Next Article in Journal
Production and Molecular Identification of Interspecific Hybrids between Phaius mishmensis (Lindl. and Paxton) Rchb. f. and Phaius tankervilliae (Banks) Blume
Next Article in Special Issue
The Effect of Botanicals with Nematicidal Activity on the Structural and Functional Characteristics of the Soil Nematode Community
Previous Article in Journal
Effects of Nitrogen Application Rate on Protein Components and Yield of Low-Gluten Rice
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Agriculture
Volume 11
Issue 4
10.3390/agriculture11040304
agriculture-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

Chemical Composition and Broad-Spectrum Insecticidal Activity of the Flower Essential Oil from an Ancient Sicilian Food Plant, Ridolfia segetum

by
Natale Badalamenti
1,
Vincenzo Ilardi
2,
Maurizio Bruno
1,
Roman Pavela
3,4,
Maria C. Boukouvala
5,
Nickolas G. Kavallieratos
5,
Filippo Maggi
6,*,
Angelo Canale
7 and
Giovanni Benelli
7
1
Department of Biological, Chemical and Pharmaceutical Sciences and Technologies (STEBICEF), University of Palermo, Viale delle Scienze, Parco d’Orleans II, 90128 Palermo, Italy
2
Department of Earth and Marine Sciences (DISTeM), University of Palermo, Via Archirafi 26, 90128 Palermo, Italy
3
Crop Research Institute, Drnovska 507, 161 06 Prague 6, Ruzyne, Czech Republic
4
Department of Plant Protection, Czech University of Life Sciences Prague, Kamycka 129, 165 00 Praha 6, Suchdol, Czech Republic
5
Laboratory of Agricultural Zoology and Entomology, Department of Crop Science, Agricultural University of Athens, 75 Iera Odos Str, 11855 Athens, Attica, Greece
6
School of Pharmacy, University of Camerino, Via Sant’Agostino 1, 62032 Camerino, Italy
7
Department of Agriculture, Food and Environment, University of Pisa, Via del Borghetto 80, 56124 Pisa, Italy
*
Author to whom correspondence should be addressed.
Agriculture 2021, 11(4), 304; https://doi.org/10.3390/agriculture11040304
Submission received: 12 March 2021 / Revised: 23 March 2021 / Accepted: 30 March 2021 / Published: 1 April 2021
(This article belongs to the Special Issue Biopesticides: The Naturally Originating Plant Protection Products and Biocides)
Versions Notes

Abstract

:
Several species of the family Apiaceae are aromatic herbs that produce essential oils usable on an industrial scale for pharmaceutical, cosmetic, and food purposes. In particular, some essential oils, such as green insecticides for example, may replace synthetic insecticides, keeping most of their efficacy and avoiding environmental pollution or human poisoning. In the present study, we explored the insecticidal potential of Ridolfia segetum (L.) Moris essential oil (EO) against three different pests: Culex quinquefasciatus Say, Musca domestica L., and Spodoptera littoralis (Boisduval). For this purpose, the EO was obtained by hydrodistillation of flowers and its composition was achieved by gas chromatography/flame ionization detection (GC/FID) and gas chromatography/mass spectrometry (GC/MS). This EO was rich in α-phellandrene (49.3%), β-phellandrene (9.2%), terpinolene (20.7%), and piperitenone oxide (5.9%). Concerning the mosquitocidal efficacy, the EO showed noteworthy toxicity against C. quinquefasciatus 3rd instar larvae, with a LC50 = 27.1 µL L−1 and LC90 = 42.5 µL L−1. Regarding M. domestica, a different toxicity of the R. segetum EO was found on male and female flies, calculating LD50 values of 10.5 and 50.8 µg adult−1, respectively. The EO was also toxic to S. littoralis 3rd instar larvae, achieving LD50 and LD90 values of 37.9 and 99.6 µg larva−1, respectively. Overall, this flower EO, extracted from a traditional Sicilian food plant, merits further investigation for the development of green insecticide formulations to be used in real world conditions, pending a careful assessment of non-target toxicity on beneficial organisms.

1. Introduction

Arthropods include numerous agricultural pests, as well as key species that play a major role as vectors of pathogens, including malaria, dengue, Zika virus, lymphatic filariasis, Lyme disease, and many others [1,2]. Their control has a long history, and it is still routinely achieved through massive applications of synthetic insecticides [3,4,5], with severe effects on human health and the environment, long-term sub-lethal effects [6,7,8,9,10], and the quick development of resistance in the targeted species [11,12,13]. In the attempt to discover novel active ingredients for insecticidal, acaricidal, and repellent formulations, botanical products have been largely investigated [14,15,16], outlining their scarce toxicity to vertebrates [17], as well as their multiple modes of action on arthropods, which strongly reduce the risk of resistance development [18,19]. Although the commercialization of botanical insecticides (BIs) seems complex and slow for the time being [17,20,21], research needs to be intensified, especially in terms of phytochemical standardization of the active ingredients, formulation of BIs to ensure long-term effectiveness, and the search for new plant species as potential sources of active substances for BIs [16,22]. In particular, considering the decreasing number of authorized active ingredients of synthetic insecticides and the greening of agricultural production, BIs are of growing relevance among the preferred products for plant protection purposes [17,20,21]. In this scenario, research focusing on the largely unexplored insecticidal potential of aromatic food plant species growing in arid environments is of special interest [23], with potential connections to the local agricultural economy of Mediterranean countries.
Ridolfia segetum (L.) Moris (Apiales: Apiaceae) is an annual plant (Terofita), 3–8 dm high, hairless, and with an unpleasant odor. It is a Mediterranean species found commonly in cereal fields and temporarily uncultivated grounds in southern Europe, Turkey, the Middle East, and North Africa [24]. In Italy, it is present in all central and southern regions, from Liguria, Tuscany, and Marche, to Sardinia, and Sicily [25,26].
In Morocco, it is cooked as a vegetable in several recipes including tajines, couscous, and beqoula [27], whereas in Sicily, this plant, locally known as “finuocchiu anitu,” is consumed raw in salads and cooked [28]; its roots and stems are eaten to treat gastric acidity [29].
Earlier research focused on the composition of the essential oils of other accessions, growing in Europe and North Africa. Some biological properties of R. segetum essential oil (EO) have also been reported. The EO of the flowers collected in Portugal showed anti-inflammatory and antioxidant activities [30] and, recently, strong antitumor potential with high capability to inhibit proliferation and induce apoptosis [31]. Jabrane et al. [32,33] and Ben Jannet and Mighri [34] showed the antibacterial activities of the EOs from plants collected in Tunisia, whereas the EO from the Sardinian population was shown to inhibit HIV-1 RT RDDP activity in a dose-dependent manner [35].
In the frame of our ongoing research on Mediterranean species belonging to the Apiaceae family [36,37,38,39,40,41], we analyzed the chemical composition of the flower EO of a Sicilian accession of R. segetum, not investigated so far, and evaluated its insecticidal activity on a panel of insect species of high economic importance, i.e., the lymphatic filariasis vector Culex quinquefasciatus Say (Diptera: Culicidae)—for which the development of novel and sustainable control tools is urgently needed [37,42]—the common housefly, Musca domestica L. (Diptera: Muscidae), which is a noxious insect being able to transmit a large number of microbial pathogens [43], and the African cotton leafworm, Spodoptera littoralis (Boisduval) (Lepidoptera: Noctuidae), which is currently considered one of the most polyphagous moth species attacking highly diverse crops tropic and sub-tropic regions, and is listed as an A2 quarantine pest [44]. For mosquitoes and moths, the third larval instar was targeted, while for houseflies we examined the EO toxicity on adults, assessing the potential difference in EO effectiveness on male and female flies.

