Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин
Aim. To synthesize new 1-alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones and study their biological activity as potential plant growth regulators.Results and discussion. 1-Alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones were obtained from the corresponding 1-alkyl-3-polyflu...
Збережено в:
| Опубліковано в: | Журнал органічної та фармацевтичної хімії |
|---|---|
| Дата: | 2023 |
| Том: | 21 |
| Випуск: | 2 |
| Сторінки: | 10-14 |
| ISSN: | 2518-1548 |
| Автори та афіліації: |
|
| Автори: | , |
| Формат: | Стаття |
| Мова: | Англійська |
| Опубліковано: |
National University of Pharmacy
2023
|
| Теми: | |
| Онлайн доступ: | https://ophcj.nuph.edu.ua/article/view/278660 |
| Теги: |
Додати тег
Немає тегів, Будьте першим, хто поставить тег для цього запису!
|
| Назва журналу: | Journal of Organic and Pharmaceutical Chemistry |
| Завантажити файл: |
|
Репозитарії
Journal of Organic and Pharmaceutical Chemistry| _version_ | 1874364447819038720 |
|---|---|
| author | Petko, Kirill I. Petrenko, Volodymyr S. |
| author_facet | Petko, Kirill I. Petrenko, Volodymyr S. |
| author_institution_txt_mv | [
{
"author": "Kirill I. Petko",
"institution": "Institute of Organic Chemistry of the National Academy of Sciences of Ukraine",
"orcid": ""
},
{
"author": "Volodymyr S. Petrenko",
"institution": "Institute of Organic Chemistry of the National Academy of Sciences of Ukraine",
"orcid": ""
}
] |
| author_sort | Petko, Kirill I. |
| baseUrl_str | https://ophcj.nuph.edu.ua/oai |
| collection | OJS |
| container_end_page | 14 |
| container_issue | 2 |
| container_start_page | 10 |
| container_title | Журнал органічної та фармацевтичної хімії |
| container_volume | 21 |
| datestamp_date | 2026-08-23T19:38:20Z |
| description | Aim. To synthesize new 1-alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones and study their biological activity as potential plant growth regulators.Results and discussion. 1-Alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones were obtained from the corresponding 1-alkyl-3-polyfluoroalkylbenzimidazolium iodides by the action of elemental selenium in the presence of a base. The preliminary biological tests for the growth-regulating activity of the compounds obtained were conducted.Experimental part. The structure of the compounds synthesized was proven by 1H and 19F NMR spectroscopy methods, as well as by the elemental analysis. The biological studies were done on model plants of winter wheat of the “bezosta” variety.Conclusions. A convenient method for obtaining 1-alkyl-3-polyfluoroalkyl-1,3-dihydro-benzimidazole-2-selenones has been developed. Biological studies have shown that the compounds synthesized have a diverse effect on the plant growth. |
| doi_str_mv | 10.24959/ophcj.23.278660 |
| first_indexed | 2025-07-23T04:43:18Z |
| format | Article |
| fulltext |
ISSN 2308-8303 (Print) / 2518-1548 (Online) 10
Original Research
http://ophcj.nuph.edu.ua
UDC 54.057:547.78:631.8
K. I. Petko, V. S. Petrenko
Institute of Organic Chemistry of the National Academy of Sciences of Ukraine,
5 Academician Kukhar str., 02660 Kyiv, Ukraine
The Synthesis of 1-Alkyl-3-polyfluoroalkyl-
1,3-dihydrobenzimidazole-2-selenones as Potential Plant
Growth Regulators
Abstract
Aim. To synthesize new 1-alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones and study their biological activity
as potential plant growth regulators.
Results and discussion. 1-Alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones were obtained from the corre-
sponding 1-alkyl-3-polyfluoroalkylbenzimidazolium iodides by the action of elemental selenium in the presence of a base.
The preliminary biological tests for the growth-regulating activity of the compounds obtained were conducted.
Experimental part. The structure of the compounds synthesized was proven by 1H and 19F NMR spectroscopy methods, as
well as by the elemental analysis. The biological studies were done on model plants of winter wheat of the “bezosta” variety.
Conclusions. A convenient method for obtaining 1-alkyl-3-polyfluoroalkyl-1,3-dihydro-benzimidazole-2-selenones has been
developed. Biological studies have shown that the compounds synthesized have a diverse effect on the plant growth.
