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Insecticidal Activity of Plant Secondary Metabolites

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A special issue of Plants (ISSN 2223-7747). This special issue belongs to the section "Phytochemistry".

Deadline for manuscript submissions: closed (30 June 2022) | Viewed by 36416

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Prof. Dr. Filippo Maggi

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Guest Editor

School of Pharmacy, University of Camerino, 62032 Camerino, Italy
Interests: medicinal and aromatic plants; essential oils; green extraction; phytochemistry; bioactivity
Special Issues, Collections and Topics in MDPI journals

Dr. Giovanni Benelli

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Guest Editor

Department of Agriculture, Food and Environment, University of Pisa, Via del Borghetto 80, 56124 Pisa, Italy
Interests: insect behaviour; biological control; chemical ecology; mating disruption; ecotoxicology; integrate pest and vector management; One Health
Special Issues, Collections and Topics in MDPI journals

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Dear Colleagues,

Plant secondary metabolites display a plethora of biological functions, among which the biochemical defense against insects and other organisms is one of the most important ones. For this purpose, they synthesize alkaloids, terpenoids, and phenolics which act as allelochemicals through highly diverse modes of action leading to major changes on the arthropods’ physiology and behavior. Thus, they represent a complementary and alternative strategy to manage populations of pests and vectors. In this framework, the present Special Issue welcomes original research articles and reviews shedding light on recent advancements about the use of plant secondary metabolites and related formulations against arthropod targets of health and agricultural importance. This Special Issue welcomes contributions on the following topics:

- Phytochemical analysis and biological evaluation of plant-borne secondary metabolites;

- Lethal and sub-lethal effects of plant-borne insecticides and acaricides;

- Repellent effects of plant-borne secondary metabolites on insects and mites;

- Modes of action of green insecticides, acaricides, and repellents;

- Toxicity of green insecticides and acaricides on non-target species, including aquatic organisms;

- Structure–activity relationships characterizing green insecticides and acaricides;

- Synergistic and antagonistic studies focusing on green insecticides and acaricides;

- Development of insecticidal and acaricidal formulations with extended shelf-life and prolonged bioactivity in the field.

Prof. Dr. Filippo Maggi
Dr. Giovanni Benelli
Guest Editors

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Keywords

botanicals
secondary metabolites
formulations
insect vectors
insect pests
crop protection
ticks
integrated pest management

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Published Papers (11 papers)

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Editorial

Jump to: Research, Review

2 pages, 194 KiB

Open AccessEditorial

Insecticidal Activity of Plant Secondary Metabolites

by Giovanni Benelli and Filippo Maggi

Plants 2022, 11(20), 2804; https://doi.org/10.3390/plants11202804 - 21 Oct 2022

Cited by 6 | Viewed by 1622

Abstract

Plant-insect interactions are one of the most fascinating fields of research attracting biologists, entomologists, botanists, as well as a wide range of multidisciplinary researchers [...] Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

Research

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14 pages, 323 KiB

Open AccessArticle

Essential Oils from Cameroonian Aromatic Plants as Effective Insecticides against Mosquitoes, Houseflies, and Moths

by Joice G. Nkuimi Wandjou, Cecilia Baldassarri, Marta Ferrati, Filippo Maggi, Roman Pavela, Nole Tsabang, Riccardo Petrelli, Renato Ricciardi, Nicolas Desneux and Giovanni Benelli

Plants 2022, 11(18), 2353; https://doi.org/10.3390/plants11182353 - 9 Sep 2022

Cited by 12 | Viewed by 3081

Abstract

Recently, spices have attracted the attention of scientists and agrochemical companies for their potential as insecticidal and acaricidal agents, and even as repellents to replace synthetic compounds that are labeled with detrimental impacts on environment and human and animal health. In this framework, the aim of this study was to evaluate the insecticidal potential of the essential oils (EOs) obtained from three Cameroonian aromatic plants, namely Monodora myristica (Gaertn.) Dunal, Xylopia aethiopica (Dunal) A. Rich., and Aframomum citratum (J. Pereira) K. Schum. They were produced by hydrodistillation, with yields of 3.84, 4.89, and 0.85%, respectively. The chemical composition was evaluated by GC-MS analysis. The EOs and their major constituents (i.e., geraniol, sabinene, α-pinene, p-cymene, α-phellandrene, and β-pinene) were tested against the polyphagous moth pest, i.e., Spodoptera littoralis (Boisd.), the common housefly, Musca domestica L., and the filariasis and arbovirus mosquito vector, Culex quinquefasciatus Say. Our results showed that M. myristica and X. aethiopica EOs were the most effective against M. domestica adults, being effective on both males (22.1 µg adult⁻¹) and females (LD₅₀: 29.1 µg adult⁻¹). The M. myristica EO and geraniol showed the highest toxicity on S. littoralis, with LD₅₀₍₉₀₎ values of 29.3 (123.5) and 25.3 (83.2) µg larva⁻¹, respectively. Last, the EOs from M. myristica and X. aethiopica, as well as the major constituents p-cymene and α-phellandrene, were the most toxic against C. quinquefasciatus larvae. The selected EOs may potentially lead to the production of cheap and effective botanical insecticides for African smallholders, although the development of effective formulations, a safety evaluation, and an in-depth study of their efficacy on different insect species are needed. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