2. Materials and Methods

2.1. Plant Material

Flowers of R. segetum were collected in June 2019, at Borgo Eras, Collesano, Palermo (Sicily) at 600 m of altitude (37°53′34.84″ N and 13°54′41.08″ E). Typical specimens (PAL 109714), collected and identified by Prof. Vincenzo Ilardi, have been deposited in Herbarium Mediterraneum Panormitanum of the “Orto Botanico,” Palermo, Italy.

2.2. Essential Oil Extraction

350 g of flowers of R. segetum were subjected to hydrodistillation for 3 h using a Clevenger type apparatus [45]. The EO (yield 0.9% (v/w)) was dried with anhydrous sodium sulphate, filtered, and stored in the freezer at − 20 °C, until the time of analysis.

2.3. GC-FID Analysis of the Essential Oil

An Agilent 4890D gas chromatograph coupled with an ionization flame detector (FID) was used. The separation stationary phase was represented by a HP-5 capillary column (5% phenylmethylpolysiloxane, 25 m, 0.32 mm i.d.; 0.17 μm f.t.) (Agilent, Folsom, CA, USA). The mobile phase was helium (99.999%) flowing at 1.0 mL/min. The oven temperature programmer was as follows: 60 °C isothermal for 5 min, then ramp (4 °C/min) to 220 °C, and ramp (11 °C/min) to 280 °C. The EO was diluted to 1:100 in hexane and the volume injected was 1 μL in split mode (1:34). The injector and detector temperatures were set to 280 °C. A commercial mix of n-alkanes (C8–C30) purchased from Supelco (Bellefonte, CA, USA) was used to determine the peak linear retention index (RI). Quantitative values, expressed as percentages, were obtained following the procedure by Cecchini et al. [46]; they were the mean of three determinations.

2.4. GC-MS Analysis of the Essential Oil

An Agilent 6890N gas chromatograph equipped with a 5973N single quadrupole mass spectrometer (MS) was employed. The stationary phase was a HP-5MS capillary column (30 m, 0.25 mm i.d., 0.1 μm f.t.) (Agilent). The operative conditions and the mobile phase were the same of those reported above. The injector and transfer line temperatures were 280 and 250°C, respectively. Same dilution of that reported above was injected into the GC-MS system in split mode (1:50). Mass spectra were acquired in electron impact (EI) mode in the range of 29–400 m/z. The identification was carried out by combination of mass spectra (MS) matching and RI overlapping against the Adams [47], NIST 17 [48] and FFNSC 2 [49] libraries. The comparison with available authentic standards (Sigma-Aldrich, Milan, Italy) was also used for α-pinene, camphene, sabinene, β-pinene, myrcene, α-phellandrene, p-cymene, limonene, γ-terpinene, terpinolene, camphor, and terpinen-4-ol.

2.5. Insect Rearing

Populations of C. quinquefasciatus, M. domestica, and S. littoralis were reared following the methods described by Pavela [50,51,52]. Experimental colonies of mosquitoes from the Crop Research Institute (Prague, Czech Republic) were established. Adult mosquitoes were maintained in entomological cages (40×40×40 cm) and fed a 10% sucrose solution. Egg hatching was achieved in tap water. Larvae were reared in plastic trays (30 × 35 × 25 cm, about 100 larvae/L). The larvae were fed on dog biscuits and yeast powder at 3:1 (w:w) ratio [50]. All stages were held at 25 ± 2 °C, 65–75% R.H., and a 12:12 h (L:D) photoperiod.

2.6. Insecticidal Activity on Culex quinquefasciatus

The R. segetum flower EO was diluted in dimethyl sulfoxide (DMSO) and tested against early 3rd instar larvae of C. quinquefasciatus following the WHO method [53], with minor changes by Benelli et al. [54]. The larvae were selected and transferred in 25 mL of distilled water. The EO was diluted in DMSO obtaining the following test concentrations: 10, 20, 30, 40, and 50 µL L−1. For experimental treatments, 1 mL of each serial EO dilution was added to 224 mL of distilled water in a 500-mL glass bowl, and shaken lightly to ensure a homogenous test solution. Then, the selected larvae were transferred from distilled water into a bowl of the test solution with a final surface area of 125 cm2 (25 larvae/beaker). Each concentration was replicated 4 times on groups of 25 larvae each. Distilled water with the same amount of DMSO used for dissolving the EO was the negative control. Larval mortality was recorded after 24 h in a growth chamber (photoperiod 16:8, 24 ± 1 °C). No food was offered to the larvae during the testing and resting phases.

2.7. Insecticidal Activity on Musca domestica

The R. segetum flower EO was tested on adult females and males (3–6 days old) through topical application, following Benelli et al. [55]. One μL of acetone (Sigma-Aldrich, Germany) plus the EO at 5, 10, 20, 40, 60, 80, 100, 120, 140, and 160 µg adult−1 (each concentration was tested on 4 groups of 20 males or females each), was applied using a microelectric applicator (Hardy Step Electronic, Brand, Czech Republic) to the pronotum of flies anesthetized with carbon dioxide. The number and range of doses were determined from preliminary experiments. Acetone was the negative control. The flies were moved to a recovery box (10 × 10 × 12 cm, placed in a growth chamber, photoperiod 16:8, 24 ± 1 °C) for 24 h, then mortality was recorded for males and females.

2.8. Insecticidal Activity on Spodoptera littoralis

The R. segetum flower EO diluted in acetone was tested through topical application to S. littoralis early 3rd instar larvae (weight 20–25 mg larva−1). According to Pavela et al. [23], each larva was treated on the dorsum with 1 μL of acetone containing 20, 30, 40, 50, 70, 90, and 100 µg larva−1 of R. segetum EO. Each concentration was replicated 4 times (n = 20 larvae replicate−1). The number and range of individual doses were determined from preliminary experiments. Acetone was the negative control. All treated larvae from each replication were transferred to the relevant diet in plastic boxes (10 × 10 × 7 cm) for 24 h and stored in a growth chamber (photoperiod 16:8, 24 ± 1 °C). Each box had a perforated cap to avoid any fumigation effect of the EO or acetone.

2.9. Statistical Analysis

Lethal doses or lethal concentrations were estimated using Probit analysis [56]. The calculation also included a possible correction of mortality according to Abbott [57]. Calculations were performed using statistical software BioStat Pro (version 5.8.9.).

3. Results and Discussion

3.1. Flower Essential Oil Yield and Its Chemical Composition

Hydro-distillation of the flowers of R. segetum gave a pale yellow EO with a yield of 0.9% (v/w). Overall, 27 compounds were identified, representing 99.9% of the total compositions. The components are listed in Table 1 according to their retention indices on a HP-5MS column and are classified based on their chemical structures into four classes. This EO was extremely rich in monoterpene hydrocarbons (90.1%). α-Phellandrene (49.3%) was, by far, the main component of this class as well as of the EO, followed by terpinolene (20.7%) and β-phellandrene (9.2%). These 3 components made up about 80% of the total composition. Oxygenated monoterpenes were present in lower amounts (6.1%), with piperitenone oxide (5.9%) as the main compound of the class, whereas sesquiterpene derivatives were practically absent. Among other compounds, it is worthy to point out the occurrence of a good quantity of dill apiole (3.7%).
Based on composition of EOs of different accessions of R. segetum studied so far, it is possible to identify three distinct chemotypes: the first one is largely dominated by monoterpene hydrocarbons, usually α-phellandrene, terpinolene, and p-cymene [35,58,59,60]; a second one which contains phenylpropanoids, usually myristicin and/or dillapiol as major compounds [33,34,61]; and a third one rich in dillapiole and o-cymene [62].
The composition of R. segetum EO clearly indicates that the Sicilian accession belongs to the first chemotype. In fact, the comparison with the EOs from flowers of other populations shows a high similitude with those from Sardinia [(a-phellandrene (24.7%), terpinolene (19.9%)] [58], Andalusia, Spain [(a-phellandrene (54.7–44.5%), terpinolene (27.6–20.1%)] [59], Castillia la Mancha, Spain [(a-phellandrene (33.8–32.0%), terpinolene (21.4–18.0%)] [60] and Kroussia, Tunisia [(a-phellandrene (34.7%), terpinolene (23.7%)] [32]. On the other hand, the oil from M’saken, Tunisia [34] and Morocco [61,63], rich in dillapiole and myristicin, showed a completely different profile with respect to our sample.
Table S1 reviews the composition of EOs of different accessions of R. segetum studied so far (Supplementary Material).