Keywords: N-polyfluoroalkylazoles; benzimidazole-2-selenones; plant growth regulation
К. І. Петко, В. С. Петренко
Інститут органічної хімії Національної академії наук України,
вул. Академіка Кухаря, 5, м. Київ, 02660, Україна
Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних
регуляторів росту рослин
Анотація
Мета. Синтезувати нові 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенони та вивчити їхню рістрегулю-
вальну активність відносно рослин.
Результати та їх обговорення. Синтезовано нові 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенони дією
елементарного селену на відповідні 1-алкіл-3-поліфлуороалкілбензімідазолій йодиди в присутності основи. Було про-
ведено попередні біологічні випробування на рістрегулювальну активність отриманих сполук.
Експериментальна частина. Структуру одержаних сполук доведено методами 1Н та 19F ЯМР, а також елементним ана-
лізом. Біологічні дослідження виконували з використанням насіння озимої пшениці сорту Безоста.
Висновки. Розроблено зручний метод синтезу 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів. Біологічні
випробування засвідчили, що отримані сполуки мають різноплановий вплив на ріст рослин.
Ключові слова: N-поліфлуороалкілазоли; бензімідазол-2-селенони; рістрегулювальна активність
Citation: Petko, K. I.; Petrenko, V. S. The synthesis of 1-alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones as Potential Plant
Growth Regulators. Journal of Organic and Pharmaceutical Chemistry 2023, 21 (2), 10 – 14.
https://doi.org/10.24959/ophcj.23.278660
Received: 15 March 2023; Revised: 22 April 2023; Accepted: 25 April 2023
Copyright© 2023, K. I. Petko, V. S. Petrenko. This is an open access article under the CC BY license
(http://creativecommons.org/licenses/by/4.0).
Funding: The authors received no specific funding for this work.
Conflict of interests: The authors have no conflict of interests to declare.
ISSN 2308-8303 (Print) / 2518-1548 (Online) 11
Journal of Organic and Pharmaceutical Chemistry 2023, 21 (2)
■ Introduction
Selenium compounds play an important role
in the physiological processes of many living or-
ganisms. It has been shown that selenium is con-
tained (in the form of a selenocysteine fragment)
in some enzymes, such as glutathione peroxida-
se, glycine reductase, and some others [1, 2].
Selenium was found to be incorporated into bac-
terial transfer RNA bases (probably following sul-
fur pathways) when Escherichia coli was grow-
ing in a medium containing [75Se]selenite [3].
Natural nucleosides containing a selenouracil frag-
ment were also isolated [4]. Additions of seleno-
urea derivatives increase the quality of straw-
berries and radishes [5]. It has been also found
that selenium micro-additions to the soil increase
the resistance of plants to UV radiation [6].
Although an excessive amount of selenium neg-
atively affects the growth and development of
plants, the effect of selenium compounds on the
development of plant organisms, as well as the
problem of selenium accumulation in food prod-
ucts, is the subject of Finbey’s review [7]. There
are no fluorinated preparations among the men-
tioned selenium-containing plant growth regu-
lators. However, fluorine-containing compounds
are widely used in agrochemistry, in particular,
the known herbicides Sulfentrazone and Carfen-
trazone, which are difluoromethyl derivatives of
triazole.
We previously studied the chemical proper-
ties of fluorine-containing imidazolium and ben-
zimidazolium salts and showed the ways of their
transformation through carbene intermediates
into the corresponding thiones [8]. Since it is known
that the introduction of fluorine atom into the
molecule of a biologically active compound often
leads to an increase in the biological activity, and
imidazolium and benzimidazolium thiones, as well
as selenones are structural analogs of the corre-
sponding thioureas and thiouracils, the urgent
task was to synthesize and study the effect of
similar selenones on the plant development.
■ Results and discussion
We chose benzimidazole derivatives – 1-difluo-
romethylbenzimidazole (1a) [9] and 1-(2,2-dichlo-
ro-1,1,2-trifluoromethyl)benzimidazole (1b) [10]
as starting compounds. The latter were introduced
into the interaction with iodoalkanes – iodome-
thane, iodoethane, and 2-iodopropane (Scheme).
