Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family
New insecticidal natural products are required to find compounds with higher intrinsic activities to lower field application rates, and with novel modes of action to combat insect pest species which have developed resistance to current commercial insecticides. Using a taxonomic approach, studies...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
1998
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| Online Access: | https://eprints.nottingham.ac.uk/30648/ |
| _version_ | 1848794030332182528 |
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| author | Beddie, David G. |
| author_facet | Beddie, David G. |
| author_sort | Beddie, David G. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | New insecticidal natural products are required to find compounds with higher intrinsic activities to lower field application rates, and with novel modes of action to combat insect pest species which have developed resistance to current commercial insecticides.
Using a taxonomic approach, studies on plants of the Myrtaceae family led to the isolation and characterisation of a range of insecticidal natural products 1 - 9 (figure 1). These compounds are all structurally related as they contain a tetramethylcyclohexenedione group, attached to either a terpene or a phloroglucinol moiety. Seven of the nine compounds (1 - 6, 9) are novel. For compounds 7 and 8, no synthesis had been previously reported.
The compounds are active against a range of insect species, although in general they are less active than commercial natural products. Further tests show some of the compounds are potent antifeedants.
Synthesis of seven of the nine natural products (1 - 5, 7, 8) by short, convergent, stereospecific and high yielding routes was achieved. The synthetic routes were devised to mimic the postulated biosynthesis of the compounds. Reaction of syncarpic acid, an aldehyde and pyrrollidine formed a Mannich base, which on elimination gave a key alkylidene intennediate. This key intermediate was reacted, with either terpenes in Diels-Alder reactions or with phloroglucinols in aromatic alkylation reactions, to synthesise seven of the natural products. |
| first_indexed | 2025-11-14T19:09:42Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-30648 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T19:09:42Z |
| publishDate | 1998 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-306482025-02-28T11:37:10Z https://eprints.nottingham.ac.uk/30648/ Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family Beddie, David G. New insecticidal natural products are required to find compounds with higher intrinsic activities to lower field application rates, and with novel modes of action to combat insect pest species which have developed resistance to current commercial insecticides. Using a taxonomic approach, studies on plants of the Myrtaceae family led to the isolation and characterisation of a range of insecticidal natural products 1 - 9 (figure 1). These compounds are all structurally related as they contain a tetramethylcyclohexenedione group, attached to either a terpene or a phloroglucinol moiety. Seven of the nine compounds (1 - 6, 9) are novel. For compounds 7 and 8, no synthesis had been previously reported. The compounds are active against a range of insect species, although in general they are less active than commercial natural products. Further tests show some of the compounds are potent antifeedants. Synthesis of seven of the nine natural products (1 - 5, 7, 8) by short, convergent, stereospecific and high yielding routes was achieved. The synthetic routes were devised to mimic the postulated biosynthesis of the compounds. Reaction of syncarpic acid, an aldehyde and pyrrollidine formed a Mannich base, which on elimination gave a key alkylidene intennediate. This key intermediate was reacted, with either terpenes in Diels-Alder reactions or with phloroglucinols in aromatic alkylation reactions, to synthesise seven of the natural products. 1998 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/30648/1/299578.pdf Beddie, David G. (1998) Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family. PhD thesis, University of Nottingham. insecticidal natural products Myrtaceae tetramethylcyclohexenedione botanical insecticides |
| spellingShingle | insecticidal natural products Myrtaceae tetramethylcyclohexenedione botanical insecticides Beddie, David G. Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family |
| title | Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family |
| title_full | Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family |
| title_fullStr | Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family |
| title_full_unstemmed | Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family |
| title_short | Isolation, characterisation and synthesis of insecticidal natural products of the Myrtaceae family |
| title_sort | isolation, characterisation and synthesis of insecticidal natural products of the myrtaceae family |
| topic | insecticidal natural products Myrtaceae tetramethylcyclohexenedione botanical insecticides |
| url | https://eprints.nottingham.ac.uk/30648/ |