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Synthesis and larvicidal and adult topical activity of some hydrazide-hydrazone derivatives against Aedes aegypti

Year 2014, Volume: 18 Issue: 3, 120 - 125, 12.09.2014

Abstract

A series of novel hydrazide-hydrazone derivatives were

synthesized and evaluated for their larvicidal and adult

topical activity against Aedes aegypti. The proposed

structures of all the synthesized compounds were confirmed

using elemental analysis, UV, IR, 1H-NMR, 13C-NMR and

mass spectroscopy. Compounds 4a-h were screened in larval

bioassays at concentrations of 100, 50 and 25 ppm in a dose

dependent manner and data for their mortality was recorded.

Among the tested compounds, 1-(4-nitrophenyl)-3-(4-{2-

oxo-2-[2-(2-oxo-1,2-dihydro-3H-ylidene)hydrazinyl] ethyl}

phenyl)urea (4b) showed noteworthy larvacidal activity

against Aedes aegypti. Dose-response data of compound 4b

showed LC50 and LC90 values of 30.5 (15.4 – 22.7) and 95.9

(73.8 – 139.4) ppm, respectively. Screening of compounds

4a-h at four doses by topical bioassay indicated a range of

activity between 10000 and 1000 ppm.

Keywords: Hydrazide-hydrazone, mosquito control, Aedes

aegypti, larvicidal activity, adult topical activity

References

  • Katritzky AR, Wang Z, Slavov S, Tsikolia M, Dobchev D, Akhmedov NG, Hall CD, Bernier UR, Clark GG, Linthicum KJ. Synthesis and bioassay of improved mosquito repellents predicted from chemical structure. P.N.A.S. 2008; 105:7359-64.
  • Hoel D, Pridgeon JW, Bernier UR, Chauhan K, Meepagala K, Cantrell C. Departments of Defense and Agriculture team up to develop new insecticides for mosquito control. Wingbeats 2010; 21: 19–
  • Carroll JF, Tabanca N, Kramer M, Elejalde NM, Wedge DE, Bernier UR, Co M, Becnel J, Demirci B, Başer KHC, Zhang S. Essential oils of Cupressus funebris, Juniperus communis, and J. Chinensis (Cupressaceae) as repellents against ticks (Acari: Ixodidae) and mosquitoes (Diptera: Culicidae) and as toxicants against mosquitoes. J. Vector. Ecol. 2011; 36: 258–268.
  • Tabanca N, Bernier UR, Ali A, Wang M, Demirci B, Blythe EK, Khan SI, Başer KHC, Khan IA. Bioassay-guided investigation of two monarda essential oils as repellents of yellow fever mosquito aedes aegypti. J Agric Food Chem 2013; 61: 38573−80.
  • Tabanca N, Bernier UR, Tsikolia M, Becnel JJ, Sampson B, Werle C, Demirci B, Başer KHC, Blythe EK, Pounders C, Wedge DE. Eupatorium capillifolium Essential Oil: Chemical composition, antifungal activity, and insecticidal activity. Nat Prod Commun 2010; 5: 1409–15.
  • Tabanca N, Abbas A, Bernier UR, Khan IA, Kocyigit-Kaymakcioglu B, Oruc-Emre EE, Unsalan S, Rollas S. Biting deterrence and insecticidal activity of hydrazide-hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles against Aedes aegypti. Pest Manag Sci 2013; 69: 703–8.
  • Tabanca N, Wedge DE, Ali S, Khan IA, Kaplancikli ZA, Altintop MD. Antifungal, mosquito deterrent, and larvicidal activity of N-(benzylidene)-3-cyclohexylpropionic acid hydrazide derivatives. Med Chem Res 2013; 22: 2602–9.
  • Kocyigit-Kaymakcioglu B, Celen AO, Tabanca N, Ali A, Khan SI, Khan IA, Wedge DE. Synthesis and biological activity of substituted urea and thiourea derivatives containing 1,2,4-triazole moieties. Molecules 2013; 8: 3562–76.
  • Narasimhan B, Kumar P, Sharma D. Biological activities of hydrazide derivatives in the new millennium. Acta Pharma Sci 2010; 52: 169–
  • Olayinka A, Obafemi C, Nwinyi O, Akinpelu D. Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives. Bioorg Med Chem 2010; 18: 214–21.
  • Abdel-Aal MT, El-Sayed WA, El-Ashry EH. Synthesis and antiviral evaluation of some sugar arylglycinoylhydrazones and their oxadiazoline derivatives. Arch Pharm Chem Life Sci 2006; 339: 656–63.
  • Koçyiğit-Kaymakçıoğlu B, Oruç E, Unsalan S, Rollas S. Synthesis and antituberculosis activity of hydrazide–hydrazones. Med Chem Res 2009; 118: 277–86.
  • Rostom SAF, Shalaby MA, El-Demellawy MA. Polysubstituted pyrazoles, part 5. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. Eur J Med Chem 2003; 38: 959–74.
  • Koçyigit-Kaymakcioglu B, Oruc E, Unsalan S, Kandemirli F, Shvets N, Rollas S, Dimoglo A. Synthesis and characterization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. Eur J Med Chem 2006; 41: 1253–61.
  • Koçyiğit-Kaymakçıoğlu B, Oruç-Emre EE, Ünsalan S, Tabanca N, Wedge DE, Khan SI, Demirci F, Rollas S. Synthesis and biological activity of hydrazide–hydrazones and their corresponding 3-acetyl2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles. Med Chem Res 2012; 21: 3499–508.
  • Boger M, Dur D, Gsell L, Hall RG, Karrer F, Kristiansen O, Maienfisch P, Pascual A, Rindlisbacher A. Synthesis and structure activity relationships of benzophenone hydrazone derivatives with insecticidal activity. Pest Manag Sci 2001; 57: 191–202.
  • Liu M, Wang Y, Wangyang WZ, Liu F, Cui YL, Duan YS, Wang M, Liu SZ, Rui CH. Design, synthesis and insecticidal activities of phthalamides containing a hydrazone substructure. J Agric Food Chem 2010; 58: 6859–63.
  • Wu J, Song BA, Hu DY, Yue M, Yang S. Design synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures. Pest Manag Sci 2012; 68: 801–10.
  • Aggarwal G, Kumar R, Srivatva C, Dureja P, Khurana JM. Synthesis of nalidixic acid based hydrazones as novel pesticides. J Agric Food Chem 2010; 58: 3056–61.
  • Yanga C, Shao Y, Zhi X, Huana Q, Yua X, Yao X, Xu H. Semisynthesis and quantitative structure–activity relationship (QSAR) study of some cholesterol-based hydrazone derivatives as insecticidal agents. Bioorg Med Chem 2013; 23: 4806–12.
  • Pridgeon JW, Becnel JJ, Clark GG, Linthicum KJ. A high throughput screening method to identify potential pesticides for mosquito control. J Med Entomol 2009; 46: 335–41.
  • SAS Institute. 2007. SAS Online Doc., version 9.2. SAS Institute, Cary, NC.
  • Abbott WS. A method of computing the effectiveness of an insecticide. J Econ Entomol 1925; 18: 265–7.
  • Pridgeon JW, Becnel JJ, Clark GG, Linthicum KJ. Permethrin induces overexpression of multiple genes in Aedes aegypti. J Med Entomol 2009; 46: 580-7.