Only the reactions of similar imidazolium salts
were studied earlier [8]. It has turned out that,
as in the case of fluorine-containing imidazole
derivatives, the alkylation of 1-polyfluoroalkylb-
enzimidazoles takes place during the prolonged
period of reflux in acetonitrile. The reaction time
is significantly reduced in the case of 1-difluoro-
methylbenzimidazole compared to 1-(2,2-dichlo-
ro-1,2,2-trifluoromethyl)benzimidazole since the
latter contains a more electron-withdrawing sub-
stituent near the nitrogen atom, and therefore,
it is a weaker base. The interaction of 1-(2,2-di-
chloro-1,2,2-trifluoromethyl)benzimidazole with
the least reactive 2-iodopropane under the reac-
tion conditions was extremely slow, so we were
unable to obtain the corresponding salt in pre-
parative quantities.
The 1-alkyl-3-polyfluoroalkylbenzimidazolium
iodides 2a – e synthesized were introduced into
the interaction with elemental selenium in pyri-
dine in the presence of potassium carbonate.
Although the reaction was accompanied by the
substantial tar formation, the target products
were easily purified by flash chromatography of
organic extracts. Thus, the target 1-alkyl-3-poly-
fluoroalkylbezimidazolium-2-selenones 3a – e were
obtained with the yields of 50 – 60 %. They are
N
N
RF
R
N
N
RF
R
I
Se, K2CO3
N
N
RF
R
Se
1a,b 2a-e 3a-e
1a: RF = CF2H
1b: RF = CF2CFCl2
2a 3a, : RF = CF2H, R = Me (a)
2b 3b, : RF = CF2H, R = Et (b)
2c 3c, : RF = CF2H, R = Pr (c)i
2d 3d, : RF = CF2CFCl2, R = Me (d)
2e 3e, : RF = CF2CFCl2, R = Et (d)
I
MeCN, reflux Py
Scheme. Synthesis of 1-alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones
ISSN 2308-8303 (Print) / 2518-1548 (Online) 12
Журнал органічної та фармацевтичної хімії 2023, 21 (2)
stable crystalline compounds that are well solu-
ble in most organic solvents and can be crystal-
lized from hexane.
We conducted screening studies of the com-
pounds synthesized for plant growth regulating
and herbicidal effects. The tests were carried out
on model plants of winter wheat of the “bezosta”
variety according to the Sergiyeva method [11].
Experiments were performed in Petri dishes in
the agar medium. Solutions of the compounds
synthesized with a mass fraction of the test
compound of 1×10–2, 1×10–3, and 1×10–4 % were
studied. The same amount of nutrients was add-
ed to the control samples as in the test plants,
but without the test compounds. Experiments
were performed in four repetitions. The results
of the experiment were calculated on the 9th day
from the experiment start. Experimental data are
presented in Table.
The analysis of the results shows that all com-
pounds synthesized affect the growth and deve-
lopment of plants. Judging by the results of the
study, selenone 3a containing methyl and difluo-
romethyl groups exhibits the growth-regulating
activity. At the concentration of 1×10–4 %, this pre-
paration increases the growth of the root system
of winter wheat of the “bezosta” variety by 26 %
and increases the total weight compared to con-
trol plants, practically without affecting seed ger-
mination. The patented drug Ivin (2,6-dimethyl-
pyridine-1-oxide) when applied to the soil in the
same concentration leads to an increase in the
growth of the plant root system (on beans) by
21 % [12]; therefore, it can be argued that com-
pound 3a is close in its activity to the known drug.
Thus, 1-methyl-3-difluoromethyl-1,3-dihydro-ben-
zimidazole-2-selenone (3a) can be regarded as
a potential plant growth regulator. In high con-
centrations compound 3a along with other sele-
nones synthesized displayed an inhibiting effect
on the plant growth. An increase in the size of
both alkyl and polyfluoroalkyl radicals in the sele-
none molecule leads to undesirable changes in
the biological activity. In these cases, the seleno-
nes obtained lose their growth-stimulating pro-
perties and behave only as plant growth inhibi-
tors. For example, compound 3b, with difluoro-
methyl and ethyl groups in the concentration of
1×10–2 % exhibits herbicide properties, reducing
the rate of the root system development by three
times. Selenones with a dichlorotrifluoroethyl group
show a low biological activity.
The acute toxicity of the compounds obtained
was also studied on white mice weighing 20 – 23 g
by oral administration of solutions of the com-
pounds under research in DMSO. The research
results were calculated in 24 hours. It has been
shown that selenones 3a – e have approximately
the same toxicity – they are moderately toxic sub-
stances (LD50 = 400 – 450 mg kg–1).