3.2. Insecticidal Activity

The R. segetum flower EO showed relevant insecticidal activity against the three tested insect species (Table 2). Concerning mosquitoes, the EO showed a considerable efficacy against 3rd instar larvae of the studied species C. quinquefasciatus, with a LC50 = 27.1 µL L−1 and LC90 = 42.5 µL L−1 (Table 2). These values are lower if compared with those obtained testing many plant EOs as larvicides on the same mosquito species (e.g., Curcuma zedoaria (Christm.) Roscoe EO, LC50 = 37.29 µL L−1 [64]; Blumea mollis (D. Don) Merr. EO, LC50 = 71.71 µL L−1 [65]); Zingiber collinsii Mood & Theilade EO, LC50 = 50.11 mg L−1 [66]. On the other hand, it should also be noted that—even if several EOs have been found more effective against C. quinquefasciatus larvae (e.g., Lippia berlandieri Schauer and Pimpinella anisum L. oils, both LC50 < 7 mg L−1 [67])—the LC50 value calculated here for the R. segetum EO is of interest for further studies. Indeed, according to Pavela [68], EO-based mosquito larvicides achieving LC50 values < 50 µL L−1 can be considered promising for further development of mosquitocidal products. Further efforts to boost the EO stability and efficacy in the field are still needed [22] to allow its real-world use, with special reference to the encapsulation in nanoemulsions to boost bioactivity and stability in the field [69,70].
Regarding M. domestica, a different toxicity of the R. segetum flower EO was found on male and female flies, calculating LD50 values of 10.5 and 50.8 µg adult−1, respectively (LD90 = 75.2 and 147.5 µg adult−1, respectively), with not overlapping 95% confidence intervals (Table 2). Even if a number of promising botanicals have been tested against M. domestica larvae, with successful results [71,72,73], adult flies should also be targeted by proper control action, since they are the vehicle of reproduction and also cause nuisance to humans and livestock, as other muscoid fly species [74,75].
The tested EO showed relatively promising efficacy against M. domestica. Based on LC90 values estimated for less sensitive females, we would be able to achieve at least 90% adult mortality approximately with a 15–20% essential oil-based preparation. The different sensitivity between the sexes of M. domestica is also confirmed by other studies [52]. In general, females are always less sensitive to chemicals than males. Therefore, in biological tests, it is important to monitor each sex separately, or only females, which are more important in terms of fertility [76,77]. However, even sub-lethal EO concentrations applied to M. domestica adults can have a significant impact on the population density of this pest, because they can significantly reduce the fecundity, longevity, and overall vitality of adults as it has been demonstrated for other EOs [52,76,78]. Investigating this phenomenon for the EO of R. segetum will be a subject of our further research.
The R. segetum flower EO was found significantly toxic to S. littoralis 3rd instar larvae, achieving LD50 and LD90 values of 37.9 and 99.6 µg larva−1 (Table 2). Its efficacy seems good against this important pest. Compared to other EOs, the one from R. segetum seems to provide average up to superior efficacy when compared to the EO from Echinophora spinosa L. (Apiales: Apiaceae) or some EOs obtained from plants of the genus Thymus [79,80]. It will also be necessary to determine whether the EO from R. segetum causes any phytotoxicity in the treated plants. High concentrations of EOs are known for their potential to exhibit herbicidal activity [81]. However, also it is known that although low doses of plant EOs may not show acute toxicity against S. littoralis larvae, they can cause chronic toxicity, as demonstrated, for example, for EOs extracted from Pimenta racemosa (Mill.) J.W. Moore, Origanum vulgare L., Salvia sclarea L., and Thymus vulgaris L. Indeed, when these EOs were applied at doses corresponding to the estimated LD30 value, this led to an overall mortality of S. littoralis larvae > 70%. In addition, these EOs significantly reduced longevity, fecundity, fertility, and natality of the surviving adults [82]. This phenomenon therefore deserves further studies, including efforts to evaluate the EO of R. segetum. It is also important to focus on an appropriate formulation of the botanical insecticide, since the latter can significantly increase the biological efficacy of an EO, thus reducing the needed application concentration. For example, a nanoformulation of the EO from Mentha spicata L. (Lamiales: Lamiaceae) increased its efficacy against Culex pipiens L. (Diptera: Culicidae) and M. domestica by more than 71 and 52%, respectively [70]. The prospects of green micro- and nano-emulsions, increasing the EOs efficacy as well as safety, have also been confirmed by other studies [22,83].
About 80% of the total composition was made up of three constituents, namely α-phellandrene (49.3%), terpinolene (20.7%), and β-phellandrene (9.2%). Thus, it is assumed that the insecticidal effects displayed on the three targets strictly depend on these compounds. α-Phellandrene and terpinolene were proven to be effective as larvicides against Aedes aegypti L. and Ae. albopictus (Skuse) (Diptera: Culicidae) with LC50 values of 16.6 and 39.9, and 28.4 and 35.6 mg L−1, respectively [84]. Terpinolene was also tested by Pavela et al. [85] on C. quinquefasciatus, highlighting an LC50 of 25.7 µL L−1. β-Phellandrene exhibited contact and fumigant toxicity against the stored-product beetle Sitophilus zeamais (Motschulsky) (Coleoptera: Curculionidae), with LD50 and LC50 of 2.2 μg adult−1 and 3.6 mg L−1, respectively [86]. However, even if it should be noted that the majority of components are generally considered to be responsible for biological activity, it is possible that there are synergistic or antagonistic relationships between them, including with minor compounds [87,88,89,90,91]. Further research into this phenomenon is therefore needed.
As for their potential mode of action, evidence from the literature suggests their involvement in cholinergic transmission, leading to an impairment of insect nerve conduction and coordination of neuromuscular system. This can cause an alteration of the insect behavior, lack of motor coordination, and even death [92]. Actually, β-phellandrene has been found to exert inhibition on the acetylcholinesterase activity in the German cockroach, Blattella germanica (L.) (Blattodea: Ectobiidae) [93].
EOs have been often found scarcely toxic to non-target species [17,94,95]. However, in several cases they exhibit relevant toxicity to non-target aquatic species [96,97], pollinators, and biological control agents [98,99]. Therefore, further research assessing the R. segetum EO potential toxicity of non-target species, as well as its long-term effects on physiology and behavior, is needed.