14 pages, 696 KiB

Open AccessEditor’s ChoiceArticle

Insecticidal Activity of Four Essential Oils Extracted from Chilean Patagonian Plants as Potential Organic Pesticides

by Cristiano Giordani, Eleonora Spinozzi, Cecilia Baldassarri, Marta Ferrati, Loredana Cappellacci, Daniela Santibañez Nieto, Roman Pavela, Renato Ricciardi, Giovanni Benelli, Riccardo Petrelli and Filippo Maggi

Plants 2022, 11(15), 2012; https://doi.org/10.3390/plants11152012 - 2 Aug 2022

Cited by 7 | Viewed by 2659

Abstract

Patagonia is a geographical area characterized by a wide plant biodiversity. Several native plant species are traditionally used in medicine by the local population and demonstrated to be sources of biologically active compounds. Due to the massive need for green and sustainable pesticides, this study was conducted to evaluate the insecticidal activity of essential oils (EOs) from understudied plants growing in this propitious area. Ciprés (Pilgerodendron uviferum), tepa (Laureliopsis philippiana), canelo (Drimys winteri), and paramela (Adesmia boronioides) EOs were extracted through steam distillation, and their compositions were analyzed through GC–MS analysis. EO contact toxicity against Musca domestica L., Spodoptera littoralis (Boisd.), and Culex quinquefasciatus Say was then evaluated. As a general trend, EOs performed better on housefly males over females. Ciprés EO showed the highest insecticidal efficacy. The LD₅₀₍₉₀₎ values were 68.6 (183.7) and 11.3 (75.1) µg adult⁻¹ on housefly females and males, respectively. All EOs were effective against S. littoralis larvae; LD₅₀ values were 33.2–66.7 µg larva⁻¹, and tepa EO was the most effective in terms of LD₉₀ (i.e., <100 µg larva⁻¹). Canelo, tepa, and paramela EOs were highly effective on C. quinquefasciatus larvae, with LC₅₀ values < 100 µL L⁻¹. Again, tepa EO achieved LD₉₀ < 100 µL L⁻¹. This EO was characterized by safrole (43.1%), linalool (27.9%), and methyl eugenol (6.9%) as major constituents. Overall, Patagonian native plant EOs can represent a valid resource for local stakeholders, to develop effective insecticides for pest and vector management, pending a proper focus on their formulation and nontarget effects. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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9 pages, 829 KiB

Open AccessArticle

Acaricidal Activity of Bufadienolides Isolated from Drimia pancration against Tetranychus urticae, and Structural Elucidation of Arenobufagin-3-O-α-L-rhamnopyranoside

by Natale Badalamenti, Maurizio Bruno, Roman Pavela, Filippo Maggi, Oliviero Marinelli, Laura Zeppa, Giovanni Benelli and Angelo Canale

Plants 2022, 11(13), 1629; https://doi.org/10.3390/plants11131629 - 21 Jun 2022

Cited by 9 | Viewed by 2054

Abstract

Chemical characterization of the bulbs of Drimia pancration was conducted to isolate four steroidal saponins (1–4). Earlier, we focused on the structural elucidation of compounds 1–3. Herein, by means of ¹H-NMR, ¹³C-NMR, Nuclear Overhauser Effects (NOE), and 2D-NMR spectra, the full stereochemical structure of 4 is reported, and all the ¹H and ¹³C signals are assigned. Compounds 1–4 were tested for their acaricidal properties against the two-spotted spider mite Tetranychus urticae. Our results showed excellent activity of compound 1, with an LD₅₀ (µg/cm²) of 0.29 and a LD₉₀ (µg/cm²) of 0.96, whereas compounds 2, 3, and 4 showed moderate activity. Furthermore, the acaricidal and cytotoxic properties of the crude extract were also investigated. Of note, after 96 h of exposure, the acaricidal activity of compound 1 was higher than that of the positive control, hexythiazox. Indeed, for compound 1, LD₅₀ and LD₉₀ were 0.29 and 0.96 µg/cm², respectively, while hexythiazox LD₅₀₍₉₀₎ was 18.7 (132.5) µg/cm². Additionally, D. pancration extract, after 72 h, induced a high cytotoxic effect in HaCaT and THP-1 cell lines, with an IC₅₀ of 7.37 ± 0.5 µg/mL and 3.50 ± 0.15 µg/mL, respectively. Overall, D. pancration can be considered as a green source of novel acaricides effective against mites of agricultural importance, such as T. urticae, pending proper field validation and the assessment of non-target effects on other invertebrate species. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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17 pages, 490 KiB