■ Conclusions
Thus, one of the fluorine-containing benzimi-
dazole-2-selenone derivatives (1-methyl-3-difluo-
romethyl-1,3-dihydro-benzimidazole-2-selenone)
studied has been shown to exhibit a high growth-
stimulating activity. This compound shows ac-
tivity at the level of well-known patented prepa-
rations and can be considered as a promising
Таble 1. The biological activity of 1-alkyl-3-polyfluoroalkyl-1,3-dihydro-benzimidazole-2-selenones
Cmp Concentration, %
The effect on the growth of the plants studied
Root, % to control Stem length, %
to control
Plant mass, % to
control
Germination %
to control
3а
1×10–2 72.7 78.6 73.2 91.9
1×10–3 108.6 91.3 99.3 100.0
1×10–4 126.3 98.9 105.9 100.0
3b
1×10–2 33.3 76.6 45.4 101.7
1×10–3 94.5 94.1 88.2 101.0
1×10–4 97.4 98.0 92.3 103.4
3c
1×10–2 88.3 95.5 91.6 100.0
1×10–3 89.6 93.2 93.7 101.4
1×10–4 90.6 97.4 93.2 103.4
3d
1×10–2 84.1 95.6 83.2 101.7
1×10–3 90.3 90.3 93.4 103.4
1×10–4 93.9 99.3 98.8 103.4
3e
1×10–2 60.2 58.6 72.1 100.0
1×10–3 81.8 85.7 89.5 103.5
1×10–4 98.6 98.4 92.6 101.7
ISSN 2308-8303 (Print) / 2518-1548 (Online) 13
Journal of Organic and Pharmaceutical Chemistry 2023, 21 (2)
plant growth stimulator. A trend to decrease the
growth-stimulating activity with an increase in
the size of substituents was observed.
■ Experimental part
Melting points were measured in open capil-
lary tubes and were given uncorrected. 1H NMR
(300 MHz, CDCl3 or DMSO-d6) and 19F NMR
(288 MHz, CDCl3 or DMSO-d6) spectra were re-
corded on a Varian-Mercury-300 spectrometer using
TMS and CCl3F as internal standards, respec-
tively. The elemental analysis was performed in
the Analytical Chemistry Laboratory of the In-
stitute of Organic Chemistry, National Academy
of Sciences of Ukraine. The reaction progress
was controlled by TLC on Silufol 254 plates by
UV light.
The procedure for biological tests
The studies were carried out according to the
method [11]. Quartz sand (2 – 3 mm) previously
washed with hydrochloric acid and distilled wa-
ter was placed on the bottom of Petri dishes,
agar-agar (2 – 3 mm) was added and placed on
top of 4 awned wheat seeds of the “bezosta” va-
riety and covered with filter paper. The filter pa-
per was impregnated with an emulsion of a test
drug in water at the test concentration. In par-
allel, the control experiment was carried out by
impregnating filter paper with distilled water.
The Petri dishes were covered with glass and
distilled water, or an emulsion of the test prepa-
ration was periodically added for 9 days, ensur-
ing that the sand and agar-agar were constantly
wet. Nine days later, measurements were taken
by finding the arithmetic mean of the four seeds
under study.
The general procedure for the synthesis of
1-alkyl-3-polyfluoroalkylbenzimidazolium
iodides (2a – e)
A mixture of the corresponding 1-polyfluoro-
alkylbenzimidazole (0.05 mol) and iodoalkane
(0.1 mol) in 50 mL of anhydrous acetonitrile
was boiled for: 2a – 5 hours, 2b – 18 hours,
2c – 30 hours, 2d – 12 hours, 2d – 56 hours.
The precipitate formed upon cooling was filtered
off, washed with diethyl ether, and dried giving
an analytically pure product.
1-Methyl-3-difluoromethylbenzimidazolium
iodide (2а)
A white solid. Yield – 93 %. M. p. 227 – 229 ºС.
Anal. Calcd for C9H9F2IN2, %: I 41.07. Found, %:
I 40.96. 1H NMR (300 MHz, DMSO-d6), δ, ppm:
4.05 (3Н, s, СН3); 7.62 – 7.75 (2Н, m, ArH);
7.79 – 7.85 (2Н, m, ArH); 7.88 (1Н, t, 2JH-F = 59 Hz,
CF2H); 10.02 (1Н, s, СH). 19F NMR (288 MHz,
DMSO-d6), δ, ppm: -97.6 (2F, d, 2JH-F = 59 Hz,
NCF2Н).
