English

• 5-Arylidene-2, 3-diaryl-thiazolidin-4-one derivati-ve is a very important class of heterocyclic compounds and exhibits various biological activities, such as antitumor activity^[1], antiinflammatory activity^[2], antimalarial activity^[3]and antiparasite activity^[4]. However, to the best of our knowledge, little attention has been paid to the investigation of the antifungal activities of 5-arylidene-2, 3-diaryl-thiazolidin-4-ones against phytopathogenic fungi. Therefore, we designed and prepared some 5-arylidene-2, 3-diaryl-4- thiazolidinones, followed by investigations of their antifungal activities against phytopathogenic fungi.

  Generally, 5-arylidene-2, 3-diaryl-thiazolidin-4-ones were prepared with refluxing in EtOH for a long time^[5] or using of toxic reagents^[6]. Recently, we reported a new and efficient method via microwave irradiation to form 5-arylidene-2, 3-diphenyl-thiazolidin-4-ones^[7]. Encouraged by the results and as a consequence, in continuation of our previous work of microwave-assisted synthesis, herein 5-arylidene-2, 3- diphenyl-thiazolidin-4-ones were synthesized under microwave irradiation.

  1.   Experimental

  1.1   General experiment

  All reagents and solvents were of reagent grade or purified according to standard methods before use. Analytical thin-layer chromatography (TLC) and preparative thin-layer chromatography (PTLC) were performed with silica gel plates using silica gel 60 GF₂₅₄ (Qingdao Haiyang Chemical Co., Ltd., China). Melting points (mp) were determined on a XT-4 digital melting point apparatus (Beijing Tech Instrument Co., Ltd., Beijing, China) and tempeature was uncorrected. ¹H NMR were recorded in CDCl₃ on a Bruker Avance 500 MHz instrument, and tetrameth-ylsilane (TMS) was used as the internal standard. Electrospraylonization mass spectrometry (ESI-MS) was carried out with a Thermo DSQ GC/MS instrument.

  1.2   Syntheses

  The preparation of 2, 3-diaryl-thiazolidin-4-ones (3a~g) had been reported in Ref. 8^[8].

  Preparation of 5-Arylidene-2, 3-diaryl-thiazolidin-4- ones (4a~4r): A mixture of 3a~g (1.0 mmol), aldehydes (1.0 mmol), anhydrous K₂CO₃(1.0mmol), TBAB (0.2mmol) and H₂O (2mL) were placed in a 10mL glass tube, which was sealed with a septum and placed into the microwave cavity. Microwave irradiation of 50 W for 90℃ or 100 W for 140℃ was used with the temperature being raised from r.t. to 90 or 140℃. Once the given temperature was reached, the reaction mixture was held at this temperature for 30~90 min. The reaction progress was checked by TLC at the end of each irradiation period. When the reaction was completed according to the TLC analysis, the vessel was allowed to cool to room temperature, and the mixture was poured into ice water (20mL) and extracted with DCM (3×40mL). Then the organic phases were combined and dried over anhydrous Na₂SO₄, concentrated in vacuo, and purified by silica gel column chromatography to give the pure products (4a~4r). All compounds were characterized by ¹H NMR (500MHz), ESI-MS and mp.

  Structure information of 4a~4d had been reported in Ref. 7^[7].

  2-(4-Methoxyphenyl)-3-phenyl-5-(phenylme-thylene)-thiazolidin-4-one (4e): yield 61%, white solid, mp 168~169℃; ¹H NMR (500 MHz, CDCl₃) δ: 7.67 (s, 1H), 7.54 (d, J=7.5Hz, 2H), 7.40 (t, J =7.5Hz, 2H), 7.29 (t, J =7.5Hz, 3H), 7.18~7.24 (m, 5H), 6.78 (d, J=8.5Hz, 2H), 6.24 (s, 1H), 3.74(s, 3H); MS (ESI, m/z): 374.05 ([M+H]⁺, 100).

  5-[4-Methoxyphenylmethylene]-2-(4-metho-xyphenyl)-3-phenyl-4-thiazolidin-4-one (4f): yield 64%, white solid, mp 176~177℃; ¹H NMR (500 MHz, CDCl₃) δ: 7.63 (s, 1H), 7.49 (d, J=8.5Hz, 2H), 7.29~7.32 (m, 2H), 7.23~7.25 (m, 4H), 7.17~7.20 (m, 1H), 6.94 (d, J=8Hz, 2H), 6.78 (d, J=8Hz, 2H), 6.23 (s, 1H), 3.84 (s, 3H), 3.75 (s, 3H); MS (ESI, m/z): 404.15 ([M+H]⁺, 100).

