salicylates and geraniol

Aphids have been mainly controlled by traditional chemical insecticides, resulting in unamiable risk to the environment over the last decades. Push-pull strategy is regarded as a promising eco-friendly approach for aphid management through repelling aphid away and attracting their natural enemy. Methyl salicylate (MeSA), one of typical HIPVs (herbivore-induced plant volatiles), can repel aphids and attract ladybugs. Our previous studies discovered a new lead compound 3e, a salicylate-substituted carboxyl (E)-β-farnesene derivative that had effective aphid-repellent activity. However, whether 3e has attractive activity to ladybug like MeSA is unknown. Meanwhile, to discover a new derivative for both deterring aphid and recruiting ladybug is meaningful for green control of aphids.. Through the structural optimization of 3e, 14 new derivatives were designed and synthesized. Among them, compounds 4e and 4i had good aphid (Acyrthosiphon pisum) repellent activity, and compounds 3e, 4e and 4i had significant ladybug (Harmonia axyridis) attractive activity to males. Particularly, 4i exhibited manifest attractive effect on the females as well. Binding mechanism showed that 4i not only bound effectively with the aphid (Acyrthosiphon pisum) target ApisOBP9 thanks to its multiple hydrophobic interactions and hydrogen-bond, but also had strong binding affinity with ladybug target HaxyOBP15 due to the suitable steric space. Additionally, 4i displayed low toxicity to bee Apis mellifera.. Compound 3e does exhibit attractive activity to male ladybug as MeSA. However, the new derivative 4i, with both pleasant aphid-repellent and ladybug-attraction activities, can be considered as a novel potential push-pull candidate for aphid control in sustainable agriculture. © 2022 Society of Chemical Industry.

Topics: Acyclic Monoterpenes; Animals; Aphids; Bees; Coleoptera; Insect Repellents; Salicylates

Plants have evolved sophisticated defense mechanisms to overcome their sessile nature. However, if and how volatiles from cold-stressed plants can trigger interplant communication is still unknown. Here, we provide the first evidence for interplant communication via inducible volatiles in cold stress. The volatiles, including nerolidol, geraniol, linalool, and methyl salicylate, emitted from cold-stressed tea plants play key role(s) in priming cold tolerance of their neighbors via a C-repeat-binding factors-dependent pathway. The knowledge will help us to understand how plants respond to volatile cues in cold stress and agricultural ecosystems.

Topics: Acyclic Monoterpenes; Camellia sinensis; Cold-Shock Response; Salicylates; Sesquiterpenes

Moths recognize a wide range of volatile compounds, which they use to locate mates, food sources, and oviposition sites. These compounds are recognized by odorant receptors (OR) located within the dendritic membrane of sensory neurons that extend into the lymph of sensilla, covering the surface of insect antennae. We have identified 3 genes encoding ORs from the tortricid moth, Epiphyas postvittana, a pest of horticulture. Like Drosophila melanogaster ORs, they contain 7 transmembrane helices with an intracellular N-terminus, an orientation in the plasma membrane opposite to that of classical GPCRs. EpOR2 is orthologous to the coreceptor Or83b from D. melanogaster. EpOR1 and EpOR3 both recognize a range of terpenoids and benzoates produced by plants. Of the compounds tested, EpOR1 shows the best sensitivity to methyl salicylate [EC(50) = 1.8 x 10(-12) M], a common constituent of floral scents and an important signaling compound produced by plants when under attack from insects and pathogens. EpOR3 best recognizes the monoterpene citral to low concentrations [EC(50) = 1.1 x 10(-13) M]. Citral produces the largest amplitude electrophysiological responses in E. postvittana antennae and elicits repellent activity against ovipositing female moths. Orthologues of EpOR3 were found across 6 families within the Lepidoptera, suggesting that the ability to recognize citral may underpin an important behavior.

