Synthesis, formulation, evaluation of insecticidal activity of chromen derivatives against cotton leafworm Spodoptera littoralis (Lepidoptera: Noctuidae) and their mode of action under laboratory conditions
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Abstract
The toxicity of benzothiazole derivatives obtained from 2-cyanomethyl benzothiazole against cotton leafworm Spodoptera littoralis 2nd and 4th instar larvae has been documented. The main objective of this research was to formulate two previously reported chromen derivatives and test their biological activity against cotton leafworm S. littoralis 2nd and 4th instar larvae under laboratory conditions. According to the standard method, two chromen derivatives with two distinct substituents (salicylaldehyde and 2-hydroxy-1-naphthaldehyde) were synthesized. Their physical and chemical properties were evaluated, and both were formulated as 10 and 9.5 percent dustable powder formulations. Both formulae were then evaluated in the laboratory on cotton leafworm S. littoralis 2nd and 4th instar larvae for mortality and developmental effect percentage. Formulation (F2) was more efficient than formulation (F3) in both cases and for both stages. Furthermore, when comparing the developmental effects on the 2nd and 4th instar larvae, the 4th instar larvae demonstrated marked tolerance. Both stages were unable to complete their life cycle. Histopathological analysis of samples from the affected stages was performed to assess the mode of action of these formulations on 4th instar larvae at their LC50 values. Experimental data showed that Formulation (F3) resulted in epidermal cells separated from the cuticular layer, necrosis, ruptured columnar cells with pyknotic nuclei, disrupted basement membrane, and weak epicuticle necrosis and separation. In comparison, formulation (F2) revealed a midgut with vacuoles, damaged columnar, muscle cell necrosis, and a ruined peritrophic matrix. Thus, the cotton leafworm S. littoralis could be combated with the newly prepared formulations (F2) and (F3).
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Keywords
Biological efficacy, Chemical substitution, Dustable powder, Spodoptera littoralis, Thiazole
References
Abbot, W. S. A. (1925). A method of computing the effectiveness of an insecticide; J. Econ. Ent., 18(2): 265-267. https://doi.org/10.1093/jee/18.2.265a
Abdel-Mageed, A., El-bokl, M., Khidr, A. & Said, R. (2018): Disruptive effects of selected chitin synthesis inhibitors on cotton leaf worm Spodoptera littoralis (Boisd.). Australian Journal of Basic and Applied Sciences, 12(1): 4-9. https://doi.org/10.22587/ajbas.2018.12.1.2
Abdel-Salam, M. E. & El-Sayed Negm M. A. M. (2009). The Egyptian cotton; current constraints and future opportunities, Textile Industries Holding Co. www.icac.org/econ_stats/country_facts/e_egyptian_cons traints_opportu nities
Ahmed Y. N. & Delin H. (2019). Current situation of Egyptian cotton: econometrics study using ARDL Model. Journal of Agricultural Science, 11(10), 88-97. https://doi.org/10.5539/jas.v11n10p88
Ahmed, M. A. I., Abdel-Galil, F. A., Temerak, S. A. S. & Manna, S. H. M. (2015a). Bioresidual activity of selected biopesticides in comparison with the conventional insecticide Dursban against Cotton leafworm, Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae). American-Eurasian Journal of Sustainable Agriculture, 9 (1), 9-14.
Ahmed, M. A. I., Temerak, S. A. S., Abdel-Galil, F. A. & Manna S. H. M. (2015b). Effect of selected host plants on the efficacy of spinosad pesticide on Cotton leafworm, Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae) under laboratory conditions. Advances in Environmental Biology, 9: 372–375.
Allam, E. A. Y., Manaa, S. H., Dahi, H. F., Ahmed, M. M. A. & Yones, M. S. (2021). Threshold Temperatures and Thermal Requirements of Cotton Leafworm, Spodoptera littoralis Hb. Egypt. Acad. J. Biolog. Sci., 14(3):103-113.
