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Eucalyptus dives leaf oil, representing the piperitone chemotype, was characterized by GC/MS and evaluated for insecticidal efficacy against larval and adult stages of Tribolium castaneum and Plodia interpunctella. GC/MS analysis revealed that piperitone comprised 47.09% of the oil, followed by α-phellandrene (16.96%) and p -cymene (9.01%). The piperitone-rich E. dives oil exhibited fumigant- and contact-dependent insecticidal activity against P. interpunctella and T. castaneum , with toxicity varying by species, developmental stage, and exposure mode. Adult P. interpunctella showed high susceptibility to fumigant exposure, whereas T. castaneum displayed comparatively lower sensitivity across both life stages. Adult P. interpunctella exhibited an order-of-magnitude greater susceptibility to fumigant exposure than larvae, highlighting vapor-phase uptake as a dominant driver of toxicity in piperitone-rich chemotypes. Piperitone, corresponding to the dominant constituent identified in the oil, was confirmed as a contact-active compound, showing stronger larvicidal activity against T. castaneum than P. interpunctella . Comparative evaluation of selected 2-cyclohexen-1-one analogues, used as simplified structural models of the piperitone cyclohexenone core, revealed consistent structure–activity relationships (SARs), with 3-methyl-substituted analogues exhibiting higher toxicity than other structural variants. By integrating chemotype-resolved composition analysis, component-level bioassays, and parallel fumigant and contact assays across two pests and life stages, this study delineated how ketone-dominant Eucalyptus chemotypes translate structural features into exposure-dependent insecticidal outcomes. Across the cyclohexenone analogues, empirical SARs indicated higher toxicity for analogues bearing smaller substituents at the 3-position than at the 4-position. These findings underscore the potential of piperitone-rich E. dives oil and cyclohexenone analogues as environmental grain protectants.

Fusarium spp. are considered as one of the most devastating plant pathogenic fungi worldwide. In this study, the effect of essential oil (EO) of Mentha longifolia, M. spicata, Achillea sp. and Foeniculum vulgare, ethanolic extract of Propolis (EEP), and Trichoderma harzianum T447 and T. hamatum T622 was investigated against five phytopathogenic Fusarium species. The results showed that the fungal species, the type of EO, and concentrations play a substantial role in inhibiting the mycelial growth of Fusarium spp. GC–MS analysis of the EOs showed that the piperitone oxide and cis-piperitone oxide were found as the main components of M. longifolia. Our results also revealed that EEP possessed the growth inhibitory effect against Fusarium spp. It was observed that the extracellular secretions of T. harzianum T447 showed very high inhibition against the fungi. Our results highlighted the need for further research to apply them as a safe alternative to the chemical pesticides.

The postharvest life of most fruit, vegetables and cereals is limited by fungal proliferation. The chemical composition of Mentha piperita, M. spicata and M. suaveolens essential oils (EO), and the antifungal activity against four pathogenic and post-harvest fungi isolated from food, were herein investigated to evaluate their potential as natural food preservatives. The EO were obtained by hydrodistillation of aerial parts leaves, stems and inflorescences (except for peppermint oil, which was purchased in a specialized store) and submitted to GC-MS and GC-FID analysis. Regarding the EO composition, carvone (41.1%) and limonene (14.1%) were the major compounds in M. spicata, menthol (47.0%) and menthone (23.1%), as well as other menthol derivatives (neomenthol -3.6%- and menthofurane -3.7%-) in M. piperita, and piperitone oxide (40.2%) and piperitenone oxide (31.4%) in M. suaveolens.Botryotinia fuckeliana was the most sensitive fungus. The three studied EO inhibited growth by 92–100%. The highest dose of M. suaveolens EO, 400 µg/mL, produced 100% MGI in all the studied fungi, except Fusarium oxysporum with 94.21%. The M. suaveolens EO can be considered to develop a low-risk enviro-friendly botanical biofungicide.

The present study assessed the phytotoxic and cytotoxic potential of the essential oil (EO) extracted from aboveground parts of Mentha longifolia (L.) Huds. Gas chromatography–mass spectrometry revealed 39 compounds constituting 99.67% of the EO. The EO was rich in monoterpenoids (mostly oxygenated monoterpenes), which accounted for 89.28% of the oil. The major components in EO were monoterpene ketones such as piperitone oxide (53.83%) and piperitenone oxide (11.52%), followed by thymol (5.80%), and ( E )-caryophyllene (4.88%). The phytotoxic activities of EO were estimated against Cyperus rotundus , Echinochloa crus-galli , and Oryza sativa (rice) through pre- and post-emergence assays at concentrations ranging from 10 to 250 μg/ml and 0.5–5%, respectively. In pre-emergence assay, the phytotoxic effect of EO was most pronounced on C. rotundus , thereby significantly affecting percent germination, plantlet growth, and chlorophyll content. On the contrary, the impact was comparatively lesser on rice, with ~ 40% germination in response to 250 μg/ml of EO treatment. In the post-emergence assay, the spray treatment of EO caused a loss of chlorophyll and wilting in test plants, and subsequently affected the growth of plants, even leading to death in some cases. The cytotoxic activity of EO (at 2.5–50 μg/ml) was studied in meristem cells in onion ( Allium cepa L.) root tips. EO exposure to the onion roots induced various chromosomal aberrations such as chromosomal bridges, c-mitosis, stickiness, vagrant chromosomes, etc., and negatively affected the mitotic index. At 50 μg/ml, EO treatment triggered the complete death of roots. The study concludes that M. longifolia EO has phytotoxic activities due to the mito-depressive effect, along with other physiological effects on target plants. Therefore, EO of M. longifolia could be developed into a novel bioherbicide for sustainable management of weeds in agricultural systems.

Bio-degradable and eco-friendly essential oils (EOs) extracted from Mentha longifolia, Salsola imbricata, Erigeron bonariensis, E. canadensis, Ailanthus altissima, and Zanthoxylum armatum were investigated for their repellent and larvicidal potential against Aedes aegypti mosquitoes. The EOs of M. longifolia, S. imbricata, E. bonariensis, E. canadensis, A. altissima, and Z. armatum exhibited 99.0%, 96.8%, 40.2%, 41.7%, 29.1%, and 13.2% repellency against mosquitoes at a tested dose of 33.3 μg/cm2, respectively. In time span bioassays, the EOs of M. longifolia, S. imbricata, E. bonariensis, and E. canadensis showed more than 40% repellency for 60 min at a tested dose of 330 μg/cm2. Larvicidal bioassays revealed that larvae of Ae. aegypti were the most susceptible to M. longifolia (LC50, 39.3 mg/L), E. bonariensis (LC50, 26.0 mg/L), E. canadensis (LC50, 35.7 mg/L), and Z. armatum (LC50, 35.9 mg/L) EOs upon 48 h exposure. The most abundant constituents in the EOs of M. longifolia, S. imbricata, E. bonariensis, E. canadensis and A. altissima were piperitone oxide (45.5%), carvone (39.9%), matricaria ester (43.1%), (31.7%) and eugenol (24.4%), respectively. Our study demonstrates that EOs of M. longifolia, S. imbricata, E. bonariensis, and E. canadensis might be used to control Ae. aegypti mosquitoes without harming humans or the environment.

Plant-based essential oils have gained attention as a natural alternative for controlling mosquitoes due to their repellent, larvicidal and oviposition deterrent properties. We tested repellent, larvicidal, and oviposition deterrent effects of essential oils (EOs) of Mentha spicata (L.), Ocimum basilicum (L.), and Abutilon indicum (L.) against three mosquito species (Diptera: Culicidae) including Aedes aegypti (L.), Anopheles gambiae s. l. Giles, and Culex quinquefasciatus Say by using contact-based technique. In screening bioassays, M. spicata I, M. spicata II, O. basilicum I, O. basilicum II, and A. indicum EOs showed higher repellency against Cx. quinquefasciatus as compared to Ae. aegypti and An. gambiae when tested at 33.3 μg/cm2. In time-span bioassays performed at 33.3 μg/cm2, EO of M. spicata I exhibited 100% repellence up to 45, 30, and 75 min against Ae. aegypti, An. gambiae, and Cx. quinquefasciatus, respectively. Interestingly, at this tested dose, M. spicata I and M. spicata II showed higher repellence compared to DEET against Ae. aegypti and Cx. quinquefasciatus after 45 and 75 min, respectively. Their repellency was observed up to 150 and 210 min against Ae. aegypti and Cx. quinquefasciatus, respectively. In larvicidal bioassays, M. spicata I EO proved more toxic against 2nd instar larvae of Ae. aegypti, An. gambiae, and Cx. quinquefasciatus (LC50 = 11.0, 42.9, and 12.6 mg/L, respectively) compared to other tested EOs. In oviposition bioassays, M. spicata I exhibited the highest activity, showing 60%, 46%, and 79% oviposition deterrence against Ae. aegypti, An. gambiae, and Cx. quinquefasciatus, respectively, tested at a dose of 600 µg/cm2. Major compounds of M. spicata I, M. spicata II, O. basilicum I, and O. basilicum II EOs were piperitenone oxide (38.8%), piperitone oxide (35.4%), estragole (55.3%), and linalool (43.8%), respectively. In conclusion, M. spicata EO could be used to control mosquitoes and their bites.

Anethum graveolens L. (Dill) is an aromatic, medicinal, and food plant that is widely known in the world. This paper presents the results of the study of the essential oil of A. graveolens, which was cultivated in the Stavropol region (Russia, North Caucasus) to restore its growth. Herb of A. graveolens, variety “Scythian”, was collected in different fields of the limited company “Cossack agriculture “Staropavlovskoe”. The essential oil was obtained by Clevenger distillation. The chemical composition of the essential oils was studied by the GC/MS method. 25 compounds were detected in essential oil: carvone; 3.9-epoxy-1-p-menthene; ipsdienol; 2-hydroxycineol; allyl caprate; carveol; 6-camphenol; 5-isopropenyl-2-methyl-7-oxabicyclo [4.1.0] heptane-2-ol; piperitone oxide; 3-methyl-2-pent-2-enyl-cyclopent-2-enone; cis-p-mentha-2.8-dien-1-ol; 2-cyclol piperitone oxidehydroxy-3-methyl-6-(1- methyleth); limonene-6-ol, pivalate; isopulegol acetate; z-(13,14-epoxy) tetradec-11-en-1-ol acetate. The major component in the oil detected was arvone (36.9–44.5%). The obtained data confirmed the positive result of the cultivation of A.graveolens with the content of carvone in the essential oil of herbs comparable to the content of carvone in fruits.

Mint species are one of the most traded medicinal plants with a wide array of applications in the food, pharmaceutical, and perfumery industries. Here, a field experiment based on completely randomized block design (RCBD) aimed to compare drug yield, antioxidant properties, and essential-oil (EO) quality of three newly introduced mints (i.e., ginger mint, pineapple mint, and grapefruit mint) with a chiefly cultivated one (i.e., peppermint). The results manifested that dry-weight yield and EO yield of grapefruit mint (310 g/m2 and 5.18 g/m2, respectively) was approximately 2 times more than that of others. The highest EO content (i.e., 3.12%, v/w)) was obtained from the ginger mint; however, there were no significant differences among the other three mints. The highest total flavonoids content and 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity of both methanolic and ethanolic extracts were found in pineapple and grapefruit mint. Methanolic extract of ginger mint yielded the highest total polyphenol content, whereas the ethanolic extract of pineapple mint showed the highest total polyphenol content. According to mean comparisons, the EO of ginger mint exhibited the highest antioxidant activity (EC50 value = 2.23 µL/mL), while EO of peppermint showed the lowest antioxidant activity (EC50 value = 48.23 µL/mL). Gas chromatography analysis identified four EO types among these mints: (i) grapefruit mint EO rich in linalool (51.7%) and linalyl acetate (28.38%); (ii) ginger mint EO rich in linalool (59.16%); (iii) pineapple mint EO rich in piperitone oxide (77.65%); and (iv) peppermint EO rich in menthol (35.65%). The findings of the present study provide new insights into the cultivation of preferable mints possessing desired characteristics for food and drug industries.

Mentha longifolia L. (horsemint) is one of the most famous wild perennial herbs of the Lamiaceae family, which has broad usage in therapeutic and pharmaceutical services. In this research, screening of twenty Mentha longifolia L. accessions was assessed according to the physio-chemical variability under low water irrigation. The investigation was a split plot arranged in a completed randomized block design in three replications with two water treatments of full irrigation (100% field capacity as control) and deficit irrigation (60% FC). The interaction effects of water deficit and accessions indicated that drought stress meaningfully ( P  ≤ 0.01) altered physiological parameters such as CGR, NAR, RGR, LAR, SLA electrolyte leakage, element content, stomatal conductivity, essential oil content, antioxidant activities, proline, relative water content, chlorophyll, and carotenoid content. The main volatile components as 1,8-cineole, (Z)-β-ocimene, menthon, menthol, pulegone, trans-piperitone epoxide, piperitenone, and piperitone oxide were analyzed. The HPLC analysis disclosed the existence of rosmarinic acid, caffecic acid, 2,3-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, ferulic acid, chlorogenic acid, vanillic acid, p-coumaric acid, and rutin as predominant phenolic and flavonoid compounds in horsemint accessions. Results showed that the drought stress not only enhanced the values of rosmarinic acid, ferulic acid, caffeic acid, rutin, 2,3-dihydroxybenzoic acid, and 3,4-dihydroxybenzoic acid but also triggered p -coumaric acid that did not exist in some accessions under full irrigation conditions. However, the findings were affected by the accession type. Cluster analysis based on all the traits categorized the accessions into two main groups, in which the comparisons of the dendrograms between normal and water deficit conditions showed 0.23 entanglement. The analysis showed that ML13, ML17, and ML2 accessions could be offered as tolerant accessions. Regarding the various reactions to drought stress and the variability among the accessions, the results of the current research could be a primary stage in recognizing and obtaining high-yield, drought-tolerance, and elite accessions and can promote horsemint breeding programs and domestication.

This study is focused on the analysis of regional variation of the chemical compositions of three Clinopodium menthifolium subsp. ascendens (Jord.) Govaerts Tunisian accession, as well as their inhibition toward fungi and insect pests. The diversity of the chemical constituents and biological activities in front of the aforementioned variations was found to be remarkable. Essential oils were obtained by hydrodistillation of the aerial parts and analyzed by gas chromatography-mass spectrometry (GC-MS). A total of 41, 42, and 30 compounds were identified respectively from Clinopodium menthifolium essential oils harvested from three Tunisian regions, namely Ain-Draham (ADEO), Babouch (BEO), and Tabarka (TEO). All analyzed oils were rich in oxygenated monoterpenes with different major constituents. Piperitenone (34.5%), cis -piperitone oxide (26.1%), and pulegone (47.9%) were the dominant compounds in the three volatile oils, respectively. The antifungal activity was investigated in vitro using six targeted fungal strains ( Aspergillus flavus , Aspergillus terreus , Candida albicans , Microsporum canis , Microsporum gypseum , and Trichophyton mentagrophytes ). The toxicity and repellency of essential oils were evaluated against the stored product pest Tribolium confusum . The tested samples were differently effective toward the target fungi and the pest depending on the variability of their chemical compositions. BEO exhibited the highest fungitoxic properties toward A . terreus mold, M. canis dermatophyte, and C. albicans yeast (the MIC values ranged from 40 to 400 μg mL −1 ). In addition, the data showed that TEO repelled T. confusum moderately (PR = 42.5% at 2 h after exposure). Concerning the contact treatment, both ADEO and BEO were proved to possess slightly toxic effects toward T. confusum pest (% of mortality 27.5–32.5% at 5% concentration). The results showed that the geographic origin greatly influenced the chemical composition and the associated bioactivities of Clinopodium menthifolium subsp. ascendens.