SYNTHESIS OF FERROCENYL CHALCONES AND THEIR EVALUATION AGAINST PLANT PATHOGENIC FUNGI AND ROOT KNOT NEMATODE

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dc.contributor.advisorN. A. Shakil
dc.contributor.authorDINESH KUMAR YADAV
dc.date.accessioned2020-11-27T09:04:39Z
dc.date.available2020-11-27T09:04:39Z
dc.date.issued2020
dc.descriptionT-10332en_US
dc.description.abstractChalcones and their derivatives are conventionally known to possess biological activity due to their highly reactive unsaturated carbonyl group. Chalcone nucleus containing compounds have been a subject of interest for the scientists all over the world and research is directed towards the development of potent crop protection chemicals based on this nucleus. However, poor solubility is a major concern and prevents their use in crop protection. In order to overcome this, thirty four substituted ferrocenyl chalcones have been synthesized by microwave method (MM) and compared the reaction time and yield of products with that of conventional method (CM). Microwave Assisted Organic Synthesis (MAOS) has provided a great impetus to organic synthesis during the last few decades and has become most useful for functional group inter conversions. The use of microwave has several advantages such as shorter reaction times, higher yields, ease of manipulation and lower costs. Furthermore, reactions under microwave have great advantage of not using organic solvents (solvent-free) and thus such reactions are environment friendly and generate less waste. Environmentally benign character of the microwave method is desirable for large scale industrial applications. A series of ferrocenyl chalcones was synthesized by base-catalyzed condensation of acetylferrocene with different benzaldehydes and ferrocenecarboxyaldehyde with different acetophenones. All the products were obtained in appreciable amounts and the yields for different compounds were higher in microwave method (77-92%) as compared to conventional method (71-87%). The synthesized compounds were characterized by various spectroscopic techniques viz. IR, 1H-NMR, 13C-NMR and LC-HRMS. All synthesised compounds were tested against root knot nematode, Meloidogyne incognita. Although all the compounds possessed activity against M. incognita, but compounds 3b, 3f, 3h, 3m, 3o, 6g, 6h, 6j, 6k and 6p were found to be more potent. However, all the synthesized compounds were found to be less active than commercially available carbofuran and velum prime. Pot study revealed that, all plant growth parameters (shoot length, shoot weight, root length, root weight, average no. of galls/plant and yield (g)) were positively influenced by these compounds. As the nematicial activity of test compounds increased, plant growth parameters were also increased. The activity was highest in compounds 3f, 3h, 6g, and 6h @ 80 ppm at 30 DAI and 60 DAI. The activity was higher in soil drenching method compared to root dipping method. All the synthesized compounds showed antifungal activity. Among (3a-3p) series compounds, 3o i.e. (2E)-1-Ferrocenyl-3-(2,6-dichlorophenyl)-prop-2-en-1-one showed highest fungicidal activity against Sclerotium rolfsii with ED50 of 23.24 ppm. But in case of Alternaria solani, among (3a-3p) series compounds, 3c i.e. (2E)-1- Ferrocenyl-3-(4-fluorophenyl)-prop-2-en-1-one, having value ED50 = 29.9 ppm showed highest activity. Among (6a-6r) series compounds, 6o i.e. (2E)-1-(5-Chloro-2-hydroxyphenyl)- 3-ferrocenyl-prop-2-en-1-one showed highest fungicidal activity against S. rolfsii with ED50 of 21.50 ppm. In case of A. solani, among (6a-6r) series compounds, 6b i.e. (2E)- 1-(4-Bromophenyl)-3-ferrocenyl-prop-2-en-1-one showed highest fungicidal activity with ED50 of 31.14 ppm. Based on in vitro results, three most effective compounds 3b, 3o and 6o were chosen for pot experiment against S. rolfsii. The study revealed that shoot length was significantly increased as compared to control. The shoot length wasfound to be highest (24.50 cm) in plants treated with 3b followed by 3o and 6o @ 1000 ppm at 60 DAI. The percent disease incidence was significantly decreased as compared to control. The percent disease incidence was found to be minimum in plants treated with 3b @ 1000 ppm. The disease incidence was minimum in soil drenching method compared to root dipping method. In conclusion, this is the first attempt to synthesise a series of ferrocenyl chalcones by Microwave Synthesis Reactor. Study revealed that microwave method was quick and green method as compared to conventional method. All the synthesized compounds were found to have good to moderate nematicidal and fungicidal activity. Keywords:en_US
dc.identifier.urihttps://krishikosh.egranth.ac.in/handle/1/5810155895
dc.keywordsFerrocenyl chalcones, Microwave method ,Antifungal activity , Nematicidal activityen_US
dc.language.isoEnglishen_US
dc.publisherDIVISION OF AGRICULTURAL CHEMICALS ICAR-INDIAN AGRICULTURAL RESEARCH INSTITUTE NEW DELHIen_US
dc.subAgricultural Chemicalsen_US
dc.themeSYNTHESIS OF FERROCENYL CHALCONES AND THEIR EVALUATION AGAINST PLANT PATHOGENIC FUNGI AND ROOT KNOT NEMATODEen_US
dc.these.typePh.Den_US
dc.titleSYNTHESIS OF FERROCENYL CHALCONES AND THEIR EVALUATION AGAINST PLANT PATHOGENIC FUNGI AND ROOT KNOT NEMATODEen_US
dc.typeThesisen_US
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