Synthesis, Characterization and Insecticidal Activity against Cotton Leaf Worm of New Heterocyclics Which Scaffold on Hydrazide-Hydrazone Derivative

References

• A. F. El-Aswad, S. A. M. Abdelgaleil, and M. Nakatani, “Feeding Deterrent and Growth Inhibitory Properties of Limonoids from Khaya Senegalensis against the Cotton Leafworm, Spodoptera littoralis,”Pest Management Science 60, no. 2 (2004): 199–203.
   PubMed Web of Science ®Google Scholar
• L. Sannino, “Spodoptera littoralis in Italy: Possible Reasons for Its Increasing Spread and Control Measures,” Informatore Fitopatologico 53 (2003): 28–31.
   Google Scholar
• H. F. Dahi, “Egyptian Cotton Leafworm Spodoptera littoralis Development on Artificial Diet in Relation to Heat Unit Requirements” (The Third International Conference on IPM Role in Integrated Crop management and Impacts on Environment and Agricultural Products, Plant Protection Research Institute, ARC, Dokki, Giza, Egypt, 2005).
   Google Scholar
• T. R. Amin, “The Effect of Host Plants on the Susceptibility of the Cotton Leafworm, Spodoptera littoralis (Biosd.) to Insecticidal Treatments,” Egyptian Journal of Agricultural Research 85, no. 6 (2007): 2005–15.
   Google Scholar
• A. Lanzoni, G. G. Bazzocchi, F. Reggiori, F. Rama, L. Sannino, and S. Maini, “Spodoptera littoralis Male Capture Suppression in Processing Spinach Using Two Kinds of Synthetic Sex-Pheromone Dispensers,” Bulletin of Insectology 65 (2012): 311–8.
   Web of Science ®Google Scholar
• M. A. A. Abd El-Razik, and Z. M. S. Mostafa, “Joint Action of Two Novel Insecticides Mixtures with Insect Growth Regulators, Synergistic Compounds and Conventional Insecticides against Spodoptera littoralis (Boisd.) Larvae,” American Journal of Biochemistry and Molecular Biology 3, no. 4 (2013): 369–78.
   Google Scholar
• M. A. M. Osman, and M. F. Mahmoud, “Effects of Bio-Rational Insecticides on Selected Biological Aspects of the Egyptian Cotton Leaf Worm Spodptera littoralis (Boisd.) (Lepidoptera: Noctuidae),” Journal of Plant Protection Research 49, no. 2 (2009): 135–40.
   Google Scholar
• Croft B. A, ““Arthropod Biological Control Agents and Pesticides,” Wiley, New York,” Environmental Entomology 20, no. 5 (1990): 1492.
   Google Scholar
• M. A. Kandil, N. F. Abdel-Aziz, and E. A. Sammour, “Comparative Toxicity of Chlofluazuron and Lufenuron against Cotton Leafworm, Spodoptera littoralis,” Egyptian Journal of Agricultural Research NRC 2 (2003): 645–61.
   Google Scholar
• H. S. Abd-El-Aziz, and S. Z. Sayed, “Effects of Certain Insecticides on Eggs of Spodoptera littoralis,” Egyptian Journal of Agricultural Research 92, no. 3 (2014): 875–84.
   Google Scholar
• F. Vandenbussche, N. Yu, W. Li, L. Vanhaelewyn, M. Hamshou, D. Van Der Straeten, and G. Smagghe, “An Ultraviolet B Condition That Affects Growth and Defense in Arabidopsis,” Plant Science: An International Journal of Experimental Plant Biology 268 (2018): 54–63.
   PubMed Web of Science ®Google Scholar
• B. A. Sallam, S. A. El-Dossouki, S. E. M. El-Naggar, and M. M. Shibel, “Effect of Gamma Irradiation and Dose Accumulation on the Histology of Spodoptera littoralis (Boisd.) Male Testes” (Proceedings of Seventh Conference of Nuclear Sciences & Applications, Cairo, Egypt, February 6–10, 2000), 1249–1257.