Open AccessArticle

Chemical Profiles and Insecticidal Potential of Essential Oils Isolated from Four Thymus Species against Rhyzopertha dominica (F.)

by Asgar Ebadollahi, Bahram Naseri, Zahra Abedi and William N. Setzer

Plants 2022, 11(12), 1567; https://doi.org/10.3390/plants11121567 - 14 Jun 2022

Cited by 13 | Viewed by 2362

Abstract

Although chemical pesticides have been efficiently used to manage insect pest, their overuse has led to environmental contamination and threats to human health, enticing researchers to introduce eco-friendly and effective agents. In this study, the insecticidal effectiveness of essential oils isolated from Thymus species, including T. eriocalyx, T. kotschyanus, T. fallax, and T. vulgaris, was evaluated against the adults of Rhyzopertha dominica. The terpenes p-cymene, 1,8-cineole, linalool, α-terpineol, and carvacrol were the prominent compounds in the hydrodistilled essential oils. All essential oils produced significant fumigant at 24, 48, and 72-exposure times. The energy reserves protein by all essential oils, glycogen by T. kotschyanus and T. vulgaris, and lipid by T. fallax and T. vulgaris were significantly decreased compared to control. All essential oils except T. vulgaris affected the amylolytic and proteolytic activity of the pest. The pest increased the α- and β-esterase enzyme activity in response to the essential oils. Nutritional indices of adults were also affected by essential oils, in which feeding deterrence index was calculated from 20.41% to 61.11%. Accordingly, based on lethal and extensive sub-lethal insecticidal activities, T. eriocalyx, T. kotschyanus, T. fallax, and T. vulgaris essential oils can be considered as efficient agents for R. dominica management. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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11 pages, 2095 KiB

Open AccessArticle

Acaricidal, Larvacidal, and Repellent Activity of Elettaria cardamomum Essential Oil against Hyalomma anatolicum Ticks Infesting Saudi Arabian Cattle

by Abdullah D. Alanazi, Mourad Ben Said, Abdullah F. Shater and Mohammad Nafi Solaiman Al-Sabi

Plants 2022, 11(9), 1221; https://doi.org/10.3390/plants11091221 - 30 Apr 2022

Cited by 4 | Viewed by 2417

Abstract

Background: In this experimental study, we aimed to assess the acaricidal effects of Elettaria cardamomum L. essential oil (ECEO) against Hyalomma anatolicum tick in cattle from Saudi Arabia. Methods: Gas chromatography-mass spectrometry (GC-MS) was performed to identify the chemical composition of ECEO. The acaricidal, larvicidal, and repellent activity of ECEO against H. anatolicum was studied through the adult immersion test (AIT), the larval packet test (LPT), the vertical movement behavior of tick’s larvae technique, anti-acetylcholinesterase (AChE) activity, and oxidative enzyme activity. Results: By GC/MS, the most compounds were 1,8-cineole (34.3%), α-terpinyl acetate (23.3%), and α-pinene (17.7%), respectively. ECEO significantly (p < 0.001) increased the mortality rate as a dose-dependent response. After ECEO Treatment, number of eggs, egg weight, and hatchability significantly declined as a dose-dependent response. ECEO at concentrations of 5 µL/mL and above completely killed the larva. The LC₅₀ and LC₉₀ values for ECEO were 1.46 and 2.68 µL/mL, respectively. ECEO at concentrations of 10, 20, and 40 µL/mL showed 100% repellency activity up to 60, 120, and 360 min incubation, respectively. ECEO, especially at ½ LC₅₀ and LC_50, significantly inhibited GST and AChE activities of H. anatolicum larvae compared to the control group. Conclusions: We found promising adulticidal, larvicidal, and repellent effects of ECEO against H. anatolicum as a vector of theileriosis in Saudi Arabia. We also found that ECEO displayed these activities through inhibiting AChE and GST. Nevertheless, additional investigations are required to confirm the accurate mechanisms and the relevance of ECEO in practical application. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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11 pages, 460 KiB

