Separation of OH-containing compounds from the essential oil mixture via a one-pot synthesis of carbamates, antimicrobial evaluation and dynamic 1H NMR study of their derivatives

Separation of OH-containing compounds from the essential oil mixture via a one-pot synthesis of carbamates, antimicrobial evaluation and dynamic 1H NMR study of their derivatives | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Separation of OH-containing compounds from the essential oil mixture via a one-pot synthesis of carbamates, antimicrobial evaluation and dynamic 1H NMR study of their derivatives Farhang Farhadi-Ghalati, Ghasem Marandi, Mohammad Nikbin, Zahra Ahani, and 5 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-4010880/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract A series of various carbamate derivatives were synthesized using essential oils of various plants and cyclohexyl or phenyl isocyanate under solvent-free conditions. Carvacrol , Thymol and Eugenol were chosen for synthesis that exist in Satureja bachtiarica Bunge , Satureja hortensis L ., Trachyspermum ammi and Caryophyllus aromaticus , respectively. Essential oils after extraction and identification by GC-MS, were used as raw material for synthesis of carbamate derivatives. Antimicrobial activity of synthesized compounds was examined against four Gram-negative and Gram-positive bacteria as well as three fungal strains. Good inhibitory activities were observed with synthesized compounds. Also 1 H NMR dynamic of synthetic carbamates were investigated for this compounds. Green synthesis essential oil carvacrol thymol eugenol carbamate antibacterial and antifungal activities Dynamic 1H NMR Introduction Carbamates are derived from carbamic acids that represent an important class of compounds showing various interesting properties and have been extensively used in pharmaceuticals agrochemicals and as intermediates in organic synthesis (Chaturvedi 2012 ). Structurally, the carbamate functionality is related to amide-ester hybrid features and, in general, displays very good chemical and proteolytic stabilities. Organic carbamates can be used as anticancer, antimicrobial and antimalarial agents. Substitution on the O- and N-termini of a carbamate offers opportunities for modulation of biological properties and improvement in stability and pharmacokinetic properties. Organic carbamates play an important role in organic synthesis, especially as subunits of biologically active compounds. A number of methods have been developed for the synthesis of carbamates. Hofmann rearrangement of amides (Borah et al. 2012; Gogoi et al. 2077; Huang et al. 1997 ), the Curtius rearrangement of acyl azides (Gómez-Sánchez et al. 2005; Singh et al. 2016 ), the reductive carbonylation of nitroaromatics (Li et al. 2016 ; Santi 1997; Bontempi et al. 1987 ), the carbonylation of amines (Gadge et al. 2014), carbon dioxide alkylation (Barzagli et al. 2016 ; Riley et al. 1994 ) and the reaction of alcohols with isocyanates (Farkas et al. 1965; Christian et al. 2004 ; Ion et al. 2008 ). Factors such as climate change, genetic changes, pollution etc. caused some bacteria have become resistant to drugs and antibiotics, for example methicillin-resistant staphylococcus aureus and vancomycin-resistant enterococci (Krátký et al. 2016). Much research has been done for the synthesis of new medicines and antibiotics that to replace the existing antibiotics. Since one of the features of carbamates are their antimicrobial properties (Elliott et al. 1998 ; Zadrazilova et al. 2015 ), therefore, the desire to synthesize of these compounds has increased. Recently, there has been an increasing interest in the use of natural substances. Essential oils (EOs) are liquid mixtures of volatile compounds obtained from aromatic plants, most commonly by steam distillation. They have beneficial properties, for example, antiseptic (Bauroth et al. 2003 ), antioxidant (Amorati et al. 2013 ; Viuda-Martos et al. 2010 ), antimicrobial (Mimica-Dukic et al. 2004 ; Sivropoulou et al. 1997 ) and anti-inflammatory (Chao et al. 2005 ). Chemical compositions of essential oils include isoprenoid compounds, mainly mono- and sesquiterpenes. Natural monoterpenes such as Thymol , Carvacrol , Citronellol and menthol due to having OH functional groups are good starting materials for the synthesis carbamate. These components can react with isocyanates to form carbamate. Since these compounds are natural, hence, not dangerous for the environment. Essential oil can contain about 20–60 components at quite different concentrations. They are characterized by two or three major components at fairly high concentrations (20–70%) compared to other components present in trace amounts. Therefore, we can examine any reaction on the essential oil. Thus, according to our previous work that the synthesis of some thiazolidin-4-one was carried out using essential oils of Anethum graveolens seeds as starting material (Ahani et al. 2018 ), herein, we report the synthesis of carbamate depravities by essential oil of some plants containing compounds with the OH functional group which have the highest abundance in essential oil. In addition, this procedure gives us a chance to separate essence with OH groups from the others in a simple route. Results and discussion In this article, synthesis of various derivatives carbamates was investigated by using essential oil of some plants and cyclohexyl and phenyl isocyanate. Due to the desired starting material should be containing OH functional group, thus the plants that essential oil of them having OH functional group were chosen. There are Carvacrol , Eugenol and Thymol as the dominant composition in S. bachtiarica Bunge (Sefidkon et al. 2000; Falsafi et al. 2015), S. hortensis L . (Sefidkon et al. 2006; Güllüce et al. 2003; Deans et al. 1989), C. aromaticus (Jalali eta al. 2016) and seed of T. ammi (Vitali et al. 2016), respectively. Most previous works were based on the reaction of compounds isolated from essential oil, but we tried that the mixture of essential oils to be used as a starting material that the advantage over previous work, fewer number of reaction steps, less use of chemicals, being easier of methods and purification. Essential oil of each plants were extracted by distillation method. Yields of essential oils extracted from 100 gr of raw material were 1.07% S. bachtiarica Bunge , 0.9% in S. hortensis L ., 2.58% in C. aromaticus and 1.57% in T. ammi . Chemical composition of essential oils of tested plants were shown in tables (1-4). As shown in Table 1 Eugenol 66.95% has high concentration in essential oil of C. aromaticus . The next important component in this oil is Caryophyllene 20.91% that due to the absence of OH functional groups does not participate in this reaction. Table 1. Chemical composition of essential oil of C. aromaticus. No. Compounds RT(min) Percentage 1 5-Methyl-2-hexanone 3.504 0.111 2 2-Heptanol acetate 8.489 0.079 3 Benzyl acetate 11.928 0.105 4 Methyl salicylate 12.805 0.172 5 (-)-Carvone 14.174 0.085 6 4-(2-propenyl)-Phenol 14.367 0.124 7 Eugenol 17.485 66.952 8 α -Copaene 17.801 0.443 9 Caryophyllene 18.988 20.913 10 Humulene 19.769 2.965 11 γ -Muurolene 20.299 0.146 12 α -Selinene 20.999 0.125 13 Eugenol acetate 21.502 7.076 15 Caryophyllene oxide 22.882 0.446 16 Apiol 23.759 0.092 The desired compound Carvacrol in the essential oil of S. bachtiarica Bunge and S. hortensis L . have high concentration 42.22% and 37.98%, respectively (Table 2,3). Table 2. Chemical composition of essential oil of S. bachtiarica Bunge . No. Compounds RT(min) Percentage 1 β -Thujene 5.585 0.252 2 α-Pinene 5.756 5.756 3 Camphene 6.117 0.600 4 β -Pinene 7.132 0.468 5 α -Terpinene 7.832 0.557 6 m-Cymene 8.062 18.242 7 D-Limonene 8.164 0.262 8 γ -Terpinene 8.983 2.794 9 Linalool 10.109 4.546 10 Isopinocarveol 11.243 0.116 11 Endo-Borneol 11.999 3.364 12 Terpinene-4-ol 12.323 0.939 13 p-Cymene-8-ol 12.522 0.272 14 α -Terpineol 12.692 0.133 15 Thymol 15.453 7.484 16 Carvacrol 15.796 42.229 17 Eugenol 17.241 8.538 18 Caryophyllene 18.901 4.109 19 p-tert-Buthylcatechol 19.380 0.140 20 Humulene 19.747 0.351 21 Eugenol acetate 21.449 0.563 22 (-)-Spathulenol 22.734 0.197 23 Caryophyllene oxide 22.880 1.708 24 Isoaromadendrene epoxide 24.834 0.094 Table 3. Chemical composition of essential oil of S. hortensis L . No. Compounds RT(min) Percentage 1 β -Thujene 5.538 1.006 2 α -Pinene 5.710 0.427 3 β -Pinene 6.773 0.761 4 β -Myrcene 7.083 1.247 5 α-Terpinene 7.780 3.007 6 D-Limonene 8.001 12.195 7 γ -Terpinene 8.945 35.083 8 Thymol 15.391 2.676 9 Carvacrol 15.680 37.984 10 β -Bisabolene 20.997 0.597 Table 4. Chemical composition of essential oil of T. ammi. No. Compounds RT(min) Percentage 1 α -Pinene 5.535 1.689 2 Sabinene 6.765 4.531 3 β -Pinene 7.085 1.466 4 α -Terpinene 7.791 1.226 5 o-Cymene 8.082 30.927 6 β -Thujene 8.158 1.400 7 γ -Terpinene 9.050 37.604 8 Thymol 15.473 19.514 9 Carvacrol 15.665 0.448 Although γ -Terpinene 37.60% and o-Cymene 30.92% have high concentration in T. ammi oil, but due to lack of functional groups are neutral and not participate in this reaction, therefore, Thymol do this reaction (Table 4). Triethylamine (Et 3 N) to act as base and take the proton of OH functional group. Created ion attack to carbonyl group of isocyanate and the negative charge is moved on nitrogen. Finally, nitrogen with taking the proton of Et 3 NH + be neutral and carbamate is synthesized. The reaction results are presented in Table 5. 