   Google Scholar
• M. B. Isman, “Insect Antifeedants,”Pesticide Outlook 13, no. 4 (2002): 152–7. 1039/B206507J.
   Google Scholar
• A. Bavaresco, M. S. Garcia, A. D. Grützmacher, R. Ringenberg, and J. Foresti, “Adequação de Uma Dieta Artificial Para a Criação de Spodoptera Cosmioides (Walk.)(Lepidoptera: Noctuidae) em Laboratório,” [Adaptation of an Artificial Diet for Spodoptera Cosmioides (Walk.)(Lepidoptera: Noctuidae) Laboratory Rearing],” Neotropical Entomology 33, no. 2 (2004): 155–61.
   Web of Science ®Google Scholar
• M. A. Khedr, H. M. Al-Shannaf, H. M. Mead, and S. A. E.-A. Shaker, “Comparative Study to Determine Food Consumption of Cotton Leaf-Worm, Spodoptera littoralis, on Some Cotton Genotypes,” Journal of Plant Protection Research 55, no. 3 (2015): 312–21.
   Google Scholar
• G. Smagghe, S. Pineda, B. Carton, P. Del Estal, F. Budia, and E. Viñuela, “Toxicity and Kinetics of Methoxyfenozide in Greenhouse-Selected Spodoptera exigua (Lepidoptera: Noctuidae),” Pest Management Science 59, no. 11 (2003): 1203–9.
   PubMed Web of Science ®Google Scholar
• R. Lasa, I. Pagola, I. Ibañez, J. E. Belda, T. Williams, and P. Caballero, “Efficacy of Spodoptera exigua Multiple Nucleopolyhedrovirus as a Biological Insecticide for Beet Armyworm Control in Greenhouses of Southern Spain,” Biocontrol Science and Technology 17, no. 3 (2007): 221–32.
   Web of Science ®Google Scholar
• L. A. Lacey, D. Grzywacz, D. I. Shapiro-Ilan, R. Frutos, M. Brownbridge, and M. S. Goettel, “Insect Pathogens as Biological Control Agents: Back to the Future,” Journal of Invertebrate Pathology 132 (2015): 1–41.
   PubMed Web of Science ®Google Scholar
• E. S. El-Sheikh, “Comparative Toxicity and Sublethal Effects of Emamectin Benzoate, Lufenuron and Spinosad on Spodoptera littoralis Boisd. (Lepidoptera: Noctuidae),” Crop Protection 67 (2015): 228–34.
   Web of Science ®Google Scholar
• J. Su, Z. Wang, K. Zhang, X. Tian, Y. Yin, X. Zhao, A. Shen, and C. F. Gao, “Status of Insecticide Resistance of the White-Backed Planthopper, Sogatella furcifera (Hemiptera: Delphacidae),”Florida Entomologist 96, no. 3 (2013): 948–56.
   Web of Science ®Google Scholar
• W. T. Garrood, C. T. Zimmer, K. J. Gorman, R. Nauen, C. Bass, and T. G. Davies, “Field‐Evolved Resistance to Imidacloprid and Ethiprole in Populations of Brown Planthopper Nilaparvata lugens Collected from across South and East Asia,” Pest Management Science 72, no. no. 1 (2016): 140–9.
   PubMed Web of Science ®Google Scholar
• J. E. Casida, “Pest Toxicology: The Primary Mechanisms of Pesticide Action,” Chemical Research in Toxicology 22, no. 4 (2009): 609–19.
   PubMed Web of Science ®Google Scholar
• R. N. C. Guedes, G. Smagghe, J. D. Stark, and N. Desneux, “Pesticide-Induced Stress in Arthropod Pests for Optimized Integrated Pest Management Programs,” Annual Review of Entomology 61 (2016): 43–62.
