CC BY
12Chemical Journal of Kazakhstan
Volume 1, Number 81(2023), 15-23 https://doi.org/10.51580/2023-1.2710-1185.02
УДК 547.496.2 +615.281+282
SYNTHESIS, BACTERICIDAL AND FUNGICIDAL ACTIVITY OF N-(4-METHOXYPHENYL) ACETAMIDE AND N-PHENYLACETAMIDE DERIVATIVES
E.S. Sycheva1*, D.B. Markina1, M.S. Mukanova1, L.A. Boltayeva2, O.T. Seilkhanov3
'JSC« A.B. Bekturov Institute of Chemical Sciences», Almaty, Kazakhstan 2Zh. Zhiembaev Kazakh Research Institute of Plant Protection and Quarantine, Almaty, Kazakhstan 3Sh. Ualikhanov Kokshetau State University, Kokshetau, Kazakhstan E-mail: yelena-sycheva@yandex.kz
Abstract. Introduction. Particular attention in the cultivation of industrial and agricultural crops is paid to the fight against pathogenic fungi, which not only lead to significant yield losses, but they are also dangerous to humans. The purpose of this work is the synthesis of biologically active compounds in the series of aromatic dithiocarbamic acids based on N-(4-methoxyphenyl)acetamide and N-phenylacetamide and the study of their antifungal and antibacterial activities. Results and discussion. Biologically active aromatic sodium dithiocarbamates have been synthesized by the reaction of (N-(4-methoxyphenyl)acetamide and N-phenylacetamide) with carbon disulfide in the presence of NaOH in ethanol at 22 °C in 78 and 85% yields. Thioanhydrides have been synthesized by the acylation of sodium acetyl(4-methoxyphenyl)carbamodithioate and sodium acetyl(phenyl)carbamodithioate with acid chlorides (benzoic, 3,4-dimethoxybenzoic, 2-bromobenzoic, and 4-nitrobenzoic) in chloroform at a temperature of 22 °C. The structure of the synthesized compounds has been established on the basis of elemental analysis data, IR spectra, ^ and ^ NMR spectroscopy. Conclusion. Antifungal and bactericidal properties of the synthesized compounds were studied against phytopathogenic fungi and bacteria Fusarium oxysporum and Pectobacterium carotovorum bacteria. It has been found that sodium acetyl(4-methoxyphenyl)carbamodithioate exhibits high fungicidal and bactericidal activityies compared to the control and standards tetramethylthiuram disulfide (TMTD) and Fitolavin. It has been established that sodium acetyl(4-methoxyphenyl)carbamodithioate at a concentration of 0.4% has a high fungicidal activity and completely inhibits the growth of the Fusarium oxysporum phytopathogen. The maximum zone of inhibition (18 mm) of Pectobacterium carotovorum bacteria has been at a concentration of 0.4%.
Keywords: N-phenylacetamide, dithiocarbamates, thioanhydrides, fungicidal and bactericidal activity
Sycheva Yelena Sergeevna Candidate of Chemical Sciences; E-mail: yelena-sycheva@yandex. kz
Markina Dariay Bazarbekovna Master of Engineering Sciences; E-mail:dimels 946@list. ru
Mukanova Meruyert Sisenbekovna Candidate of Chemical Sciences; E-mail: chem mukan@mail ru
Boltayeva Lyazat Agabayevna Master of Agricultural Sciences; E-mail: LJAZAT19 81@mail ru
Seilkhanov Olzhas Tulegenovich Master of Natural Sciences; E-mail:seilkhanov@mail.ru
Citation: Sycheva E.S., Mukanova M.S., Markina D.B., Boltayeva L.A., Seilkhanov O.T. Synthesis and antibacterial activity of N-(4-methoxyphenyl)acetamide and N-phenylacetamide derivatives. Chem. J. Kaz., 2023, 1(81), 15-23. DOI: https://doi.org/10.51580/2023-1.2710-1185.02
1. Introduction
In agricultural practice, the main control means against plant fungal diseases, which guarantees high yields, the preservation of seed material and the quality of agricultural products, is still fungicide treatment.