  5-(2-Furanylmethylene)-2-(4-methoxy-phe-nyl)-3-phenyl-thiazolidin-4-one (4g): yield 67%, white solid, mp 156~158℃; ¹H NMR (500MHz, CDCl₃) δ: 7.54 (s, 1H), 7.48 (s, 1H), 7.28~7.31 (m, 2H), 7.22~7.23 (m, 4H), 7.17~7.20 (m, 1H), 6.78 (d, J=8Hz, 2H), 6.57 (s, 1H), 6.51 (s, 1H), 6.22 (s, 1H), 3.74(s, 3H); MS (ESI, m/z): 364.21 ([M+H]⁺, 100).

  2-(4-Methoxyphenyl)-5-[4-nitrophenyl methylene]-3-phenyl-thiazolidin-4-one (4h): yield 60%, yellow solid, mp 172~173℃; ¹H NMR (500MHz, CDCl₃) δ: 8.26 (d, J=9Hz, 2H), 7.66 (d, J =8Hz, 3H), 7.31~7.35 (m, 2H), 7.22~7.24 (m, 5H), 6.80 (d, J =8.5Hz, 2H), 6.28 (s, 1H), 3.76 (s, 3H); MS (ESI, m/z): 419.08 ([M+H]⁺, 100).

  3-(4-Nitrophenyl)-2-phenyl-5-(phenylme-thylene)-thiazolidin-4-one (4i): yield 50%, yellow solid, mp 234~235℃; ¹H NMR (500 MHz, CDCl₃) δ: 8.22 (d, J=9Hz, 2H), 7.86 (d, J =8.5Hz, 2H), 7.65 (s, 1H), 7.59 (d, J=7.5Hz, 2H), 7.48~7.51 (m, 2H), 7.44 (d, J=7.5Hz, 2H), 7.38 (t, J=7.5Hz, 1H), 7.31~7.34 (m, 2H), 7.26~7.29 (m, 1H), 7.12 (s, 1H); MS (ESI, m/z): 388.96 ([M+H]⁺, 100).

  5-[(4-Nitrophenyl)methylene]-2, 3-bis(4-nitrophenyl)-thiazolidin-4-one e (4j): yield 66%, yellow solid, mp 273~274℃; ¹H NMR (500 MHz, CDCl₃) δ: 8.31 (d, J=8.5Hz, 2H), 8.24 (d, J =9Hz, 2H), 8.16 (d, J =8.5Hz, 2H), 7.85~7.89 (m, 4H), 7.38~7.81 (m, 3H), 7.33 (s, 1H); MS (ESI, m/z): 479.06 ([M+H]⁺, 100).

  2, 3-Bis(4-nitrophenyl)-5-(phenylmethylene) -thiazolidin-4-one (4k): yield 52%, yellow solid, mp 211~212℃; ¹H NMR (500 MHz, CDCl₃) δ: 8.19~8.22 (m, 4H), 7.77 (s, 1H), 7.61 (d, J =9Hz, 2H), 7.50~7.53 (m, 4H), 7.43 (t, J=7.5Hz, 2H), 7.35~7.38 (m, 1H), 6.52 (s, 1H); MS (ESI, m/z): 434.02 ([M+H]⁺, 100).

  2-(4-Methoxyphenyl)-3-(4-methylphenyl)-5-(phenylmethylene)-thiazolidin-4-one (4l): yield 56%, white solid, mp 176~177℃; ¹H NMR (500 MHz, CDCl₃) δ: 7.65 (s, 1H), 7.54 (d, J=7.5Hz, 2H), 7.39~7.42 (m, 2H), 7.28~7.31 (m, 1H), 7.22 (d, J=9Hz, 2H), 7.07~7.11 (m, 4H), 6.78 (d, J=8.5Hz, 2Hz), 6.19 (s, 1H), 3.75 (s, 3H), 2.27 (s, 3H); MS (ESI, m/z): 388.10 ([M+H]⁺, 100).