4. Conclusions

In conclusion, the present work explored the insecticidal potential of R. segetum, a Mediterranean species found commonly in cereal fields and uncultivated grounds. GC and GC-MS analyses showed the significant presence of monoterpene hydrocarbons (90.1%), allowing us to classify the EO in the chemotype dominated by α-phellandrene, terpinolene, and p-cymene. Although developing novel insecticides from the flower EO from R. segetum requires further research, the present study clearly outlines that this traditional food plant provides an effective EO, which can be used for the development and subsequent production of botanical insecticides against highly diverse and harmful insect species. These prospects are also enhanced by the possibility of growing the plant even in arid or rather dry areas [77], an issue that may provide yields similar to those of the analogous habitat and growth of F. vulgare. This potentially alternative crop provides relatively high yields of EO (about 1%), and is both a food and medicinal plant, therefore applications of botanical insecticides based on the EO from R. segetum does not give rise to any concerns.

Supplementary Materials

The following are available online at https://www.mdpi.com/article/10.3390/agriculture11040304/s1, Table S1: Current knowledge about the main compounds (≥2%) detected in the essential oils extracted from different plant parts of Ridolfia segetum.

Author Contributions

Conceptualization, M.B., R.P., F.M., and G.B.; methodology, V.I., R.P., F.M., A.C., and G.B.; software, R.P. and G.B.; validation, R.P., M.C.B, N.G.K., F.M., and A.C.; formal analysis, R.P., F.M., and G.B.; investigation, N.B., R.P., F.M., and G.B.; resources, N.B., V.I., and R.P.; data curation, N.B. and G.B.; writing—original draft preparation, N.B. and G.B.; writing—review and editing, R.P., M.C.B., N.G.K., F.M., A.C., and G.B.; visualization, R.P., M.C.B., N.G.K., A.C., and G.B.; supervision, F.M., R.P., A.C., and G.B.; project administration, M.B. and R.P.; funding acquisition, M.B. and R.P. All authors have read and agreed to the published version of the manuscript.

Funding

This work was supported by grant from MIUR-ITALY PRIN 2017 (Project N. 2017A95NCJ) (M. Bruno). R. Pavela would like to thank the Ministry of Agriculture of the Czech Republic for its financial support concerning botanical pesticide and basic substances research (Project MZE-RO0418).

Acknowledgments

We are grateful to N. Ntalli for inviting this article as part of her Agriculture Special Issue “Biopesticides: The Naturally Originating Plant Protection Products and Biocides”.