Bazı Hidrazit-Hidrazon Türevlerinin Sentezi ve Larvasidal Etkileri

Year 2014, Volume: 18 Issue: 3, 120 - 125, 12.09.2014

Abstract

Bir seri hidrazit-hidrazon türevi bileşik sentezlenmiş ve
bunların larvisidal ve yüzeyel etkisi Aedes aegypti türüne
karşı ölçülmüştür. Sentezlenen tüm bileşiklerin yapıları
elementel analiz, UV, IR, 1H-NMR, 13C-NMR ve kütle
spektroskopisi kullanılarak doğrulanmıştır. 4a-h
bileşiklerinin biyolojik analizleri 100, 50 and 25 ppm
konsantrasyonlarında taranmış ve mortalite oranları
kaydedilmiştir. Test edilen bileşikler arasında 1-(4-nitrofenil)-
3-(4-{2-okso-2-[2-(2-okso-1,2-dihidro-3H-iliden)hidrazinil]
etil} fenil)üre (4b) Aedes aegypti türüne karşı kaydadeğer
larvisidal aktivite göstermiştir. 4b bileşiğinin doz yanıt
verileri, LC50 ve LC90 değerlerini sırasıyla 30.5 (15.4 – 22.7)
ve 95.9 (73.8 – 139.4) ppm olarak göstermiştir. Taranan 4a-h
bileşiklerinin dört dozla yapılan biyolojik analizinde aktivite
aralığının 10000 ve 1000 ppm arasında olduğu belirlenmiştir.