  5-[(4-Methoxyphenyl)methylene]-2-(4-methoxyphenyl)-3-(4-methylphenyl)-thiazolidin-4-one (4m): yield 61%, white solid, mp 171~172℃; ¹H NMR (500 MHz, CDCl₃) δ: 7.61 (s, 1H), 7.49 (d, J=8.5Hz, 2H), 7.22 (d, J=8.5Hz, 2H), 7.07~7.12 (m, 4H), 6.93 (d, J=8.5Hz, 2H), 6.78(d, J=8.5Hz, 2Hz), 6.18 (s, 1H), 3.83 (s, 3H), 3.75 (s, 3H), 2.27 (s, 3H); MS (ESI, m/z): 418.14 ([M+H]⁺, 100).

  5-(2-Furanylmethylene)-2-(4-methoxyph-enyl)-3-(4-methylphenyl)-thiazolidin-4-one (4n): yield 59%, white solid, mp 148~149℃; ¹H NMR (500 MHz, CDCl₃) δ: 7.53 (s, 1H), 7.47 (s, 1H), 7.21 (d, J=8.5Hz, 2H), 7.07~7.10 (m, 4H), 6.78 (d, J=8.5Hz, 2Hz, 2H), 6.55 (d, J=3.5Hz, 1H), 6.49~6.50 (m, 1H), 6.17 (s, 1H), 3.75 (s, 3H), 2.27 (s, 3H); MS (ESI, m/z): 378.05 ([M+H]⁺, 100).

  3-(4-Methylphenyl)-2-phenyl-5-(phenylmeth-ylene)-thiazolidin-4-one (4o): yield 63%, white solid, mp 189~190℃; ¹H NMR (500 MHz, CDCl₃) δ: 7.67 (s, 1H), 7.54 (d, J=7.5Hz, 2H), 7.39~7.42 (m, 2H), 7.25~7.32 (m, 6H), 7.08~7.13 (m, 4H), 6.22 (s, 1H), 2.27 (s, 3H); MS (ESI, m/z):358.33 ([M+H]⁺, 100).

  5-[4-Methoxyphenylmethylene]-3-(4-methyl-phenyl)-2-phenyl-thiazolidin-4-one (4p): yield 69%, white solid, mp 186~187℃; ¹H NMR (500 MHz, CDCl₃) δ: 7.62 (s, 1H), 7.48 (d, J=9Hz, 2H), 7.27~7.32 (m, 5H), 7.08~7.12 (m, 4H), 6.93 (d, J =8.5Hz, 2H), 6.22 (s, 1H), 3.83 (s, 3H), 2.26 (s, 3H); MS (ESI, m/z): 388.11 ([M+H]⁺, 100).

  5-(2-Furanylmethylene)-3-(4-methylphenyl)-2-phenyl-thiazolidin-4-one (4q): yield 63%, white solid, mp 156~157℃; ¹H NMR (500 MHz, CDCl₃) δ: 7.53 (s, 1H), 7.47 (s, 1H), 7.26~7.31 (m, 5H), 7.07~7.12 (m, 4H), 6.56 (d, J =3.5Hz, 1H), 6.49~6.50 (m, 1H), 6.21 (s, 1H), 2.26 (s, 3H); MS (ESI, m/z): 348 ([M+H]⁺, 100).

  5-[(4-Nitrophenyl)methylene]-3-(4-methyl-phenyl)-2-phenyl-thiazolidin-4-one (4r): yield 57%, yellow solid, mp 206~207℃; ¹H NMR (500 MHz, CDCl₃) δ: 8.25 (d, J=9Hz, 2H), 7.66~7.68 (m, 3H), 7.29~7.35 (m, 5H), 7.10~7.13 (m, 4H), 6.27 (s, 1H), 2.28 (s, 3H); MS (ESI, m/z): 403.08 ([M+H]⁺, 100).