7c (60.5%) and 6c (48.2%) had the highest and lowest yields that were obtained from the reaction of Thymol in T. ammi’s essential oil with phenyl and cyclohexyl isocyanate, respectively. Compounds 6a and 6b are similar product with the same starting material from two different plants that were produced by the reaction Carvacrol with cyclohexyl isocyanate and their yields were 56.6% and 50.1%, respectively. Also the reaction of essential oil of same plants with phenyl isocyanate, 7a (54.6%) and 7b (56.4%) were synthesized. The reaction of Thymol and Carvacrol with cyclohexyl isocyanate was done at 80 ℃ and with phenyl isocyanate at room temperature, but Eugenol in C. aromaticus was reacted with both isocyanate derivatives at 80 ℃ and the reaction was not carried out at room temperature. Table 5. Synthesis of carbamates 6a-d and 7a-d from cyclohexyl and phenyl isocyanate respectively. Entry Ar Compound Time (min) T (°C) m.p (°C) Yield (%) 1 Carvacrol a 6a 5 80 113-115 56.6 2 Carvacrol b 6b 3 80 112-114 50.1 3 Thymol 6c 5 80 119-120 35.5 4 Eugenol 6d 5 80 92-94 48.2 5 Carvacrol a 7a 3 r.t 128-130 54.6 6 Carvacrol b 7b 1 r.t 128-130 56.4 7 Thymol 7c 3 r.t 98-100 60.5 8 Eugenol 7d 5 80 88-90 43.1 a Carvacrol in S. bachtiarica Bunge, b Carvacrol in S. hortensis L . Antimicrobial and antifungal activities Inhibitory property of the newly synthesized compounds ( 6a - d and 7a - d ) was studied against a variety of Gram-positive and -negative pathogenic bacteria as well as fungal strains. Moderate to good activities of carbamates (except 6d ) were obtained according to inhibition zone diameter (IZD), minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC) values presented in Table 6 and Table 7 . Antibiotics amikacin and gentamicin, and antifungal drugs terbinafine and fluconazole were used as positive controls. Derivative 6d exhibited no inhibitory activities against all tested bacteria; however, analogue 7d including phenyl substituent could inhibit growth of Listeria monocytogenes and Bacillus cereus . Two equivalent carbamates 6a and 7a were effective against Listeria monocytogenes and Bacillus subtilis subsp . spizizenii , respectively. Based on the results obtained, carbamates having anilino substituents ( 7d , 7c and 7a ) showed better and more broad-spectrum antibacterial effects than carbamates containing cyclohexylamino groups ( 6d , 6c and 6a ). No inhibitory activity of carbamates 6d , 7d and 6a was observed against three tested fungi. Antifungal effects of carbamates 6c and 7a were proven against these microorganisms. It deduced that cyclohexylamino and aniliyno substituents were respectively improved antifungal effects in carbamate skeletons 6c and 6a . Table 6. Antibacterial activity of carbamates 6a - d and 7a - d . Bacteria/productsa 6d 7d 6c 7c 6a 7a Amikacin Gentamicin 1297/ IZD -b 11.61 - - 10.11 - 12.74 18.71 1297/MIC - 128 - - 512 - 1 2 1297/MBC - 256 - - 1024 - 2 2 1665/IZD - 14.97 15.21 8.14 - - 20.12 25.51 1665/MIC - 128 64 64 - - 0.5 0.5 1665/MBC - 1024 512 1024 - - 0.5 4 1290/IZD - 14.76 - - - 16.10 21.78 1290/MIC - - 16 - - - 0.125 4 1290/MBC - - 128 - - - 0.125 4 1023/IZD - - - 10.18 - 10.56 17.19 28.57 1023/MIC - - - 32 32 4 0.063 1023/MBC - - - 128 - 128 8 0.063 a IZD (mm), MIC (μg/mL), MBC (μg/mL). b (-): indicates that not detected noticeable antibacterial effect at the initial concentrations. Table 7. Antifungal activity of carbamates 6a - d and 7a - d . Fungi/productsa 6d 7d 6c 7c 6a 7a Terbinafine Fluconazole 5009/ IZD -b - 12.52 9.73 - 12.23 29.18 21.13 5009/MIC - - 512 1024 - 512 32 32 5009/MBC - - 1024 2048 - 1024 32 64 5027/IZD - - 8.35 - - 11.98 36.24 14.81 5027/MIC - - 2048 - - 512 32 256 5027/MBC - - 4096 - - 1024 64 512 5115/IZD - 11.17 10.96 - 9.84 23.94 15.23 5115/MIC - - 256 256 - 512 32 128 5115/MBC - - 512 512 - 1024 64 256 a IZD (mm), MIC (μg/mL), MBC (μg/mL). b (-): indicates that not detected noticeable antifungal effect at the initial concentrations. Dynamic NMR study of synthesized carbamates In continuation of our studies about the carbamates (Marandi et al. 2015) we reported examinations on conformational behaviours of synthesized carbamates. We observed that the compound 7d shows dynamic effects on its 1 H NMR spectrum. The 1 H NMR spectrum of compound 7d shows a broad doublet for the two geminal protons of allylic system at ambient temperature which are sharpened at high temperatures (higher than +35 °C) and converts to doublet of doublet with uneven ratio in low temperatures (lower than 0 °C). The coalescence temperature for this process was observed at +11 °C. Investigation of such behaviors at variable temperatures allowed us to calculate ΔG ‡ for restricted rotational process around the C Ar -O single bond. Rate of exchange at coalescence temperature for this process obtained using the equation of first-order rate constant (k = Δνπ/√2). By further investigations at variable temperatures another dynamic effects have been observed on variable temperature 1 H-NMR (VT- 1 H NMR) spectra (Scheme 3). When the temperature decreased from the ambient temperature signal methoxy protons split to separate signals near +15 °C. The coalescence temperature for this process was observed at +18 °C. This process attributed to restricted rotational barrier around the N Ar −C carbonyl in compound 7d . Scheme 3 illustrates the pathways for observed dynamic processes in compound 7d . Other details involving k, ΔG ‡ and etc. are presented in Table 8. Table 8. Selected 1 H chemical shifts at 400.1 MHz, in ppm, Me 4 Si) along with other activation parameters for the restricted rotational processes around the C Ar -O single bond and N Ar —C carbonyl in compound 7d . Process Tc(K) δ (ppm) Δν (Hz) kc (s-1) ΔG‡ (kJ/mol) C Ar —O single bond 284 293 3.14, 3.39, 3.36, 3.34 3.40, 3.38 19.2 42.7 60.47 N Ar —C carbonyl 281 293 3.85, 3.79 3.84 10.9 24.4 61.12 Experiment section General experimental procedures Petroleum ether, dimethyl sulfoxide (DMSO) and ethyl acetate were obtained from Merck (Darmstadt, Germany). Phenyl isocyanate, cyclohexyl isocyanate, triethylamine and MgSO4 were purchased from Sigma-Aldrich Chemical Company, UK. All other chemicals and solvents were of analytical grade and are available commercially. Melting points were recorded on an Electrothermal-9100 apparatus. FT-IR spectra were recorded on a JASCO FT-IR 460 plus spectrometer. The 1 H NMR spectra were recorded on a BRUKER DRX-400 & 300 Avance spectrometer using CDCl 3 and DMSO-d 6 as solvent. Mass spectra were recorded on an Agilent Technologies MS-5973 (70 eV) mass spectrometer. Extraction of essential oil Aerial parts of S. bachtiarica Bunge (Voucher number: 55059, Herbarium of Shiraz University (HSU) collected in summer 2015) and S. hortensis L. (Voucher number: 55058, HSU, collected in summer 2016), flower buds of C. aromaticus (collected in March 2014) and seed of T. ammi (Voucher number: 55029, HSU, collected in August 2016) were used as the raw source, dried in the shade and powdered by the grinder. 100 grams of dried powder was distilled for 3h using a Clevenger type apparatus. The obtained essential oil was collected and anhydrous magnesium sulfate was used to absorb the small amount of water containing essential oil. The essential oil was then stored at 4 °C until use. GC/MS analysis Analysis of the essential oil was performed using a GC/MS Agilent Technologies (GC: 7890B, MS: 5977AMSD). HP-5MS capillary column (30 m, 0.25 mm i.d., 0.25-µm film thickness) was used. The carrier gas was helium at 1 mL/ minutes with following temperature program: at 60 °C for 1 minute, increased to 240 °C at the rate of 5 °C /minutes held for 5 minutes. Samples were injected at a temperature of 270 °C. An electron impact ionization system with ionization energy of 70 eV and electron ionization spectra with a mass scan range of 30-500 m/z were used. The chemical compositions of essential oil would be identified by NIST mass spectral libraries. Synthesis of carbamate To synthesis of carbamate (Shriner et al. 2003), cyclohexyl isocyanate 1 or phenyl isocyanate 2 was added (1:1) to essential oil containing OH functional group ( Carvacrol 3 , Thymol 4 and Eugenol 5 ) and 2-3 drops of trimethylamine was added to this solution. In most reactions after the addition of catalyst (Et 3 N) the mixture reaction were heated at 80 ℃ and immediately placed in an ice bath and the product was formed and then washed by n -Hexane to be purified. 5-isopropyl-2-methylphenyl cyclohexylcarbamate ( 6a ). White crystal; Yield: 56.6%; m.p= 113-115 ℃; IR υ (cm -1 ): 677, 707, 893, 1015, 1233, 1547, 1574, 1626, 1706, 1743, 2852, 2932, 3058, 3289; 1 HNMR (DMSO-d 6 , 400 MHz,) δ ppm: 2.19 (3H, s, CH 3 ), 2.82-2.96 (1H, m, CH 3 -CH-CH 3 ), 3.46-3.64 (1H, m, CH of cyclohexyl), 4.96-4.98 (1H, d, NH), 6.96, 6.99-7.02, 7.13-7.15 (3H, CH, aromatic protons). 2-isopropyl-5-methylphenyl cyclohexylcarbamate ( 6c ). White crystal; Yield: 35.5%; m.p= 119-120 ℃; IR υ (cm -1 ): 681, 812, 1229, 1536, 1703, 1736, 2854, 2933, 3049, 3296; 1 HNMR (DMSO-d 6 , 400 MHz,) δ ppm: 2.33 (3H, s, CH 3 ), 3.04-3.13 (1H, m, CH 3 -CH-CH 3 ); 3.49-3.64 (1H, m, CH of cyclohexyl), 4.92-4.94 (1H, d, NH), 6.90, 7.00-7.02, 7.17-7.20 (3H, CH, aromatic protons). 4-allyl-2-methoxyphenyl cyclohexylcarbamate (6d) . White crystal; Yield: 48.2%; m.p= 92-94 ℃; IR υ (cm -1 ): 577, 681, 812, 892, 1018, 1229, 1536, 1703, 1736, 2854, 2933, 2962, 3049, 3296; 1 HNMR (DMSO-d 6 , 400 MHz,) δ ppm: 3.38-3.40 (2H, d, Ar-CH 2 -CH), 3.52-3.63 (1H, m, CH of cyclohexyl), 3.85 (3H, s, OCH 3 ), 4.99-5.02 (1H, d, NH), 5.1 (2H, d, CH 2 =CH-), 5.91-6.05 (1H, m, CH 2 =CH-CH 2 -), 6.76-6.79, 7.02-7.05, 7.29 (3H, CH, aromatic protons). 5-isopropyl-2-methylphenyl phenylcarbamate (7a). White crystal; Yield: 54.6%; m.p= 128-130 ℃; IR υ (cm -1 ): 507, 760, 1016, 1116, 1224, 1445, 1544, 1602, 1712, 2872, 2962, 3060, 3306; 1 HNMR (DMSO-d 6 , 400 MHz,) δ ppm: 1.26-1.28 (2H, 2d, CH 3 -CH-CH 3 ), 2.26 (3H, s, CH 3 ), 2.87-2.97 (1H, m, CH 3 -CH-CH 3 ), 7.02-7.21, 7.34-7.39, 7.48-7.50, (3H, CH, aromatic protons), 7.29 (1H, s, NH). 2-isopropyl-5-methylphenyl phenylcarbamate (7c). White crystal; Yield: 60.5%; m.p= 98-100 ℃; IR υ (cm -1 ): 654, 756, 1018, 1109, 1219, 1445, 1545, 1603, 1714, 2871, 2966, 3060, 3336; 1 HNMR (DMSO-d 6 , 400 MHz,) δ ppm: 1.16-1.18 (6H, 2d, CH 3 -CH-CH 3 ); 2.29 (3H, s, CH 3 ), 3.02-3.11 (1H, m, CH 3 -CH-CH 3 ), 6.65-7.55 (3H, CH, aromatic protons), 10.25 (1H, s, NH). 4-allyl-2-methoxyphenyl phenylcarbamate (7d). White crystal; Yield: 43.1%; m.p= 88-90 ℃; IR υ (cm -1 ): 507, 579, 824, 1018, 1109, 1219, 1317, 1445, 1545, 1603, 1714, 2871, 2927, 2966, 3060, 3336; 1 HNMR (DMSO-d 6 , 400 MHz,) δ ppm: 3.42-3.44 (2H, d, Ar-CH 2 -CH-), 3.87 (3H, s, OCH 3 ), 5.13-5.20 (2H, d, CH 2 =CH-), 5.94-6.08 (1H, m, CH 2 =CH-CH 2 -), 6.82-6.84, 7.10-7.14, 7.29-7.37, 7.46-7.48 (3H, CH, aromatic protons), 7.21 (1H, s, NH). In Vitro Antibacterial Assay Antibiotics and antifungal agents were purchased from Sigma-Aldrich. The concentration of bacterial and fungal suspensions was determined by using Jenway 6405 UV-Vis spectrophotometer. Gram-positive bacterial strains including Listeria monocytogenes (PTCC 1297), Bacillus cereus (PTCC 1665) and Bacillus subtilis subsp . spizizenii (PTCC 1023), and Gram-negative Klebsiella pneumoniae (PTCC 1290), and fungi including Aspergillus fumigatus (PTCC 5009), Candida albicans (PTCC 5027) and Fusarium oxysporum (PTCC 5115) were prepared from the Persian Type Culture Collection (PTCC), Karaj, Iran. Broth microdilution, disk diffusion and time-kill susceptibility tests were performed according to CLSI (Clinical and Laboratory Standards Institute) guidelines M07-A9, M26-A, M02-A11, M44-A and M27-A2 (Beyzaei et al. 2017; Arikan 2007). Solution of all carbamates were prepared in 10% DMSO at initial concentrations of 10240 μg/mL, antibiotics and antifungal drugs were dissolved in double-distilled water at concentrations of 17.6 and 10240 μg/mL, respectively. The IZD (inhibition zone diameter) values were measured at initial concentrations. All tests were repeated three times and the results were expressed as the average of three independent experiments. Conclusions In summary, we report a one-pot, solvent-free synthesis of some carbamate derivatives using essential oil mixture. The OH functional groups in the essential oil compounds are good starting item for synthesis of various compounds by this method. Another advantage of this method are low cost, eco-friendly and easy work-up. The synthesized carbamates show good antimicrobial activities in against four Gram-negative and Gram-positive bacteria. Declarations Availability of data and materials All data generated or analyzed during this study are included in this published article [and its supplementary information files]. Acknowledgements We gratefully acknowledge financial support from the Research Council of the University of Sistan and Baluchestan. Competing interests The authors declare no competing interests. Author contributions All authors studied and designed the report, interpreted the results, and contributed to the writing of the manuscript. M.T. Maghsoodlou supervised the study in synthetic and chemical area, Z. Bameri and J. Valizadeh supervised the study in biological field. F. Farhadi-Ghalati and Z. Ahani, carried out all chemical reactions. H. Beyzaei and M. Moghadam-Manesh analyzed all obtained data to gather with G. Marandi, M.T. Maghsoodlou and J. Valizadeh. G. Marandi is the advisor of the study and analyzed the dynamic VT NMR results and performed this paper with M. Nikbin. References Ahani Z, Nikbin M, Maghsoodlou MT, Farhadi-Ghalati F, Valizadeh J, Beyzaei H, Moghadam-Manesh M (2018) Semi-synthesis, antibacterial and antifungal activities of three novel thiazolidin-4-one by essential oil of Anethum graveolens seeds as starting material. J Iran Chem Soc 15:2423–2430. https://doi.org/10.1007/s13738-018-1431-y Amorati R, Foti MC. 