Open AccessArticle

Contact and Fumigant Activities of Citrus aurantium Essential Oil against the Stable Fly Stomoxys calcitrans (Diptera: Muscidae)

by Tanasak Changbunjong, Sookruetai Boonmasawai, Sivapong Sungpradit, Thekhawet Weluwanarak and Arpron Leesombun

Plants 2022, 11(9), 1122; https://doi.org/10.3390/plants11091122 - 21 Apr 2022

Cited by 10 | Viewed by 3008

Abstract

The stable fly, Stomoxys calcitrans (L.), is a cosmopolitan hematophagous fly of medical and veterinary importance. It is widely considered a major livestock pest that can cause significant economic losses. This study aimed to evaluate the insecticidal activity of Citrus aurantium (L.) essential oil against S. calcitrans based on contact and fumigant toxicity tests. Chemical analysis by gas chromatography-mass spectrometry of the essential oil showed the dominance (93.79%) of limonene in the total essential oil composition. Furthermore, the insecticidal test results showed that the mortality of flies increased with concentration and time within 24 h of exposure. In the contact toxicity test, the median lethal dose was 105.88 µg/fly, while the 90% lethal dose was 499.25 µg/fly. As for the fumigant toxicity test, the median lethal concentration was 13.06 mg/L air, and the 90% lethal concentration was 43.13 mg/L air. These results indicate that C. aurantium essential oil exhibits insecticidal activity against S. calcitrans. Therefore, it can be used as an alternative to synthetic insecticides for achieving stable fly control. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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25 pages, 2262 KiB

Open AccessArticle

Secondary Metabolites in Basil, Bio-Insecticide, Inhibition Effect, and In Silico Molecular Docking against Proteolytic Enzymes of the Red Palm Weevil (Rhynchophorus ferrugineus)

by Hossam Moustafa Darrag, Hani Taher Almuhanna and Emadaldeen Hamad Hakami

Plants 2022, 11(8), 1087; https://doi.org/10.3390/plants11081087 - 16 Apr 2022

Cited by 15 | Viewed by 3600

Abstract

The purpose of this work was to determine the secondary metabolites generated by O. basilicum cell suspensions, as well as their insecticide and inhibitory activity against R. ferrugineus. The growth kinetics with inoculation Verticillium dahliae were determined and identified using LC-MS. Determination of total phenolic components (TFC), flavonoids (TF), and condensed tannins (TCT) were measured. Insecticidal activity of O. basilicum extract against R. ferrugineus (larva and adult) and proteolytic enzymes activity were assessed (in vitro and in vivo). The O.basilicum extract had an LC₅₀ of 1238 µg/mL and an LD₅₀ of 13.4 µg/larva. The LC₅₀ of chicoric acid, ursolic acid, salvigenin, quercetin-3-O-rutinoside, rosmarinyl glucoside, and nepetoidin B demonstrated activity at an LC₅₀ of 1132, 1167, 1189, 1214, 1275, and 1317 µg/mL, respectively. Chicoric acid, salvigenin, nepetoidin B, and rosmarinic acid demonstrated an LD₅₀ activity of 10.23, 11.4, 11.9, and 12.4 µg/larva, respectively. The active extract of O. basilicum inhibited total protease, trypsin-like serine proteinases, elastase, cysteine, and metalloprotease activity with an IC₅₀ (in vitro) of 119.4, 91, 102.4, 76.4, and 52.4 µg/mL, respectively. In silico studies of compounds were conducted, such as molecular docking and ADMET analysis. The study proposes using an efficient cell suspension technique to produce O. basilicum extract containing active secondary metabolites and accessible using as bio-insecticide. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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13 pages, 1826 KiB

Open AccessArticle

Origanum vulgare Essential Oil against Tenebrio molitor (Coleoptera: Tenebrionidae): Composition, Insecticidal Activity, and Behavioral Response

by Angelica Plata-Rueda, José Cola Zanuncio, José Eduardo Serrão and Luis Carlos Martínez