Dithiocarbamates receive considerable attention due to their biological activity and their key role in agriculture [1, 2]. Mancozeb, maneb, ziram, metiram, zineb, ferbam are well-known dithiocarbamate fungicides that are widely used in agricultural practice as antifungal agents for cereal and legume crops, vegetables, fruits and ornamental plants [3, 4].
Dithiocarbamate pesticides are used to treat and prevent a wide range of plant fungal diseases such as powdery mildew and septoria leaf spot, late blight, downy mildew, gray mold, scab and bacterial spot [5-11]. Their use improves seed yield and quality as a post-harvest treatment to prevent fungus or mold causing food rot during storage or transport. Dithiocarbamates are non-systemic fungicides that remain on the surface of crops after treatment and prevent fungus growth without penetrating into plant tissue.
In this regard, there is an increasing interest in the synthesis of new dithiocarbamates with a wide spectrum of action, which have a protective effect against diseases and adverse factors.
2. Experimental part
The progress of the reactions and the purity of the products were monitored by thin-layer chromatography on Silufol UV-254 plates with the display of spots of the compounds with iodine vapor, eluent ethanol:acetone/hexane (1/3). IR spectra were recorded on a Nicolet 5700 spectrometer in tablets with KBr. The melting points of the compounds were determined on a Hanon MP450 instrument. The :H and 13C NMR spectra of the compounds were recorded on a JNM-ECA 400 spectrometer (Jeol) with the operating frequency of 400 (1H) and 100 MHz (13C) of the deuterated DMSOd and CDCh solutions. All reagents and solvents were received from Sigma-Aldrich and used without further purification. Elemental analysis was carried out on a Rapid Micro N Cube elemental analyzer (Elementar, Germany, 2015).
Sodium acetyl(4-methoxyphenyl)carbamodithioate (1). A solution of 2.4 g (0.06 mol) of NaOH in 5 ml of distilled water was added to a mixture of 10 g (0.06 mol) N-(4-methoxyphenyl)acetamide in 40 ml of ethanol. Then a solution of 4.6 g (0.06 mol) carbon disulfide was added dropwise. The reaction mixture was stirred at r.t. at 22 °C for 4 h. The solvent was distilled off in a water-jet pump vacuum. The product was purified by recrystallization from acetonitrile. Yield of compound 1 was 17.27 g (78.5%), f.83 (ethanol). Found, %: C 45.55; H 3.95; N 5.47; S 24.23. C10H^NNaO2S2. Calculated, %: C 45.61; H 3.83; N 5.32; S 24.36. NMR spectra (DMSO-d6), 5, ppm: 1.95 (s, 3H, CH3); 3.62 (s, 3H, OCH3); 6.77 (d, 2H, Arm); 7.42 (d, 2H, Ar„). NMR 13C spectra (DMSOd), 5, ppm: 24.2 (CH3); 55.6 (O-CH3); 114.3, 121.2, 132.9, 143.6, 155.6 (Ar); 168.5 (C=0); 230.6 (C=S).
Sodium acetyl(phenyl)carbamodithioate (2). Yield 14.6 g (85%), Rf 0.80 (ethanol). Found, %: C 46.45; H 3.55; N 5.87; S 27.33. C9H8NNaOS2. Calculated, %: C 46.34; H 3.46; N 6.00; S 27.49. IR spectra (KBr), v, cm-1: 1651 (C=0), 1036 (C=S), 685 (C-S). NMR 13C spectra (DMSOd), 5, ppm: 24.3 (CH3); 119.7, 129.0, 139.2 (Ar); 169.4 (C=0); 230.6 (C=S).
Benzoic acetyl(phenyl)carbamothioic thioanhydride (3). A solution of 1.2 g (0.0085 mol) of benzoyl chloride was added dropwise to a solution of 2 g (0.0085 mol) sodium acetyl(phenyl)carbamodithioate in 25 ml of chloroform with stirring. The mixture was stirred at room temperature of 22 °C for two hours. The solvent was distilled off in a water-jet pump vacuum, the product was isolated by recrystallization from hexane. Yield 1.49 g (56%), Rf 0.62 (acetone/hexane, 1/3), an oil. Found, %: C 60.85; H 4.27; N 4.35; S 20.41. C16H13NO2S2. Calculated, %: C 60.93; H 4.15; N 4.44; S 20.33. IR spectra (KBr), v, cm-1: 1695, 1787 (C=0), 1004 (C=S), 683 (C-S). NMR 13C spectra (CDCI3), 5, ppm: 24.5 (CH3); 128.1, 128.4, 129.6, 130.6, 134.5, 134.7 (Ar); 166.6 (C^C=0); 171.8 (SC=0); 205.0 (C=S).