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Phytomedicine 22:173–177. doi: 10.1016/j.phymed.2014.11.012 Farkas A, Strohm PF (1965) Mechanism of Amine-Catalyzed Reaction of Isocyanates with Hydroxyl Compounds. Ind. Eng. Chem. Fund. 4:32–38. https://doi.org/10.1021/i160013a005 Gadge ST, Bhanage BM (2014) Recent developments in palladium catalysed carbonylation reactions. RSC Advances 4:10367–10389. https://doi.org/10.1039/C3RA46273K Gogoi P, Konwar D (2007) An efficient modification of the Hofmann rearrangement: synthesis of methyl carbamates. Tetrahedron lett. 48, 531–533. https://doi.org/10.1016/j.tetlet.2006.11.134 Güllüce M, Sökmen M, Daferera D, Agar G, Özkan H, Kartal N, Polissiou M, Sökmen A, Sahin F (2003) In vitro antibacterial, antifungal, and antioxidant activities of the essential oil and methanol extracts of herbal parts and callus cultures of Satureja hortensis L. J Agric Food Chem 51:3958–3965. doi: 10.1021/jf0340308 Gómez-Sánchez E, Marco-Contelles J (2005) Synthesis and transformations of alkyl N -(1-cyclohex-3-enyl)carbamates prepared from cyclohex-3-ene carboxylic acid via Curtius rearrangement. Tetrahedron 61:1207–1219. https://doi.org/10.1016/j.tet.2004.11.037 Huang X, Seid M, Keillor JW (1997) A Mild and Efficient Modified Hofmann Rearrangement. J Org Chem 62:7495–7496. https://doi.org/10.1021/jo9708553 Ion A, Van Doorslaer C, Parvulescu V, Jacobs P, De Vos D (2008) Green synthesis of carbamates from CO 2 , amines and alcohols. Green Chem 10:111–116. https://doi.org/10.1039/B711197E Jalali N, Ariiai P, Fattahi E (2016) Effect of alginate/carboxyl methyl cellulose composite coating incorporated with clove essential oil on the quality of silver carp fillet and Escherichia coli O157:H7 inhibition during refrigerated storage. J Food Sci techno 53:757–765. https://doi.org/10.1007/s13197-015-2060-4 Krátký M, Vinšová J (2016) Salicylanilide N-monosubstituted carbamates: Synthesis and in vitro antimicrobial activity. Bioorg Med Chem 24:1322–1330. https://doi.org/10.1039/B711197E Li Q, Wang P, Liu S, Fei Y, Deng Y (2016) Catalytic degradation of polyurea: synthesis of N -substituted carbamates with CuO–ZnO as the catalyst. Green Chem 18:6091–6098. https://doi.org/10.1039/C6GC01884J Marandi G, Maghsoodlou MT, Saravani H, Shokouhian M, Mofarrah E (2015) Synthesis of Stable Carbamate Phosphorus Ylides by a Four-Component Reaction And Dynamic 1 H-Nmr Study of the Energy Barriers for the Rotation around the Carbon–Nitrogen Single Bond and the Carbon–Carbon Double Bond. Phosphorus Sulfur and Silicon 190:1410–1421. https://doi.org/10.1080/10426507.2014.986267 Mimica-Dukic N, Bozin B, Sokovic M, Simin N (2004) Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil. J Agric Food Chem 52:2485–2489. doi: 10.1021/jf030698a (2004). Riley, D., McGhee, W. D. & Waldman, T. Generation of urethanes and isocyanates from amines and carbon dioxide. ACS Symp. Ser. 577,122–132. doi: 10.1021/bk-1994-0577.ch010 (1994). Sefidkon F, Abbasi K, Khaniki GB (2006) Influence of drying and extraction methods on yield and chemical composition of the essential oil of Satureja hortensis . Food Chem 99:19–23. doi: 10.1016/j.foodchem.2005.07.026 Sefidkon F, Jamzad Z (2000) Essential Oil of Satureja bachtiarica Bunge. J Essen Oil Res 12:545–546. https://doi.org/10.1080/10412905.2000.9712155 Santi R, Romano AM, Panella F, Santini C (1997) Palladium and silver reductive catalyzed carbonylation of nitrobenzene to methyl N -phenylcarbamate. J Mol Catal A Chem 127:95–99. https://doi.org/10.1016/S1381-1169(98)80131-3 Shriner RL, Hermann CKF, Morrill TC, Curtin DY, Fuson RC, The Systematic Identification of Organic Compounds, 8th Eds (2003). Singh AS, Kumar D, Mishra N, Tiwari VK (2016) An efficient one-pot synthesis of N , N ′-disubstituted ureas and carbamates from N -acylbenzotriazoles. RSC Advances 6:84512–84522. https://doi.org/10.1039/C6RA14131E Sivropoulou A, Nikolaou C, Papanikolaou E, Kokkini S, Lanaras T, Arsenakis M (1997) Antimicrobial, Cytotoxic, and Antiviral Activities of Salvia fructicosa Essential Oil. J Agric Food Chem 45:3197–3201. https://doi.org/10.1021/jf970031m Vitali LA, Beghelli D, Nya PCB, Bistoni O, Cappellacci L, Damiano S, Lupidi G, Maggi F, Orsomando G, Papa F, Petrelli D, Petrelli R, Quassinti L, Sorci L, Majd Zadeh M, Bramucci M (2016) Diverse biological effects of the essential oil from Iranian Trachyspermum ammi. Arab J Chem 9:775–786. https://doi.org/10.1016/j.arabjc.2015.06.002 Viuda-Martos M, El Gendy AENG, Sendra E, Fernandez-Lopez J, Abd El Razik K, Omer EA, Pérez-Alvarez JA (2010) Chemical Composition and Antioxidant and Anti- Listeria Activities of Essential Oils Obtained from Some Egyptian Plants. J. Agric. Food Chem. 58, 9063–9070. https://doi.org/10.1021/jf101620c Zadrazilova I, Pospisilova S, Masarikova M, Imramovsky A, Ferriz JM., Vinsova J, Cizek A (2015) Jampilek, J. Salicylanilide carbamates: Promising antibacterial agents with high in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA). Eur . J . Pharm . Sci . 77, 197–207. doi: 10.1016/j.ejps.2015.06.009 (2015). Schemes Schemes 1-3 are available in the Supplementary Files section. Additional Declarations No competing interests reported. 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05:18:56","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":92066,"visible":true,"origin":"","legend":"","description":"","filename":"Schemes.docx","url":"https://assets-eu.researchsquare.com/files/rs-4010880/v1/b1fa85efc00074015e6a8cea.docx"},{"id":52122488,"identity":"cb393837-4aa9-4480-a64a-d7436163b019","added_by":"auto","created_at":"2024-03-07 05:18:56","extension":"pdf","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":2000527,"visible":true,"origin":"","legend":"","description":"","filename":"SupplementaryMaterial.pdf","url":"https://assets-eu.researchsquare.com/files/rs-4010880/v1/3d10e83d54cdae942f773353.pdf"}],"financialInterests":"No competing interests reported.","formattedTitle":"Separation of OH-containing compounds from the essential oil mixture via a one-pot synthesis of carbamates, antimicrobial evaluation and dynamic 1H NMR study of their derivatives","fulltext":[{"header":"Introduction","content":"\u003cp\u003eCarbamates are derived from carbamic acids that represent an important class of compounds showing various interesting properties and have been extensively used in pharmaceuticals agrochemicals and as intermediates in organic synthesis (Chaturvedi \u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e2012\u003c/span\u003e). Structurally, the carbamate functionality is related to amide-ester hybrid features and, in general, displays very good chemical and proteolytic stabilities. Organic carbamates can be used as anticancer, antimicrobial and antimalarial agents. Substitution on the O- and N-termini of a carbamate offers opportunities for modulation of biological properties and improvement in stability and pharmacokinetic properties. Organic carbamates play an important role in organic synthesis, especially as subunits of biologically active compounds. A number of methods have been developed for the synthesis of carbamates. Hofmann rearrangement of amides (Borah et al. 2012; Gogoi et al. 2077; Huang et al. \u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e1997\u003c/span\u003e), the Curtius rearrangement of acyl azides (G\u0026oacute;mez-S\u0026aacute;nchez et al. 2005; Singh et al. \u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e2016\u003c/span\u003e), the reductive carbonylation of nitroaromatics (Li et al. \u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e2016\u003c/span\u003e; Santi 1997; Bontempi et al. \u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e1987\u003c/span\u003e), the carbonylation of amines (Gadge et al. 2014), carbon dioxide alkylation (Barzagli et al. \u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e2016\u003c/span\u003e; Riley et al. \u003cspan citationid=\"CR27\" class=\"CitationRef\"\u003e1994\u003c/span\u003e) and the reaction of alcohols with isocyanates (Farkas et al. 1965; Christian et al. \u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e2004\u003c/span\u003e; Ion et al. \u003cspan citationid=\"CR21\" class=\"CitationRef\"\u003e2008\u003c/span\u003e). Factors such as climate change, genetic changes, pollution etc. caused some bacteria have become resistant to drugs and antibiotics, for example methicillin-resistant \u003cem\u003estaphylococcus aureus\u003c/em\u003e and vancomycin-resistant \u003cem\u003eenterococci\u003c/em\u003e (Kr\u0026aacute;tk\u0026yacute; et al. 2016). Much research has been done for the synthesis of new medicines and antibiotics that to replace the existing antibiotics. Since one of the features of carbamates are their antimicrobial properties (Elliott et al. \u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e1998\u003c/span\u003e; Zadrazilova et al. \u003cspan citationid=\"CR36\" class=\"CitationRef\"\u003e2015\u003c/span\u003e), therefore, the desire to synthesize of these compounds has increased.