MD4740C1 - Use of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazole-1-yl)pent-1-en-3-one as an active compound against phytopathogenic bacteria - Google Patents
Use of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazole-1-yl)pent-1-en-3-one as an active compound against phytopathogenic bacteria Download PDFInfo
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- MD4740C1 MD4740C1 MDA20200056A MD20200056A MD4740C1 MD 4740 C1 MD4740 C1 MD 4740C1 MD A20200056 A MDA20200056 A MD A20200056A MD 20200056 A MD20200056 A MD 20200056A MD 4740 C1 MD4740 C1 MD 4740C1
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- HSYXNSUUVTWJTP-JYRVWZFOSA-N (z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1/C(C(=O)C(C)(C)C)=C\C1=CC=C([N+]([O-])=O)C=C1 HSYXNSUUVTWJTP-JYRVWZFOSA-N 0.000 title claims abstract description 8
- 241000894006 Bacteria Species 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 title claims description 10
- 230000003032 phytopathogenic effect Effects 0.000 title claims description 8
- 241000588698 Erwinia Species 0.000 claims description 4
- 241000589634 Xanthomonas Species 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 16
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003899 bactericide agent Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 9
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 7
- 239000005787 Flutriafol Substances 0.000 description 7
- 125000001376 1,2,4-triazolyl group Chemical class N1N=C(N=C1)* 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 6
- 241000588701 Pectobacterium carotovorum Species 0.000 description 5
- 150000003852 triazoles Chemical class 0.000 description 5
- 239000005822 Propiconazole Substances 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241000588694 Erwinia amylovora Species 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000815873 Xanthomonas euvesicatoria Species 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FHOIVKVRWCOMTB-UHFFFAOYSA-N 1-(2h-triazol-4-yl)prop-2-en-1-one Chemical class C=CC(=O)C=1C=NNN=1 FHOIVKVRWCOMTB-UHFFFAOYSA-N 0.000 description 1
- FMWWRALTYIWZEB-UHFFFAOYSA-N 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C)(C)C(=O)CN1C=NC=N1 FMWWRALTYIWZEB-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 235000002567 Capsicum annuum Nutrition 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000588921 Enterobacteriaceae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000220222 Rosaceae Species 0.000 description 1
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 1
- 241000589636 Xanthomonas campestris Species 0.000 description 1
- 241000589652 Xanthomonas oryzae Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 208000013435 necrotic lesion Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- -1 vinyltriazole ketone Chemical class 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Invenţia se referă la aplicarea compuşilor heterociclici, derivaţi ai 1,2,4-triazolului, în calitate de remediu antibacterian şi poate fi utilizată în agricultură.Esenţa invenţiei revendicate constă în aplicarea în calitate de compus activ contra bacteriilor fitopatogene din genul Erwinia şi Xanthomonas a (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-onei cu formula:.Valorile concentraţiei minime bactericide constituie 0,4...2,0 µg/mL.The invention relates to the application of heterocyclic compounds, derivatives of 1,2,4-triazole, as an antibacterial remedy and can be used in agriculture. (Z) -4,4-dimethyl-1- (4-nitrophenyl) -2- (1H-1,2,4-triazol-1-yl) pent-1-en-3-one of the formula: .Concentration values minimum bactericides are 0.4 ... 2.0 µg / mL.
Description
Invenţia se referă la aplicarea compuşilor heterociclici, derivaţi ai 1,2,4-triazolului, în calitate de remediu antibacterian şi poate fi utilizată în agricultură. The invention refers to the application of heterocyclic compounds, derivatives of 1,2,4-triazole, as an antibacterial remedy and can be used in agriculture.