3,4-Dimethoxybenzoic acetyl(phenyl)carbamothioic thioanhydride (4) was synthesized in a similar way. Yield 2.4 g (75%), Rf 0.24 (acetone/hexane, 1/3), m.p. 92 0C. Found, %: C 57.65; H 4.67; N 3.69; S 17.21. C18H17NO4S2. Calculated, %: C 57.58; H 4.56; N 3.73; S 17.08. IR spectra (KBr), v, cm-1: 1664, 1761 (C=0), 1059 (C=S), 605 (C-S). NMR 1H spectra (CDCh), 5, ppm: 2.11 (s, 3H, CH3); 3.89 (s, 6H, OCH3); 6.91 (d, 1H); 7.03 (t, 2H); 7.22 (t, 1H); 7.50 (d, 1H); 7.57 (s, 1H), 7.74 (d, 1H). NMR 13C spectra (CDCI3), 5, ppm: 24.3 (CH3); 56.1 (OCH3); 110.6, 112.5, 120.3, 124.3, 125.3, 128.9, 138.2, 148.5, 149.1 (Ar);
169.6 (CH3C=0); 170.7 (SC=0); 203.1 (C=S).
2-Bromobenzoic acetyl(phenyl)carbamothioic thioanhydride (5) was synthesized in a similar way. Yield 1.85 r (88%), Rf 0.67 (acetone/hexane, 1/3), m.p. 80 0C. Found, %: C 48.65; H 3.19; N 3.69; S 16.35. C16H^BrNO2S2. Calculated, %: C 48.74; H 3.07; N 3.55; S 16.26. IR spectra (KBr), v, cm-1: 1691, 1784 (C=0), 1022 (C=S), 628 (C-S). NMR 1H spectra (CDCl3), 5, ppm: 2.13 (s, 3H, CH3); 7.05 (t, 2H); 7.25 (t, 1H); 7.42 (t, 2H); 7.49 (d, 1H); 7.80 (d, 1H). NMR 13C spectra (CDCI3), 5, ppm: 24.5 (CH3); 120.1, 124.3, 128.9, 129.4, 132.0, 138.17, 141.1 (Ar); 169.1 (CftC=0); 184.3 (SC=0); 202.7 (C=S).
4-Nitrobenzoic acetyl(4-methoxyphenyl)carbamothioic thioanhydride (6) was synthesized in a similar way. Yield 1.27 r (49%), Rf 0.47 (acetone/hexane, 1/3), m.p. 109-110 0C. Found, %: C 52.42; H 3.79; N 7.09; S 16.35. C17H14N2O5S2. Calculated, %: C 52.30; H 3.61; N 7.17; S 16.43. IR spectra (KBr), v, cm-1: 1687, 1765 (C=0), 1055 (C=S), 678 (C-S). NMR 1H spectra (DMSOd), 5, ppm: 1.95 (s, 3H, CH3); 3.64 (s, 3H, OCH3); 6.78 (d, 2H); 7.42 (d, 2H); 8.09 (d, 2H); 8.22 (d, 2H). NMR 13C spectra (DMSOd), 5, ppm: 24.1 (CH3); 55.6 (O-CH3); 114.2, 121.0, 124.0, 131.1, 133.0, 150.5, 155.5 (Ar); 166.2 (CftC=0); 168.2 (SC=0);
201.7 (C=S).
The fungicidal activity of the synthesized compounds was studied at the Kazakh Research Institute of Plant Protection and Quarantine named after Zh. Zhiembaev.
The study of fungicidal properties was carried out by the disk-diffusion method on Potato Dextrose Agar (PDA). Test object: pure culture of the fungus Fusarium Sp. Paper discs 10 mm in diameter were placed in Petri dishes with PDA agar medium at a distance of 2 mm from the edge of the dish and at an equal distance from each other, impregnated with a solution of the test substance. Afterwards micromycetes were sown in Petri dishes on a nutrient medium by the surface method. Incubation lasted for 7-14 days in a thermostat at a temperature of 27 °C. The presence of a inhibition zone of fungal growth was noted after 3 days. At the end of the incubation was measured the zone of fungal growth inhibition around the disk.
