Antinemic activity of ferrocenyl chalcones against Meloidogyne incognita infestation in tomato

DINESH K YADAV; KAILASH PATI TRIPATHI; PANKAJ PANKAJ; PRASHANT KAUSHIK; VIRENDRA S RANA; DILIP KHATRI; NAJAM A SHAKIL

doi:10.56093/ijas.v91i2.111644

Authors

DINESH K YADAV ICAR-Indian Agricultural Research Institute, New Delhi 110 012, India
KAILASH PATI TRIPATHI ICAR-Indian Agricultural Research Institute, New Delhi 110 012, India
PANKAJ PANKAJ ICAR-Indian Agricultural Research Institute, New Delhi 110 012, India
PRASHANT KAUSHIK ICAR-Indian Agricultural Research Institute, New Delhi 110 012, India
VIRENDRA S RANA ICAR-Indian Agricultural Research Institute, New Delhi 110 012, India
DILIP KHATRI ICAR-Indian Agricultural Research Institute, New Delhi 110 012, India
NAJAM A SHAKIL ICAR-Indian Agricultural Research Institute, New Delhi 110 012, India

https://doi.org/10.56093/ijas.v91i2.111644

Keywords:

Ferrocenyl chalcones, Meloidogyne incognita, Root dipping, Root-knot nematode, Soil drenching

Abstract

A series of ferrocenyl chalcones using acetylferrocene with different aldehydes were synthesized and their in vitro evaluation against Meloidogyne incognita was reported. The present study was carried out in net house conditions, Division of Nematology, ICAR-IARI, during rabi 2018-19, the bioefficacy evaluation of most effective compounds, identified by in vitro results, along with Carbofuran 3G in pot cultured tomato is reported. The identified, five most effective compounds, (2E)-1-Ferrocenyl-3-(4-bromophenyl)-prop-2-en-1-one (3b), (2E)-1-Ferrocenyl-3-(4- methoxyphenyl)-prop-2-en-1-one (3f), (2E)-1-Ferrocenyl-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one (3h), (2E)-1- Ferrocenyl-3-(4-nitrophenyl) prop-2-en-1-one (3m) and (2E)-1-Ferrocenyl-3-(2,6-dichlorophenyl)-prop-2-en-1-one (3o) were undertaken for pot experiment at different concentrations, viz. 20, 40 and 80 ppm and by soil drenching and root dipping methods. The study revealed that all plant growth parameters were positively influenced by these compounds. It was also observed that the presence of electron releasing group positively influences the efficacy and the activity was highest in compound 3f and 3h @ 80 ppm at 30 DAI and 60 DAI. The activity was higher in soil drenching compared to root dipping method.

Downloads

Download data is not yet available.

References

Abad P, Gouzy J, Aury J M, Castagnone S P, Danchin E G, Deleury E and Caillaud M C. 2008. Genome sequence of the metazoan plant parasitic nematode Meloidogyne incognita. Nature biotechnology 26(8): 909–15. DOI: https://doi.org/10.1038/nbt.1482

Abada K A, Mostafa S H and Mervat R. 2008. Effect of some chemical salts on suppressing the infection by early blight disease of tomato. Egyptian Journal of Applied Science 23(20): 47–58.

Anonymous, Indian Horticulture Database. 2011. National Horticulture Board, Department of Agriculture Co-operation and Farmers Welfare, Ministry of Agriculture and Farmer Welfare, New Delhi.

Attar S, O’Brien Z, Alhaddad H, Golden M L and Calderon- Urrea A. 2011. Ferrocenyl chalcones versus organic chalcones: a comparative study of their nematocidal activity. Bioorganic and Medicinal Chemistry 19(6): 2055–73. DOI: https://doi.org/10.1016/j.bmc.2011.01.048

Bag S, Ramar S and Degani M S. 2009. Synthesis and biological evaluation of α, β-unsaturated ketone as potential antifungal agents. Medicinal Chemistry Research 18(4): 309–16. DOI: https://doi.org/10.1007/s00044-008-9128-x

Bose A, Shakil N A, Pankaj, Kumar J and Singh M K. 2010. Biocatalytic amidation of carboxylic acids and their antinemic activity. Journal of Environmental Science and Health Part B 45(3): 254–61. DOI: https://doi.org/10.1080/03601231003613716

Caboni P, Aissani N, Demurtas M, Ntalli N and Onnis V. 2016. Nematicidal activity of acetophenones and chalcones against Meloidogyne incognita and structure activity considerations. Pest Management Science 72(1): 125–30. DOI: https://doi.org/10.1002/ps.3978

Jayasinghe L, Balasooriya B A I S, Padmini W C, Hara N and Fujimoto Y. 2004. Geranyl chalcone derivatives with antifungal and radical scavenging properties from the leaves of Artocarpus nobilis. Phytochemistry 65(9): 1287–90. DOI: https://doi.org/10.1016/j.phytochem.2004.03.033

Kalirajan R, Sivakumar S U, Jubie S, Gowramma B and Suresh B. 2009. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. International Journal of Chemtech Research 1(1): 27–34.