Topics: Acyclic Monoterpenes; Amino Acid Sequence; Animals; Female; Gene Expression Profiling; Molecular Sequence Data; Moths; Phylogeny; Receptors, Odorant; Salicylates; Sequence Alignment; Terpenes; Volatile Organic Compounds

The Y-olfactometer bioassays showed that the volatiles from tea aphids and tea aphid-damaged tea shoots (PHC) strongly attracted Sphaerophoria menthastri and Chrysopa septempunctata. At the dosage of 10(-4) g x ml(-1), S. menthastri selected geraniol and methyl salicylate from PHC, n-octanol from intact tea shoots (ITS), nerol from tea flowers (P < 0.01), and (E)-2-hexen-1-ol, E-2-hexenal, 1,3,6-octatriene-3,7-dimethyl and linalool from PHC (P < 0.05), while C. septempunctata selected n-octanol and hexanal from ITS (P < 0.05). At the dosage of 10(-2) g x ml(-1), S. menthastri selected hexanal, nerol and benzaldehyde from PHC (P < 0.05), while C. septempunctata selected hexanal, benzaldehyde, geraniol and (E)-2-hexen-1-ol (P < 0.05). The experimental results showed that besides aldehydes and methyl salicylate, geraniol, n-octanol and (E)-2-hexen-1-ol were significantly attractive to the natural enemies. The selective responses of natural enemies were restricted by thresholds. Both dosages of hexanal significantly attracted C. septempunctata. Nerol might be an infochemicals seducing S. menthastri to orient to tea flowers.

Topics: 1-Octanol; Acyclic Monoterpenes; Animals; Behavior, Animal; Chemotactic Factors; Chemotaxis; Diptera; Dose-Response Relationship, Drug; Flowers; Insecta; Monoterpenes; Odorants; Plant Extracts; Plant Shoots; Salicylates; Tea; Terpenes; Volatilization

Subjects rated the overall perceived intensity of concentrations of the odorants cineole, geraniol, hexyl salicylate, and linalyl acetate smelled alone and in binary mixtures. The subjects also rated intensity of specified constituents (e.g. amount of cineole in cineole, and in mixtures of cineole and linalyl acetate). The intensity of the stronger component alone offered a close description of perceived intensity. In addition to the Stronger Component model, two other psychological models (Vector and U model) and two psychophysical models (UPL2 and Equiratio Mixture model) offered descriptions ranging from fair to very good. Psychological models gave better fits, but lack explanatory power. Some results indicated that weaker odors add more potently than stronger odors, an outcome incompatible with these models. The psychophysical models, based on the additivity of single components, generally overestimated perceived intensity. Judgments of individual qualities gave only slight encouragement to any expectation of differences in masking or maskability among odorants. The results highlight the need to test particular critical hypotheses regarding how people perceive mixtures.

Topics: Acyclic Monoterpenes; Adolescent; Adult; Cyclohexanols; Dose-Response Relationship, Drug; Eucalyptol; Female; Humans; Male; Menthol; Middle Aged; Models, Biological; Monoterpenes; Odorants; Perception; Perfume; Salicylates; Sensory Thresholds; Smell; Terpenes

A novel method is proposed for the evaluation of the activity of an antifungal agent administered as a gas. This system is composed of a batch-flow type reaction vessel, a gas flow system, and a microscopic observation system. The agar plate was prepared on the ceiling of the reaction vessel, and the mycelium of a fungus (Aspergillus niger or Rhizoctonia solani) was inoculated onto it. After preincubation at 25 degrees C for 24 h, the reaction vessel was connected to the gas flow system. An appropriate hypha was selected, and its elongation rate was measured. Then a sample holder containing an antifungal compound was inserted into the reaction vessel from the side hole to saturate the atmosphere inside with its vapor. The retardation or inhibition of the hypha elongation was observed on a television monitor and recorded on a video tape recorder. The antifungal compound was then removed, and the reaction vessel was flushed with air. If the hypha lived, it began to elongate again. By this method, antifungal activity of seven odor compounds could be evaluated quantitatively within several hours.

Topics: Acrolein; Acyclic Monoterpenes; Antifungal Agents; Aspergillus niger; Benzaldehydes; Cyclohexanols; Cyclohexenes; Eucalyptol; Limonene; Menthol; Microbial Sensitivity Tests; Monoterpenes; Rhizoctonia; Salicylates; Terpenes; Volatilization