Determination of bactericidal properties was carried out by the well method on Potato Agar (PA). Test object: pure culture of bacteria Pectobacterium carotovorum, which was identified by PCR analysis. A daily culture of the test object was inoculated into Petri dishes with a nutrient medium, turbidity standard was 10-9. In the center of the Petri dish inoculated with the test object, 12 mm wells were made, into which solutions of the compounds were added. Petri dishes were placed in a thermostat at a temperature of 25-26 °C, which was optimal for bacterial growth. The presence of a zone of inhibition of bacterial growth was noted after 2 days.
Lab experience options:
1. Control (water);
2. TMTD (standard), (0.4%);
3. Phytolavin (standard), (0.5%);
4. Compound 1 (0.1%, 0.2%, 0.4%);
5. Compound 6 (0.1%, 0.2%, 0.4%).
3. Results and discussion
The aim of the study is the targeted synthesis of new potential biologically active aromatic dithiocarbamic acids.
Sodium dithiocarbamates were obtained by reacting amines (N-(4-methoxyphenyl)acetamide and N-phenylacetamide) with carbon disulfide in the presence of NaOH in ethanol at 25 °C. Sodium acetyl(4-methoxyphenyl)carbamodithioate 1 (78.5%) and sodium acetyl(phenyl)carbamodithioate 2 (85%) were individually isolated after completion of the reactions and appropriate treatment of the reaction mixtures.
New carbonyl derivatives of thioangirides were synthesized by acylation of sodium dithiocarbamates. Acylation of dithiocarbamates 1, 2 was carried out by reacting sodium acetyl(4-methoxyphenyl)carbamodithioate 1 and sodium acetyl(phenyl)carbamodithioate 2 with acid chlorides (benzoic, 3,4-dimethoxybenzoic, 2-bromobenzoic and 4-nitrobenzoic) in chloroform medium at a temperature of 25 °C within 3 h.
As a result of isolation from reaction mixtures, thioanhydrides 3-6 were obtained individually in 49-88% yields, respectively.
h3C H3C H3C
)=0 CS2, NaOH r=° R2COCl ' '°
c2H5OH • Ri"AL>N>=s M1>\=S
NaS S
1,2 3-6 \ Q
r2
1: Rj = OCHj; 2: R, = H; 3: R, = H; R2 = C6H5; 4: R, = H; R2 = 3,4-(OCH3)2C6H3;
5: R! = H; R2 = 2-BrC6H4; 6: R! = OCH3; R2 = 4-N02C6H4;
The composition of the synthesized compounds was confirmed by elemental analysis, thin layer chromatography and physicochemical characteristics. The structure of the compounds 3-6 was established based on the analysis of IR and :H, 13C NMR spectroscopy data. The characteristic signals of protons and carbon atoms in the synthesized molecules 1 -6 are presented in the experimental part.
The synthesized compounds 1 and 6 were tested for antibacterial activity against the phytopathogen Fusarium oxysporum and bacteria Pectobacterium carotovorum (Table 1, Figure 1).
Table 1 - Fungicidal and bactericidal properties of compounds 1 and 6
Preparation Concentration, % Suppression zone, mm Fusarium Sp. Suppression zone, mm P. carotovorum
Control (Water) - -
TMTD (Standard) 0.4 5 -
Phytolavin (Standard) 0.5 - 4
Compound 1 0.1 10 12
0.2 17 15
0.4 clean 18
Compound 6 0.1 - 3
0.2 - 3
0.4 - 3
Note - «-» - No zone of suppression of fungal and bacterial infection.
Analysis of the test results shows that compound 1 exhibits the highest fungicidal and bactericidal activity compared to the control and standards TMTD and Phytolavin.
The highest degree of antimicrobial activity was shown by compound 1 at the concentration of 0.4% against Fusarium Sp. completely inhibited the growth of the phytopathogen and P. carotovorum the zone of inhibition was 18 mm.
