Essential Oil of Rosmarinus officinalis Ecotypes and Their Major Compounds: Insecticidal and Histological Assessment Against Drosophila suzukii and Their Impact on a Nontarget Parasitoid.

Essential oils (EOs) produced by plants in the Lamiaceae family may provide new insecticidal molecules. Novel control compounds are needed to control Drosophila suzukii (Matsumura), a severe economic invasive pest of thin-skinned fruit crops. Thus, we characterized the main compounds of EOs from three rosemary Rosmarinus officinalis ecotypes (ECOs) and evaluated their toxicity to D. suzukii adults, deterrence of oviposition behavior, and histological alterations in larvae. Additionally, we analyzed the lethal and sublethal effect on the pupal parasitoid Trichopria anastrephae. The main compounds identified in the R. officinalis ECOs were α-pinene, camphor and 1,8-cineole. In bioassays via topical application or ingestion, ECOs and their major compounds showed high toxicity on D. suzukii adults and a lower concentration could kill 50% and 90% of flies compared to spinetoram. The dry residues of a-pinene, 1,8-cineole, and camphor provided a repellent effect by reducing D. suzukii oviposition by ~47% compared to untreated fruit. Histological sections of 3rd instar larval D. suzukii posttreatment revealed damage to the fat body, Malpighian tubules, brain, salivary gland, and midgut, which contributed to high larval and pupal mortality. Survival and parasitism by adult T. anastrephae were not affected. Thus, R. officinalis EO and their compounds have potential for developing novel insecticides to manage D. suzukii.

Insecticidal and oviposition deterrent effects of essential oils of Baccharis spp. and histological assessment against Drosophila suzukii (Diptera: Drosophilidae).

The diverse flora of the Atlantic Forest is fertile ground for discovering new chemical structures with insecticidal activity. The presence of species belonging to the genus Baccharis is of particular interest, as these species have shown promise in pest management applications. The objective of this study is to chemically identify the constituents expressed in the leaves of seven species of Baccharis (B. anomala DC., B. calvescens DC., B. mesoneura DC., B. milleflora DC., B. oblongifolia Pers., B. trimera (Less) DC. and B. uncinella DC.) and to evaluate the toxicological and morphological effects caused by essential oils (EOs) on the larvae and adults of Drosophila suzukii (Diptera: Drosophilidae). Chemical analysis using gas chromatography-mass spectrometry (GC-MS) indicated that limonene was the main common constituent in all Baccharis species. This constituent in isolation, as well as the EOs of B. calvescens, B. mesoneura, and B. oblongifolia, caused mortality in over 80% of adults of D. suzukii at a discriminatory concentration of 80 mg L-1 in bioassays of ingestion and topical application. These results are similar to the effect of spinosyn-based synthetic insecticides (spinetoram 75 mg L-1) 120 h after exposure. Limonene and EOs from all species had the lowest LC50 and LC90 values relative to spinosyn and azadirachtin (12 g L-1) in both bioassays. However, they showed the same time toxicity over time as spinetoram when applied to adults of D. suzukii (LT50 ranging from 4.6 to 8.7 h) in a topical application bioassay. In olfactometry tests, 92% of D. suzukii females showed repellent behavior when exposed to the EOs and limonene. Likewise, the EOs of B. calvescens, B. mesoneura, and B. oblongifolia significantly reduced the number of eggs in artificial fruits (≅ 7.6 eggs fruit-1), differing from the control treatment with water (17.2 eggs fruit-1) and acetone (17.6 eggs fruit-1). According to histological analyses, the L3 larvae of D. suzukii had morphological and physiological alterations and deformations after exposure to treatments containing EOs and limonene, which resulted in high larval, pupal, and adult mortality. In view of the results, Baccharis EOs and their isolated constituent, limonene, proved to be promising alternatives for developing bioinsecticides to manage of D. suzukii.

Identification of Zingiberenol and Murgantiol as Components of the Aggregation-Sex Pheromone of the Rice Stink Bug, Mormidea v-luteum (Heteroptera: Pentatomidae).