1-Ethyl-3-difluoromethylbenzimidazolium
iodide (2b)
A white solid. Yield – 82 %. M. p. 202 – 204 ºС.
Anal. Calcd for C10H11F2IN2, %: I 39.19. Found, %:
I 39.06. 1H NMR (300 MHz, DMSO-d6), δ, ppm:
1.48 (3Н t, 3JHH = 5 Hz, СН3); 4.13 (2Н, q, 3JHH =
5 Hz, СН2); 7.45 – 7.54 (2Н, m, ArH); 7.65 – 7.77
(2Н, m, ArH); 7.88 (1Н, t, 2JHF = 59 Hz, CF2H);
9.79 (1Н, s, СH). 19F NMR (288 MHz, DMSO-d6),
δ, ppm: -98.1 (2F, d, 2JHF = 59 Hz, NCF2Н).
1-iso-Propyl-3-difluoromethylbenzimidazolium
iodide (2c)
A white solid. Yield – 72 %. M. p. 182 – 184 ºС.
Anal. Calcd for C11H13F2IN2, %: I 37.86. Found, %:
I 38.02. 1H NMR (300 MHz, DMSO-d6), δ, ppm:
1.42 (6Н d, 3JHH = 4 Hz, СН3); 5.18 (1Н m, СН);
7.45 – 7.54 (2Н, m, ArH); 7.65 – 7.77 (2Н, m, ArH);
7.87 (1Н, t, 2JHF = 59 Hz, CF2H); 9.98 (1Н, s, СH).
19F NMR (288 MHz, DMSO-d6), δ, ppm: -98.1 (2F,
d, 2JHF = 59 Hz, NCF2Н).
1-Methyl-(2,2-dichloro-1,1,2-trifluoroethyl)-
benzimidazolium iodide (2d)
A white solid. Yield – 87 %. M. p. 218 – 220 ºС.
Anal. Calcd for C10H8Cl2F2IN2, %: I 30.90. Found, %:
I 31.20. 1H NMR (300 MHz, DMSO-d6), δ, ppm: 4.20
(3Н, s, СН3); 7.64 – 7.72 (2Н, m, ArH); 7.76 – 7.84
(2Н, m, ArH); 10.45 (1Н, s, СH). 19F NMR (288 MHz,
DMSO-d6), δ, ppm: -75.2 (1F, s, CFCl2), -92.6 (2F,
s, NCF2).
1-Ethyl-(2,2-dichloro-1,1,2-trifluoroethyl)-
benzimidazolium iodide (2e)
A white solid. Yield – 52 %. M. p. 205 – 207 ºС.
Anal. Calcd for C10H8Cl2F2IN2, %: I 29.81. Found, %:
I 30.02. 1H NMR (300 MHz, DMSO-d6), δ, ppm:
1.37 (3Н, t, 3JHH = 5 Hz, СН3); 4.14 (2Н, q, 3JHH =
5 Hz, СН2); 7.45 – 7.54 (2Н, m, ArH); 7.65 – 7.77 (2Н,
m, ArH); 10.07 (1Н, s, СH). 19F NMR (288 MHz,
DMSO-d6), δ, ppm: -75.6 (1F, s, CFCl2); -92.7 (2F,
s, NCF2).
The general procedure for the synthesis
of 1-alkyl-3-polyfluoroalkyl-1,3-dihydro-
benzimidazole-2-selenones (3a – d)
Finely ground selenium (0.8 g, 0.015 mol)
and potassium carbonate (1.4 g, 0.01 mol) were
added to a solution of the corresponding salt
2a – d (0.01 mol) in 15 mL of pyridine. The reac-
tion mixture was heated with intensive stirring,
gradually increasing the temperature to 115 ºС,
and then the reaction mixture was refluxed for
an hour. Water (100 mL) was then added, and
ISSN 2308-8303 (Print) / 2518-1548 (Online) 14
Журнал органічної та фармацевтичної хімії 2023, 21 (2)
the resulting precipitate was extracted with
chloroform (2×50 mL), washed with water, and
dried over MgSO4. After filtering the solution,
the solvent was evaporated to a residual volume
of 10 mL and chromatographed on a column
(MN-Kieselgel-60) to isolate the first compound
with the highest Rf. The eluent is chloroform.
1-Methyl-3-difluoromethyl-1,3-dihydrobenzimi-
dazole-2-selenone (3а)
A white solid. Yield – 61 %. M. p. 151 – 153 ºС.