Kaushik P, Shakil N A and Pankaj 2015. Biocatalytic amidation of phenolic acids and their antinemic activity. Indian Journal of Nematology 45(2): 241–44.

Kaushik P, Shakil N A, Pankaj and Kumar J. 2019. Systemic acquired resistance (Sar) study of phenolic acid amides against Meloidogyne graminicola infestation in rice. Indian Journal of Nematology 49(1): 1–8.

Kromann H, Larsen M, Boesen T, Schonning K and Nielsen S F. 2004. Synthesis of prenylated benzaldehydes and their use in the synthesis of analogues of licochalcone A. European Journal of Medicinal Chemistry 39(11): 993–1000. DOI: https://doi.org/10.1016/j.ejmech.2004.07.004

Kumar V, Khan M R and Walia R K. 2020. Crop loss estimations due to plant parasitic nematodes in major crops in india. National Academy Science Letters 43(5): 409–12. DOI: https://doi.org/10.1007/s40009-020-00895-2

Liu G, Lin X, Xu S, Liu G, Liu F and Mu W. 2020. Screening, identification and application of soil bacteria with nematicidal activity against root-knot nematode (Meloidogyne incognita) on tomato. Pest Management Science 76(6): 2217–24. DOI: https://doi.org/10.1002/ps.5759

Mishra S, Zhang W, Lin Z, Pang S, Huang Y, Bhatt P and Chen S. 2020. Carbofuran toxicity and its microbial degradation in contaminated environments. Chemosphere 127419. DOI: https://doi.org/10.1016/j.chemosphere.2020.127419

National Horticulture Board. 2018. Horticultural statistics at a glance. Department of Agriculture Co-operation and Farmers Welfare, Ministry of Agriculture and Farmer Welfare, New Delhi.

Nielsen S F, Larsen M, Boesen T, Schonning K and Kromann H. 2005. Cationic chalcone antibiotics. Design, synthesis and mechanism of action. Journal of Medicinal Chemistry 48(7): 2667–77. DOI: https://doi.org/10.1021/jm049424k

Shakil N A, Kumar J, Pandey R K and Saxena D B. 2008. Nematicidal prenylated flavanones from Phyllanthus niruri. Phytochemistry 69(3): 759–64. DOI: https://doi.org/10.1016/j.phytochem.2007.08.024

Shakil N A, Singh M K, Sathiyendiran M and Kumar J. 2011. Microwave accelerated solvent-free synthesis and antifungal evaluations of flavanones. Archives of Phytopathology and Plant Protection 44(20): 1958–65. DOI: https://doi.org/10.1080/03235408.2010.544467

Shakil N A, Singh M K, Sathiyendiran M, Kumar J and Padaria J C. 2013. Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen- 1-one and 2H-indazol-3-ol derivatives. European Journal of Medicinal Chemistry 59: 120–31. DOI: https://doi.org/10.1016/j.ejmech.2012.10.038

Yadav D K, Kaushik P, Pankaj, Rana V S, Kamil D, Khatri D and Shakil N A. 2019. Microwave assisted synthesis, characterization and biological activities of ferrocenyl chalcones and their QSAR analysis. Frontiers in Chemistry 7: 1–15. DOI: https://doi.org/10.3389/fchem.2019.00814

Yadav D K, Tripathi K P, Kaushik P, Pankaj, Rana, V S, Kamil D, Khatri D and Shakil N A. 2020. Microwave assisted synthesis, characterization and biological activities of ferrocenyl chalcones and their QSAR analysis: Part II. Journal of Environmental Science and Health, Part B 56(1): 82–97. DOI: https://doi.org/10.1080/03601234.2020.1838828

Zhou L, Yuen G, Wang Y, Wei L and Ji G. 2016. Evaluation of bacterial biological control agents for control of root-knot nematode disease on tomato. Crop Protection 84: 8–13. DOI: https://doi.org/10.1016/j.cropro.2015.12.009