Asian Journal of Chemistry; Vol. 27, No. 7 (2015), 2356-2358
A
SIAN
J
OURNAL OF HEMISTRY
C
Synthesis and Activity of Novel Fungicide 2-(3-Chlorophenylcarbamoyl)phenyl Acetate
1
1
1
2
1,*
CHIXIANG ZHANG , ZHOU WANG , BO PU , XUESONG WANG and SHIRONG JIAO
1School of Bioengineering, Xihua University, Chengdu 610039, P.R. China
2School of Physics and Chemistry, Xihua University, Chengdu 610039, P.R. China
*Corresponding author: Tel: +86 13882002899; E-mail: 15208372274@163.com
Received: 16 April 2014;
Accepted: 24 June 2014;
Published online: 30 March 2015;
AJC-17032
In the present study, 2-(3-chlorophenylcarbamoyl)phenyl acetate was synthesized by the ammonolysis of 2-(chlorocarbonyl)phenyl acetate.
Its structure was confirmed by IR and 1H NMR. Its antifungal activity against Sclerotinia sclerotiorum and Helminthosprium maydis has
been determined in the laboratory. The results showed that it had good antifungal activity against the two different pathogenic fungi of
plants. Its median effective concentrations (EC50) reached 2 and 3.80 mg L-1, respectively.
Keywords: Antifungal activity, 2-(3-Chlorophenylcarbamoyl)phenyl acetate.
Synthesis of target compound: The target compound
was synthesized according to the reaction shown in Fig. 1.
3-chloroaniline (0.02 mol) and pyridine (0.02 mol) were
dissolved in CH2Cl2 (15 mL). The mixture was stirred and
heated to 35-45 °C. 2-(chlorocarbonyl)phenyl acetate (0.02
mol) with CH2Cl2 (15 mL) was slowly added to the above
mixture under stirring until the reaction was complete. The
precipitate was filtered and washed with distilled water. The
pure compound was obtained by re-crystallization in anhydrous
ethanol.
Synthesized compound (C15H12O3NCl): White crystals;
yield: 27 %; m.p. 126-127 °C; IR (KBr, νmax, cm-1): 3296, 3261,
3187, 3115, 3077, 1770, 1743, 1676, 1666, 1593, 1537, 1484,
1450, 1368, 1316, 1203, 1162, 1135, 784, 775, 751, 696, 583;
1H NMR (400 MHz, CDCl3) δ (ppm): 2.31 (s, 3H), 7.12 (t, J =
8.0 Hz, 2H), 7.23-7.27 (m, 1H), 7.31 (t, J = 8.0 Hz, 1H), 7.39
(d, J = 8.0 Hz, 1H), 7.49 (t, J = 8.0 Hz, 2H), 7.76 (t, J = 8.0
Hz, 1H), 8.18 (s, 1H).
INTRODUCTION
Sclerotinia sclerotiorum is a harmful disease of cole1. For
a long period, benzimidazole fungicides have been mostly used
to prevent it. In recent years, however, it has developed resis-
tance to the fungicides2-5. Moreover, its scope of resistance
continues to develop and has already included many new
fungicides6-8.
Likewise, Helminthosprium maydis is a pathogenic fungus
of plants that has serious harm to vegetables and flowers. Over
the past decades, synthetic fungicides including carbendazim
have been used to prevent it. Nevertheless, the development
of its resistance to all the fungicides has reduced the efficacy
of fungicidal treatment9-14
.
It is well-known that since aspirin (acetylsalicylic acid)
was first marketed in 1899, it has been widely used for the
treatment of pains, fever and colds15-23. Thus, 2-(3-chloro-
phenylcarbamoyl)phenyl acetate was synthesized on the basis
of it. In the meantime, its antifungal activity has been evaluated
in the laboratory to find novel fungicides with high efficacy
and low toxicity.
Assay of antifungal activity: Antifungal activity of the
synthesized compound against Sclerotinia sclerotiorum and
Helminthosprium maydis was determined using the plate
growth rate method24.
EXPERIMENTAL
The synthesized compound and carbendazim (purity 90 %)
were dissolved in dimethyl sulfoxide (DMSO), respectively.
The two solutions were diluted into five different concentra-
tions with distilled water, respectively. They were added to
the sterile culture medium (PDA) at 45 °C, mixed to homo-
geneity and transferred to sterile petri dishes to solidify. A
mycelium agar disc (5 mm in diameter) of the target fungi
was placed in the center of PDA plates. They were incubated
Sclerotinia sclerotiorum and Helminthosprium maydis were
obtained from the Chinese Academy of Agricultural Sciences.
They were preserved at 4 °C. All chemicals and solvents were
purchased from commercial sources unless specified otherwise.
IR spectra were recorded on a Thermofisher Nicolet-6700
spectrophotometer. 1H NMR spectra were taken on aVarian Unity
Inova-400 instrument using deuteron-chloroform as the solvent.
Zhang, Chixiang