Anonymous (1965): Mollusicidal screening & evaluation. Bull. WHO, 33 (4), 567 - 581. https://apps.who.int/iris/handle/10665/262863
Aydin, H. M. & Gurkan, O. R. (2006). The efficacy of spinosad on different strains of Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae). Turkish J. Biol., 30, 5-9.
Baffes, J. (2005). The cotton problem, The World Bank Research Observer, 20 (1), 109-144, www.jsto r.org.ezpro xy.library.ubc.ca/stable/4126 1411. https://doi.org/10.10 93/wbro/lki004
CABI (2019). Spodoptera littoralis. Invasive Species Compendium. Retrieved from www. Cabi.org/isc
Czwartkowski, K., Wierzbic, A. & Golimowski, W. (2022). Quality, key production factors, and consumption volume of niche edible oils marketed in the European Union, Sustainability, 14, 1846. https://doi.org/10.3390/su14031846
Dobrat, W. & Martijn, A. (1995). Collaborative International Pesticides Analytical Council CIPAC hand book, F, Physicochemical Methods for Technical and Formulated Pesticides
El-Defrawi, M. F, Toppozada, A., N. Mansour & Zaid M. (1964). Toxicological studies on the Egyptian cotton leafworm, Prodenia litura I susceptibility of different larval instars of Prodenia to insecticides J. Econ. Entomol, 57(4):591-593. https://doi.org/10.1093/jee/57.4.591
El-Geddawy, A. M. H., Ahmed, M. A. I. & Mohamed, S. H. (2014). Toxicological evaluation of selected biopesticides and one essential oil in comparison with Indoxacarb pesticide on cotton leafworm, Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae) under laboratory conditions. American-Eurasian Journal of Sustainable Agriculture, 8 (2), 58–64.
El-Hamidi, M. & Zaher, F. A. (2018). Production of vegetable oils in the world and in Egypt: an overview. Bulletin of the National Research Centre, 42(19), 1-9. https://doi.org/10.1186/s42269-018-0019-0
El-Kholy, R.M.A., El-Bamby, M. M. M., El-Tawil, M. F. & Abouamer, W. L. (2014). Effect of Three Plant Extracts on Some Biological Aspects of Cotton Leafworm, Spodoptera littoralis (Boisd.), Middle East Journal of Applied Sciences, 4(2): 243-251.
El-Sheikh, T. A. A. (2012): Biological, biochemical and histological effects of spinosad, Bacillus thuringiensis var. kurstaki and cypermethrin on the Cotton leafworm, Spodoptera littoralis (Boisd.). Egyptian Academic Journal of Biological Sciences, 4(1), 113–124. https://doi.org/ 10.21608/EAJBSC.2012.16130
El-Zemaity, M. S., El-Deeb, W. M., Osman, Y. A. and Hussien, A. I. (2003). Development of resistance of Spodoptera littoralis to certain bioinsecticides. Journal of Environmental Sciences, 6: 793–810. [ResearchGate]
El-Zoghby, Fadia, A., Salem, M. H., Gadelhak, G. G. and El-Sabrout, A. M. (2011). Effects of Melilotus indica crude extracts and cascade (IGR) on Spodoptera littoralis (Lepidoptera: Noctuidae) Reproductive Organs. Bull. ent. Soc. Egypt, Econ. Ser., 37: 121-136. [ResearchGate]
Fadda, A. A., Abd El-Mageed, A. M., Hamouda, S. E.S & ElSharkawy, R. A. (2020). Efficacy of some benzothiazole derivatives and their formulation against cotton leafworm Spodoptera littoralis (Lepidoptera: Noctuidae). Egypt. J. Plant Prot. Res. Inst., 3 (2), 662 - 672
Finney, D. J. (1971). Probit Analysis, A statistical Treatment of the Sigmoid Response Curve, 7th Ed., Cambridge Univ. Press, England.
Food and Agriculture Organization and World Health Organization, FAO and WHO, 1st 2nd rev. MT 186 (2010) Manual on Development and Use of FAO and WHO Specifications for Pesticides.
Food and Agriculture Organization and World Health Organization, FAO and WHO, 1st 2nd rev. MT 191 (2010) Manual on Development and Use of FAO and WHO Specifications for Pesticides.