Speciile de bacterii fitopatogene pot provoca diferite boli ale plantelor agricole, în special din genurile Erwinia şi Xanthomonas. De exemplu, Erwinia amylovora, bacteria gram-negativă din familia Enterobacteriaceae, este agentul cauzal al focului bacterian, o boală devastatoare a plantelor care afectează o gamă largă de specii din cadrul genului Rosaceae şi este o ameninţare globală majoră pentru producţia comercială de mere şi pere (Piqué N., Miñana-Galbis D., Merino S. M. Tomás J.. Virulence Factors of Erwinia amylovora: A Review. Int. J. Mol. Sci., 2015, 16(6), p. 12836-12854). O altă specie, E. carotovora, cauzeaza putregaiul moale la culturile economico-importante, precum cartofi, roşii, castraveţi. În cazul cartofului se produce putregaiul moale al tulpinii şi tuberculilor până şi după recoltare, astfel reducând considerabil randamentul roadei (Benada M., Boumaaza B., Boudalia S., Khaladi O., Guessas B. Variability of aggressiveness and virulence of Erwinia carotovora subsp. carotovorum causing the soft rot on potato tubers in the western of Algeria. Int. J. of Plant Biology, 2018, vol. 9:7568, p. 52-56). Xanthomonas campestris pv. vesicatoria este o bacterie gram-negativă biotrofică şi este agentul care provoacă pătarea bacteriană a tomatelor (Solanum lycopersicum L.) sau a ardeiului (Capsicum annuum), o boală care este prezentă la nivel mondial. Simptomele infectării bacteriene includ desfolierea şi leziunile necrotice clorotice pe frunze, tulpini, fructe şi flori, care conduc ulterior la un randament redus al roadei (Tamir-Ariel D., Navon N., and Burdman S. Identification of Genes in Xanthomonas campestris pv. vesicatoria induced during its interaction with tomato. J. Bacteriol., 2007, 189(17), p. 6359-6371). Species of phytopathogenic bacteria can cause different diseases of agricultural plants, especially from the genera Erwinia and Xanthomonas. For example, Erwinia amylovora, the gram-negative bacterium of the Enterobacteriaceae family, is the causative agent of fire blight, a devastating plant disease that affects a wide range of species within the genus Rosaceae and is a major global threat to commercial apple and pear production. (Piqué N., Miñana-Galbis D., Merino S. M. Tomás J.. Virulence Factors of Erwinia amylovora: A Review. Int. J. Mol. Sci., 2015, 16(6), p. 12836-12854). Another species, E. carotovora, causes soft rot in economically important crops, such as potatoes, tomatoes, cucumbers. In the case of potato, the soft rot of the stem and tubers occurs even after harvesting, thus considerably reducing the yield of the fruit (Benada M., Boumaaza B., Boudalia S., Khaladi O., Guessas B. Variability of aggressiveness and virulence of Erwinia carotovora subsp . carotovorum causing the soft rot on potato tubers in the western of Algeria. Int. J. of Plant Biology, 2018, vol. 9:7568, p. 52-56). Xanthomonas campestris pv. vesicatoria is a biotrophic gram-negative bacterium and is the agent that causes bacterial spotting of tomatoes (Solanum lycopersicum L.) or pepper (Capsicum annuum), a disease that is present worldwide. Symptoms of bacterial infection include defoliation and chlorotic necrotic lesions on leaves, stems, fruits and flowers, which subsequently lead to reduced fruit yield (Tamir-Ariel D., Navon N., and Burdman S. Identification of Genes in Xanthomonas campestris pv. vesicatoria induced during its interaction with tomato. J. Bacteriol., 2007, 189(17), p. 6359-6371).