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Mazzi, D.; Dorn, S. Movement of insect pests in agricultural landscapes. Ann. Appl. Biol. 2012, 160, 97–113. [Google Scholar] [CrossRef]
  2. Di Giovanni, F.; Wilke, A.B.B.; Beier, J.C.; Pombi, M.; Mendoza-Roldan, J.A.; Desneux, N.; Canale, A.; Lucchi, A.; Dantas-Torres, F.; Otranto, D.; et al. Parasitic strategies of arthropods of medical and veterinary importance. Entomol. Gen. 2021. [Google Scholar] [CrossRef]
  3. Zhang, C.; Hu, R.; Shi, G.; Jin, Y.; Robson, M.G.; Huang, X. Overuse or underuse? An observation of pesticide use in China. Sci. Total. Environ. 2015, 538, 1–6. [Google Scholar] [CrossRef]
  4. Deligeorgidis, N.P.; Kavallieratos, N.G.; Malesios, C.; Sidiropoulos, G.; Deligeorgidis, P.N.; Benelli, G.; Papanikolaou, N.E. Evaluation of combined treatment with mineral oil, fenoxycarb and chlorpyrifos against Cydia pomonella, Phyllonorycter blancardella and Synanthedon myopaeformis in apple orchards. Entomol. Gen. 2019, 39, 117–126. [Google Scholar] [CrossRef]
  5. Humann-Guilleminot, S.; Binkowski, Ł.J.; Jenni, L.; Hilke, G.; Glauser, G.; Helfenstein, F. A nation-wide survey of neonicotinoid insecticides in agricultural land with implications for agri-environment schemes. J. Appl. Ecol. 2019, 56, 1502–1514. [Google Scholar] [CrossRef]
  6. Gul, H.; Ullah, F.; Biondi, A.; Desneux, N.; Qian, D.; Gao, X.; Song, D. Resistance against clothianidin and associated fitness costs in the chive maggot, Bradysia odoriphaga. Entomol. Gen. 2019, 39, 81–92. [Google Scholar] [CrossRef]
  7. Ullah, F.; Gul, H.; Desneux, N.; Gao, X.; Song, D. Imidacloprid-induced hormetic effects on demographic traits of the melon aphid, Aphis gossypii. Entomol. Gen. 2019, 39, 325–337. [Google Scholar] [CrossRef]
  8. Ullah, F.; Gul, H.; Desneux, N.; Tariq, K.; Ali, A.; Gao, X.; Song, D. Clothianidin-induced sublethal effects and expression changes of vitellogenin and ecdysone receptors genes in the melon aphid, Aphis gossypii. Entomol. Gen. 2019, 39, 137–149. [Google Scholar] [CrossRef]
  9. Ullah, F.; Gul, H.; Desneux, N.; Qu, Y.; Xiao, X.; Khattak, A.M.; Gao, X.; Song, D. Acetamiprid-induced hormetic effects and vitellogenin gene (Vg) expression in the melon aphid, Aphis gossypii. Entomol. Gen. 2019, 39, 259–270. [Google Scholar] [CrossRef]
  10. Varikou, K.; Garantonakis, N.; Birouraki, A. Exposure of Bombus terrestris L. to three different active ingredients and two application methods for olive pest control. Entomol. Gen. 2019, 39, 53–60. [Google Scholar] [CrossRef]
  11. Desneux, N.; Decourtye, A.; Delpuech, J.M. The sublethal effects of pesticides on beneficial arthropods. Annu. Rev. Entomol. 2007, 52, 81–106. [Google Scholar] [CrossRef]
  12. Naqqash, M.N.; Gökçe, A.; Bakhsh, A.; Salim, M. Insecticide resistance and its molecular basis in urban insect pests. Parasitol. Res. 2016, 115, 1363–1373. [Google Scholar] [CrossRef] [PubMed]
  13. Benelli, G.; Wilke, A.B.; Bloomquist, J.R.; Desneux, N.; Beier, J.C. Overexposing mosquitoes to insecticides under global warming: A public health concern? Sci. Total. Environ. 2021, 762, 143069. [Google Scholar] [CrossRef] [PubMed]
  14. Benelli, G.; Pavela, R. Repellence of essential oils and selected compounds against ticks—A systematic review. Acta Trop. 2018, 179, 47–54. [Google Scholar] [CrossRef] [PubMed]
  15. Benelli, G.; Pavela, R. Beyond mosquitoes—Essential oil toxicity and repellency against bloodsucking insects. Ind. Crops Prod. 2018, 117, 382–392. [Google Scholar] [CrossRef]
  16. Pavela, R.; Maggi, F.; Iannarelli, R.; Benelli, G. Plant extracts for developing mosquito larvicides: From laboratory to the field, with insights on the modes of action. Acta Trop. 2019, 193, 236–271. [Google Scholar] [CrossRef]
  17. Pavela, R.; Benelli, G. Essential oils as ecofriendly biopesticides? Challenges and constraints. Trends Plant Sci. 2016, 21, 1000–1007. [Google Scholar] [CrossRef]
  18. Jankowska, M.; Rogalska, J.; Wyszkowska, J.; Stankiewicz, M. Molecular targets for components of essential oils in the insect nervous system—A review. Molecules 2017, 23, 34. [Google Scholar] [CrossRef] [Green Version]
  19. Jankowska, M.; Lapied, B.; Jankowski, W.; Stankiewicz, M. The unusual action of essential oil component, menthol, in potentiating the effect of the carbamate insecticide, bendiocarb. Pestic. Biochem. Phys. 2019, 158, 101–111. [Google Scholar] [CrossRef]
  20. Isman, M.B.; Grieneisen, M.L. Botanical insecticide research: Many publications, limited useful data. Trends Plant Sci. 2014, 19, 140–145. [Google Scholar] [CrossRef]
  21. Isman, M.B. Botanical insecticides in the twenty-first century—Fulfilling their promise? Annu. Rev. Entomol. 2020, 65, 233–249. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  22. Pavoni, L.; Pavela, R.; Cespi, M.; Bonacucina, G.; Maggi, F.; Zeni, V.; Canale, A.; Lucchi, A.; Bruschi, F.; Benelli, G. Green micro-and nanoemulsions for managing parasites, vectors and pests. Nanomaterials 2019, 9, 1285. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  23. Pavela, R.; Morshedloo, M.R.; Mumivand, H.; Khorsand, G.J.; Karami, A.; Maggi, F.; Desneux, N.; Benelli, G. Phenolic monoterpene-rich essential oils from Apiaceae and Lamiaceae species: Insecticidal activity and safety evaluation on non-target earthworms. Entomol. Gen. 2020, 40, 421–435. [Google Scholar] [CrossRef]
  24. Euro + Med Plantbase. Available online: http://euromed.luomus.fi/euromed_map.php?taxon=343528&size=medium (accessed on 22 March 2021).
  25. Pignatti, S. Flora d’Italia; Edagricole: Milan, Italy, 1982; Volume 2, p. 220. [Google Scholar]
  26. Pignatti, S. Flora d’Italia; Edagricole-New Business Media: Milan, Italy, 2018; Volume 3, p. 592. [Google Scholar]
  27. Tbatou, M.; Kabil, M.; Belahyan, A.; Belahsen, R. Dietary potential of some forgotten wild leafy vegetables from Morocco. Int. Food Res. J. 2018, 25, 1829–1836. [Google Scholar]
  28. Lentini, F.; Venza, F. Wild food plants of popular use in Sicily. J. Ethnobiol. Ethnomed. 2007, 3, 15. [Google Scholar] [CrossRef] [Green Version]
  29. Tuttolomondo, T.; Licata, M.; Leto, C.; Savo, V.; Bonsangue, G.; Gargano, M.L.; Venturella, G.; La Bella, S. Ethnobotanical investigation on wild medicinal plants in the Monti Sicani regional park (Sicily, Italy). J. Ethnopharmacol. 2014, 153, 568–586. [Google Scholar] [CrossRef]
  30. Cabral, C.; Poças, J.; Gonçalves, M.J.; Cavaleiro, C.; Cruz, M.T.; Salgueiro, L. Ridolfia segetum (L.) Moris (Apiaceae) from Portugal: A source of safe antioxidant and anti-inflammatory essential oil. Ind. Crops Prod. 2015, 65, 56–61. [Google Scholar] [CrossRef] [Green Version]
  31. Beeby, E.; Magalhães, M.; Lemos, M.F.L.; Pires, I.M.; Cabral, C. Cytotoxic effects of Ridolfia segetum (L.) Moris phytoproducts in cancer cells. J. Ethnopharmacol. 2020, 267, 113515. [Google Scholar] [CrossRef]
  32. Jabrane, A.; Ben Jannet, H.; Harzallah-Skhiri, F.; Casanova, J.; Mighri, Z. GC, GC-MS and 13C NMR spectroscopy integrated analyses and in vitro antibacterial activity of Ridolfia segetum essential oils from Tunisia. J. Essent. Oil-Bear. Plants 2009, 12, 521–530. [Google Scholar] [CrossRef]
  33. Jabrane, A.; Ben Jannet, H.; Mastouri, M.; Mighri, Z.; Casanova, J. Chemical composition and in vitro evaluation of antioxidant and antibacterial activities of the root oil of Ridolfia segetum (L.) Moris from Tunisia. Nat. Prod. Res. 2010, 24, 491–499. [Google Scholar] [CrossRef]
  34. Ben Jannet, H.; Mighri, Z. Hydrodistillation kinetic and antibacterial effect studies of the flower essential oil from the Tunisian Ridolfia segetum (L.). J. Essent. Oil Res. 2007, 19, 258–261. [Google Scholar] [CrossRef]
  35. Bicchi, C.; Rubiolo, P.; Ballero, M.; Sanna, C.; Matteodo, M.; Esposito, F.; Zinzula, L.; Tramontano, E. HIV-1-inhibiting activity of the essential oil of Ridolfia segetum and Oenanthe crocata. Planta Med. 2009, 75, 1331–1335. [Google Scholar] [CrossRef] [PubMed]
  36. Casiglia, S.; Riccobono, L.; Bruno, M.; Rosselli, S.; Senatore, F.; Senatore, F. Chemical composition of the essential oil from Thapsia garganica L. (Apiaceae) grown wild in Sicily and its antimicrobial activity. Nat. Prod. Res. 2016, 30, 1042–1052. [Google Scholar] [CrossRef] [PubMed]
  37. Pavela, R.; Maggi, F.; Lupidi, G.; Cianfaglione, K.; Dauvergne, X.; Bruno, M.; Benelli, G. Efficacy of sea fennel (Crithmum maritimum L., Apiaceae) essential oils against Culex quinquefasciatus Say and Spodoptera littoralis (Boisd.). Ind. Crops Prod. 2017, 109, 603–610. [Google Scholar] [CrossRef]
  38. Di Napoli, M.; Varcamonti, M.; Basile, A.; Bruno, M.; Maggi, F.; Zanfardino, A. Anti-Pseudomonas aeruginosa activity of hemlock (Conium maculatum, Apiaceae) essential oil. Nat. Prod. Res. 2019, 33, 3436–3440. [Google Scholar] [CrossRef] [PubMed]
  39. Badalamenti, N.; Bruno, M.; Gagliano Candela, R.; Maggi, F. Chemical composition of the essential oil of Elaeoselinum asclepium (L.) Bertol subsp. meoides (Desf.) Fiori (Umbelliferae) collected wild in Central Sicily and its antimicrobial activity. Nat. Prod. Res. 2020, in press. [Google Scholar] [CrossRef] [PubMed]