It was found that sodium dithiocarbamate 1 has a high antimicrobial activity against Fusarium Sp. and Pectobacterium carotovorum. Whereas dithiocarbamic acid thioanhydride 6 showed no activity.
Compound 1 (0.1%) Compound 1 (0.2%) Compound 1 (0.4%)
Figure 1 - Fungicidal and bactericidal properties of compound 1.
4. Conclusion
As a result of this research, new thioanhydrides of aromatic dithiocarbamates based on N-(4-methoxyphenyl)acetamide and N-phenylacetamide were
synthesized. The structure of the compounds was established based on the analysis of :Н and 13С NMR spectroscopy data. It was established that sodium acetyl(4-methoxyphenyl)carbamodithioate has a high antibacterial activity compared to the well-known preparations TMTD and Phytolavin.
Acknowledgements: The SC MHES RK supported this work within the framework of the grant project for young scientists No. AR09057956 (2021-2023) "Development of bioorganic complexes with natural polysaccharides as an ecologically safe plant protection product".
Conflict of Interests: All authors declare that they have no conflict of interest.
СИНТЕЗ, БАКТЕРИЦИДНАЯ И ФУНГИЦИДНАЯ АКТИВНОСТЬ ПРОИЗВОДНЫХ ^(4-МЕТОКСИФЕНИЛ)АЦЕТАМИДА И N-ФЕНИЛАЦЕТAМИДА
Е.С. Сычева1*, Д. Б. Маркина1, М.С. Муканова1, Л. А Болтаева2, О. Т. Сейлханов3
1 Институт химических наук имени А.Б. Бектурова, Алматы, Казахстан 2Казахский научно-исследовательский институт защиты и карантина растений имени Ж. Жиембаева, Алматы, Казахстан
3Кокшетауский государственный университет имени Ш. Уалиханова, Кокшетау, Казахстан E-mail: yelena-sycheva@yandex.kz
Резюме. Введение. Особое внимание при выращивании технических и сельскохозяйственных культур уделяется борьбе с патогенными грибами, которые не только приводят к значительным потерям урожайности, но и опасны для человека. Целью данной работы является синтез биологически активных веществ в ряду ароматических дитиокарбаминовых кислот на основе N-(4-метоксифенил)ацетамида и N-фенилацетамида, и изучение их противогрибковой и антибактериальной активности. Результаты и обсуждение. Биологически активные ароматические дитиокарбаматы натрия с выходами 78 и 85% синтезированы взаимодействием аминов (Ы-(4-метоксифенил)ацетамида и N-phenylacetamide) с сероуглеродом в присутствии гидроксида натрия в этиловом спирте при температуре 22 оС. Тиоангидриды синтезированы ацилированием ацетил(4-метоксифенил)карбамодитиоата натрия и ацетил(фенил)карбамодитиоата натрия хлорангидридами (бензойный, 3,4-диметоксибензойный, 2-бромбензойный и 4-нитробензойный) в среде хлороформа при температуре 22 оС. Структура синтезированных соединений установлена на основании данных элементного анализа, ИК-спектров и спектроскопии ЯМР 1Н и 13С. Заключение. Изучены противогрибковые и бактерицидные свойства синтезированных соединений в отношении фитопатогенных грибов и бактерий Fusarium oxysporum и Pectobacterium can^orum. Выявлено, что ацетил(4-метоксифенил)карбамодитиоат натрия проявляет высокую фунгицидную и бактерицидную активность по сравнению с контролем и эталонами тетраметилтиурамдисульфид (ТМТД) и Фитолавин. Установлено, что ацетил(4-метоксифенил)карбамодитиоат натрия в концентрации 0.4% обладает высокой фунгицидной активностью и полностью ингибурует рост фитопатогена Fusarium oxysporum. Максимальная зона ингибирования (18 мм) бактерий Pectobacterium carоtоvorum составила при концентрации 0.4 %.