În calitate de remedii contra unor fitopatogeni pot servi compuşii heterociclici din clasa triazolilor derivatizaţi sau fuzionaţi cu alte grupări ciclice [1]. Triazolii reprezintă o clasă de compuşi heterociclici cu catena de 5 atomi ce conţine trei atomi de azot în ciclu situaţi în poziţiile 1,2,4 sau 1,2,3. Proprietăţile antimicrobiene ale triazolilor depind puternic de natura substituenţilor şi de conformarea lor. Sunt cunoscuţi mii de derivaţi triazolici, doar unii din ei manifestă activitate suficientă contra agenţilor fitopatogeni şi sunt utilizaţi în agricultură, în special în calitate de fungicide. De exemplu, propinacozolul (1-[[2-(2,4-diclorofenil)-4-propil-1,3-dioxolan-2-il]metil]-1,2,4-triazol) [2] sau derivatul terţ-alcoolic flutriafol (alcoolul (RS)-2,4′-difluoro-α-(1H-1,2,4-triazol-1-ilmetil)benzhidrilic) [3]. De asemenea au fost depistate proprietăţi antifungice la un şir de derivaţi din grupul de viniltriazolilcetone, totodată ele au manifestat proprietăţi erbicide şi de reglare a creşterii plantelor [4]. Este necesar de menţionat că în calitate de agenţi contra putregaiului moale, cauzat de bacteria Erwinia carotovora, au fost propuşi un grup de compuşi fungicizi cu diverse structuri chimice, şi care nu sunt activi contra bacteriei sus-menţionate în caz de aplicare directă pe bacterie, dar sunt activi contra putregaiului moale în caz de aplicare pe solul adiacent prin acţiune fungicidă. Printre compuşii propuşi se regăseşte şi unul din clasa 1,2,4-triazolilor cu grupări sulfonamidice în poziţiile 1 şi 4 [5]. Prin urmare, prezenţa ciclului 1,2,4-triazolic nu conferă obligator proprietăţi antibacteriene compusului, care se manifestă ca fungicid. Heterocyclic compounds from the class of triazoles derivatized or fused with other cyclic groups can serve as remedies against some phytopathogens [1]. Triazoles represent a class of heterocyclic compounds with a chain of 5 atoms containing three nitrogen atoms in the ring located in positions 1,2,4 or 1,2,3. The antimicrobial properties of triazoles strongly depend on the nature of the substituents and their conformation. Thousands of triazole derivatives are known, only some of them show sufficient activity against phytopathogenic agents and are used in agriculture, especially as fungicides. For example, propinacozole (1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole) [2] or the third derivative -flutriafol alcohol ((RS)-2,4′-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol) [3]. Antifungal properties were also detected in a series of derivatives from the group of vinyltriazolyl ketones, at the same time they showed herbicidal and plant growth regulating properties [4]. It is necessary to mention that as agents against soft rot, caused by the bacterium Erwinia carotovora, a group of fungicidal compounds with various chemical structures have been proposed, and which are not active against the above-mentioned bacterium in case of direct application to the bacterium, but they are active against soft rot when applied to the adjacent soil through fungicidal action. Among the proposed compounds is one from the class of 1,2,4-triazoles with sulfonamide groups in positions 1 and 4 [5]. Therefore, the presence of the 1,2,4-triazole ring does not necessarily confer antibacterial properties to the compound, which manifests itself as a fungicide.
În calitate de remediu contra bacteriilor fitopatogene din specia Xanthomonas oryzae a fost propus derivatul 1,4-pentandien-3-onic legat prin gruparea 3-tioeterică cu nucleul de 1,2,4-triazol [6]. Un dezavantaj al acestui compus constă în faptul că el posedă o structură destul de complecxă şi ca urmare este relativ greu de sintetizat. The 1,4-pentandien-3-onic derivative linked by the 3-thioether group with the 1,2,4-triazole nucleus was proposed as a remedy against the phytopathogenic bacteria of the Xanthomonas oryzae species [6]. A disadvantage of this compound is that it has a rather complex structure and as a result is relatively difficult to synthesize.
Problema pe care o rezolvă invenţia constă în lărgirea arsenalului de remedii antibacteriene contra fitopatogenilor din genul Erwinia şi Xanthomonas care conţin compuşi 1,2,4-triazolici, care pot fi obţinuţi relativ simplu. The problem that the invention solves consists in widening the arsenal of antibacterial remedies against phytopathogens of the genus Erwinia and Xanthomonas that contain 1,2,4-triazole compounds, which can be obtained relatively simply.
Esenţa invenţiei constă în aceea că se propune aplicarea în calitate de compus activ contra bacteriilor fitopatogene din genul Erwinia şi Xanthomonas a Z-izomerului viniltriazolcetonei, şi anume, (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona. The essence of the invention is that the Z-isomer of vinyltriazole ketone, namely, (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2 -(1H-1,2,4-triazol-1-yl)pent-1-en-3-one.