  40. Badalamenti, N.; Ilardi, V.; Rosselli, S.; Bruno, M.; Maggi, F.; Leporini, M.; Falco, T.; Loizzo, M.R.; Tundis, R. Ferulago nodosa subsp. geniculata (Guss.) Troia & Raimondo: Isolation of essential oil and evaluation of its bioactivity. Molecules 2020, 25, 3249. [Google Scholar] [CrossRef]
  41. Bruno, M.; Ilardi, V.; Lupidi, G.; Quassinti, L.; Bramucci, M.; Fiorini, D.; Venditti, A.; Maggi, F. Composition and biological activities of the essential oil from a Sicilian accession of Prangos ferulacea (L.) Lindl. Nat. Prod. Res. 2020, in press. [Google Scholar] [CrossRef]
  42. Wilke, A.B.B.; Beier, J.C.; Benelli, G. Filariasis vector control down-played due to the belief the drugs will be enough—Not true! Entomol. Gen. 2020, 40, 15–24. [Google Scholar] [CrossRef]
  43. Khamesipour, F.; Lankarani, K.B.; Honarvar, B.; Kwenti, T.E. A systematic review of human pathogens carried by the housefly (Musca domestica L.). BMC Public Health 2018, 18, 1–15. [Google Scholar] [CrossRef]
  44. OEPP/EPPO. EPPO Standards PM 7/124 (1) Diagnostic Protocol for Spodoptera littoralis, Spodoptera litura, Spodoptera frugiperda, Spodoptera eridania. OEPP/EPPO Bull. 2015, 34, 257–270. [Google Scholar]
  45. EDQM (Council of Europe). European Pharmacopoeia, 6th ed.; EDQM: Strasbourg, France, 2008. [Google Scholar]
  46. Cecchini, C.; Coman, M.M.; Cresci, A.; Tirillini, B.; Cristalli, G.; Papa, F.; Sagratini, G.; Vittori, S.; Maggi, F. Essential oil from fruits and roots of Ferulago campestris (Besser) Grecescu (Apiaceae): Composition and antioxidant and anti-Candida activity. Flavour Frag. J. 2010, 25, 493–502. [Google Scholar] [CrossRef]
  47. Adams, R. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, 4th ed.; Allured Publishing Corp.: Carol Stream, IL, USA, 2007. [Google Scholar]
  48. NIST 17. Mass Spectral Library; (NIST/EPA/NIH); National Institute of Standards and Technology: Gaithersburg, MD, USA, 2017. [Google Scholar]
  49. FFNSC 2. Flavors and Fragrances of Natural and Synthetic Compounds. Mass Spectral Database; Shimadzu Corps: Kyoto, Japan, 2012. [Google Scholar]
  50. Pavela, R. Insecticidal properties of Pimpinella anisum essential oils against the Culex quinquefasciatus and the non-target organism Daphnia magna. J. Asia Pac. Entomol. 2014, 17, 287–293. [Google Scholar] [CrossRef]
  51. Pavela, R. Lethal and sublethal effects of thyme oil (Thymus vulgaris L.) on the house fly (Musca domestica Lin.). J. Essent. Oil -Bear. Plants 2007, 10, 346–356. [Google Scholar] [CrossRef]
  52. Pavela, R. Acute, synergistic and antagonistic effects of some aromatic compounds on the Spodoptera littoralis Boisd. (Lep., Noctuidae) larvae. Ind. Crops Prod. 2014, 60, 247–258. [Google Scholar] [CrossRef]
  53. WHO. Report of the WHO Informal Consultation on the Evaluation and Testing of Insecticides; CTD/WHOPES /IC /96.1; WHO: Geneva, Switzerland, 1996; p. 69. [Google Scholar]
  54. Benelli, G.; Maggi, F.; Canale, A.; Mehlhorn, H. Lyme disease is on the rise—How about tick repellents? A global view. Entomol. Gen. 2019, 39, 61–72. [Google Scholar] [CrossRef]
  55. Benelli, G.; Pavela, R.; Zorzetto, C.; Sánchez-Mateo, C.C.; Santini, G.; Canale, A.; Maggi, F. Insecticidal activity of the essential oil from Schizogyne sericea (Asteraceae) on four insect pests and two non-target species. Entomol. Gen. 2019, 39, 9–18. [Google Scholar] [CrossRef]
  56. Finney, D.J. Probit Analysis; Cambridge University: London, UK, 1971; pp. 68–78. [Google Scholar]
  57. Abbott, W.S. A method of computing the effectiveness of an insecticide. J. Econ. Entomol. 1925, 18, 265–267. [Google Scholar] [CrossRef]
  58. Marongiu, B.; Piras, A.; Porcedda, S.; Tuveri, E.; Maxia, A. Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris. Nat. Prod. Res. 2007, 21, 412–417. [Google Scholar] [CrossRef] [PubMed]
  59. Palá-Paúl, J.; Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Ramos-Vázquez, P. Volatile constituents of Ridolfia segetum (L.) Moris gathered in southern Spain, Andalucia province. J. Essent. Oil Res. 2002, 14, 206–209. [Google Scholar] [CrossRef]
  60. Palá-Paúl, J.; Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Vallejo, M.C.G. Volatile constituents of Ridolfia segetum (L.) Moris gathered in central Spain: Castilla la Mancha. J. Essent. Oil Res. 2005, 17, 119–121. [Google Scholar] [CrossRef]
  61. Karkouri, J.E.L.; Amalich, S.; Drioiche, A.; Fadili, K.; Eto, B.; Khabal, Y.; Zair, T. Phytochemical valuation of the umbels of Ridolfia segetum (L.) Moris of Morocco. Int. J. Adv. Res. 2017, 5, 1780–1788. [Google Scholar] [CrossRef] [Green Version]
  62. Božović, M.; Garzoli, S.; Baldisserotto, A.; Andreotti, E.; Cesa, S.; Pepi, F.; Vertuani, S.; Manfredini, S.; Ragno, R. Variation in essential oil content and composition of Ridolfia segetum Moris based on 30-hour prolonged fractionated extraction procedure. Nat. Prod. Res. 2020, 34, 1923–1926. [Google Scholar] [CrossRef] [PubMed]
  63. Gattefosse, J.; Igolen, G. Aromatic flora of Morocco. The essence of “harvest fennel” (Ridolfia segetum). Bull. Soc. Chim. Fr. 1946, 361–363. [Google Scholar]
  64. Sutthanont, N.; Attrapadung, S.; Nuchprayoon, S. Larvicidal activity of synthesized silver nanoparticles from Curcuma zedoaria essential oil against Culex quinquefasciatus. Insects 2019, 10, 27. [Google Scholar] [CrossRef] [Green Version]
  65. Senthilkumar, A.; Kannathasan, K.; Venkatesalu, V. Chemical constituents and larvicidal property of the essential oil of Blumea mollis (D. Don) Merr. against Culex quinquefasciatus. Parasitol. Res. 2008, 103, 959–962. [Google Scholar] [CrossRef] [PubMed]
  66. Huong, L.T.; Huong, T.T.; Huong, N.T.; Hung, N.H.; Dat, P.T.; Luong, N.X.; Ogunwande, I.A. Mosquito larvicidal activity of the essential oil of Zingiber collinsii against Aedes albopictus and Culex quinquefasciatus. J. Oleo Sci. 2020, 69, 153–160. [Google Scholar] [CrossRef]
  67. Andrade-Ochoa, S.; Sánchez-Aldana, D.; Chacón-Vargas, K.F.; Rivera-Chavira, B.E.; Sánchez-Torres, L.E.; Camacho, A.D.; Nogueda-Torres, B.; Nevárez-Moorillón, G.V. Oviposition deterrent and larvicidal and pupaecidal activity of seven essential oils and their major components against Culex quinquefasciatus Say (Diptera: Culicidae): Synergism–antagonism effects. Insects 2018, 9, 25. [Google Scholar] [CrossRef] [Green Version]
  68. Pavela, R. Essential oils for the development of eco-friendly mosquito larvicides: A review. Ind. Crops Prod. 2015, 76, 174–187. [Google Scholar] [CrossRef]
  69. Sundararajan, B.; Moola, A.K.; Vivek, K.; Kumari, B.R. Formulation of nanoemulsion from leaves essential oil of Ocimum basilicum L. and its antibacterial, antioxidant and larvicidal activities (Culex quinquefasciatus). Microb. Pathog. 2018, 125, 475–485. [Google Scholar] [CrossRef]
  70. Mohafrash, S.M.; Fallatah, S.A.; Farag, S.M.; Mossa, A.T.H. Mentha spicata essential oil nanoformulation and its larvicidal application against Culex pipiens and Musca domestica. Ind. Crops Prod. 2020, 157, 112944. [Google Scholar] [CrossRef]
  71. Xie, Y.; Huang, Q.; Rao, Y.; Hong, L.; Zhang, D. Efficacy of Origanum vulgare essential oil and carvacrol against the housefly, Musca domestica L. (Diptera: Muscidae). Environ. Sci. Pollut. Res. 2019, 26, 23824–23831. [Google Scholar] [CrossRef]
  72. Chere, J.M.C.; Dar, M.A.; Pandit, R.S. Evaluation of some essential oils against the larvae of house fly, Musca domestica by using residual film method. Biotechnol. Microb. 2018, 9, 555752. [Google Scholar] [CrossRef]
  73. Xie, Y.; Jin, H.; Yang, X.; Gu, Q.; Zhang, D. Toxicity of the essential oil from Thymus serpyllum and thymol to larvae and pupae of the housefly Musca domestica L. (Diptera: Muscidae). Environ. Sci. Pollut. Res. 2020, 27, 35330–35340. [Google Scholar] [CrossRef]
  74. Hazarika, H.; Tyagi, V.; Krishnatreyya, H.; Islam, J.; Boruah, D.; Kishor, S.; Chattopadhyaya, P.; Zaman, K. Essential oil based controlled-release non-toxic evaporating tablet provides effective repellency against Musca domestica. Acta Trop. 2020, 210, 105620. [Google Scholar] [CrossRef] [PubMed]
  75. Scalerandi, E.; Flores, G.A.; Palacio, M.; Defagó, M.T.; Carpinella, M.C.; Valladares, G.; Bertoni, A.; Palacios, S.M. Understanding synegistic toxicity of terpenes as insecticides: Contribution of metabolic detoxification in Musca domestica. Front. Plant Sci. 2018, 9, 1579. [Google Scholar] [CrossRef] [Green Version]
  76. Benelli, G.; Pavela, R.; Giordani, C.; Casettari, L.; Curzi, G.; Cappellacci, L.; Petrelli, R.; Maggi, F. Acute and sub-lethal toxicity of eight essential oils of commercial interest against the filariasis mosquito Culex quinquefasciatus and the housefly Musca domestica. Ind. Crops Prod. 2018, 112, 668–680. [Google Scholar] [CrossRef]