Mormidea v-luteum (Lichtenstein, 1796) feeds on commercial crops, such as rice and ryegrass, causing damage that slows growth and reduces productivity. With the aim of developing an eco-friendly control technique, we investigated the compounds involved in chemical communication in this species. The volatiles produced by a group of seven males or females allocated to different aerated glass chambers were collected for 24 h and analyzed by gas chromatograph/mass spectrometry and gas chromatography/Fourier transform infrared spectroscopy. The analyses showed six male-specific compounds, identified as two isomers of zingiberenol (compounds 1 and 2), three isomers of murgantiol (3, 5 and 6) and sesquipiperitol (4). Compounds 1 and 5 were the major components and were produced in a ratio of 6:4. The absolute stereochemistry of the two isomers of zingiberenol was established as (1S,4R,1'S)-1 and (1R,4R,1'S)-2 by chiral gas chromatography. Stereochemistry was not determined for all the other molecules. To confirm the attractiveness of these chemicals, bioassays were performed in a Y-tube olfactometer, first using crude extracts and, subsequently, synthetic compounds. Male volatiles were attractive to both sexes, demonstrating an aggregation pheromone. In bioassays with synthetic compounds, (1'S)-zingiberenol was highly attractive to both males and females. However, when (1'S)-murgantiol was tested, only females were attracted. Interestingly, when a mixture of zingiberenol and murgantiol isomers was tested, it was attractive to both sexes, with females more attracted to the mixture than to zingiberenol alone; males did not distinguish between treatments. Thus, the bioassay data suggest that the molecules have different functions in chemical communication of this species: zingiberenol acts primarily as an aggregation pheromone, while murgantiol plays a role as a sex pheromone.

Camphor and Borneol as the Male-Produced Sex Pheromone of the Shield Bug, Orsilochides leucoptera (Hemiptera: Scutelleridae).

The ability of stink bugs to release high amounts of strong-smelling and irritating defensive compounds is related to their metathoracic gland (MTG), which is an exocrine gland with defensive, sexual, alarm and aggregation signal functions. Orsilochides leucoptera (Scutelleridae) is a widespread species in the Neotropical region that feeds on plants of the families Malvaceae, Poaceae and Euphorbiaceae. A series of compounds (ketones, alcohols and esters) have been identified in the MTGs among the three species of Scutelleridae whose MTG secretions have been investigated thus far; however, no sex pheromone compounds have been described for any scutellerid species. The aim of this work was to study sex pheromone communication within this family of stink bugs, and identify the compounds present in the MTG of O. leucoptera. Analysis by gas chromatography/mass spectrometry (GC/MS) revealed two male specific compounds identified as (R)-camphor (1) and (R)-borneol (2), which were attractive to females in Y-tube olfactometer bioassays. Also, GC/MS analysis of secretions from MTG of males and females of O. leucoptera, identified eight additional compounds: 2-(E)-hexenal (3), (E)-4-oxo-2-hexenal (4), (E)-hex-2-enyl acetate (5), (R)-linalool (6), (R)-α-terpineol (7), dodecane (8), 1-tridecene (9) and n-tridecane (10). From these, (R)-α-terpineol was detected only in the gland of males, and is probably a biosynthetic intermediate of the pheromone components. Most of the MTG compounds identified in O. leucoptera have been identified in other heteropteran species. Camphor is often a toxic and repellent compound for insects. However, we report it, for the first time, as a sex pheromone component of an insect.

Chemical composition of essential oils of selected species of Piper and their insecticidal activity against Drosophila suzukii and Trichopria anastrephae.

The present study aimed to analyze the chemical composition of five species of the genus Piper (P. aduncum L.; P. crassinervium Kunth.; P. malacophyllum Prels.; P. gaudichaudianum Kunth.; P. marginatum L.), and assess their toxicity to the adults of Drosophila suzukii (Diptera: Drosophilidae) and the pupal parasitoid Trichopria anastrephae Lima (Hymenoptera: Diapriidae). The major compounds were monoterpene hydrocarbons (5.3-60.9%); oxygenated monoterpenes (13.3%); sesquiterpenes hydrocarbons (8.3-45.3%), oxygenated sesquiterpenes (5.2-58.8%); and arylpropanoids (15.2-29.6%). In bioassays of ingestion and topical application, essential oils (EOs) from P. aduncum, P. gaudichaudianum, and P. marginatum killed approximately 100% of adults of D. suzukii, similarly to the insecticide based on spinetoram (75 mg L-1) (96.2% of mortality). Besides, the dry residues from P. aduncum, P. gaudichaudianum, and P. marginatum provided a repellent effect on oviposition (≅ 7 eggs/fruits) and negative effects on egg viability (≅ 2 larvae/fruits) of D. suzukii on artificial fruits. Based on the estimate of the lethal concentration required to kill 90% of exposed flies, EOs from P. aduncum, P. crassinervium, P. gaudichaudianum, P. malacophyllum, and P. marginatum provided low toxicity to the parasitoid T. anastrephae in a bioassay of ingestion and topical application (mortality < 20%), similarly to the water treatment (≅ 5% of mortality). EOs of Piper species tested in this work showed to be promising plant insecticides for the management of D. suzukii.