Sinteza acestui izomer este bine elaborată, se desfăşoară stereospecific în două etape, din intermediari uşor accesibili şi cu un randament mare (70%), conform brevetului MD 4515 B1 2017.09.30. Compusul dezvăluit posedă proprietăţi antituberculoase (MD 4519 B1 2017.10.31). The synthesis of this isomer is well developed, it takes place stereospecifically in two stages, from easily accessible intermediates and with a high yield (70%), according to patent MD 4515 B1 2017.09.30. The disclosed compound possesses anti-tuberculosis properties (MD 4519 B1 2017.10.31).
Exemplu de realizare a invenţiei Example of realization of the invention
În calitate de compus iniţial în sinteza Z-izomerului antibacterian (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona se utilizează cetona 3,3-dimetil-1-(1H-1,2,4-triazol-1-il)butan-2-ona, obţinută conform brevetului MD 4505 B1 2017.08.31. As a starting compound in the synthesis of the antibacterial Z-isomer (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1- en-3-one, the ketone 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one is used, obtained according to patent MD 4505 B1 2017.08.31.
Procedeul de sinteză stereospecifică a Z-izomerului prevede interacţiunea cetonei sus-menţionate cu 4-nitrobenzaldehida în benzen în prezenţa piperidinei şi acidul acetic în cantităţi catalitice, conform protocolului descris în brevetul MD 4515 B1 2017.09.30. The procedure for the stereospecific synthesis of the Z-isomer provides for the interaction of the above-mentioned ketone with 4-nitrobenzaldehyde in benzene in the presence of piperidine and acetic acid in catalytic amounts, according to the protocol described in patent MD 4515 B1 2017.09.30.
Activitatea antibacteriană Antibacterial activity
(Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona a fost testată in vitro pentru determinarea activităţii antibacteriane împotriva tulpinilor Erwinia amylovora, Erwinia carotovora şi Xantomonas campestris. Ca standard de control în testele de inhibare in vitro au fost folosite preparatele comerciale din clasa triazolilor propiconazolul şi flutriafolul. (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one was tested in vitro for determination of antibacterial activity against Erwinia amylovora, Erwinia carotovora and Xantomonas campestris strains. Commercial preparations from the triazole class, propiconazole and flutriafol, were used as a control standard in the in vitro inhibition tests.
Pentru evaluarea activităţii antimicrobiene a fost utilizată metoda diluţiilor succesive duble (http://www.dntpasteur.ru/metodic2_4_2_2.php), care constă în aceea că la etapa iniţială se iau şiruri de 10 eprubete în care se introduc câte 1 mL de bulion peptonat pentru bacterii. Ulterior se picură 1 mL de preparat (dizolvat în DMSO) în prima eprubetă (din şirul de 10 eprubete). Se pipetează amestecul obţinut, după care 1 mL din acesta se transferă în eprubeta următoare, astfel că procedura se repetă până la eprubeta nr. 10 a şirului. În aşa mod, concentraţia preparatului iniţial se micşorează de 2 ori în fiecare eprubetă următoare. În acelaşi timp, se prepară culturi de 24 ore de microorganisme-test. Se prepară iniţial suspensii de culturi bacteriene cu densităţile optice (D.O.) de 2,0 şi 7,0, respectiv, în conformitate cu indicele McFarland. Ulterior, se transferă 1 mL de suspensie bacteriană obţinută într-o eprubetă ce conţine 9 mL de apă distilată sterilă. Se amestecă conţinutul obţinut, după care se transferă 1 mL în eprubeta nr. 2 din şirul de 5 eprubete ce conţin câte 9 mL de apă distilată sterilă. Din eprubeta nr. 5 a şirului se ia câte 0,1 mL de suspensie bacteriană, ceea ce reprezintă doza de însămânţare, şi se adaugă în fiecare eprubetă care conţine preparatele titrate. Ulterior, eprubetele cu preparatele titrate, în care s-au introdus dozele de însămânţare ale bacteriilor, se plasează în termostat la temperatura de 35°C timp de 24 ore. A 2-a zi se analizează preliminar rezultatele obţinute. Ultima eprubetă din şir în care nu se atestă o creştere vizibilă a bacteriilor se consideră a fi concentraţia minimă inhibitorie (CMI) a preparatului. Pentru aprecierea concentraţiei minime bactericide (CMB), conţinutul eprubetelor cu CMI şi a eprubetelor cu concentraţii