References

  • Katritzky AR, Wang Z, Slavov S, Tsikolia M, Dobchev D, Akhmedov NG, Hall CD, Bernier UR, Clark GG, Linthicum KJ. Synthesis and bioassay of improved mosquito repellents predicted from chemical structure. P.N.A.S. 2008; 105:7359-64.
  • Hoel D, Pridgeon JW, Bernier UR, Chauhan K, Meepagala K, Cantrell C. Departments of Defense and Agriculture team up to develop new insecticides for mosquito control. Wingbeats 2010; 21: 19–
  • Carroll JF, Tabanca N, Kramer M, Elejalde NM, Wedge DE, Bernier UR, Co M, Becnel J, Demirci B, Başer KHC, Zhang S. Essential oils of Cupressus funebris, Juniperus communis, and J. Chinensis (Cupressaceae) as repellents against ticks (Acari: Ixodidae) and mosquitoes (Diptera: Culicidae) and as toxicants against mosquitoes. J. Vector. Ecol. 2011; 36: 258–268.
  • Tabanca N, Bernier UR, Ali A, Wang M, Demirci B, Blythe EK, Khan SI, Başer KHC, Khan IA. Bioassay-guided investigation of two monarda essential oils as repellents of yellow fever mosquito aedes aegypti. J Agric Food Chem 2013; 61: 38573−80.
  • Tabanca N, Bernier UR, Tsikolia M, Becnel JJ, Sampson B, Werle C, Demirci B, Başer KHC, Blythe EK, Pounders C, Wedge DE. Eupatorium capillifolium Essential Oil: Chemical composition, antifungal activity, and insecticidal activity. Nat Prod Commun 2010; 5: 1409–15.
  • Tabanca N, Abbas A, Bernier UR, Khan IA, Kocyigit-Kaymakcioglu B, Oruc-Emre EE, Unsalan S, Rollas S. Biting deterrence and insecticidal activity of hydrazide-hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles against Aedes aegypti. Pest Manag Sci 2013; 69: 703–8.
  • Tabanca N, Wedge DE, Ali S, Khan IA, Kaplancikli ZA, Altintop MD. Antifungal, mosquito deterrent, and larvicidal activity of N-(benzylidene)-3-cyclohexylpropionic acid hydrazide derivatives. Med Chem Res 2013; 22: 2602–9.
  • Kocyigit-Kaymakcioglu B, Celen AO, Tabanca N, Ali A, Khan SI, Khan IA, Wedge DE. Synthesis and biological activity of substituted urea and thiourea derivatives containing 1,2,4-triazole moieties. Molecules 2013; 8: 3562–76.
  • Narasimhan B, Kumar P, Sharma D. Biological activities of hydrazide derivatives in the new millennium. Acta Pharma Sci 2010; 52: 169–
  • Olayinka A, Obafemi C, Nwinyi O, Akinpelu D. Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives. Bioorg Med Chem 2010; 18: 214–21.
  • Abdel-Aal MT, El-Sayed WA, El-Ashry EH. Synthesis and antiviral evaluation of some sugar arylglycinoylhydrazones and their oxadiazoline derivatives. Arch Pharm Chem Life Sci 2006; 339: 656–63.
  • Koçyiğit-Kaymakçıoğlu B, Oruç E, Unsalan S, Rollas S. Synthesis and antituberculosis activity of hydrazide–hydrazones. Med Chem Res 2009; 118: 277–86.
  • Rostom SAF, Shalaby MA, El-Demellawy MA. Polysubstituted pyrazoles, part 5. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. Eur J Med Chem 2003; 38: 959–74.
  • Koçyigit-Kaymakcioglu B, Oruc E, Unsalan S, Kandemirli F, Shvets N, Rollas S, Dimoglo A. Synthesis and characterization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. Eur J Med Chem 2006; 41: 1253–61.
  • Koçyiğit-Kaymakçıoğlu B, Oruç-Emre EE, Ünsalan S, Tabanca N, Wedge DE, Khan SI, Demirci F, Rollas S. Synthesis and biological activity of hydrazide–hydrazones and their corresponding 3-acetyl2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles. Med Chem Res 2012; 21: 3499–508.
  • Boger M, Dur D, Gsell L, Hall RG, Karrer F, Kristiansen O, Maienfisch P, Pascual A, Rindlisbacher A. Synthesis and structure activity relationships of benzophenone hydrazone derivatives with insecticidal activity. Pest Manag Sci 2001; 57: 191–202.
  • Liu M, Wang Y, Wangyang WZ, Liu F, Cui YL, Duan YS, Wang M, Liu SZ, Rui CH. Design, synthesis and insecticidal activities of phthalamides containing a hydrazone substructure. J Agric Food Chem 2010; 58: 6859–63.
  • Wu J, Song BA, Hu DY, Yue M, Yang S. Design synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures. Pest Manag Sci 2012; 68: 801–10.
  • Aggarwal G, Kumar R, Srivatva C, Dureja P, Khurana JM. Synthesis of nalidixic acid based hydrazones as novel pesticides. J Agric Food Chem 2010; 58: 3056–61.
  • Yanga C, Shao Y, Zhi X, Huana Q, Yua X, Yao X, Xu H. Semisynthesis and quantitative structure–activity relationship (QSAR) study of some cholesterol-based hydrazone derivatives as insecticidal agents. Bioorg Med Chem 2013; 23: 4806–12.
  • Pridgeon JW, Becnel JJ, Clark GG, Linthicum KJ. A high throughput screening method to identify potential pesticides for mosquito control. J Med Entomol 2009; 46: 335–41.
  • SAS Institute. 2007. SAS Online Doc., version 9.2. SAS Institute, Cary, NC.
  • Abbott WS. A method of computing the effectiveness of an insecticide. J Econ Entomol 1925; 18: 265–7.
  • Pridgeon JW, Becnel JJ, Clark GG, Linthicum KJ. Permethrin induces overexpression of multiple genes in Aedes aegypti. J Med Entomol 2009; 46: 580-7.
There are 24 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Kadriye Akdağ This is me