  1.3   Antifungal assay

  The antifungal activities of the 5-Arylidene-2, 3- diaryl-thiazolidin-4-one derivatives against seven phytopathogenic fungi (Fusarium graminearum, Alternaria alternata, Fusarium oxysporium f. sp. vasinfectum, Pyricularia oryzae, Valsa mali, Alternaria solani and Alternaria brassicae) were investigated in vitro by poisoned food technique^[8]. Potato dextrose agar (PDA) medium was prepared in the flasks and sterilized. Compounds 4a~4r were dissolved in acetone before mixing with PDA, and the concentrations of test compounds in the medium were fixed at 100μg/mL. The medium was then poured into sterilized Petri dishes. All types of fungi were incubated in PDA at (28±1)℃ for 4 days to obtain new mycelium for the antifungal assays, and a mycelia disk of approximately 5 mm diameter cut from culture medium was picked up with a sterilized inoculation needle and inoculated in the center of the PDA Petri dishes. The inoculated Petri dishes were incubated at (28±1)℃ for 4 days. Acetone without any compounds mixed with PDA was served as a control, while hymexazol, a commercial agricultural fungicide were used as positive controls. For each treatment, three replicates were conducted. The radial growths of the fungal colonies were measured and the data were statistically analyzed. The inhibitory effects of the tested compounds on these fungi in vitro were calculated by the formula: Inhibition rate (%)=(C-T)·100/C. where C represents the diameter of fungi growth on untreated PDA, and T represents the diameter of fungi on treated PDA.

  2.   Results and Discussion

  As show in Scheme 1, we had reported a new and efficient method via microwave irradiation to form 5-arylidene-2, 3-diphenyl-thiazolidin-4-ones^[7]. Under optimized conditions of K₂CO₃ as base, H₂O as solvent, TBAB as the catalyst, 5-arylidene-2, 3-diphenyl- thiazolidin-4-ones could be successfully obtained in excellent yields from 2, 3-diphenyl-thiazolidin-4-ones. Using this method, we synth-esized 18 kinds of new 5-arylidene-2, 3-diphenyl-thiazolidin-4-ones (4a~4r) from 2, 3-diphenyl-thiazolidin-4-ones. All compounds were characterized for structural confirmation by ¹H NMR, mp and ESI-MS.

  Scheme 1

  

  图式 1.  5-亚甲基-2, 3-二芳基噻唑-4-酮类衍生物(4a~r)的合成路线和化学结构

  Scheme 1.  Synthetic route and chemical structures of 5-arylidene-2, 3-diphenyl-thiazolidin-4-ones (4a~r)

  下载: 全尺寸图片 幻灯片

  As shown in Tab. 1, among all the derivatives, 4g and 4n exhibited excellent broad-spectrum antifungal activities against the above-mentioned seven phytopathogenic fungi. For example, the percentage inhibitions of 4g on the growth of Fusarium graminearum, Alternaria alternata, Fusarium oxysporium f. sp. vasinfectum, Pyricularia oryzae, Valsa mali, Alternaria solani and Alternaria brassicae were 34.94%, 40.97%, 38.33%, 45.04%, 43.44%, 41.96%, and 47.53%, respectively, and the percentage inhibitions of 4n were 49.26%, 56.49%, 43.77%, 52.76%, 46.52%, 46.48% and 61.31%, respectively. As shown in the comparative study above, the introduction of heterocyclic groups could generally increase the inhibition rates. On the other hand, some compounds have moderate activity against some phytopathogenic fungi. For example, compounds 4a and 4c inhibited the growth of Fusarium graminearum by 33.23% and 30.70%, respectively. Compounds 4a, 4c, 4e and 4k inhibited the growth of Alternaria solani by 42.28%, 37.93%, 32.68% and 35.87%, respectively.

  Table 1

  

  表 1  5-芳亚甲基-2, 3-二芳基噻唑-4-酮类衍生物对7种植物病原菌的抑菌活性

  Table 1.  Antifungal activities of 5-Arylidene-2, 3-diaryl-thiazolidin-4-ones against phytopathogenic fungi at 100μg/mL in vitro

  下载: 导出CSV

  Compound	Inhibition rate/%a
  	Fusarium graminearum	A.. alternata Alternaria alternata	Fusarium oxysporium f. sp. vasinfectum	Pyricularia oryzae	Valsa mali	Alternaria solani	Alternaria brassicae
  4a	33.23(±0.38)	24.74(±0.41)	20.75(±1.61)	31.46(±1.39)	28.96(±0.41)	42.28(±0.54)	43.14(±1.80)
  4b	27.10(±0.93)	24.07(±0.49)	29.78(±0.89)	32.60(±1.52)	20.09(±0.46)	32.32(±1.02)	32.37(±0.84)
  4c	30.70(±1.62)	24.42(±0.49)	32.32(±1.02)	33.01(±0.57)	31.13(±0.43)	37.93(±0.54)	35.81(±0.49)
  4d	27.82(±1.54)	26.14(±0.98)	25.43(±0.89)	33.01(±0.57)	26.83(±0.00)	25.80(±1.02)	31.68(±0.49)
  4e	27.24(±1.30)	23.23(±1.01)	20.93(±0.51)	28.11(±0.70)	20.64(±1.48)	32.68(±0.51)	25.12(±0.28)
  4f	27.00(±1.16)	29.55(±0.83)	27.09(±1.00)	28.48(±0.59)	30.54(±0.81)	21.19(±0.97)	20.74(±0.74)
  4g	34.94(±1.01)	40.97(±0.85)	38.33(±0.51)	45.04(±1.52)	43.44(±0.43)	41.96(±0.89)	47.53(±0.84)
  4h	25.25(±0.93)	29.89(±1.27)	30.64(±1.50)	28.69(±0.51)	29.69(±0.40)	23.17(±1.12)	23.43(±0.69)
  4i	24.39(±1.35)	25.67(±1.00)	32.50(±1.61)	26.98(±1.05)	15.30(±1.19)	15.79(±0.29)	16.26(±0.58)
  4j	12.05(±0.85)	26.61(±0.96)	27.85(±0.51)	22.31(±1.34)	26.82(±1.10)	15.93(±0.90)	14.57(±0.54)
  4k	29.88(±0.62)	31.92(±0.96)	29.22(±0.50)	28.48(±1.19)	30.54(±1.61)	35.87(±0.56)	31.27(±0.69)
  4l	18.85(±1.16)	17.87(±0.85)	19.78(±0.89)	13.41(±1.00)	17.13(±0.43)	7.97(±1.02)	16.15(±0.49)
  4m	16.54(±0.19)	14.74(±0.41)	11.29(±1.75)	11.83(±0.91)	13.43(±1.09)	18.70(±0.00)	18.36(±1.22)
  4n	49.26(±0.62)	56.49(±0.49)	43.77(±1.02)	52.76(±0.57)	46.52(±0.43)	46.48(±1.54)	61.31(±0.49)
  4o	11.73(±1.79)	16.50(±0.00)	13.19(±0.87)	13.02(±1.03)	13.99(±0.40)	11.19(±0.97)	16.37(±0.69)
  4p	16.87(±0.77)	17.52(±0.83)	13.55(±0.50)	5.12(±0.59)	11.71(±0.70)	11.19(±0.97)	13.43(±0.69)
  4q	9.88(±1.23)	11.59(±0.83)	15.67(±1.00)	8.90(±0.59)	12.25(±0.40)	3.17(±1.12)	10.29(±1.20)
  4r	12.04(±0.31)	11.25(±0.96)	15.85(±0.53)	17.64(±0.59)	12.54(±0.40)	13.89(±0.56)	17.84(±1.39)
  Hymexazole	60.20(±0.79)	65.62(±0.93)	46.76(±1.16)	64.17(±0.59)	35.54(±0.41)	37.32(±1.38)	57.09(±0.70)
  Acetoneb	0	0	0	0	0	0	0
  a Values are means of three experiments, standard deviations are given in parentheses; b Control.

  Some structure-activity relationships of the 5-arylidene-2, 3-diphenyl-thiazolidin-4-ones against phy-topathogenic fungi were observed. The introduction of an electron-donating group on the substituents R¹, R² and R³ generally made no difference in the inhibition rates as compared with 4a (e.g., 4m, 4p). On the contrary, the introduction of an electron-withdrawing group (cyano) on the R¹ and R² of 4a could generally increase the inhibitory potency (e.g., 4c and 4k).

  3.   Conslusion

  In conclusion, via microwave irradiation a series of 5-arylidene-2, 3-diphenyl-thiazolidin-4-ones from 2, 3-diphenyl-thiazolidin-4-ones were synthesized and characterized for structural confirmation by ¹H NMR, mp and ESI-MS. The activity test results of the target compounds against seven phytopathogenic fungi, namely Fusarium graminearum, Alternaria alternata, Fusarium oxysporium f. sp. vasinfectum, Pyricularia oryzae, Valsa mali, Alternaria solani and Alternaria brassicae, indicated that the 4g and 4n exhibited potential antifungal activities against the phytopathogenic fungi. Introduction of heterocyclic groups could generally increase the inhibition rates.

  
  
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• 

  Scheme 1  Synthetic route and chemical structures of 5-arylidene-2, 3-diphenyl-thiazolidin-4-ones (4a~r)

  下载: 全尺寸图片 幻灯片

  Table 1.  Antifungal activities of 5-Arylidene-2, 3-diaryl-thiazolidin-4-ones against phytopathogenic fungi at 100μg/mL in vitro

  Compound	Inhibition rate/%a
  	Fusarium graminearum	A.. alternata Alternaria alternata	Fusarium oxysporium f. sp. vasinfectum	Pyricularia oryzae	Valsa mali	Alternaria solani	Alternaria brassicae
  4a	33.23(±0.38)	24.74(±0.41)	20.75(±1.61)	31.46(±1.39)	28.96(±0.41)	42.28(±0.54)	43.14(±1.80)
  4b	27.10(±0.93)	24.07(±0.49)	29.78(±0.89)	32.60(±1.52)	20.09(±0.46)	32.32(±1.02)	32.37(±0.84)
  4c	30.70(±1.62)	24.42(±0.49)	32.32(±1.02)	33.01(±0.57)	31.13(±0.43)	37.93(±0.54)	35.81(±0.49)
  4d	27.82(±1.54)	26.14(±0.98)	25.43(±0.89)	33.01(±0.57)	26.83(±0.00)	25.80(±1.02)	31.68(±0.49)
  4e	27.24(±1.30)	23.23(±1.01)	20.93(±0.51)	28.11(±0.70)	20.64(±1.48)	32.68(±0.51)	25.12(±0.28)
  4f	27.00(±1.16)	29.55(±0.83)	27.09(±1.00)	28.48(±0.59)	30.54(±0.81)	21.19(±0.97)	20.74(±0.74)
  4g	34.94(±1.01)	40.97(±0.85)	38.33(±0.51)	45.04(±1.52)	43.44(±0.43)	41.96(±0.89)	47.53(±0.84)
  4h	25.25(±0.93)	29.89(±1.27)	30.64(±1.50)	28.69(±0.51)	29.69(±0.40)	23.17(±1.12)	23.43(±0.69)
  4i	24.39(±1.35)	25.67(±1.00)	32.50(±1.61)	26.98(±1.05)	15.30(±1.19)	15.79(±0.29)	16.26(±0.58)
  4j	12.05(±0.85)	26.61(±0.96)	27.85(±0.51)	22.31(±1.34)	26.82(±1.10)	15.93(±0.90)	14.57(±0.54)
  4k	29.88(±0.62)	31.92(±0.96)	29.22(±0.50)	28.48(±1.19)	30.54(±1.61)	35.87(±0.56)	31.27(±0.69)
  4l	18.85(±1.16)	17.87(±0.85)	19.78(±0.89)	13.41(±1.00)	17.13(±0.43)	7.97(±1.02)	16.15(±0.49)
  4m	16.54(±0.19)	14.74(±0.41)	11.29(±1.75)	11.83(±0.91)	13.43(±1.09)	18.70(±0.00)	18.36(±1.22)
  4n	49.26(±0.62)	56.49(±0.49)	43.77(±1.02)	52.76(±0.57)	46.52(±0.43)	46.48(±1.54)	61.31(±0.49)
  4o	11.73(±1.79)	16.50(±0.00)	13.19(±0.87)	13.02(±1.03)	13.99(±0.40)	11.19(±0.97)	16.37(±0.69)
  4p	16.87(±0.77)	17.52(±0.83)	13.55(±0.50)	5.12(±0.59)	11.71(±0.70)	11.19(±0.97)	13.43(±0.69)
  4q	9.88(±1.23)	11.59(±0.83)	15.67(±1.00)	8.90(±0.59)	12.25(±0.40)	3.17(±1.12)	10.29(±1.20)
  4r	12.04(±0.31)	11.25(±0.96)	15.85(±0.53)	17.64(±0.59)	12.54(±0.40)	13.89(±0.56)	17.84(±1.39)
  Hymexazole	60.20(±0.79)	65.62(±0.93)	46.76(±1.16)	64.17(±0.59)	35.54(±0.41)	37.32(±1.38)	57.09(±0.70)
  Acetoneb	0	0	0	0	0	0	0
  a Values are means of three experiments, standard deviations are given in parentheses; b Control.

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