mai înalte ale preparatelor se însămânţează pe agarul peptonat solid din cutiile Petri cu ajutorul ansei bacteriologice. Cutiile însămânţate se plasează în termostat la temperatura de 35°C pentru 24 ore. Concentraţia preparatelor care nu permit creşterea nici a unei colonii bacteriene se consideră a fi concentraţia minimă bactericidă a preparatului. To evaluate the antimicrobial activity, the method of double successive dilutions was used (http://www.dntpasteur.ru/metodic2_4_2_2.php), which consists in the fact that at the initial stage rows of 10 test tubes are taken into which 1 mL of broth is inserted peptonate for bacteria. Afterwards, drop 1 mL of the preparation (dissolved in DMSO) into the first test tube (from the row of 10 test tubes). The obtained mixture is pipetted, after which 1 mL of it is transferred to the next test tube, so the procedure is repeated until test tube no. 10 of the string. In this way, the concentration of the initial preparation is reduced by 2 times in each subsequent test tube. At the same time, 24-hour cultures of test microorganisms are prepared. Bacterial culture suspensions are initially prepared with optical densities (O.D.) of 2.0 and 7.0, respectively, according to the McFarland index. Afterwards, transfer 1 mL of the obtained bacterial suspension into a test tube containing 9 mL of sterile distilled water. Mix the contents obtained, after which transfer 1 mL into test tube no. 2 of the row of 5 test tubes each containing 9 mL of sterile distilled water. From test tube no. 5 of the row, take 0.1 mL of the bacterial suspension, which represents the seeding dose, and add it to each test tube containing the titrated preparations. Afterwards, the test tubes with the titrated preparations, in which the seeding doses of the bacteria were introduced, are placed in the thermostat at a temperature of 35°C for 24 hours. On the 2nd day, the obtained results are preliminarily analyzed. The last test tube in the row in which there is no visible growth of bacteria is considered to be the minimum inhibitory concentration (MIC) of the preparation. To assess the minimum bactericidal concentration (MBC), the contents of the test tubes with MIC and of the test tubes with higher concentrations of the preparations are seeded on the solid peptone agar in the Petri dishes with the help of the bacteriological loop. The seeded boxes are placed in the thermostat at a temperature of 35°C for 24 hours. The concentration of preparations that do not allow the growth of any bacterial colony is considered to be the minimum bactericidal concentration of the preparation.
Rezultatele determinării activităţii contra bacteriilor fitopatogene sunt expuse în Tabelul de mai jos. The results of determining the activity against phytopathogenic bacteria are presented in the Table below.
Tabel Table
Concentraţiile bactericide minime (CBM) ale Z-izomerului sus-menţionat şi ale compuşilor de referinţă Minimum bactericidal concentrations (CBM) of the above-mentioned Z-isomer and reference compounds
Tulpina de bacterii CBM (µg/mL ) (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona Propiconazol Flutriafol Erwinia amylovora 0,4...2,0 62,5...125,0 62,5...125,0 Erwinia carotovora 0,4...2,0 62,5...125,0 62,5...125,0 Xanthomonas campestris 0,4...2,0 62,5...125,0 62,5...125,0 Bacterial strain CBM (µg/mL ) (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en- 3-ona Propiconazol Flutriafol Erwinia amylovora 0.4...2.0 62.5...125.0 62.5...125.0 Erwinia carotovora 0.4...2.0 62.5.. .125.0 62.5...125.0 Xanthomonas campestris 0.4...2.0 62.5...125.0 62.5...125.0
Rezultatul determinării activităţii antibacteriene, exprimat în concentraţia minimă bactericidă (100% inhibiţie), a constituit 0,4...2,0 µg/mL pentru Z-viniltriazolcetona revendicată. Totodată pentru compuşii de referinţă propiconazol şi flutriafol acest procent de inhibiţie constituie respectiv 62,5...125,0 µg/mL. The result of determining the antibacterial activity, expressed in the minimum bactericidal concentration (100% inhibition), was 0.4...2.0 µg/mL for the claimed Z-vinyltriazole ketone. At the same time, for the reference compounds propiconazole and flutriafol, this percentage of inhibition is respectively 62.5...125.0 µg/mL.