Anal. Calcd for C9H8F2N2Se, %: Se 30.27. Found, %:
Se 30.21. 1H NMR (300 MHz, CDCl3), δ, ppm: 3.80
(3Н, s, СН3); 7.34 – 7.45 (2Н, m, ArH); 7.71 – 7.84
(2Н, m, ArH); 8.25 (1Н, CF2H, t, 2JHF = 59 Hz).
19F NMR (288 MHz, CDCl3), δ, ppm: -102.9 (2F,
d, 2JHF = 59 Hz, NCF2Н).
1-Ethyl-3-difluoromethyl-1,3-dihydrobenzi-
midazole-2-selenone (3b)
A white solid. Yield – 72 %. M. p. 77 – 79 ºС.
Anal. Calcd for C10H10F2N2Se, %: Se 28.73. Found, %:
Se 29.01. 1H NMR (300 MHz, CDCl3), δ, ppm:
1.38 (3Н t, 3JHH = 5 Hz, СН3); 4.52 (2Н q, 3JHH =
5 Hz, СН2); 7.40 – 7.50 (2Н, m, ArH); 7.68 – 7.79
(2Н, m, ArH); 8.24 (1Н, t, 2JHF = 59 Hz CF2H).
19F NMR (288 MHz, CDCl3), δ, ppm: -103.7 (2F,
d, 2JHF = 59 Hz, NCF2Н).
1-iso-Propyl-3-difluoromethyl-1,3-dihydroben-
zimidazole-2-selenone (3c)
A white solid. Yield – 49 %. M. p. 101 – 102 ºС.
Anal. Calcd for C11H12F2N2Se, %: Se 27.33. Found, %:
Se 27.41. 1H NMR (300 MHz, CDCl3), δ, ppm:
1.59 (6Н d, 3JHH = 4 Hz СН3); 5.32 (1Н m, СН);
7.33 – 7.44 (2Н, m, ArH); 7.55 – 7.62 (2Н, m, ArH);
8.21 (1Н, t, 2JHF = 59 Hz, CF2H). 19F NMR (288 MHz,
CDCl3), δ, ppm: -104.0 (2F, d, 2JHF = 59 Hz, NCF2Н).
1-Methyl-(2,2-dichloro-1,1,2-trifluoroethyl)-
1,3-dihydrobenzimidazole-2-selenone (3d)
A white solid. Yield – 44 %. M. p. 104 – 105 ºС.
Anal. Calcd for C10H7Cl2F2N2Se, %: Se 21.82.
Found, %: Se 21.90. 1H NMR (300 MHz, CDCl3),
δ, ppm: 3.88 (3Н, s, СН3); 7.64 – 7.72 (2Н, m, ArH);
7.76 – 7.84 (2Н, m, ArH). 19F NMR (288 MHz, CDCl3),
δ, ppm: -70.2 (1F, s, CFCl2), -90.2 (2F, s, NCF2).
1-Ethyl-(2,2-dichloro-1,1,2-trifluoroethyl)-
1,3-dihydrobenzimidazole-2-selenone (3e)
A white solid. Yield – 42 %. M. p. 71 – 72 ºС. Anal.
Calcd for C11H9Cl2F2N2Se, %: Se 21.01. Found, %:
Se 21.27. 1H NMR (300 MHz, CDCl3), δ, ppm:
1.39 (3Н, t, 3JHH = 5 Hz, СН3); 4.70 (2Н, q, 3JHH =
5 Hz, СН2); 7.25 – 7.34 (2Н, m, ArH); 7.55 – 7.64
(2Н, m, ArH). 19F NMR (288 MHz, CDCl3), δ, ppm:
-69.9 (1F, s, CFCl2); -89.1 (2F, s, NCF2).
■ References
1. Stadtman, T. C., Selenium-Dependent Enzymes. Annu. Rev. Biochem 1980, 49 (1), 93 – 110. https://doi.org/10.1146/annurev.bi.49.070180.000521.
2. Sliwkowski, M. X.; Stadtman, T. C., Incorporation and distribution of selenium into thiolase from Clostridium kluyveri. The Journal of
biological chemistry 1985, 260 (5), 3140 – 4. https://doi.org/10.1016/S0021-9258(18)89484-4.
3. Saelinger, D. A.; Hoffman, J. L.; McConnell, K. P., Biosynthesis of selenobases in transfer RNA by Escherichia coli. J. Mol. Biol. 1972, 69 (1),
9 – 17. https://doi.org/10.1016/0022-2836(72)90020-4.