   PubMed Web of Science ®Google Scholar
• R. N. C. Guedes, S. S. Walse, and J. E. Throne, “Sublethal Exposure, Insecticide Resistance, and Community Stress,” Current Opinion in Insect Science 21 (2017): 47–53.
   PubMed Web of Science ®Google Scholar
• V. M. Rahman, S. Mukhtar, W. H. Ansari, and G. Lemiere, “Synthesis, Stereochemistry and Biological Activity of Some Novel Long Alkyl Chain Substituted Thiazolidin-4-Ones and Thiazan-4-One from 10 Undecenoic Acid Hydrazide,” European Journal of Medicinal Chemistry 40, no. 2 (2005): 173–84.
   PubMed Web of Science ®Google Scholar
• J. R. Dimmock, S. C. Vashishtha, and J. P. Stables, “Anticonvulsant Properties of Various Acetylhydrazones, Oxamoylhydrazones and Semicarbazones Derived from Aromatic and Unsaturated Carbonyl Compounds,” European Journal of Medicinal Chemistry 35, no. 2 (2000): 241–8.
   PubMed Web of Science ®Google Scholar
• Yong Xia, Chuan-Dong Fan, Bao-Xiang Zhao, Jing Zhao, Dong-Soo Shin, and Jun-Ying Miao, “Synthesis and Structure Activity Relationships of Novel 1-Arylmethyl-3-Aryl-1H-Pyrazole-5-Carbohydrazide Hydrazone Derivatives as Potential Agents A549 Lung Cancer Cells,” European Journal of Medicinal Chemistry 43, no. 11 (2008): 2347–53.
   PubMed Web of Science ®Google Scholar
• Patricia Melnyk, Virginie Leroux, Christian Sergheraert, and Philippe Grellier, “Design, Synthesis and in Vitro Antimalarial Activity of an Acylhydrazone Library,” Bioorganic & Medicinal Chemistry Letters 16, no. 1 (2006): 31–5.
   PubMed Web of Science ®Google Scholar
• O. O. Ajani, C. A. Obafemi, O. C. Nwinyi, and D. A. Akinpelu, “Microwave Assisted Synthesis and Antimicrobial Activity of 2- Quinoxalinone-3-Hydrazone Derivatives,” Bioorganic & Medicinal Chemistry 18, no. 1 (2010): 214–21.
   PubMed Web of Science ®Google Scholar
• L. W. Zheng, L. L. Wu, B. X. Zhao, W. L. Dong, and Y. J. Miao, “Synthesis of Novel Substituted Pyrazole-5-Carbohydrazide Hydrazone Derivatives and Discovery of a Potent Apoptosis Inducer in A549 Lung Cancer Cells,” Bioorganic & Medicinal Chemistry 17, no. 5 (2009): 1957–62.
   PubMed Web of Science ®Google Scholar
• M. G. Saulnier, U. Velaprthi, and K. Zimmermann, “Five-Membered Ring Systems: With N and S (Se) Atoms,” In Progress In Heterocyclic Synthesis, edited by G. W. Gribble, and J. A. Joule, Vol. 16 (Amsterdam, The Netherlands: Elsevier Science B.V., 2005), 228–271.
   Google Scholar
• M. Thormann, and H.-J. Hofmann, “Conformational Properties of Azapeptides,” Journal of Molecular Structure: THEOCHEM 469, no. 1–3 (1999): 63–76.
   Google Scholar
• Y.-C. Huang, G.-M. Fang, and L. Liu, “Chemical Synthesis of Proteins Using Hydrazide Intermediates,” National Science Review 3, no. 1 (2016): 107–16.
   Web of Science ®Google Scholar
• D. A. Evans, K. A. Manley, and K. V. Mc, “Genetic Control of Isoniazid Metabolism in Man,” British Medical Journal 2, no. 5197 (1960): 485–91.
   PubMedGoogle Scholar
• K. A. Rickman, K. L. Swancutt, S. P. Mezyk, and J. J. Kiddle, “Isoniazid: Radical-Induced Oxidation and Reduction Chemistry,” Bioorganic & Medicinal Chemistry Letters 23, no. 10 (2013): 3096–100.