Furmidge, C. G. L. (1972). General principles governing the behavior of granular formulation, Pestic. Sci., 3(6), 745-751. https://doi.org/10.1002/ps.2780030612
Hamouda, S. E. S, El-Sharkawy, R. A. &, Moustafa, H. Z. (2021). Study the potential activity of some newly synthesized thiazolidine derivatives and its 10% dustable powder formulation against pink bollworm Pectinophora gossypiella (Saunders) (Lepidoptera: Gelechiidae), International Journal of Entomology Research, 6(4), 231-236.
Hassan, H. A. (2009). Efficiency of some new insecticides on physiological, histological and molecular level of cotton leafworm.Egypt. Acad. J. biolog. Sci., (A- Entomology), 2 (2): 197- 209. https://doi.org/10.21608/EAJBSA.2009.154 43
Hatab, A. A. (2009). Performance of Egyptian cotton exports in international market. Agricultural Economics Research Review,22, 225-235.
Hatem, A. E., Abdel-Samad, S. S. M., Saleh, H. A., Soliman, M. H. A. & Hussien, A. I. (2009). Toxicologyical and physiological activity of plant extracts against Spodoptera littoralis (Boisduval) (Lepidoptera: Noctuidae) Larvae. Boletín de Sanidad Vegetal Plagas, 35, 517-531. [ResearchGate]
Hazra, D. K. & Purkait, K. (2019). Role of pesticide formulations for sustainable crop protection and environment management: A review. Journal of Pharmacognosy and Phytochemistry, 8(2), 686-693. http://krishikosh.egra nth.ac.in/handle/1/5810096400
Huang. B., Chen, F., Shen, Y., Qian, K., Wang, Y., Sun, C., Zhao, X., Cui, B., Gao, F., Zeng, Z. & Cui, H., (2018). Advances in targeted pesticides with environmentally responsive controlled release by nanotechnology. Nanomaterials, 8 (2), 102. https://doi.org/10.3390/nano802 0102. [PubMed]
Karvy. (2009). Cotton seasonal report. retrieved from http://www.karvycomtrade.com
Li, Y. (2018). Understanding the physical and biological effects of dust-induced insect death, PH. D Thesis, School of Veterinary and Life Sciences, Murdoch University Perth, Western Australia, Australia, 1-230.
Lillie, R. D. (1965). Histopathologic technique and practical histochemistry, 3rd ed., Mc Graw-Hill Book Co., New York.
Lynch, M. J., Raphael, S. S., Mellor, L. D., Spare, P. D. & Inwood, M. J. (1969). Medical laboratory technology and clinical pathology, 2nd ed., W B Saunders Co., Philadelphia London Toronto.
Malina, A. M. A. G., Oldnan, L. Tradman & Polou, P. B. (1956): Deactvation of mineral carriers for stable heptachlor formulations, J. Agric. Food Chem., 4(1),1038-1042. https://doi.org/10.1021/jf60070a008
McKinley, N., Kijima, S., Cook, G., & Sherrod, D. (2002). Avaunt (Indoxacarb): a new mode of action insecticide for control of several key orchard pests. Proc. 76th Ann. Western Orchard Pest & Disease Manag. Conf. 9-11 January 2002, Portland, Washington State Univ., New Products DuPont Crop Protection, Wilmington, DE.
Nelson, F. C., & Fiero, G. W. (1954). Pesticide formulations, a selected aromatic fraction naturally occurring in petroleum as a pesticide solvent. Journal of Agricultural and Food Chemistry, 2(14), 735-737. https://doi.org/10.1021/jf60034a005
Nkya, T. E., Idir, A., Rodolphe, P., Bernard, B., Franklin, M., Stephen M., William, K. & JeanPhilippe, D. (2014). Insecticide resistance mechanisms associated with different environments in the malaria vector Anopheles gambiae: a case study in Tanzania. Malaria Journal, 13(1), 28. https://doi.org/10.1186/1475-2875-13-28 [PubMed]
Racané, L., Pavelić, S.K., Ratkaj, I., Stepanić, V., Pavelić, K.; Kulenović, V. T. & Zamola, G. K. (2012). Synthesis and antiproliferative evaluation of some new amidino-substituted bis-benzothiazolyl-pyridines and pyrazine. Eur J. Med Che., 55, 108-116.
