Structure–Activity of Valencenoid Derivatives and Their Repellence to the Formosan Subterranean Termite

@article{Zhu2004StructureActivityOV,
  title={Structure–Activity of Valencenoid Derivatives and Their Repellence to the Formosan Subterranean Termite},
  author={Betty C. R. Zhu and Gregg Henderson and Anne M. Sauer and Ying Yu and William E. Crowe and Roger A. Laine},
  journal={Journal of Chemical Ecology},
  year={2004},
  volume={29},
  pages={2695-2701}
}
Eight valencenoid derivatives were evaluated for their repelling activity against Formosan subterranean termites, Coptotermes formosanus Shiraki. Among them, 1,10-dihydronootkatone was the strongest repellent, and valencene was the weakest. Results of the structure–repellency relationships indicated (1) reduction of the ketone group to the alcohol on position 2 of nootkatone curtailed the activity; (2) because of the low activity of valencene relative to nootkatone that the ketone group was… 
View on Springer
ncbi.nlm.nih.gov
26 Citations
Background Citations
9

26 Citations

Structural requirements for repellency: norsesquiterpenes and sesquiterpenoid derivatives of nootkatone against the Formosan subterranean termite (Isoptera: Rhinotermitidae).
TLDR
Four derivatives of nootkatone have very high repellency and toxicity to C. formosanus, 9 times the potency of the primary compound nootaton, and the relationships between structure and activity are discussed.
Antitermite activity of 7-alkoxycoumarins and related analogs against Coptotermes formosanus Shiraki
Antifeedant and Termiticidal Activities of 6-Alkoxycoumarins and Related Analogs Against Coptotermes formosanus Shiraki
TLDR
The findings indicate that the presence of alkenyloxy and alkynyloxy groups was important for the termiticidal activity, while the incorporation of alkoxy groups with longer alkyl chains tended to reduce both the Termiticidal and antifeedant activities.
Antitermite Activities of Coumarin Derivatives and Scopoletin from Protium javanicum Burm. f.
TLDR
Several coumarin derivatives whose chemical structures are similar to scopoletin were synthesized in order to investigate the structure-activity relationship (SAR) of the methoxy and hydroxy groups at the C-6 and C-7 positions of the Coumarin skeleton.
Chemical structures of p-menthane monoterpenes with special reference to their effect on seed germination and termite mortality
TLDR
The bioactivity of the p-menthane monoterpenoids was dependent upon the presence and position of certain functional groups and the degree of saturation in the functional group of the side chain.
Seven herbs against the stored product insect: Toxicity evidence and the active sesquiterpenes from Atractylodes lancea.
Antitermite Activities of C. decidua Extracts and Pure Compounds against Indian White Termite Odontotermes obesus (Isoptera: Odontotermitidae)
TLDR
Antitermite responses of Capparis decidua stem, root, flower, and fruit extracts and pure compounds to Odontotermes obesus in various bioassays are tested.
Quantitative structure-activity relationship of botanical sesquiterpenes: spatial and contact repellency to the yellow fever mosquito, Aedes aegypti.
TLDR
12 of these plant-derived sesquiterpenes have been isolated, purified, and assayed for spatial and contact repellency against the yellow fever mosquito, Aedes aegypti, to develop quantitative structure-activity relationships that identified key properties of the sesQuiterpene molecule.
Insect Antifeedant and Ixodicidal Compounds from Senecio adenotrichius
Nine eremophilane sesquiterpenes 1 – 9, two flavonoids 11 and 12, and two known pirrolizidine alkaloids 13 and 14, were isolated from Senecio adenotrichius DC. Their structures were elucidated on the…
Stepwise engineering of Saccharomyces cerevisiae to produce (+)-valencene and its related sesquiterpenes
(+)-Valencene and (+)-nootkatone are high value-added sesquiterpenoids found in grapefruit. The synthesis of (+)-nootkatone by chemical oxidation from (+)-valencene cannot meet the increasing demand…
...
...

References

SHOWING 1-10 OF 30 REFERENCES
Toxicity of monoterpenoids and other natural products to the Formosan subterranean termite (Isoptera: Rhinotermitidae)
TLDR
Monoterpenoid alcohols, particularly eugenol, were the most effective as termiticides against C. formosanus and was also more effective as a fumigant than citral and geraniol.
Synthetic experiments in the eremophilane sesquiterpene group. Synthesis of (±)-7-epi-nootkatone and partial synthesis of valerianol. The structure of nardostachone
Although the Robinson annelation of cis-4-isopropenyl-2-methylcyclohexanone with trans-pent-3-en-2-one affords (±)-nootkatone [4βH,5α-eremophila-1(10),11-dien-2-one] in low yield, the major product…
Structural Requirements for Monoterpenoid Activity Against Insects
TLDR
The topical, fumigant and ovicidal activity of fourteen monoter penoids and thirty-one monoterpenoid derivatives were evaluated using the house fly, Musca domestica to determine structure-activity relationships involving the monoterPenoids' structural shape, type of functional group, and degree of saturation.
Evaluation of Vetiver Oil and Seven Insect-Active Essential Oils Against the Formosan Subterranean Termite
TLDR
Vetiver oil is a promising novel termiticide with reduced environmental impact for use against subterranean termites and chemical volatility were inversely associated.
Vapour Toxicity and Repellency of Some Oils and Terpenoids to the Termite, Odontotermes brunneus
TLDR
Several terpenoids and oils were screened for vapour toxicity and repellency against the termite, Odontotermes brunneus and among the compounds screened, eucalyptus oil produced the fastest knockdown while ß-ionone was found to be the least effective.
Insecticidal and repellent properties of nine volatile constituents of essential oils against the American cockroach, Periplaneta americana (L.)
The toxic and repellent properties of nine major constituents of essential oils, comprising benzene derivatives and terpenes, were evaluated against Periplaneta americana (L.). Contact and fumigant…
Repellency of Essential Oils Against the Domiciliary Cockroach, Periplaneta Americana
TLDR
Dose-dependent repellency ranging from 57.1 to 100% was exhibited by all six extracts at the lowest concentration tested (12 ppm) of essential oil extracts evaluated for repellent activity against Periplaneta americana using a modification of the “two-cylinders” method.
Evaluation of the Anti-termitic Activity of Hydroxyquinoline and Naphthol Derivative Formulations using Reticulitermes in Laboratory and Field Experiments
TLDR
Mixtures of hydroxyquinoline compounds with naphthol compounds were most intensely and consistently repellent to termites even in low concentrations (<100 ppm).
Insecticidal properties of monoterpenoid derivatives to the house fly (diptera: Muscidae) and red flour beetle (coleoptera: Tenebrionidae)
TLDR
Fluoroacetates of cyclic monoterpenoids were the most effective house fly fumigants, followed by acetates, and trichloroacetates, which were both more insecticidal and more effective than haloacetates in the topical, red flour beetle fumigation and ovicidal bioassays.
Insecticidal sesquiterpene from Alpinia oxyphylla against Drosophila melanogaster.
TLDR
An MeOH extract of Alpinia oxyphylla was found to possess insecticidal activity against larvae of Drosophila melanogaster Meigen, indicating that the carbonyl group at the 2-position in 1 was the important function for enhanced activity of 1.
...
...