Aceste rezultate demonstrează că (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona manifestă o acţiune antibacteriană sporită contra tulpinilor fitopatogene din genul Erwinia şi Xanthomonas. Această activitate este una neevidentă, reieşind din activitatea manifestată de triazolii comerciali. These results demonstrate that (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one exhibits a increased antibacterial action against phytopathogenic strains of the genus Erwinia and Xanthomonas. This activity is not obvious, emerging from the activity shown by commercial triazoles.
Aşadar, a fost stabilit că activitatea bactericidă a Z-izomerului propus faţă de tulpinile fitopatogene sus-menţionate este de 31 de ori mai mare faţă de cea a pesticidelor de referinţă propiconazol şi flutriafol. Prin urmare, (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona poate fi utilizată în calitate de compus activ în remediile antibacteriene pentru agricultură. Therefore, it was established that the bactericidal activity of the proposed Z-isomer against the above-mentioned phytopathogenic strains is 31 times higher than that of the reference pesticides propiconazole and flutriafol. Therefore, (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one can be used as an active compound in agricultural antibacterial remedies.
1. Subhas Sahoo, K.N. Sindhu, K. Sreeveena. The Significance of 1, 2, 4 Triazoles in Agriculture Science: A Review. Research J. Pharm. Techn., 2019, 12(10), p. 5091-5097. Regăsit în Internet la 2020.05.19, URL: <https://rjptonline.org/HTMLPaper.aspx?Journal=Research%20Journal%20of%20Pharmacy%20and%20Technology;PID=2019-12-10-92> 1. Subhas Sahoo, K.N. Sindhu, K. Sreeveena. The Significance of 1, 2, 4 Triazoles in Agriculture Science: A Review. Research J. Pharm. Techn., 2019, 12(10), pp. 5091-5097. Retrieved on the Internet on 2020.05.19, URL: <https://rjptonline.org/HTMLPaper.aspx?Journal=Research%20Journal%20of%20Pharmacy%20and%20Technology;PID=2019-12-10-92>
2. Propinocazole. Wikipedia, The Free Encyclopedia. Regăsit în Internet la 2020.05.18, URL: <https://en.wikipedia.org/wiki/Propiconazole> 2. Propinocazole. Wikipedia, The Free Encyclopedia. Retrieved from the Internet on 2020.05.18, URL: <https://en.wikipedia.org/wiki/Propiconazole>
3. JMPR2005- FAO of UN. FLUTRIAFOL. Regăsit în Internet la 2020.05.19, URL: <http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/JMPR/Report11/Flutriafol.pdf> 3. JMPR2005- FAO of UN. FLUTRIAFOL. Retrieved on the Internet on 2020.05.19, URL: <http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/JMPR/Report11/Flutriafol.pdf>
4. US 4554007 A 1985.11.19 4. US 4554007 A 1985.11.19
5. WO 2012011287 A2 2012.01.26 5. WO 2012011287 A2 2012.01.26
6. CN 109721559 A 2019.05.07 6. CN 109721559 A 2019.05.07
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Owner name: INSTITUTIA PUBLICA UNIVERSITATEA DE STAT DIN MOLDOVA, MD STR. A. MATEEVICI NR. 60, MD-2009, CHISINAU, REPUBLICA MOLDOVA Free format text: PREVIOUS NAME OF PROPRIETOR: INSTITUTUL DE CHIMIE AL MEC, MD |