Plants 2021, 10(11), 2513; https://doi.org/10.3390/plants10112513 - 19 Nov 2021

Cited by 16 | Viewed by 5292

Abstract

Tenebrio molitor is one of the main stored product pests. This study characterized oregano essential oil (OEO) by gas chromatography (GC/FID and GC/MS) and assessed its insecticidal properties against T. molitor. Mortality, survival, respiration, and behavioral response in larva, pupa, and adult of this insect were determined. The major components of OEO were carvacrol (25.6%), p-cymene (12.3%), linalool (8.71%), thymol (7.22%), γ-terpinene (7.21%), caryophyllene oxide (4.67%), α-pinene (2.71%), and eucalyptol (2.69%). OEO caused high contact toxicity in larvae (LD₅₀ = 3.03 µg insect^–1), pupae (LD₅₀ = 5.01 µg insect^–1), and adults (LD₅₀ = 5.12 µg insect⁻¹) of T. molitor. Survival rates were 100% in larvae, pupae, and adults of T. molitor not treated with OEO, declining to 65–54%, 38–44%, 30–23%, and 6–2% in insects treated with LD₂₅, LD₅₀, LD₇₅, and LD₉₀, respectively. Low respiration rates of T. molitor at different developmental stages was observed after OEO exposure. Additionally, OEO exposure affects behavioral avoidance response and causes repellency in larvae and adults. These findings show that OEO exerts insecticidal and repellent effects against T. molitor, suggesting a potent alternative to synthetic insecticides for controlling the beetle. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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20 pages, 3504 KiB

Open AccessArticle

Potential of Essential Oils from Anise, Dill and Fennel Seeds for the Gypsy Moth Control

by Igor Kostić, Jelica Lazarević, Darka Šešlija Jovanović, Miroslav Kostić, Tatjana Marković and Slobodan Milanović

Plants 2021, 10(10), 2194; https://doi.org/10.3390/plants10102194 - 15 Oct 2021

Cited by 22 | Viewed by 2855

Abstract

The gypsy moth (Lymantria dispar L. (Lepidoptera: Erebidae)) is a serious pest of hardwood forests. In the search for an environmentally safe means of its control, we assessed the impact of different concentrations of essential oils (EOs) from the seeds of three Apiaceae plants (anise Pimpinella anisum, dill Anethum graveolens, and fennel Foeniculum vulgare) on behavior, mortality, molting and nutritional physiology of gypsy moth larvae (GML). EOs efficacy was compared with commercial insecticide NeemAzal^®-T/S (neem). The main compounds in the Eos were trans-anethole in anise; carvone, limonene, and α-phellandrene in dill; and trans-anethole and fenchone in fennel seed. At 1% EOs concentration, anise and fennel were better antifeedants and all three EOs were more toxic than neem. Neem was superior in delaying 2nd to 3rd larval molting. In the 4th instar, 0.5%, anise and fennel EOs decreased relative consumption rate more than neem, whereas all three EOs were more effective in reducing growth rate, approximate digestibility and efficiency of conversion of food into body mass leading to higher metabolic costs to GML. Decrease in consumption and metabolic parameters compared to control GML confirmed that adverse effects of the EOs stem from both pre- and post-ingestive mechanisms. The results indicate the potential of three EOs to be used for gypsy moth control. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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Review

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22 pages, 15459 KiB

Open AccessFeature PaperEditor’s ChoiceReview

A Review of the Chemistry and Biological Activities of Acmella oleracea (“jambù”, Asteraceae), with a View to the Development of Bioinsecticides and Acaricides

by Eleonora Spinozzi, Marta Ferrati, Cecilia Baldassarri, Loredana Cappellacci, Margherita Marmugi, Alice Caselli, Giovanni Benelli, Filippo Maggi and Riccardo Petrelli

Plants 2022, 11(20), 2721; https://doi.org/10.3390/plants11202721 - 14 Oct 2022

Cited by 15 | Viewed by 5019

Abstract

Human pathologies, environmental pollution, and resistance phenomena caused by the intensive use of chemical pesticides have shifted the attention of the agrochemical industries towards eco-friendly insecticides and acaricides. Acmella oleracea (L.) R. K. Jansen (jambù) is a plant native to South America, widely distributed and cultivated in many countries due to its numerous pharmacological properties. This review analyzes literature about the plant, its uses, and current knowledge regarding insecticidal and acaricidal activity. Acmella oleracea has proven to be a potential pesticide candidate against several key arthropod pest and vector species. This property is inherent to its essential oil and plant extract, which contain spilanthol, the main representative of N-alkylamides. As a result, there is a scientific basis for the industrial exploitation of jambù in the preparation of green insecticides. However, studies related to its toxicity towards non-target species and those aimed at formulating and developing marketable products are lacking. Full article

(This article belongs to the Special Issue Insecticidal Activity of Plant Secondary Metabolites)

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