\u003c/p\u003e \u003cp\u003eRecently, there has been an increasing interest in the use of natural substances. Essential oils (EOs) are liquid mixtures of volatile compounds obtained from aromatic plants, most commonly by steam distillation. They have beneficial properties, for example, antiseptic (Bauroth et al. \u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e2003\u003c/span\u003e), antioxidant (Amorati et al. \u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2013\u003c/span\u003e; Viuda-Martos et al. \u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e2010\u003c/span\u003e), antimicrobial (Mimica-Dukic et al. \u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e2004\u003c/span\u003e; Sivropoulou et al. \u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e1997\u003c/span\u003e) and anti-inflammatory (Chao et al. \u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e2005\u003c/span\u003e). Chemical compositions of essential oils include isoprenoid compounds, mainly mono- and sesquiterpenes. Natural monoterpenes such as \u003cem\u003eThymol\u003c/em\u003e, \u003cem\u003eCarvacrol\u003c/em\u003e, \u003cem\u003eCitronellol\u003c/em\u003e and menthol due to having OH functional groups are good starting materials for the synthesis carbamate. These components can react with isocyanates to form carbamate. Since these compounds are natural, hence, not dangerous for the environment.\u003c/p\u003e \u003cp\u003eEssential oil can contain about 20\u0026ndash;60 components at quite different concentrations. They are characterized by two or three major components at fairly high concentrations (20\u0026ndash;70%) compared to other components present in trace amounts. Therefore, we can examine any reaction on the essential oil. Thus, according to our previous work that the synthesis of some thiazolidin-4-one was carried out using essential oils of \u003cem\u003eAnethum graveolens\u003c/em\u003e seeds as starting material (Ahani et al. \u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e2018\u003c/span\u003e), herein, we report the synthesis of carbamate depravities by essential oil of some plants containing compounds with the OH functional group which have the highest abundance in essential oil. In addition, this procedure gives us a chance to separate essence with OH groups from the others in a simple route.\u003c/p\u003e"},{"header":"Results and discussion","content":"\u003cp\u003eIn this article, synthesis of various derivatives carbamates was investigated by using essential oil of some plants and cyclohexyl and phenyl isocyanate. Due to the desired starting material should be containing OH functional group, thus the plants that essential oil of them having OH functional group were chosen. There are \u003cem\u003eCarvacrol\u003c/em\u003e, \u003cem\u003eEugenol\u003c/em\u003e and \u003cem\u003eThymol\u003c/em\u003e as the dominant composition in \u003cem\u003eS. bachtiarica Bunge\u003c/em\u003e (Sefidkon\u0026nbsp;et al. 2000;\u0026nbsp;Falsafi\u0026nbsp;et al. 2015), \u003cem\u003eS. hortensis L\u003c/em\u003e. (Sefidkon\u0026nbsp;et al. 2006;\u0026nbsp;G\u0026uuml;ll\u0026uuml;ce\u0026nbsp;et al. 2003;\u0026nbsp;Deans\u0026nbsp;et al. 1989), \u003cem\u003eC. aromaticus\u003c/em\u003e (Jalali\u0026nbsp;eta al. 2016) and seed of \u003cem\u003eT. ammi\u003c/em\u003e (Vitali\u0026nbsp;et al. 2016), respectively. Most previous works were based on the reaction of compounds isolated from essential oil, but we tried that the mixture of essential oils to be used as a starting material that the advantage over previous work, fewer number of reaction steps, less use of chemicals, being easier of methods and purification. Essential oil of each plants were extracted by distillation method. Yields of essential oils extracted from 100 gr of raw material were 1.07% \u003cem\u003eS. bachtiarica Bunge\u003c/em\u003e, 0.9% in \u003cem\u003eS. hortensis L\u003c/em\u003e., 2.58% in \u003cem\u003eC. aromaticus\u003c/em\u003e and 1.57% in \u003cem\u003eT. ammi\u003c/em\u003e. Chemical composition of essential oils of tested plants were shown in tables (1-4). As shown in Table 1 Eugenol 66.95% has high concentration in essential oil of \u003cem\u003eC. aromaticus\u003c/em\u003e. The next important component in this oil is \u003cem\u003eCaryophyllene\u003c/em\u003e 20.91% that due to the absence of OH functional groups does not participate in this reaction.\u003c/p\u003e\n\u003cp\u003e\u0026nbsp;\u003cstrong\u003eTable 1.\u0026nbsp;\u003c/strong\u003eChemical composition of essential oil of\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003eC. aromaticus.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003eNo.\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eCompounds\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003eRT(min)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003ePercentage\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003e5-Methyl-2-hexanone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e3.504\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.111\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003e2-Heptanol acetate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e8.489\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.079\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eBenzyl acetate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e11.928\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.105\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eMethyl salicylate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e12.805\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.172\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003e(-)-Carvone\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e14.174\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.085\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003e4-(2-propenyl)-Phenol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e14.367\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.124\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eEugenol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e17.485\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e66.952\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026alpha;\u003c/em\u003e-Copaene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e17.801\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.443\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eCaryophyllene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e18.988\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e20.913\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eHumulene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e19.769\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e2.965\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026gamma;\u003c/em\u003e-Muurolene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e20.299\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.146\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026alpha;\u003c/em\u003e-Selinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e20.999\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.125\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eEugenol acetate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e21.502\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e7.076\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eCaryophyllene oxide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e22.882\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.446\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.606060606060606%\"\u003e\n \u003cp\u003e16\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"43.43434343434343%\"\u003e\n \u003cp\u003eApiol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.68686868686869%\"\u003e\n \u003cp\u003e23.759\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.272727272727273%\"\u003e\n \u003cp\u003e0.092\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003eThe desired compound \u003cem\u003eCarvacrol\u003c/em\u003e in the essential oil of \u003cem\u003eS. bachtiarica Bunge\u003c/em\u003e and \u003cem\u003eS. hortensis L\u003c/em\u003e. have high concentration 42.22% and 37.98%, respectively (Table 2,3).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 2.\u0026nbsp;\u003c/strong\u003eChemical composition of essential oil of \u003cem\u003eS. bachtiarica\u003c/em\u003e \u003cem\u003eBunge\u003c/em\u003e.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003eNo.\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eCompounds\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003eRT(min)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003ePercentage\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026beta;\u003c/em\u003e-Thujene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e5.585\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.252\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003e\u0026alpha;-Pinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e5.756\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e5.756\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eCamphene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e6.117\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.600\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026beta;\u003c/em\u003e-Pinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e7.132\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.468\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026alpha;\u003c/em\u003e-Terpinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e7.832\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.557\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003em-Cymene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e8.062\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e18.242\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eD-Limonene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e8.164\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.262\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026gamma;\u003c/em\u003e-Terpinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e8.983\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e2.794\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eLinalool\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e10.109\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e4.546\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eIsopinocarveol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e11.243\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.116\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eEndo-Borneol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e11.999\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e3.364\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eTerpinene-4-ol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e12.323\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.939\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003ep-Cymene-8-ol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e12.522\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.272\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026alpha;\u003c/em\u003e-Terpineol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e12.692\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.133\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eThymol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e15.453\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e7.484\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e16\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eCarvacrol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e15.796\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e42.229\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e17\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eEugenol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e17.241\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e8.538\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e18\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eCaryophyllene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e18.901\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e4.109\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e19\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003ep-tert-Buthylcatechol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e19.380\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.140\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eHumulene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e19.747\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.351\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e21\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eEugenol acetate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e21.449\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.563\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e22\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003e(-)-Spathulenol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e22.734\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.197\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e23\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eCaryophyllene oxide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e22.880\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e1.708\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"8.796296296296296%\" valign=\"top\"\u003e\n \u003cp\u003e24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.75925925925926%\" valign=\"top\"\u003e\n \u003cp\u003eIsoaromadendrene epoxide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"20.833333333333332%\" valign=\"top\"\u003e\n \u003cp\u003e24.834\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.61111111111111%\" valign=\"top\"\u003e\n \u003cp\u003e0.094\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003eTable 3. Chemical composition of essential oil of S. hortensis \u003cem\u003eL\u003c/em\u003e.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003eNo.\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003eCompounds\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003eRT(min)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003ePercentage\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026beta;\u003c/em\u003e-Thujene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e5.538\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e1.006\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026alpha;\u003c/em\u003e-Pinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e5.710\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e0.427\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026beta;\u003c/em\u003e-Pinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e6.773\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e0.761\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026beta;\u003c/em\u003e-Myrcene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e7.083\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e1.247\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003e\u0026alpha;-Terpinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e7.780\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e3.007\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003eD-Limonene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e8.001\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e12.195\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026gamma;\u003c/em\u003e-Terpinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e8.945\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e35.083\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003eThymol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e15.391\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e2.676\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003eCarvacrol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e15.680\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e37.984\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.079575596816976%\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"46.94960212201592%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026beta;\u003c/em\u003e-Bisabolene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.363395225464192%\"\u003e\n \u003cp\u003e20.997\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"23.607427055702917%\"\u003e\n \u003cp\u003e0.597\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u0026nbsp;Table 4. Chemical composition of essential oil of T. ammi.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003eNo.\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003eCompounds\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003eRT(min)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003ePercentage\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026alpha;\u003c/em\u003e-Pinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e5.535\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e1.689\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003eSabinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e6.765\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e4.531\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026beta;\u003c/em\u003e-Pinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e7.085\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e1.466\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026alpha;\u003c/em\u003e-Terpinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e7.791\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e1.226\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003eo-Cymene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e8.082\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e30.927\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026beta;\u003c/em\u003e-Thujene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e8.158\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e1.400\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003e\u003cem\u003e\u0026gamma;\u003c/em\u003e-Terpinene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e9.050\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e37.604\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003eThymol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e15.473\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e19.514\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"10.354223433242506%\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"45.50408719346049%\"\u003e\n \u003cp\u003eCarvacrol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"19.891008174386922%\"\u003e\n \u003cp\u003e15.665\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"24.250681198910083%\"\u003e\n \u003cp\u003e0.448\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003eAlthough \u003cem\u003e\u0026gamma;\u003c/em\u003e-Terpinene 37.60% and o-Cymene 30.92% have high concentration in \u003cem\u003eT. ammi\u003c/em\u003e oil, but due to lack of functional groups are neutral and not participate in this reaction, therefore, \u003cem\u003eThymol\u003c/em\u003e do this reaction (Table 4).\u003c/p\u003e\n\u003cp\u003eTriethylamine (Et\u003csub\u003e3\u003c/sub\u003eN) to act as base and take the proton of OH functional group. Created ion attack to carbonyl group of isocyanate and the negative charge is moved on nitrogen. Finally, nitrogen with taking the proton of Et\u003csub\u003e3\u003c/sub\u003eNH\u003csup\u003e+\u003c/sup\u003e be neutral and carbamate is synthesized.\u003c/p\u003e\n\u003cp\u003eThe reaction results are presented in Table 5. \u003cstrong\u003e7c\u003c/strong\u003e (60.5%) and \u003cstrong\u003e6c\u003c/strong\u003e (48.2%) had the highest and lowest yields that were obtained from the reaction of \u003cem\u003eThymol\u003c/em\u003e in \u003cem\u003eT. ammi\u0026rsquo;s\u003c/em\u003e essential oil with phenyl and cyclohexyl isocyanate, respectively. Compounds \u003cstrong\u003e6a\u003c/strong\u003e and \u003cstrong\u003e6b\u003c/strong\u003e are similar product with the same starting material from two different plants that were produced by the reaction \u003cem\u003eCarvacrol\u003c/em\u003e with cyclohexyl isocyanate and their yields were 56.6% and 50.1%, respectively.\u003c/p\u003e\n\u003cp\u003eAlso the reaction of essential oil of same plants with phenyl isocyanate, \u003cstrong\u003e7a\u003c/strong\u003e (54.6%) and \u003cstrong\u003e7b\u003c/strong\u003e (56.4%) were synthesized. The reaction of \u003cem\u003eThymol\u003c/em\u003e and \u003cem\u003eCarvacrol\u003c/em\u003e with cyclohexyl isocyanate was done at 80 ℃ and with phenyl isocyanate at room temperature, but \u003cem\u003eEugenol\u003c/em\u003e in \u003cem\u003eC. aromaticus\u003c/em\u003e was reacted with both isocyanate derivatives at 80 ℃ and the reaction was not carried out at room temperature.\u003c/p\u003e\n\u003cp\u003eTable 5. Synthesis of carbamates 6a-d and 7a-d from cyclohexyl and phenyl isocyanate respectively.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003eAr\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003eCompound\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003eTime (min)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003eT (\u0026deg;C)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003em.p (\u0026deg;C)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003eYield (%)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003e\u003cem\u003eCarvacrol\u003c/em\u003e\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003e6a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003e113-115\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003e56.6\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003e\u003cem\u003eCarvacrol\u003c/em\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003e6b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003e112-114\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003e50.1\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003e\u003cem\u003eThymol\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003e6c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003e119-120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003e35.5\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003e\u003cem\u003eEugenol\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003e6d\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003e92-94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003e48.2\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003e\u003cem\u003eCarvacrol\u003c/em\u003e\u003csup\u003ea\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003e7a\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003er.t\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003e128-130\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003e54.6\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003e\u003cem\u003eCarvacrol\u003c/em\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003e7b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003er.t\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003e128-130\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003e56.4\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003e\u003cem\u003eThymol\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003e7c\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003er.t\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003e98-100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003e60.5\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"9.473684210526315%\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"18.596491228070175%\"\u003e\n \u003cp\u003e\u003cem\u003eEugenol\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.894736842105264%\"\u003e\n \u003cp\u003e7d\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"16.842105263157894%\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"10.526315789473685%\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.157894736842104%\"\u003e\n \u003cp\u003e88-90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.508771929824562%\"\u003e\n \u003cp\u003e43.1\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u003csup\u003ea\u003c/sup\u003e \u003cem\u003eCarvacrol\u0026nbsp;\u003c/em\u003ein\u0026nbsp;S. bachtiarica\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003eBunge, \u003csup\u003eb\u003c/sup\u003e \u003cem\u003eCarvacrol\u003c/em\u003e in S. hortensis L\u003cstrong\u003e.\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAntimicrobial and antifungal activities\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eInhibitory property of the newly synthesized compounds (\u003cstrong\u003e6a\u003c/strong\u003e-\u003cstrong\u003ed\u003c/strong\u003e and \u003cstrong\u003e7a\u003c/strong\u003e-\u003cstrong\u003ed\u003c/strong\u003e) was studied against a variety of Gram-positive and -negative pathogenic bacteria as well as fungal strains. Moderate to good activities of carbamates (except \u003cstrong\u003e6d\u003c/strong\u003e) were obtained according to inhibition zone diameter (IZD), minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC) values presented in Table \u003cstrong\u003e6\u003c/strong\u003e and Table \u003cstrong\u003e7\u003c/strong\u003e. Antibiotics amikacin and gentamicin, and antifungal drugs terbinafine and fluconazole were used as positive controls. \u0026nbsp;Derivative \u003cstrong\u003e6d\u003c/strong\u003e exhibited no inhibitory activities against all tested bacteria; however, analogue \u003cstrong\u003e7d\u003c/strong\u003e including phenyl substituent could inhibit growth of \u003cem\u003eListeria monocytogenes\u003c/em\u003e and \u003cem\u003eBacillus cereus\u003c/em\u003e. Two equivalent carbamates \u003cstrong\u003e6a\u003c/strong\u003e and \u003cstrong\u003e7a\u003c/strong\u003e were effective against \u003cem\u003eListeria monocytogenes\u003c/em\u003e and \u003cem\u003eBacillus subtilis subsp\u003c/em\u003e. \u003cem\u003espizizenii\u003c/em\u003e, respectively. Based on the results obtained, carbamates having anilino substituents (\u003cstrong\u003e7d\u003c/strong\u003e, \u003cstrong\u003e7c\u003c/strong\u003e and \u003cstrong\u003e7a\u003c/strong\u003e) showed better and more broad-spectrum antibacterial effects than carbamates containing cyclohexylamino groups (\u003cstrong\u003e6d\u003c/strong\u003e, \u003cstrong\u003e6c\u003c/strong\u003e and \u003cstrong\u003e6a\u003c/strong\u003e).\u003c/p\u003e\n\u003cp\u003eNo inhibitory activity of carbamates \u003cstrong\u003e6d\u003c/strong\u003e, \u003cstrong\u003e7d\u003c/strong\u003e and \u003cstrong\u003e6a\u003c/strong\u003e was observed against three tested fungi. Antifungal effects of carbamates \u003cstrong\u003e6c\u003c/strong\u003e and \u003cstrong\u003e7a\u003c/strong\u003e were proven against these microorganisms. It deduced that cyclohexylamino and aniliyno substituents were respectively improved antifungal effects in carbamate skeletons \u003cstrong\u003e6c\u003c/strong\u003e and \u003cstrong\u003e6a\u003c/strong\u003e.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e\u003cstrong\u003eTable 6.\u0026nbsp;\u003c/strong\u003eAntibacterial activity of carbamates \u003cstrong\u003e6a\u003c/strong\u003e-\u003cstrong\u003ed\u003c/strong\u003e and \u003cstrong\u003e7a\u003c/strong\u003e-\u003cstrong\u003ed\u003c/strong\u003e.\u003c/strong\u003e\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\" width=\"613\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003eBacteria/productsa\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e\u003cstrong\u003e6d\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e\u003cstrong\u003e7d\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e\u003cstrong\u003e6c\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e\u003cstrong\u003e7c\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e\u003cstrong\u003e6a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e\u003cstrong\u003e7a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003eAmikacin\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003eGentamicin\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1297/ IZD\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e11.61\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e10.11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e12.74\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e18.71\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1297/MIC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e128\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1297/MBC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e256\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e1024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1665/IZD\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e14.97\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e15.21\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e8.14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e20.12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e25.51\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1665/MIC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e128\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e64\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e64\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e0.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e0.5\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1665/MBC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e1024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e1024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e0.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1290/IZD\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e14.76\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e16.10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e21.78\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1290/MIC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e16\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e0.125\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1290/MBC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e128\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e0.125\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1023/IZD\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e10.18\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e10.56\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e17.19\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e28.57\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1023/MIC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e0.063\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"21.98697068403909%\"\u003e\n \u003cp\u003e1023/MBC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"6.677524429967427%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.794788273615636%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e128\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"8.957654723127035%\"\u003e\n \u003cp\u003e128\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"12.214983713355048%\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.495114006514658%\"\u003e\n \u003cp\u003e0.063\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u0026nbsp;\u003csup\u003ea\u003c/sup\u003e IZD (mm), MIC (\u0026mu;g/mL), MBC (\u0026mu;g/mL). \u003csup\u003eb\u0026nbsp;\u003c/sup\u003e(-): indicates that not detected noticeable antibacterial effect at the initial concentrations.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 7.\u0026nbsp;\u003c/strong\u003eAntifungal activity of carbamates \u003cstrong\u003e6a\u003c/strong\u003e-\u003cstrong\u003ed\u003c/strong\u003e and \u003cstrong\u003e7a\u003c/strong\u003e-\u003cstrong\u003ed\u003c/strong\u003e.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\" width=\"613\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003eFungi/productsa\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e\u003cstrong\u003e6d\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e\u003cstrong\u003e7d\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e\u003cstrong\u003e6c\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e\u003cstrong\u003e7c\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e\u003cstrong\u003e6a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e\u003cstrong\u003e7a\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003eTerbinafine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003eFluconazole\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5009/ IZD\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-b\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e12.52\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e9.73\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e12.23\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e29.18\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e21.13\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5009/MIC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e1024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5009/MBC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e1024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e2048\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e1024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e64\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5027/IZD\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e8.35\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e11.98\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e36.24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e14.81\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5027/MIC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e2048\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e256\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5027/MBC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e4096\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e1024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e64\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5115/IZD\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e11.17\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e10.96\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e9.84\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e23.94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e15.23\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5115/MIC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e256\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e256\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e128\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"19.312602291325696%\"\u003e\n \u003cp\u003e5115/MBC\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.528641571194763%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e512\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"7.6923076923076925%\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.328968903436989%\"\u003e\n \u003cp\u003e1024\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"14.566284779050736%\"\u003e\n \u003cp\u003e64\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"15.384615384615385%\"\u003e\n \u003cp\u003e256\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u003csup\u003ea\u003c/sup\u003e IZD (mm), MIC (\u0026mu;g/mL), MBC (\u0026mu;g/mL). \u003csup\u003eb\u003c/sup\u003e (-): indicates that not detected noticeable antifungal effect at the initial concentrations.\u003c/p\u003e\n\u003cp\u003eDynamic NMR study of synthesized carbamates\u003c/p\u003e\n\u003cp\u003eIn continuation of our studies about the carbamates (Marandi et al. 2015)\u0026nbsp;we reported examinations on conformational behaviours of synthesized carbamates. We observed that the compound 7d shows dynamic effects on its \u003csup\u003e1\u003c/sup\u003eH NMR spectrum. The \u003csup\u003e1\u003c/sup\u003eH NMR spectrum of compound \u003cstrong\u003e7d\u003c/strong\u003e shows a broad doublet for the two geminal protons of allylic system at ambient temperature which are sharpened at high temperatures (higher than +35 \u0026deg;C) and converts to doublet of doublet with uneven ratio in low temperatures (lower than 0 \u0026deg;C). The coalescence temperature for this process was observed at +11 \u0026deg;C. Investigation of such behaviors at variable temperatures allowed us to calculate \u0026Delta;G\u003csup\u003e\u0026Dagger;\u003c/sup\u003e for restricted rotational process around the C\u003csub\u003eAr\u003c/sub\u003e-O single bond. Rate of exchange at coalescence temperature for this process obtained using the equation of first-order rate constant (k = \u0026Delta;\u0026nu;\u0026pi;/\u0026radic;2). By further investigations at variable temperatures another dynamic effects have been observed on variable temperature \u003csup\u003e1\u003c/sup\u003eH-NMR (VT-\u003csup\u003e1\u003c/sup\u003eH NMR) spectra (Scheme 3).\u003c/p\u003e\n\u003cp\u003eWhen the temperature decreased from the ambient temperature signal methoxy protons split to separate signals near +15 \u0026deg;C. The coalescence temperature for this process was observed at +18 \u0026deg;C. This process attributed to restricted rotational barrier around the \u003cem\u003eN\u003c/em\u003e\u003csub\u003eAr\u003c/sub\u003e\u0026minus;C\u003csub\u003ecarbonyl\u003c/sub\u003e in compound \u003cstrong\u003e7d\u003c/strong\u003e. Scheme 3 illustrates the pathways for observed dynamic processes in compound \u003cstrong\u003e7d\u003c/strong\u003e. Other details involving k, \u0026Delta;G\u003csup\u003e\u0026Dagger;\u003c/sup\u003e and etc. are presented in Table 8.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eTable 8.\u003c/strong\u003e Selected \u003csup\u003e1\u003c/sup\u003eH chemical shifts at 400.1 MHz, in ppm, Me\u003csub\u003e4\u003c/sub\u003eSi) along with other activation parameters for the restricted rotational processes around the C\u003csub\u003eAr\u003c/sub\u003e-O single bond and N\u003csub\u003eAr\u003c/sub\u003e\u0026mdash;C\u003csub\u003ecarbonyl\u003c/sub\u003e in compound \u003cstrong\u003e7d\u003c/strong\u003e.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd width=\"18.31442463533225%\"\u003e\n \u003cp\u003eProcess\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.614262560777957%\"\u003e\n \u003cp\u003eTc(K)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.228525121555915%\"\u003e\n \u003cp\u003e\u0026delta; (ppm)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.724473257698541%\"\u003e\n \u003cp\u003e\u0026Delta;\u0026nu; (Hz)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.614262560777957%\"\u003e\n \u003cp\u003ekc (s-1)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.504051863857374%\"\u003e\n \u003cp\u003e\u0026Delta;G\u0026Dagger; (kJ/mol)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"18.31442463533225%\"\u003e\n \u003cp\u003eC\u003csub\u003eAr\u003c/sub\u003e\u0026mdash;O single bond\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.614262560777957%\"\u003e\n \u003cp\u003e284\u003c/p\u003e\n \u003cp\u003e293\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.228525121555915%\"\u003e\n \u003cp\u003e3.14, 3.39, 3.36, 3.34\u003c/p\u003e\n \u003cp\u003e3.40, 3.38\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.724473257698541%\"\u003e\n \u003cp\u003e19.2\u003c/p\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.614262560777957%\"\u003e\n \u003cp\u003e42.7\u003c/p\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.504051863857374%\"\u003e\n \u003cp\u003e60.47\u003c/p\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd width=\"18.31442463533225%\"\u003e\n \u003cp\u003eN\u003csub\u003eAr\u003c/sub\u003e\u0026mdash;C\u003csub\u003ecarbonyl\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.614262560777957%\"\u003e\n \u003cp\u003e281\u003c/p\u003e\n \u003cp\u003e293\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"27.228525121555915%\"\u003e\n \u003cp\u003e3.85, 3.79\u003c/p\u003e\n \u003cp\u003e3.84\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"9.724473257698541%\"\u003e\n \u003cp\u003e10.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"13.614262560777957%\"\u003e\n \u003cp\u003e24.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd width=\"17.504051863857374%\"\u003e\n \u003cp\u003e61.12\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u003cstrong\u003eExperiment section\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eGeneral experimental procedures\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003ePetroleum ether, dimethyl sulfoxide (DMSO) and ethyl acetate were obtained from Merck (Darmstadt, Germany). Phenyl isocyanate, cyclohexyl isocyanate, triethylamine and MgSO4 were purchased from Sigma-Aldrich Chemical Company, UK. All other chemicals and solvents were of analytical grade and are available commercially. Melting points were recorded on an Electrothermal-9100 apparatus. FT-IR spectra were recorded on a JASCO FT-IR 460 plus spectrometer. The \u003csup\u003e1\u003c/sup\u003eH NMR spectra were recorded on a BRUKER DRX-400 \u0026amp; 300 Avance spectrometer using CDCl\u003csub\u003e3\u003c/sub\u003e and DMSO-d\u003csub\u003e6\u003c/sub\u003e as solvent. Mass spectra were recorded on an Agilent Technologies MS-5973 (70 eV) mass spectrometer.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eExtraction of essential oil\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAerial parts of \u003cem\u003eS. bachtiarica\u003c/em\u003e \u003cem\u003eBunge\u003c/em\u003e (Voucher number: 55059, Herbarium of Shiraz University (HSU) collected in summer 2015) and \u003cem\u003eS. hortensis L.\u003c/em\u003e (Voucher number: 55058, HSU, collected in summer 2016), flower buds of \u003cem\u003eC. aromaticus\u003c/em\u003e (collected in March 2014) and seed of \u003cem\u003eT. ammi\u003c/em\u003e (Voucher number: 55029, HSU, collected in August 2016) were used as the raw source, dried in the shade and powdered by the grinder. 100 grams of dried powder was distilled for 3h using a Clevenger type apparatus. The obtained essential oil was collected and anhydrous magnesium sulfate was used to absorb the small amount of water containing essential oil. The essential oil was then stored at 4 \u0026deg;C until use.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eGC/MS analysis\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAnalysis of the essential oil was performed using a GC/MS Agilent Technologies (GC: 7890B, MS: 5977AMSD). HP-5MS capillary column (30 m, 0.25 mm i.d., 0.25-\u0026micro;m film thickness) was used. The carrier gas was helium at 1 mL/ minutes with following temperature program: at 60 \u0026deg;C for 1 minute, increased to 240 \u0026deg;C at the rate of 5 \u0026deg;C /minutes held for 5 minutes. Samples were injected at a temperature of 270 \u0026deg;C. An electron impact ionization system with ionization energy of 70 eV and electron ionization spectra with a mass scan range of 30-500 m/z were used. The chemical compositions of essential oil would be identified by NIST mass spectral libraries.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eSynthesis of carbamate\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eTo synthesis of carbamate (Shriner\u0026nbsp;et al. 2003), cyclohexyl isocyanate \u003cstrong\u003e1\u003c/strong\u003e or phenyl isocyanate \u003cstrong\u003e2\u003c/strong\u003e was added (1:1) to essential oil containing OH functional group (\u003cem\u003eCarvacrol\u003c/em\u003e \u003cstrong\u003e3\u003c/strong\u003e, \u003cem\u003eThymol\u003c/em\u003e \u003cstrong\u003e4\u003c/strong\u003e and \u003cem\u003eEugenol\u003c/em\u003e \u003cstrong\u003e5\u003c/strong\u003e) and 2-3 drops of trimethylamine was added to this solution. In most reactions after the addition of catalyst (Et\u003csub\u003e3\u003c/sub\u003eN) the mixture reaction were heated at 80\u0026nbsp;℃\u0026nbsp;and immediately placed in an ice bath and the product was formed and then washed by \u003cem\u003en\u003c/em\u003e-Hexane to be purified.\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e5-isopropyl-2-methylphenyl cyclohexylcarbamate (\u003cstrong\u003e6a\u003c/strong\u003e).