4. Wittwer, A. J.; Tsai, L.; Ching, W. M.; Stadtman, T. C., Identification and synthesis of a naturally occurring selenonucleoside in bacte-
rial tRNAs: 5-[(methylamino)methyl]-2-selenouridine. Biochemistry 1984, 23 (20), 4650 – 4655. https://doi.org/10.1021/bi00315a021.
5. Carvalho, K. M.; Gallardo-Williams, M. T.; Benson, R. F.; Martin, D. F., Effects of Selenium Supplementation on Four Agricultural Crops.
J. Agric. Food. Chem. 2003, 51 (3), 704 – 709. https://doi.org/10.1021/jf0258555.
6. Shanker, A. K., Countering UV-B Stress in Plants: Does Selenium have a Role? Plant and Soil 2006, 282 (1), 21 – 26.
https://doi.org/10.1007/s11104-005-5249-x.
7. Finley, J. W., Selenium Accumulation in Plant Foods. Nutrition Reviews 2005, 63 (6), 196 – 202. https://doi.org/10.1111/j.1753-4887.2005.tb00137.x.
8. Yagupolskii, L. M.; Sokolenko, T. M.; Petko, K. I., Chemical properties of N-polyfluoroethylimidazole and -pyrrole derivatives. Russ. Chem.
Bull. 2005, 54 (3), 796 – 802. https://doi.org/10.1007/s11172-005-0323-3.
9. Poludnenko, V. G.; Didinskaya, O. B.; Pozharskii, A. F., Fluorine-containing azoles. 2. Reaction of imidazole, benzimidazoles, and perimi-
dines with difluorocarbene. Chem. Heterocycl. Comp. 1984, 20 (4), 422 – 425. https://doi.org/10.1007/BF00513860.
10. Petko, K. I.; Yagupolskii, L. M., Interaction of the Azole N‐Sodium Derivatives with Freon‐113: Synthesis of N‐(2,2‐dichlorotrifluoroethyl)
azoles. Synth. Commun. 2006, 36 (14), 1967 – 1972. https://doi.org/10.1080/00397910600634050.
11. Sergeeva, Т. А. Metodika laboratornyih ispyitaniy gerbitsidov [Herbicide Laboratory Testing Procedure, in Russian]. Zaschita Rastenii
1963, 2, 42 – 43.
12. Petrenko, V. S.; Danilenko, G. І.; Yavorovskii, P. P.; Schwartau, V. V.; Lysenko V. P.; Guzhova, S. V.; Ozerova, L. V.; Lozinskii, М. О. Norborn-
5-en-2-karboksy-3-karboksylat 1-oksyd-2,6-dymetylpirydynu (Ivinor) – stymuliator rostu ta rozvytku roslyn [Norbon-5-en-2-carboxy-
3-carboxylate 1-oxide-2,6-dimethylpyridine (Ivinor) plants growth and evolution stimulant, in Ukrainan]. UA Patent № 75280, Mar 15,
2006.
Information about the authors:
Kirill I. Petko (corresponding author), Ph.D. in Chemistry, Senior Researcher, Organofluorine Compounds Chemistry Department,
Institute of Organic Chemistry of the National Academy of Sciences of Ukraine; https://orcid.org/0000-0002-2522-0128;
e-mail for correspondence: kirpet@ukr.net.
Volodymyr S. Petrenko, Ph.D. in Biology, Senior Researcher, Department of Medical and Biological Testing, Institute of Organic
Chemistry of the National Academy of Sciences of Ukraine.