Ключевые слова: N-фенилацетамид, дитиокарбаматы, тиоангидриды, фунгицидная и бактерицидная активность
Сычева Елена Сергеевна Кандидат химических наук
Маркина Дария Базарбековна Магистр технических наук
Муканова Меруерт Сисенбековна Кандидат химических наук
Болтаева Лязат Агабаевна Магистр сельскохозяйственных наук
Сейлханов Олжас Тулегенович Магистр естественных наук
]\-(4-МЕТОКСИФЕНИЛ)АЦЕТАМИД ЖЭНЕ N-ФЕНИЛАЦЕТАМИД ТУЫНДЫЛАРЫНЬЩ СИНТЕЗ1, ОЛАРДЬЩ БАКТЕРИЦИДТ1К ЖЭНЕ ФУНГИЦИДТ1К БЕЛСЕНД1Л1Г1
Е. С. Сычева '*, Д.Б. Маркина 1, МС. Муканоеа Л.А. Болтаееа 2, О. Т. Сейлханое 3
'Э.Б. БектYров атындагы химия гылымдары институты, Алматы, Цазацстан 2Ж. Жиембаев атындагы К,азац всмдт цоргау жэне карантин гылъми зерттеу институты, Алматы, Цазацстан
3Ш. Уэлиханов атындагы Квкшетау ммеммлекеттт университетi, Квкшетау, Цазацстан E-mail: yelena-sycheva@yandex.kz
Туйшдеме. Kipicne. Техникалык жэне ауылшаруашылык дакылдарын ecipy кезшде патогендж сацыраукулактармен куресуге ерекше назар аударылады, бул ешмдшктщ айтарлыктай жогалуына экелiп кана коймай, адамдар Yшiн де каyiптi. Жумыстыц мацсаты Ы-(4-метоксифенил)ацетамид пен N-фенилацетамид непзшде ароматикалык дитиокарбамин кышкылдарыныц катарындагы биологиялык белсендi заттарды синтездеу жэне олардыц сацыраукулакка карсы жэне бактерияга карсы белсендiлiгiн зерттеу болып табылады. Нэтижелер жэне талцылау. Биологиялык белсендi ароматикалык натрий дитиотиокарбаматтары 78 жэне 85% шыгыммен аминдердщ (N-(4-метоксифенил)ацетамида жэне N-фенеилацетамид) KYкiрткeмiртекпен NaOH катысында этил спиртшде 22 oC температурада синтезделш алынды. Тиоангидридтер натрий ацетил(4-метоксифенил)карбамодитиоаты жэне натрий ацетил(фенил)карбамодитиоатыныц хлорангидридтермен (бензойлы, 3,4-диметоксибензойлы, 2-бромбензойлы жэне 4-нитробензойлы) хлороформ ортасында 22 оС температурада ацилдеу аркылы синтезделдi. Синтезделген косылыстардыц курылымы элементтiк талдау, ИК^-спектрлер^ ЯМР 1Н жэне 13С спектроскопиясы негiзiнде дэлелдендг Кррытынды. Синтезделген косылыстардыц Fusarium oxysporum жэне Pectobacterium carotovorum фитопатогендi сацыраукулагына жэне бактериясына сацыраукулакка карсы жэне бактерицидтж касиеттерi зерттелiндi. Бакылаумен жэне тетраметилтиурамдисульфид (ТМТД) жэне Фитолавин эталондарымен салыстырганда натрий ацетил(4-метоксифенил)карбамодитиоаты жогары фyнгицидтiк жэне бактерицидтiк белсендiлiк керсеткеш аныкталды. Сынактар нэтижесiнде натрий ацетил(4-метоксифенил)карбамодитиоаты 0.4% концентрациясында жогары фyнгидцидтi белсендшкке ие екендiгi жэне Fusarium oxysporum фитопатогешнщ eсiмiн толыктай тежейтiнi аныкталды. Pectobacterium carotovorum бактериясыныц максималды тежелу аймагы (18 мм) 0.4 % концентрацияда болды.
ТYЙiн сездер: N-фенилацетамид, дитиокарбаматтар, тиоангидридтер, фунгицидтiк жэне бактерицидтж белсендiлiк
Сычева Елена Сергеевна Химия гылымдарыныц кандидаты
Маркина Дария Базарбековна Техникалыц гылымдар Maucmpi
Муканова Меруерт Сисенбековна Химия гылымдарыныц кандидаты
Болтаева Лязат Агабаевна Ауыл шаруашылыгы гылымдарыныц K^^mpi
Сейлханов Олжас Тулегенович Жаратылыстану гылымдарыныц мaгucmpi
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