Raza, W., Grumiller, J., Grohs, H. & Alexander, R., (2020). Austrian Foundation for Development Research (OEFSE), Value chain analysis for apparel from Egypt, Commissioned by The Centre for the Promotion of Imports from developing countries (CBI), 1-82.
Refat, H. A. & Mohamed, S. K. (2015). Efficient and convenient synthesis of pyrido [2,1-b]benzothiazole, pyrimidopyrido[2,1-b] benzothiazole and benzothiazolo[3,2-a][1,8] naphthyridine derivatives, Heterocycl. Commun. 21(4), 219-224. https://doi.org/10.1515/hc-2015-0018
Reichenberger, S., Bach, M., Skitschak, A. & Frede, H. (2007). Mitigation Strategies to Reduce Pesticide Inputs into Ground-and Surface Water and Their Effectiveness: A review. Sci. Total Environ.,384(1-3), 1-35. https://doi.org/10.1016/J.SCITOTENV.2007.04.046 [CrossRef] [PubMed]
Sun, C.J., Cui, H.X., Wang, Y., Zeng, Z.H., Zhao, X. & Cui, B. (2016). Studies on applications of nanomaterial and nanotechnology in agriculture, J. Agric. Sci. Technol, 18, 18-25. [CrossRef]
Sun, Y. P. (1950). Toxicity index an improved method of comparing the relative toxicity of insecticides, J. Econ. Entomol. 43(1), 45-53. https://doi.org/10.1093/jee/43.1.45
Temerak, S. A. (2002). Historical records of cotton leafworm (Spodoptera littoralis) resistance to conventional insecticides in the field as influenced by the resistance programs in Egypt from 1950–2002. Resistant Pest Management Newsletter, 12 (1): 7–10.
Wing, K. D., Sacher, M., Kagaya, Y., Tsurubuchi, Y., Mulderig, L., Connair, M. & Schnee, M., (2000). Bioactivation and mode of action of the oxadiazine indoxacarb in insects. Crop Protect. 19 (8-10), 537–545. https://doi.org/10.1016/S0261-2194(00)00070-3 [ScienceDirect]
World Health Organization (1979). Specification of Pesticides Used in Public Health, 5th Ed. Geneva, 1979
Zaazoua, M. H., El-Aknahal & El-Attal, Z. M. (1966). Evaluation of certain local materials for use as insecticide dust diluents and carriers 1- The physical properties and PH values. Bull. Fac. of Agric. Cairo Univ., 17(2),33-34.
Zhao, X.J., Wu, Y. & Jiang, B. G. (2006). The investigation of synthesis and decomposition of amino acid salicyadehyde schiff base. J. Dalian Natl. Univ., 30, 24-27.
Abdel-Mageed, A., El-bokl, M., Khidr, A. & Said, R. (2018): Disruptive effects of selected chitin synthesis inhibitors on cotton leaf worm Spodoptera littoralis (Boisd.). Australian Journal of Basic and Applied Sciences, 12(1): 4-9. https://doi.org/10.22587/ajbas.2018.12.1.2
Abdel-Salam, M. E. & El-Sayed Negm M. A. M. (2009). The Egyptian cotton; current constraints and future opportunities, Textile Industries Holding Co. www.icac.org/econ_stats/country_facts/e_egyptian_cons traints_opportu nities
Ahmed Y. N. & Delin H. (2019). Current situation of Egyptian cotton: econometrics study using ARDL Model. Journal of Agricultural Science, 11(10), 88-97. https://doi.org/10.5539/jas.v11n10p88
Ahmed, M. A. I., Abdel-Galil, F. A., Temerak, S. A. S. & Manna, S. H. M. (2015a). Bioresidual activity of selected biopesticides in comparison with the conventional insecticide Dursban against Cotton leafworm, Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae). American-Eurasian Journal of Sustainable Agriculture, 9 (1), 9-14.