   PubMed Web of Science ®Google Scholar
• A. C. T. Hsu, T. T. Fujimoto, and T. S. Dhadialla, “Structure-Activity Study and Conformational Analysis of RH-5992, the First Commercialized Nonsteroidal Ecdysone Agonist. In Phytochemicals for Pest Control,” American Chemical Society 658 (1997): 206–19.
   Google Scholar
• M. M. Elshahawi, A. K. EL-Ziaty, J. M. Morsy, and A. F. Aly, “Synthesis and Insecticidal Efficacy of Novel Bis Quinazolinone Derivatives,” Journal of Heterocyclic Chemistry 53, no. 5 (2016): 1443–8.
   Web of Science ®Google Scholar
• H. F. Madkour, M. E. Azab, A. F. Aly, and, and M. S. M. Khamees, “Novel Heteerocycles Based on 1, 3, 4-Thiadiazole Scaffolds as Insecticides,” Journal of Environmental Science 40, no. no. 2 (2017): 19–44.
   Google Scholar
• M. F. Ismail, H. M. F. Madkour, M. S. Salem, A. M. M. Mohamed, and A. F. Aly, “Design, Synthesis and Insecticidal Activity of New 1,3,4thiadiazole and 1,3,4-Thiadiazolo[3,2-a]Pyrimidine Derivatives under Solvent-Free Conditions,” Synthetic Communications 51, no. 17 (2021): 2644–60.
   Web of Science ®Google Scholar
• A. M. M. Mohamed, M. F. Ismail, H. M. F. Madkour, A. F. Aly, and M. S. Salem, “Straightforward Synthesis of 2-chloro-N-(5-(Cyanomethyl)-1,3,4-Thiadiazol-2-yl)Benzamide as a Precursor for Synthesis of Novel Heterocyclic Compounds with Insecticidal Activity,” Synthetic Communications 50, no. 22 (2020) : 3424–42.
   Web of Science ®Google Scholar
• N. A. Hamed, M. I. Marzouk, M. F. Ismail, and M. H. Hekal, “N'-(1-([1,1'-biphenyl]-4-yl)Ethylidene)-2-Cyanoacetohydrazide as Scaffold for the Synthesis of Diverse Heterocyclic Compounds as Prospective Antitumor and Antimicrobial Activities,” Synthetic Communications 49, no. 21 (2019): 1–3029.
   Web of Science ®Google Scholar
• M. F. Ismail, and A. A. El-Sayed, “Synthesis and in-Vitro Antioxidant and Antitumor Evaluation of Novel Pyrazole-Based Heterocycles,” Journal of the Iranian Chemical Society 16, no. 5 (2019): 921–37.
   Web of Science ®Google Scholar
• M. F. Ismail, and G. A. Elsayed, “Dodecanoyl Isothiocyanate and N’-(2-Cyanoacetyl)Dodecanehydrazide as Precursors for the Synthesis of Different Heterocyclic Compounds with Interesting Antioxidant and Antitumor Activity,” Synthetic Communications 48, no. 8 (2018): 892–905.
   Web of Science ®Google Scholar
• M. R. Mahmoud, S. A. Shiba, A. K. El-Ziaty, F. S. M. Abu El-Azm, and M. F. Ismail, “Synthesis and Reactions of Novel 2,5-Disubstituted 1,3,4-Thiadiazoles,”Synthetic Communications 44, no. 8 (2014): 1094–102.
   Web of Science ®Google Scholar
• M. R. Mahmoud, and M. F. Ismail, “Recent Developments in Chemistry of 1,3,4-Thiadiazoles,” Journal of Advances in Chemistry 10, no. 6 (2014): 2812–42.
