Antifungal, mosquito deterrent, and larvicidal activity of N -(benzylidene)-3-cyclohexylpropionic acid hydrazide derivat
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Med Chem Res (2013) 22:2602–2609 DOI 10.1007/s00044-012-0250-4
ORIGINAL RESEARCH
Antifungal, mosquito deterrent, and larvicidal activity of N(benzylidene)-3-cyclohexylpropionic acid hydrazide derivatives Nurhayat Tabanca • David E. Wedge • Abbas Ali Ikhlas A. Khan • Zafer Asım Kaplancikli • Mehlika Dilek Altintop
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Received: 30 May 2012 / Accepted: 18 September 2012 / Published online: 6 October 2012 Ó Springer Science+Business Media New York 2012
Abstract Hydrazone derivatives possess good antifungal and insecticidal activities and their structures are used in pesticide design. In the present study, for the first time, ten hydrazone derivatives (1–10) 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 3, 5, 7, and 9 showed strong antifungal activity at 30 lM against Phomopsis obscurans, whereas only two compounds (5 and 9) demonstrated strong antifungal activity against Phomopsis viticola. Compound 5 showed the highest biting deterrent activity against Ae. aegypti when compared with N,N-diethyl-meta-toluamide, the positive control at 25 nmol/cm2. Compound 9 exhibited the highest larvicidal activity in toxicity bioassay with LD50 values of 57.4 and
N. Tabanca (&) A. Ali I. A. Khan National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA e-mail: [email protected] D. E. Wedge USDA, ARS, Natural Products Utilization Research Unit, University of Mississippi, University, MS 38677, USA I. A. Khan Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA I. A. Khan Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia Z. A. Kaplancikli (&) M. D. Altintop Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskisehir 26470, Turkey e-mail: [email protected]
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4.35 ppm and LD90 values of 297.8 and 19.1 ppm, respectively, at 24 and 48 h post treatment. Compounds 5 bearing 4-fluoro substituent on benzene ring and 9 carrying a 4-isopropyl group on the benzene ring were found to be the most active compounds in both bioassays. These results could be useful information for development of new effective fungicides and insecticides in the near future. Keywords Hydrazone Fungicide Plant pathogen Phomopsis obscurans Phomopsis viticola Mosquito control Aedes aegypti
Introduction Plant pathogens and insect pests cause substantial damage to many economically important crops. Pesticides are used predominantly in agriculture and against insect vectors. In many cases, pesticides have become less effective as target organisms have developed resistance. In addition, these pesticides are threats to human health and threats to environmental through agriculture. Increased resistance to commercially available pesticides has led to a need fo
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