\u003c/em\u003e White crystal; Yield: 56.6%; m.p= 113-115\u0026nbsp;℃; IR \u0026upsilon; (cm\u003csup\u003e-1\u003c/sup\u003e): 677, 707, 893, 1015, 1233, 1547, 1574, 1626, 1706, 1743, 2852, 2932, 3058, 3289; \u003csup\u003e1\u003c/sup\u003eHNMR (DMSO-d\u003csub\u003e6\u003c/sub\u003e, 400 MHz,) \u0026delta; ppm: 2.19 (3H, s, CH\u003csub\u003e3\u003c/sub\u003e), 2.82-2.96 (1H, m, CH\u003csub\u003e3\u003c/sub\u003e-CH-CH\u003csub\u003e3\u003c/sub\u003e), 3.46-3.64 (1H, m, CH of cyclohexyl), 4.96-4.98 (1H, d, NH), 6.96, 6.99-7.02, 7.13-7.15 (3H, CH, aromatic protons).\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e2-isopropyl-5-methylphenyl cyclohexylcarbamate (\u003cstrong\u003e6c\u003c/strong\u003e).\u003c/em\u003e White crystal; Yield: 35.5%; m.p= 119-120\u0026nbsp;℃; IR \u0026upsilon; (cm\u003csup\u003e-1\u003c/sup\u003e): 681, 812, 1229, 1536, 1703, 1736, 2854, 2933, 3049, 3296; \u003csup\u003e1\u003c/sup\u003eHNMR (DMSO-d\u003csub\u003e6\u003c/sub\u003e, 400 MHz,) \u0026delta; ppm: 2.33 (3H, s, CH\u003csub\u003e3\u003c/sub\u003e), 3.04-3.13 (1H, m, CH\u003csub\u003e3\u003c/sub\u003e-CH-CH\u003csub\u003e3\u003c/sub\u003e); 3.49-3.64 (1H, m, CH of cyclohexyl), 4.92-4.94 (1H, d, NH), 6.90, 7.00-7.02, 7.17-7.20 (3H, CH, aromatic protons).\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e4-allyl-2-methoxyphenyl cyclohexylcarbamate (6d)\u003c/em\u003e. White crystal; Yield: 48.2%; m.p= 92-94\u0026nbsp;℃; IR \u0026upsilon; (cm\u003csup\u003e-1\u003c/sup\u003e): 577, 681, 812, 892, 1018, 1229, 1536, 1703, 1736, 2854, 2933, 2962, 3049, 3296; \u003csup\u003e1\u003c/sup\u003eHNMR (DMSO-d\u003csub\u003e6\u003c/sub\u003e, 400 MHz,) \u0026delta; ppm: 3.38-3.40 (2H, d, Ar-CH\u003csub\u003e2\u003c/sub\u003e-CH), 3.52-3.63 (1H, m, CH of cyclohexyl), 3.85 (3H, s, OCH\u003csub\u003e3\u003c/sub\u003e), 4.99-5.02 (1H, d, NH), 5.1 (2H, d, CH\u003csub\u003e2\u003c/sub\u003e=CH-), 5.91-6.05 (1H, m, CH\u003csub\u003e2\u003c/sub\u003e=CH-CH\u003csub\u003e2\u003c/sub\u003e-), 6.76-6.79, 7.02-7.05, 7.29 (3H, CH, aromatic protons).\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e5-isopropyl-2-methylphenyl phenylcarbamate (7a).\u003c/em\u003e White crystal; Yield: 54.6%; m.p= 128-130\u0026nbsp;℃; IR \u0026upsilon; (cm\u003csup\u003e-1\u003c/sup\u003e): 507, 760, 1016, 1116, 1224, 1445, 1544, 1602, 1712, 2872, 2962, 3060, 3306; \u003csup\u003e1\u003c/sup\u003eHNMR (DMSO-d\u003csub\u003e6\u003c/sub\u003e, 400 MHz,) \u0026delta; ppm: 1.26-1.28 (2H, 2d, CH\u003csub\u003e3\u003c/sub\u003e-CH-CH\u003csub\u003e3\u003c/sub\u003e), 2.26 (3H, s, CH\u003csub\u003e3\u003c/sub\u003e), 2.87-2.97 (1H, m, CH\u003csub\u003e3\u003c/sub\u003e-CH-CH\u003csub\u003e3\u003c/sub\u003e), 7.02-7.21, 7.34-7.39, 7.48-7.50, (3H, CH, aromatic protons), 7.29 (1H, s, NH).\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e2-isopropyl-5-methylphenyl phenylcarbamate (7c).\u0026nbsp;\u003c/em\u003eWhite crystal; Yield: 60.5%; m.p= 98-100\u0026nbsp;℃; IR \u0026upsilon; (cm\u003csup\u003e-1\u003c/sup\u003e): 654, 756, 1018, 1109, 1219, 1445, 1545, 1603, 1714, 2871, 2966, 3060, 3336; \u003csup\u003e1\u003c/sup\u003eHNMR (DMSO-d\u003csub\u003e6\u003c/sub\u003e, 400 MHz,) \u0026delta; ppm: 1.16-1.18 (6H, 2d, CH\u003csub\u003e3\u003c/sub\u003e-CH-CH\u003csub\u003e3\u003c/sub\u003e); 2.29 (3H, s, CH\u003csub\u003e3\u003c/sub\u003e), 3.02-3.11 (1H, m, CH\u003csub\u003e3\u003c/sub\u003e-CH-CH\u003csub\u003e3\u003c/sub\u003e), 6.65-7.55 (3H, CH, aromatic protons), 10.25 (1H, s, NH).\u003c/p\u003e\n\u003cp\u003e\u003cem\u003e4-allyl-2-methoxyphenyl phenylcarbamate (7d).\u003c/em\u003e White crystal; Yield: 43.1%; m.p= 88-90\u0026nbsp;℃; IR \u0026upsilon; (cm\u003csup\u003e-1\u003c/sup\u003e): 507, 579, 824, 1018, 1109, 1219, 1317, 1445, 1545, 1603, 1714, 2871, 2927, 2966, 3060, 3336; \u003csup\u003e1\u003c/sup\u003eHNMR (DMSO-d\u003csub\u003e6\u003c/sub\u003e, 400 MHz,) \u0026delta; ppm: 3.42-3.44 (2H, d, Ar-CH\u003csub\u003e2\u003c/sub\u003e-CH-), 3.87 (3H, s, OCH\u003csub\u003e3\u003c/sub\u003e), 5.13-5.20 (2H, d, CH\u003csub\u003e2\u003c/sub\u003e=CH-), 5.94-6.08 (1H, m, CH\u003csub\u003e2\u003c/sub\u003e=CH-CH\u003csub\u003e2\u003c/sub\u003e-), 6.82-6.84, 7.10-7.14, 7.29-7.37, 7.46-7.48 (3H, CH, aromatic protons), 7.21 (1H, s, NH).\u003c/p\u003e\n\u003cp\u003e\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e\u003cem\u003eIn Vitro\u003c/em\u003e\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;Antibacterial Assay\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAntibiotics and antifungal agents were purchased from Sigma-Aldrich. The concentration of bacterial and fungal suspensions was determined by using Jenway 6405 UV-Vis spectrophotometer. Gram-positive bacterial strains including \u003cem\u003eListeria monocytogenes\u003c/em\u003e (PTCC 1297), \u003cem\u003eBacillus cereus\u003c/em\u003e (PTCC 1665) and \u003cem\u003eBacillus subtilis subsp\u003c/em\u003e. spizizenii (PTCC 1023), and Gram-negative \u003cem\u003eKlebsiella pneumoniae\u003c/em\u003e (PTCC 1290), and fungi including \u003cem\u003eAspergillus fumigatus\u003c/em\u003e (PTCC 5009), \u003cem\u003eCandida albicans\u003c/em\u003e (PTCC 5027) and \u003cem\u003eFusarium oxysporum\u003c/em\u003e (PTCC 5115) were prepared from the Persian Type Culture Collection (PTCC), Karaj, Iran. Broth microdilution, disk diffusion and time-kill susceptibility tests were performed according to CLSI (Clinical and Laboratory Standards Institute) guidelines M07-A9, M26-A, M02-A11, M44-A and M27-A2 (Beyzaei et al. 2017; Arikan 2007). Solution of all carbamates were prepared in 10% DMSO at initial concentrations of 10240 \u0026mu;g/mL, antibiotics and antifungal drugs were dissolved in double-distilled water at concentrations of 17.6 and 10240 \u0026mu;g/mL, respectively. The IZD (inhibition zone diameter) values were measured at initial concentrations. All tests were repeated three times and the results were expressed as the average of three independent experiments.\u003c/p\u003e"},{"header":"Conclusions","content":"\u003cp\u003eIn summary, we report a one-pot, solvent-free synthesis of some carbamate derivatives using essential oil mixture. The OH functional groups in the essential oil compounds are good starting item for synthesis of various compounds by this method. Another advantage of this method are low cost, eco-friendly and easy work-up. The synthesized carbamates show good antimicrobial activities in against four Gram-negative and Gram-positive bacteria.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAvailability of data and materials\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u0026nbsp;All data generated or analyzed during this study are included in this published article [and its supplementary information files].\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAcknowledgements\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eWe gratefully acknowledge financial support from the Research Council of the University of Sistan and Baluchestan.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eCompeting interests\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare no competing interests.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthor contributions\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAll authors studied and designed the report, interpreted the results, and contributed to the writing of the manuscript. M.T. Maghsoodlou supervised the study in synthetic and chemical area, Z. Bameri and J. Valizadeh supervised the study in biological field. F. Farhadi-Ghalati and Z. Ahani, carried out all chemical reactions. H. Beyzaei and M. Moghadam-Manesh analyzed all obtained data to gather with G. Marandi, M.T. Maghsoodlou and J. Valizadeh. G. Marandi is the advisor of the study and analyzed the dynamic VT NMR results and performed this paper with M. Nikbin.\u0026nbsp;\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n \u003cli\u003e\u003cspan\u003eAhani Z, Nikbin M, Maghsoodlou MT, Farhadi-Ghalati F, Valizadeh J, Beyzaei H, Moghadam-Manesh M (2018) Semi-synthesis, antibacterial and antifungal activities of three novel thiazolidin-4-one by essential oil of \u003cem\u003eAnethum graveolens\u003c/em\u003e seeds as starting material. 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Salicylanilide carbamates: Promising antibacterial agents with high in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA). \u003cem\u003eEur\u003c/em\u003e. \u003cem\u003eJ\u003c/em\u003e. \u003cem\u003ePharm\u003c/em\u003e. \u003cem\u003eSci\u003c/em\u003e. 77, 197\u0026ndash;207. doi:\u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003e10.1016/j.ejps.2015.06.009\u003c/span\u003e\u003c/span\u003e (2015).\u003c/span\u003e\u003c/li\u003e\n\u003c/ol\u003e"},{"header":"Schemes","content":"\u003cp\u003eSchemes 1-3 are available in the Supplementary Files section.\u003c/p\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"Green synthesis, essential oil, carvacrol, thymol, eugenol, carbamate, antibacterial and antifungal activities, Dynamic 1H NMR","lastPublishedDoi":"10.21203/rs.3.rs-4010880/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-4010880/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eA series of various carbamate derivatives were synthesized using essential oils of various plants and cyclohexyl or phenyl isocyanate under solvent-free conditions. \u003cem\u003eCarvacrol\u003c/em\u003e, \u003cem\u003eThymol\u003c/em\u003e and \u003cem\u003eEugenol\u003c/em\u003e were chosen for synthesis that exist in \u003cem\u003eSatureja bachtiarica Bunge\u003c/em\u003e, \u003cem\u003eSatureja hortensis L\u003c/em\u003e., \u003cem\u003eTrachyspermum ammi\u003c/em\u003e and \u003cem\u003eCaryophyllus aromaticus\u003c/em\u003e, respectively. Essential oils after extraction and identification by GC-MS, were used as raw material for synthesis of carbamate derivatives. Antimicrobial activity of synthesized compounds was examined against four Gram-negative and Gram-positive bacteria as well as three fungal strains. Good inhibitory activities were observed with synthesized compounds. Also \u003csup\u003e1\u003c/sup\u003eH NMR dynamic of synthetic carbamates were investigated for this compounds.\u003c/p\u003e","manuscriptTitle":"Separation of OH-containing compounds from the essential oil mixture via a one-pot synthesis of carbamates, antimicrobial evaluation and dynamic 1H NMR study of their derivatives","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-03-07 05:18:51","doi":"10.21203/rs.3.rs-4010880/v1","editorialEvents":[{"type":"communityComments","content":1}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"e3229b14-dfee-492d-af25-4c9acf8574bd","owner":[],"postedDate":"March 7th, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[],"tags":[],"updatedAt":"2024-03-16T10:15:01+00:00","versionOfRecord":[],"versionCreatedAt":"2024-03-07 05:18:51","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-4010880","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-4010880","identity":"rs-4010880","version":["v1"]},"buildId":"qtupq5eGEP_6zYnWcrvyt","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}