   Google Scholar
• M. R. Mahmoud, A. K. El-Ziaty, F. S. M. Abu El-Azm, M. F. Ismail, and S. A. Shiba, “Utility of Cyano-N-(2-Oxo-1,2-Dihydroindol-3-Ylidene)Acetohydrazide in the Synthesis of Novel Heterocycles,” Journal of Chemical Research 37, no. 2 (2013): 80–5.
   Google Scholar
• Yanyan Wang, Fangzhou Xu, Gang Yu, Jun Shi, Chuanhui Li, A'li Dai, Zhiqian Liu, Jiahong Xu, Fenghua Wang, and Jian Wu, “Synthesis and Insecticidal Activity of Diacylhydrazine Derivatives Containing a 3-Bromo-1-(3-Chloropyridin-2-yl)-1H-Pyrazole Scaffold,” Chemistry Central Journal 11, no. 1 (2017): 50.
   PubMedGoogle Scholar
• S. H. Doss, W. W. Wardakhan, and N. A. Louca, “The Reaction of Digitoxin and Digoxin with Cyanoacetic Acid Hydrazide: synthesis of Coumarin, Thiazole, Thiophene and Pyridine Derivatives with Potential Biological Activities,” Archives of Pharmacal Research 24, no. 5 (2001): 377–84.
   PubMed Web of Science ®Google Scholar
• P. Rathelot, N. Azas, H. El-Kashef, F. Delmas, C. D. Giorgio, P. Timon-David, J. Maldonado, and P. Vanelle, “1,3-Diphenylpyrazoles: synthesis and Antiparasitic Activities of Azomethine Derivatives,” European Journal of Medicinal Chemistry 37, no. 8 (2002): 671–9.
   PubMed Web of Science ®Google Scholar
• C.-J. Xu, and Y.-Q. Shi, “Synthesis and Crystal Structure of 5-Chloro-3-Methyl-1-Phenyl-1H-Pyrazole-4-Carbaldehyde,” Journal of Chemical Crystallography 41, no. 12 (2011): 1816–9.
   Web of Science ®Google Scholar
• K. Ghoneim, Kh Hamadah, and H. Waheeb, “Bioefficacy of Farnesol, a Common Sesquiterpene, on the Survival, Growth, Development, and Morphogenesis of Spodoptera littoralis (Lepidoptera: Noctuidae),” Egyptian Academic Journal of Biological Sciences 12, no. 1 (2020): 71–99.
   Google Scholar
• K.S. Ghoneim, “Physiological Studies on Endocrine and Reproductive Systems of the Cotton Leafworm Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae)” (Ph.D. Thesis, Fac. of Sci., Al-Azhar Univ., Cairo, Egypt, 1985).
   Google Scholar
• R. F. A. Bakr, N. M. El-Barky, M. F. Abd Elaziz, M. H. Awad, and H. M. E. Abd El-Halim, “Effect of Chitin Synthesis Inhibitors (Flufenoxuron) on Some Biological and Biochemical Aspects of the Cotton Leaf Worm Spodoptera littoralis Bosid. (Lepidoptera: Noctuidae),” Egyptian Academic Journal of Biological Sciences. F, Toxicology & Pest Control 2, no. 2 (2010): 43–56.
   Google Scholar
• R. R. S. Asher, and F. Miriam, “The Residual Contact Toxicity of Bay Sir 8514 to Spodoptera littoralis, Larvae,” Phytoparasitica 9, no. 2 (1981): 133–8.
   Web of Science ®Google Scholar
• W. S. Abbott, “A Method for Computing Effectiveness of an Insecticide,” Journal of Economic Entomology 18, no. 2 (1925): 265–7.
   Google Scholar
• D. J. Finney, Propit Analysis, 3rd Ed. (London: Cambridge Univ. Press, 1971), 318.
   Google Scholar
• Y.-P. Sun, J. Hyman, and C. Denver, “Toxicity Index: An Improved Method of Comparing the Relative Toxicity of Insecticides,” Journal of Economic Entomology 43, no. 1 (1950): 45–53.
   Web of Science ®Google Scholar