  77. Pavela, R.; Zabka, M.; Bednar, J.; Triska, J.; Vrchotova, N. New knowledge for yield, composition and insecticidal activity of essential oils obtained from the aerial parts or seeds of fennel (Foeniculum vulgare Mill.). Ind. Crops Prod. 2016, 83, 275–282. [Google Scholar] [CrossRef]
  78. Kumar, P.; Mishra, S.; Malik, A.; Satya, S. Biocontrol potential of essential oil monoterpenes against housefly, Musca domestica (Diptera: Muscidae). Ecotoxicol. Environ. Saf. 2014, 100, 1–6. [Google Scholar] [CrossRef] [PubMed]
  79. Pavela, R.; Maggi, F.; Cianfaglione, K.; Canale, A.; Benelli, G. Promising insecticidal efficacy of the essential oils from the halophyte Echinophora spinosa (Apiaceae) growing in Corsica Island, France. Environ. Sci. Pollut. Res. 2020, 27, 14454–14464. [Google Scholar] [CrossRef]
  80. Pavela, R.; Bartolucci, F.; Desneux, N.; Lavoir, A.V.; Canale, A.; Maggi, F.; Benelli, G. Chemical profiles and insecticidal efficacy of the essential oils from four Thymus taxa growing in central-southern Italy. Ind. Crops Prod. 2019, 138, 111460. [Google Scholar] [CrossRef]
  81. Verdeguer, M.; Sanchez-Moreiras, A.M.; Araniti, F. Phytotoxic effects and mechanism of action of essential oils and terpenoids. Plants 2020, 9, 1571. [Google Scholar] [CrossRef]
  82. Pavela, R. Sublethal effects of some essential oils on the cotton leafworm Spodoptera littoralis (Boisduval). J. Essent. Oil-Bear. Plants 2012, 15, 144–156. [Google Scholar] [CrossRef]
  83. Pavela, R.; Benelli, G.; Pavoni, L.; Bonacucina, G.; Cespi, M.; Cianfaglione, K.; Bajalan, I.; Morshedloo, M.R.; Lupidi, G.; Romano, D.; et al. Microemulsions for delivery of Apiaceae essential oils—Towards highly effective and eco-friendly mosquito larvicides? Ind. Crops Prod. 2019, 129, 631–640. [Google Scholar] [CrossRef]
  84. Cheng, S.S.; Huang, C.G.; Chen, Y.J.; Yu, J.J.; Chen, W.J.; Chang, S.T. Chemical compositions and larvicidal activities of leaf essential oils from two Eucalyptus species. Bioresour. Technol. 2009, 100, 452–456. [Google Scholar] [CrossRef]
  85. Pavela, R.; Maggi, F.; Cianfaglione, K.; Bruno, M.; Benelli, G. Larvicidal activity of essential oils of five Apiaceae taxa and some of their main constituents against Culex quinquefasciatus. Chem. Biodivers. 2018, 15, e1700382. [Google Scholar] [CrossRef] [PubMed]
  86. Ma, S.; Jia, R.; Guo, M.; Qin, K.; Zhang, L. Insecticidal activity of essential oil from Cephalotaxus sinensis and its main components against various agricultural pests. Ind. Crops Prod. 2020, 150, 112403. [Google Scholar] [CrossRef]
  87. Benelli, G.; Pavela, R.; Iannarelli, R.; Petrelli, R.; Cappellacci, L.; Cianfaglione, K.; Afsharf, F.H.; Nicoletti, M.; Canale, A.; Maggi, F. Synergized mixtures of Apiaceae essential oils and related plant-borne compounds: Larvicidal effectiveness on the filariasis vector Culex quinquefasciatus Say. Ind. Crops Prod. 2017, 96, 186–195. [Google Scholar] [CrossRef]
  88. Tak, J.H.; Isman, M.B. Enhanced cuticular penetration as the mechanism for synergy of insecticidal constituents of rosemary essential oil in Trichoplusia ni. Sci. Rep. 2015, 5, 1–10. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  89. Tak, J.H.; Isman, M.B. Penetration-enhancement underlies synergy of plant essential oil terpenoids as insecticides in the cabbage looper, Trichoplusia ni. Sci. Rep. 2017, 7, srep42432. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  90. Liu, T.T.; Chao, L.K.P.; Hong, K.S.; Huang, Y.J.; Yang, T.S. Composition and insecticidal activity of essential oil of Bacopa caroliniana and interactive effects of individual compounds on the activity. Insects 2020, 11, 23. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  91. Benelli, G.; Pavela, R.; Canale, A.; Cianfaglione, K.; Ciaschetti, G.; Conti, F.; Nicoletti, M.; Senthil-Nathan, S.; Mehlhorn, H.; Maggi, F. Acute larvicidal toxicity of five essential oils (Pinus nigra, Hyssopus officinalis, Satureja montana, Aloysia citrodora and Pelargonium graveolens) against the filariasis vector Culex quinquefasciatus: Synergistic and antagonistic effects. Parasitol. Int. 2017, 66, 166–171. [Google Scholar] [CrossRef] [PubMed]
  92. Maggi, F.; Benelli, G. Essential Oils from Aromatic and Medicinal Plants as Effective Weapons against Mosquito Vectors of Public Health Importance. In Mosquito-borne Diseases. Parasitology Research Monographs; Benelli, G., Mehlhorn, H., Eds.; Springer: Cham, Switzerland, 2018; Volume 10. [Google Scholar] [CrossRef]
  93. Yeom, H.J.; Jung, C.S.; Kang, J.; Kim, J.; Lee, J.H.; Kim, D.S.; Kim, H.S.; Park, P.S.; Kang, K.S.; Park, I.K. Insecticidal and acetylcholine esterase inhibition activity of Asteraceae plant essential oils and their constituents against adults of the German cockroach (Blattella germanica). J. Agric. Food Chem. 2015, 63, 2241–2248. [Google Scholar] [CrossRef]
  94. Govindarajan, M.; Rajeswary, M.; Benelli, G. Chemical composition, toxicity and non-target effects of Pinus kesiya essential oil: An eco-friendly and novel larvicide against malaria, dengue and lymphatic filariasis mosquito vectors. Ecotoxicol. Environ. Saf. 2016, 129, 85–90. [Google Scholar] [CrossRef] [PubMed]
  95. Murfadunnisa, S.; Vasantha-Srinivasan, P.; Ganesan, R.; Senthil-Nathan, S.; Kim, T.J.; Ponsankar, A.; Kumar, S.D.; Chandramohan, D.; Krutmuang, P. Larvicidal and enzyme inhibition of essential oil from Spheranthus amaranthroides (Burm.) against lepidopteran pest Spodoptera litura (Fab.) and their impact on non-target earthworms. Biocatal. Agric. Biotechnol. 2019, 21, 101324. [Google Scholar] [CrossRef]
  96. Conti, B.; Flamini, G.; Cioni, P.L.; Ceccarini, L.; Macchia, M.; Benelli, G. Mosquitocidal essential oils: Are they safe against non-target aquatic organisms? Parasitol. Res. 2014, 113, 251–259. [Google Scholar] [CrossRef]
  97. Benelli, G.; Pavela, R.; Petrelli, R.; Nzekoue, F.K.; Cappellacci, L.; Lupidi, G.; Quassinti, L.; Bramucci, M.; Sut, S.; Dall’Acqua, S.; et al. Carlina oxide from Carlina acaulis root essential oil acts as a potent mosquito larvicide. Ind. Crops Prod. 2019, 137, 356–366. [Google Scholar] [CrossRef]
  98. Ferreira, T.P.; Oliveira, E.E.; Tschoeke, P.H.; Pinheiro, R.G.; Maia, A.M.S.; Aguiar, R.W.S. Potential use of Negramina (Siparuna guianensis Aubl.) essential oil to control wax moths and its selectivity in relation to honey bees. Ind. Crops Prod. 2017, 109, 151–157. [Google Scholar] [CrossRef]
  99. Melo, C.R.; Picanço, M.C.; Santos, A.A.; Santos, I.B.; Pimentel, M.F.; Santos, A.C.C.; Blank, A.F.; Araujo, A.P.A.; Cristaldo, P.F.; Bacci, L. Toxicity of essential oils of Lippia gracilis chemotypes and their major compounds on Diaphania hyalinata and non-target species. Crop Prot. 2018, 104, 47–51. [Google Scholar] [CrossRef]
Table
Table 1. Composition (%) of the essential oil of flowers of Ridolfia segetum collected in Sicily.
Table 1. Composition (%) of the essential oil of flowers of Ridolfia segetum collected in Sicily.
ComponentsLRI aLRI Lit.%Id.b
1α-Thujene9219240.4RI, MS
2α-Pinene9269323.0Co-I,RI,MS
3Camphene939946TCo-I,RI,MS
4Sabinene9659690.5Co-I,RI,MS
5β-Pinene9689742.5Co-I,RI,MS
6Myrcene9899881.1Co-I,RI,MS
7α-Phellandrene1004100249.3Co-I,RI,MS
8δ-3-Carene10081008tCo-I,RI,MS
9α-Terpinene101410140.1Co-I,RI,MS
10p-Cymene102210201.4Co-I,RI,MS
11Limonene102410250.3Co-I,RI,MS
12β-Phellandrene102510259.2RI,MS
13(Z)-β-Ocimene103710321.3Co-I,RI,MS
14(E)-β-Ocimene104710440.1Co-I,RI,MS
15γ-Terpinene105510540.2Co-I,RI,MS
16Terpinolene1086108620.7Co-I,RI,MS
17Linalool11011095tCo-I,RI,MS
181,3,8-p-Menthatriene11091108tRI, MS
19allo-Ocimene11291128tCo-I,RI,MS
20Terpinen-4-ol117311740.1Co-I,RI,MS
21p-Cymen-8-ol118311790.1RI, MS
22α-Terpineol11861186tCo-I,RI,MS
23Piperitone12501249tRI,MS
24Piperitenone13361340tRI,MS
25Piperitenone oxide136213665.9RI,MS
26Germacrene D14711484tRI,MS
27Dill apiole162116203.7RI,MS
Monoterpene hydrocarbons 90.1
Oxygenated monoterpenes 6.1
Sesquiterpene hydrocarbons t
Others 3.7
Total 99.9
a LRI: Linear retention index on a HP-5MS column; b Co-I, Co-elution with authentic standard (Sigma-Aldrich); RI, coherence respect to values reported in ADAMS library; MS, mass spectrum overlapping with those stored in ADAMS, NIST17, and FFNSC3 libraries.
Table
Table 2. Lethal concentrations (LC) and lethal doses (LD) of Ridolfia segetum flower essential oil against three key insect pests and vectors.
Table 2. Lethal concentrations (LC) and lethal doses (LD) of Ridolfia segetum flower essential oil against three key insect pests and vectors.
Insect SpeciesUnitLC/LD50CI95LC/LD90CI95χ2 (df = 4)p-Level
Culex quinquefasciatus 3rd instar larvaµL L−127.118.9–32.342.538.9–54.20.7340.574 ns
Musca domestica adult femaleµg adult−150.841.2–62.3147.5129.5–168.73.7510.289 ns
Musca domestica adult maleµg adult−110.55.8.15.675.261.8–93.62.4850.615 ns
Spodoptera littoralis 3rd instar larvaµg larva−137.928.5–42.699.687.2–152.72.7450.133 ns
CI95 = 95% confidence interval, df = degrees of freedom; ns = not significant (p > 0.05).
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Share and Cite

