Aphid‐repellent, ladybug‐attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety

Abstract

BACKGROUND 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. RESULTS 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. CONCLUSION 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.

Synthesis of 4H-Pyrazolo[3,4-d]pyrimidin-4-one Hydrazine Derivatives as a Potential Inhibitor for the Self-Assembly of TMV Particles

“…The antiviral activity data given in Tables and are the mean ± standard deviation of three replicates. A one-way analysis of variance (ANOVA) followed by Duncan’s test was used for significant differences at P < 0.05, indicating by lower case letters qRT-PCR data were analyzed using GraphPad Prism 8.0.2. Student’s t -test was used for statistical analysis …”

“…Food Chem. XXXX, XXX, XXX−XXX indicating by lower case letters46 qRT-PCR data were analyzed using GraphPad Prism 8.0.2. Student's t-test was used for statistical analysis 47.…”

Recruitment of Hippodamia variegata by active volatiles from Glycyrrhiza uralensis and Alhagi sparsifolia plants infested with Aphis atrata

“…HIPVs play a key role in the tritrophic interactions among plants, herbivores, and their natural enemies, 38 and comprehension of the chemical ecology involving Hippodamia variegata is essential for their efficient use in push–pull strategies developed for pest control 9 . In the current study, the varieties and function of the active volatiles identified in HIPVs from Glycyrrhiza uralensis and Alhagi sparsifolia plants that attracted Hippodamia variegata adults were clarified in the laboratory, and their effects were also evaluated in cotton fields.…”

Rational design, synthesis and binding mechanisms of novel benzyl geranate derivatives as potential eco‐friendly aphid repellents

“…The model of ApisOBP9 used for this study was modeled in our previous study. 30 The Surflex docking algorithm in SYBYL 7.3 software was used to perform molecular docking between the ligands and ApisOBP9. 31 Benzyl alcohol, lead compound 5i and compound T9 were employed as representative ligands.…”