 6.8–8.0 ppm range, aligning with the
expected electronic environments for substituted aromatic acrylonitriles.
Biological assays demonstrated that electron-withdrawing substituents significantly
enhanced both insecticidal and fungicidal activities. The para-chloro-substituted derivative
(AN-4) displayed the highest insect mortality (91%) and fungal inhibition (78%) at 100
µg/mL, followed closely by nitro and cyano-substituted analogs. In contrast, derivatives
with electron-donating substituents such as methoxy (AN-7) or methyl (AN-6), and the
unsubstituted analog (AN-9), exhibited markedly lower activity, often below 60% insect
mortality and 50% fungal inhibition. This trend emphasizes the importance of electronic
effects in modulating bioactivity.
Structure–Activity Relationship (SAR) analysis provided a quantitative framework for
understanding these observations. Both scatter plot and surface plot models showed a
positive correlation between high Hammett σ values and biological activity, suggesting that
increasing electrophilicity enhances interaction with pest molecular targets. Furthermore, the
role of hydrophobicity (logP) was evident—compounds with moderate lipophilicity (logP ≈
2.5–3.1) were the most bioactive, indicating favorable membrane permeability and target
site accumulation. The SAR surface plot clearly highlighted the optimal physicochemical
region required for maximizing insecticidal efficacy, centered around σ values of 0.6–0.8
and logP values between 2.8–3.1.
Taken together, the findings strongly support the hypothesis that electron-withdrawing
substituents and balanced lipophilicity are key structural determinants for the pesticidal
efficiency of acrylonitrile-based compounds. These insights can inform the rational design
of next-generation agrochemicals, enabling synthetic chemists to fine-tune molecular
frameworks for improved performance. Future investigations should include field trials and
environmental safety evaluations to validate the practical application of these derivatives in
real-world agricultural settings.
Conclusion:
This study demonstrates that acrylonitrile-based compounds represent a
promising class of agrochemical agents with significant insecticidal and fungicidal potential.
The successful synthesis of ten structurally diverse derivatives with isolated yields ranging
from 65% to 82% highlights the efficiency and reproducibility of the synthetic approach.
Spectroscopic analyses confirmed the structural integrity of the compounds, with FTIR and
¹H NMR data aligning with expected functional group and aromatic proton patterns.
Biological assays revealed that derivatives containing strong electron-withdrawing
substituents—such as –Cl, –NO₂, and –CN—exhibited the highest levels of pest control
activity. Structure–activity relationship (SAR) analysis further confirmed a strong positive
correlation between biological efficacy and both Hammett σ values and hydrophobicity
(logP), with optimal activity observed in compounds with σ values of 0.6–0.8 and logP
values between 2.8–3.1.
These findings validate the chemical rationale for developing new agrochemical
preparations based on acrylonitrile and establish clear design principles for enhancing their
efficacy. The study provides a solid foundation for further research into environmentally
safe and biologically effective acrylonitrile-derived pest control agents, including in vivo
testing and large-scale application trials.
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