MDPI and ACS Style

Badalamenti, N.; Ilardi, V.; Bruno, M.; Pavela, R.; Boukouvala, M.C.; Kavallieratos, N.G.; Maggi, F.; Canale, A.; Benelli, G. Chemical Composition and Broad-Spectrum Insecticidal Activity of the Flower Essential Oil from an Ancient Sicilian Food Plant, Ridolfia segetum. Agriculture 2021, 11, 304. https://doi.org/10.3390/agriculture11040304

AMA Style

Badalamenti N, Ilardi V, Bruno M, Pavela R, Boukouvala MC, Kavallieratos NG, Maggi F, Canale A, Benelli G. Chemical Composition and Broad-Spectrum Insecticidal Activity of the Flower Essential Oil from an Ancient Sicilian Food Plant, Ridolfia segetum. Agriculture. 2021; 11(4):304. https://doi.org/10.3390/agriculture11040304

Chicago/Turabian Style

Badalamenti, Natale, Vincenzo Ilardi, Maurizio Bruno, Roman Pavela, Maria C. Boukouvala, Nickolas G. Kavallieratos, Filippo Maggi, Angelo Canale, and Giovanni Benelli. 2021. "Chemical Composition and Broad-Spectrum Insecticidal Activity of the Flower Essential Oil from an Ancient Sicilian Food Plant, Ridolfia segetum" Agriculture 11, no. 4: 304. https://doi.org/10.3390/agriculture11040304

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop