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United States Department of Agriculture

Agricultural Research Service

Research Project: DISCOVERY AND DEVELOPMENT OF NATURAL PRODUCT FOR PHARMACEUTICAL AND AGRICHEMICAL APPLICATIONS

Location: Natural Products Utilization Research

Title: Antifungal, mosquito deterrent, and larvicidal activity of N-(benzylidene)-3-cyclohexylpropionic acid hydrazide derivatives

Authors
item Tabanca, Nurhayat -
item Wedge, David
item Ali, Abbas -
item Khan, Ikhlas -
item Kaplancikli, Zafer -
item Altintop, Mehlika -

Submitted to: Research and Reports in Medicinal Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: September 18, 2012
Publication Date: October 6, 2012
Citation: Tabanca, N., Wedge, D.E., Ali, A., Khan, I.A., Kaplancikli, Z.A., Altintop, M.D. 2012. Antifungal, misquito deterrent, and larvicidal activity of N-(benzylidene)-3-cyclohexylpropionic acid hydrazide derivatives. Research and Reports in Medicinal Chemistry. 22:2602-2609.

Interpretive Summary: Hydrazones have received considerable attention due to their biological importance in medicinal chemistry. Many studies have confirmed that hydrazone derivatives exhibit a wide spectrum of biological effects including antifungal and insectidal activity. In this study, ten hydrazone derivatives were evaluated for their antifungal activity against Colletotrichum, Botrytis, Fusarium and Phomopsis species and biting deterrent and larvicidal activity against Aedes aegypti. Compound 2e bearing 4-floro substituent on benzene ring and compound 2i carrying 4-isopropyl group on benzene ring exhibited good antifungal and larvicidal activity. Hydrazone derivatives possess good antifungal and insecticidal activities and their structure has potential in pesticide design.

Technical Abstract: Hydrazone derivatives possess good antifungal and insecticidal activities and their structure are used in pesticide design. In the present study, ten hydrazone derivatives (2a-j) were evaluated for their antifungal activity against Colletotrichum, Botrytis, Fusarium and Phomopsis species and for their biting deterrent and larvicidal activity against Aedes aegypti, the yellow mosquito. The 96-well microbioassay revealed that compounds 2c, 2e, 2g, 2i showed strong antifungal activity at 30 µM against Phomopsis obscurans, whereas only two compounds (2e and 2i) demonstrated strong antifungal activity against P. viticola. Compound 2e showed the highest biting deterrent activity when compared with N,N-diethyl-meta-toluamide (DEET), the positive control at 25 nmol/cm2. In toxicity bioassay, compound 2i exhibited the highest larvicidal activity with LD50 (95%CI) values of 57.4 and 4.35 ppm and LD90 values of 297.8 and 19.1 ppm, respectively at 24 and 48 h post treatment. Compounds 2e bearing 4-floro substituent on benzene ring and 2i carrying 4-isopropyl group on benzene ring exhibited the most active compounds in both bioassays. These results could be useful information for development of new effective antifungal and insecticides in the near future.

Last Modified: 9/2/2014
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