|
| id | oai:ojs.journals.uran.ua:article-278660 |
| institution | Journal of Organic and Pharmaceutical Chemistry |
| issn | 2518-1548 |
| keywords_txt_mv | |
| language | English |
| last_indexed | 2026-08-24T01:00:33Z |
| publishDate | 2023 |
| publisher | National University of Pharmacy |
| record_format | ojs |
| resource_txt_mv | ophcjnupheduua/49/b133d4009feabb88989bc6d0850f7c49.pdf |
| spelling | oai:ojs.journals.uran.ua:article-2786602026-08-23T19:38:20Z The Synthesis of 1-Alkyl-3-polyfluoroalkyl- 1,3-dihydrobenzimidazole-2-selenones as Potential Plant Growth Regulators Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин Petko, Kirill I. Petrenko, Volodymyr S. N-поліфлуороалкілазоли бензімідазол-2-селенони рістрегулювальна активність N-polyfluoroalkylazoles benzimidazole-2-selenones plant growth regulation Aim. To synthesize new 1-alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones and study their biological activity as potential plant growth regulators.Results and discussion. 1-Alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones were obtained from the corresponding 1-alkyl-3-polyfluoroalkylbenzimidazolium iodides by the action of elemental selenium in the presence of a base. The preliminary biological tests for the growth-regulating activity of the compounds obtained were conducted.Experimental part. The structure of the compounds synthesized was proven by 1H and 19F NMR spectroscopy methods, as well as by the elemental analysis. The biological studies were done on model plants of winter wheat of the “bezosta” variety.Conclusions. A convenient method for obtaining 1-alkyl-3-polyfluoroalkyl-1,3-dihydro-benzimidazole-2-selenones has been developed. Biological studies have shown that the compounds synthesized have a diverse effect on the plant growth. Мета. Синтезувати нові 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенони та вивчити їхню рістрегулю-вальну активність відносно рослин.Результати та їх обговорення. Синтезовано нові 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенони дієюелементарного селену на відповідні 1-алкіл-3-поліфлуороалкілбензімідазолій йодиди в присутності основи. Було проведено попередні біологічні випробування на рістрегулювальну активність отриманих сполук.Експериментальна частина. Структуру одержаних сполук доведено методами 1Н та 19F ЯМР, а також елементним аналізом. Біологічні дослідження виконували з використанням насіння озимої пшениці сорту Безоста.Висновки. Розроблено зручний метод синтезу 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів. Біологічнівипробування засвідчили, що отримані сполуки мають різноплановий вплив на ріст рослин. National University of Pharmacy 2023-08-30 Article Article application/pdf https://ophcj.nuph.edu.ua/article/view/278660 10.24959/ophcj.23.278660 Journal of Organic and Pharmaceutical Chemistry; Vol. 21 No. 2 (2023); 10-14 Журнал органической и фармацевтической химии; Том 21 № 2 (2023); 10-14 Журнал органічної та фармацевтичної хімії; Том 21 № 2 (2023); 10-14 2518-1548 2308-8303 en https://ophcj.nuph.edu.ua/article/view/278660/274353 Copyright (c) 2023 Kirill I. Petko, Volodymyr S. Petrenko http://creativecommons.org/licenses/by/4.0 |
| spellingShingle | N-поліфлуороалкілазоли бензімідазол-2-селенони рістрегулювальна активність Petko, Kirill I. Petrenko, Volodymyr S. Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин |
| title | Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин |
| title_alt | The Synthesis of 1-Alkyl-3-polyfluoroalkyl- 1,3-dihydrobenzimidazole-2-selenones as Potential Plant Growth Regulators |
| title_full | Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин |
| title_fullStr | Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин |
| title_full_unstemmed | Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин |
| title_short | Синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин |
| title_sort | синтез 1-алкіл-3-поліфлуороалкіл-1,3-дигідробензімідазол-2-селенонів як потенційних регуляторів росту рослин |
| topic | N-поліфлуороалкілазоли бензімідазол-2-селенони рістрегулювальна активність |
| topic_facet | N-поліфлуороалкілазоли бензімідазол-2-селенони рістрегулювальна активність N-polyfluoroalkylazoles benzimidazole-2-selenones plant growth regulation |
| url | https://ophcj.nuph.edu.ua/article/view/278660 |
| work_keys_str_mv | AT petkokirilli thesynthesisof1alkyl3polyfluoroalkyl13dihydrobenzimidazole2selenonesaspotentialplantgrowthregulators AT petrenkovolodymyrs thesynthesisof1alkyl3polyfluoroalkyl13dihydrobenzimidazole2selenonesaspotentialplantgrowthregulators AT petkokirilli sintez1alkíl3polífluoroalkíl13digídrobenzímídazol2selenonívâkpotencíjnihregulâtorívrosturoslin AT petrenkovolodymyrs sintez1alkíl3polífluoroalkíl13digídrobenzímídazol2selenonívâkpotencíjnihregulâtorívrosturoslin AT petkokirilli synthesisof1alkyl3polyfluoroalkyl13dihydrobenzimidazole2selenonesaspotentialplantgrowthregulators AT petrenkovolodymyrs synthesisof1alkyl3polyfluoroalkyl13dihydrobenzimidazole2selenonesaspotentialplantgrowthregulators |