Ahmed, M. A. I., Temerak, S. A. S., Abdel-Galil, F. A. & Manna S. H. M. (2015b). Effect of selected host plants on the efficacy of spinosad pesticide on Cotton leafworm, Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae) under laboratory conditions. Advances in Environmental Biology, 9: 372–375.
Allam, E. A. Y., Manaa, S. H., Dahi, H. F., Ahmed, M. M. A. & Yones, M. S. (2021). Threshold Temperatures and Thermal Requirements of Cotton Leafworm, Spodoptera littoralis Hb. Egypt. Acad. J. Biolog. Sci., 14(3):103-113.
Anonymous (1965): Mollusicidal screening & evaluation. Bull. WHO, 33 (4), 567 - 581. https://apps.who.int/iris/handle/10665/262863
Aydin, H. M. & Gurkan, O. R. (2006). The efficacy of spinosad on different strains of Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae). Turkish J. Biol., 30, 5-9.
Baffes, J. (2005). The cotton problem, The World Bank Research Observer, 20 (1), 109-144, www.jsto r.org.ezpro xy.library.ubc.ca/stable/4126 1411. https://doi.org/10.10 93/wbro/lki004
CABI (2019). Spodoptera littoralis. Invasive Species Compendium. Retrieved from www. Cabi.org/isc
Czwartkowski, K., Wierzbic, A. & Golimowski, W. (2022). Quality, key production factors, and consumption volume of niche edible oils marketed in the European Union, Sustainability, 14, 1846. https://doi.org/10.3390/su14031846
Dobrat, W. & Martijn, A. (1995). Collaborative International Pesticides Analytical Council CIPAC hand book, F, Physicochemical Methods for Technical and Formulated Pesticides
El-Defrawi, M. F, Toppozada, A., N. Mansour & Zaid M. (1964). Toxicological studies on the Egyptian cotton leafworm, Prodenia litura I susceptibility of different larval instars of Prodenia to insecticides J. Econ. Entomol, 57(4):591-593. https://doi.org/10.1093/jee/57.4.591
El-Geddawy, A. M. H., Ahmed, M. A. I. & Mohamed, S. H. (2014). Toxicological evaluation of selected biopesticides and one essential oil in comparison with Indoxacarb pesticide on cotton leafworm, Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae) under laboratory conditions. American-Eurasian Journal of Sustainable Agriculture, 8 (2), 58–64.
El-Hamidi, M. & Zaher, F. A. (2018). Production of vegetable oils in the world and in Egypt: an overview. Bulletin of the National Research Centre, 42(19), 1-9. https://doi.org/10.1186/s42269-018-0019-0
El-Kholy, R.M.A., El-Bamby, M. M. M., El-Tawil, M. F. & Abouamer, W. L. (2014). Effect of Three Plant Extracts on Some Biological Aspects of Cotton Leafworm, Spodoptera littoralis (Boisd.), Middle East Journal of Applied Sciences, 4(2): 243-251.
El-Sheikh, T. A. A. (2012): Biological, biochemical and histological effects of spinosad, Bacillus thuringiensis var. kurstaki and cypermethrin on the Cotton leafworm, Spodoptera littoralis (Boisd.). Egyptian Academic Journal of Biological Sciences, 4(1), 113–124. https://doi.org/ 10.21608/EAJBSC.2012.16130
El-Zemaity, M. S., El-Deeb, W. M., Osman, Y. A. and Hussien, A. I. (2003). Development of resistance of Spodoptera littoralis to certain bioinsecticides. Journal of Environmental Sciences, 6: 793–810. [ResearchGate]
El-Zoghby, Fadia, A., Salem, M. H., Gadelhak, G. G. and El-Sabrout, A. M. (2011). Effects of Melilotus indica crude extracts and cascade (IGR) on Spodoptera littoralis (Lepidoptera: Noctuidae) Reproductive Organs. Bull. ent. Soc. Egypt, Econ. Ser., 37: 121-136. [ResearchGate]
Fadda, A. A., Abd El-Mageed, A. M., Hamouda, S. E.S & ElSharkawy, R. A. (2020). Efficacy of some benzothiazole derivatives and their formulation against cotton leafworm Spodoptera littoralis (Lepidoptera: Noctuidae). Egypt. J. Plant Prot. Res. Inst., 3 (2), 662 - 672
Finney, D. J. (1971). Probit Analysis, A statistical Treatment of the Sigmoid Response Curve, 7th Ed., Cambridge Univ. Press, England.