Bedia Kocyıgıt-kaymakcıoglu This is me

Bedia Koçyiğit-kaymakcıoğlu This is me

Nurhayat Tabanca This is me

Abbas Ali This is me

Alden Estep This is me

James J. Becnel This is me

James Becnel This is me

Ikhlas Khan This is me

Publication Date September 12, 2014
Published in Issue Year 2014 Volume: 18 Issue: 3

Cite

APA Akdağ, K., Kocyıgıt-kaymakcıoglu, B., Koçyiğit-kaymakcıoğlu, B., Tabanca, N., et al. (2014). Synthesis and larvicidal and adult topical activity of some hydrazide-hydrazone derivatives against Aedes aegypti. Marmara Pharmaceutical Journal, 18(3), 120-125. https://doi.org/10.12991/mpj.2014187238
AMA Akdağ K, Kocyıgıt-kaymakcıoglu B, Koçyiğit-kaymakcıoğlu B, Tabanca N, Ali A, Estep A, Becnel JJ, Becnel J, Khan I. Synthesis and larvicidal and adult topical activity of some hydrazide-hydrazone derivatives against Aedes aegypti. Marmara Pharm J. November 2014;18(3):120-125. doi:10.12991/mpj.2014187238
Chicago Akdağ, Kadriye, Bedia Kocyıgıt-kaymakcıoglu, Bedia Koçyiğit-kaymakcıoğlu, Nurhayat Tabanca, Abbas Ali, Alden Estep, James J. Becnel, James Becnel, and Ikhlas Khan. “Synthesis and Larvicidal and Adult Topical Activity of Some Hydrazide-Hydrazone Derivatives Against Aedes Aegypti”. Marmara Pharmaceutical Journal 18, no. 3 (November 2014): 120-25. https://doi.org/10.12991/mpj.2014187238.
EndNote Akdağ K, Kocyıgıt-kaymakcıoglu B, Koçyiğit-kaymakcıoğlu B, Tabanca N, Ali A, Estep A, Becnel JJ, Becnel J, Khan I (November 1, 2014) Synthesis and larvicidal and adult topical activity of some hydrazide-hydrazone derivatives against Aedes aegypti. Marmara Pharmaceutical Journal 18 3 120–125.
IEEE K. Akdağ, “Synthesis and larvicidal and adult topical activity of some hydrazide-hydrazone derivatives against Aedes aegypti”, Marmara Pharm J, vol. 18, no. 3, pp. 120–125, 2014, doi: 10.12991/mpj.2014187238.
ISNAD Akdağ, Kadriye et al. “Synthesis and Larvicidal and Adult Topical Activity of Some Hydrazide-Hydrazone Derivatives Against Aedes Aegypti”. Marmara Pharmaceutical Journal 18/3 (November 2014), 120-125. https://doi.org/10.12991/mpj.2014187238.
JAMA Akdağ K, Kocyıgıt-kaymakcıoglu B, Koçyiğit-kaymakcıoğlu B, Tabanca N, Ali A, Estep A, Becnel JJ, Becnel J, Khan I. Synthesis and larvicidal and adult topical activity of some hydrazide-hydrazone derivatives against Aedes aegypti. Marmara Pharm J. 2014;18:120–125.
MLA Akdağ, Kadriye et al. “Synthesis and Larvicidal and Adult Topical Activity of Some Hydrazide-Hydrazone Derivatives Against Aedes Aegypti”. Marmara Pharmaceutical Journal, vol. 18, no. 3, 2014, pp. 120-5, doi:10.12991/mpj.2014187238.
Vancouver Akdağ K, Kocyıgıt-kaymakcıoglu B, Koçyiğit-kaymakcıoğlu B, Tabanca N, Ali A, Estep A, Becnel JJ, Becnel J, Khan I. Synthesis and larvicidal and adult topical activity of some hydrazide-hydrazone derivatives against Aedes aegypti. Marmara Pharm J. 2014;18(3):120-5.