Food and Agriculture Organization and World Health Organization, FAO and WHO, 1st 2nd rev. MT 186 (2010) Manual on Development and Use of FAO and WHO Specifications for Pesticides.
Food and Agriculture Organization and World Health Organization, FAO and WHO, 1st 2nd rev. MT 191 (2010) Manual on Development and Use of FAO and WHO Specifications for Pesticides.
Furmidge, C. G. L. (1972). General principles governing the behavior of granular formulation, Pestic. Sci., 3(6), 745-751. https://doi.org/10.1002/ps.2780030612
Hamouda, S. E. S, El-Sharkawy, R. A. &, Moustafa, H. Z. (2021). Study the potential activity of some newly synthesized thiazolidine derivatives and its 10% dustable powder formulation against pink bollworm Pectinophora gossypiella (Saunders) (Lepidoptera: Gelechiidae), International Journal of Entomology Research, 6(4), 231-236.
Hassan, H. A. (2009). Efficiency of some new insecticides on physiological, histological and molecular level of cotton leafworm.Egypt. Acad. J. biolog. Sci., (A- Entomology), 2 (2): 197- 209. https://doi.org/10.21608/EAJBSA.2009.154 43
Hatab, A. A. (2009). Performance of Egyptian cotton exports in international market. Agricultural Economics Research Review,22, 225-235.
Hatem, A. E., Abdel-Samad, S. S. M., Saleh, H. A., Soliman, M. H. A. & Hussien, A. I. (2009). Toxicologyical and physiological activity of plant extracts against Spodoptera littoralis (Boisduval) (Lepidoptera: Noctuidae) Larvae. Boletín de Sanidad Vegetal Plagas, 35, 517-531. [ResearchGate]
Hazra, D. K. & Purkait, K. (2019). Role of pesticide formulations for sustainable crop protection and environment management: A review. Journal of Pharmacognosy and Phytochemistry, 8(2), 686-693. http://krishikosh.egra nth.ac.in/handle/1/5810096400
Huang. B., Chen, F., Shen, Y., Qian, K., Wang, Y., Sun, C., Zhao, X., Cui, B., Gao, F., Zeng, Z. & Cui, H., (2018). Advances in targeted pesticides with environmentally responsive controlled release by nanotechnology. Nanomaterials, 8 (2), 102. https://doi.org/10.3390/nano802 0102. [PubMed]
Karvy. (2009). Cotton seasonal report. retrieved from http://www.karvycomtrade.com
Li, Y. (2018). Understanding the physical and biological effects of dust-induced insect death, PH. D Thesis, School of Veterinary and Life Sciences, Murdoch University Perth, Western Australia, Australia, 1-230.
Lillie, R. D. (1965). Histopathologic technique and practical histochemistry, 3rd ed., Mc Graw-Hill Book Co., New York.
Lynch, M. J., Raphael, S. S., Mellor, L. D., Spare, P. D. & Inwood, M. J. (1969). Medical laboratory technology and clinical pathology, 2nd ed., W B Saunders Co., Philadelphia London Toronto.
Malina, A. M. A. G., Oldnan, L. Tradman & Polou, P. B. (1956): Deactvation of mineral carriers for stable heptachlor formulations, J. Agric. Food Chem., 4(1),1038-1042. https://doi.org/10.1021/jf60070a008
McKinley, N., Kijima, S., Cook, G., & Sherrod, D. (2002). Avaunt (Indoxacarb): a new mode of action insecticide for control of several key orchard pests. Proc. 76th Ann. Western Orchard Pest & Disease Manag. Conf. 9-11 January 2002, Portland, Washington State Univ., New Products DuPont Crop Protection, Wilmington, DE.
Nelson, F. C., & Fiero, G. W. (1954). Pesticide formulations, a selected aromatic fraction naturally occurring in petroleum as a pesticide solvent. Journal of Agricultural and Food Chemistry, 2(14), 735-737. https://doi.org/10.1021/jf60034a005
Nkya, T. E., Idir, A., Rodolphe, P., Bernard, B., Franklin, M., Stephen M., William, K. & JeanPhilippe, D. (2014). Insecticide resistance mechanisms associated with different environments in the malaria vector Anopheles gambiae: a case study in Tanzania. Malaria Journal, 13(1), 28. https://doi.org/10.1186/1475-2875-13-28 [PubMed]
Racané, L., Pavelić, S.K., Ratkaj, I., Stepanić, V., Pavelić, K.; Kulenović, V. T. & Zamola, G. K. (2012). Synthesis and antiproliferative evaluation of some new amidino-substituted bis-benzothiazolyl-pyridines and pyrazine. Eur J. Med Che., 55, 108-116.
Raza, W., Grumiller, J., Grohs, H. & Alexander, R., (2020). Austrian Foundation for Development Research (OEFSE), Value chain analysis for apparel from Egypt, Commissioned by The Centre for the Promotion of Imports from developing countries (CBI), 1-82.
Refat, H. A. & Mohamed, S. K. (2015). Efficient and convenient synthesis of pyrido [2,1-b]benzothiazole, pyrimidopyrido[2,1-b] benzothiazole and benzothiazolo[3,2-a][1,8] naphthyridine derivatives, Heterocycl. Commun. 21(4), 219-224. https://doi.org/10.1515/hc-2015-0018
Reichenberger, S., Bach, M., Skitschak, A. & Frede, H. (2007). Mitigation Strategies to Reduce Pesticide Inputs into Ground-and Surface Water and Their Effectiveness: A review. Sci. Total Environ.,384(1-3), 1-35. https://doi.org/10.1016/J.SCITOTENV.2007.04.046 [CrossRef] [PubMed]
Sun, C.J., Cui, H.X., Wang, Y., Zeng, Z.H., Zhao, X. & Cui, B. (2016). Studies on applications of nanomaterial and nanotechnology in agriculture, J. Agric. Sci. Technol, 18, 18-25. [CrossRef]
Sun, Y. P. (1950). Toxicity index an improved method of comparing the relative toxicity of insecticides, J. Econ. Entomol. 43(1), 45-53. https://doi.org/10.1093/jee/43.1.45
Temerak, S. A. (2002). Historical records of cotton leafworm (Spodoptera littoralis) resistance to conventional insecticides in the field as influenced by the resistance programs in Egypt from 1950–2002. Resistant Pest Management Newsletter, 12 (1): 7–10.
Wing, K. D., Sacher, M., Kagaya, Y., Tsurubuchi, Y., Mulderig, L., Connair, M. & Schnee, M., (2000). Bioactivation and mode of action of the oxadiazine indoxacarb in insects. Crop Protect. 19 (8-10), 537–545. https://doi.org/10.1016/S0261-2194(00)00070-3 [ScienceDirect]
World Health Organization (1979). Specification of Pesticides Used in Public Health, 5th Ed. Geneva, 1979
Zaazoua, M. H., El-Aknahal & El-Attal, Z. M. (1966). Evaluation of certain local materials for use as insecticide dust diluents and carriers 1- The physical properties and PH values. Bull. Fac. of Agric. Cairo Univ., 17(2),33-34.
Zhao, X.J., Wu, Y. & Jiang, B. G. (2006). The investigation of synthesis and decomposition of amino acid salicyadehyde schiff base. J. Dalian Natl. Univ., 30, 24-27.
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How to Cite
Synthesis, formulation, evaluation of insecticidal activity of chromen derivatives against cotton leafworm Spodoptera littoralis (Lepidoptera: Noctuidae) and their mode of action under laboratory conditions. (2022). Journal of Applied and Natural Science, 14(2), 310-319. https://doi.org/10.31018/jans.v14i2.3359
