Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides.

A series of 19 novel eugenol derivatives containing a 1,2,3-triazole moiety was synthesized via a two-step process, with the key step being a copper(I)-catalyzed azide-alkyne cycloaddition reaction. The compounds were assessed for their antifungal activities against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. Triazoles 2k, 2m, 2l, and 2n, at 100 ppm, were the most effective, reducing mycelial growth by 88.3, 85.5, 82.4, and 81.4%, respectively. Molecular docking calculations allowed us to elucidate the binding mode of these derivatives in the catalytic pocket of C. gloeosporioides CYP51. The best-docked compounds bind closely to the heme cofactor and within the channel access of the lanosterol (LAN) substrate, with crucial interactions involving residues Tyr102, Ile355, Met485, and Phe486. From such studies, the antifungal activity is likely attributed to the prevention of substrate LAN entry by the 1,2,3-triazole derivatives. The triazoles derived from natural eugenol represent a novel lead in the search for environmentally safe agents for controlling C. gloeosporioides.

Leishmanicidal activity and 4D quantitative structure-activity relationship and molecular docking studies of vanillin-containing 1,2,3-triazole derivatives.

Aim: The assessment of the antileishmanial potential of 22 vanillin-containing 1,2,3-triazole derivatives against Leishmania braziliensis is reported. Materials & methods: Initial screening was performed against the parasite promastigote form. The most active compound, 4b, targeted parasites within amastigotes (IC50 = 4.2 ± 1.0 µmol l-1), presenting low cytotoxicity and a selective index value of 39. 4D quantitative structure-activity relationship and molecular docking studies provided insights into structure-activity and biological effects. Conclusion: A vanillin derivative with significant antileishmanial activity was identified. Enhanced activity was linked to increased electrostatic and Van der Waals interactions near the benzyl ring of the derivatives. Molecular docking indicated the inhibition of the Leishmania amazonensis sterol 14α-demethylase, using Leishmania infantum sterol 14α-demethylase as a model, without affecting the human isoform. Inhibition was active site competition with lanosterol.

Synthesis of 1,2,3-Triazole-Containing Methoxylated Cinnamides and Their Antileishmanial Activity against the Leishmania braziliensis Species.

Leishmaniasis is a group of infectious diseases caused by protozoan parasites that belong to the genus Leishmania. Currently, there is no human vaccine, and the available treatments are associated with toxicity, high cost, and the emergence of resistant strains. These factors highlight the need to identify new antileishmanial candidates. In this study, we synthesized twenty-four methoxylated cinnamides containing 1,2,3-triazole fragments and evaluated their antileishmanial activity against the Leishmania braziliensis species, which is the main etiological agent responsible for American Tegumentary Leishmaniasis (ATL). The cinnamides were synthetically prepared using nucleophilic acyl substitution and copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. The compounds were characterized using infrared, nuclear magnetic resonance, and high-resolution mass spectrometry techniques. We performed preliminary studies to evaluate the biological activity of these compounds against L. braziliensis promastigotes and axenic amastigotes. Compound 28, N-((1-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazole-4-yl) methyl)-3,4-dimethoxy cinnamide, demonstrated relevant antileishmanial activity with low toxicity in murine cells. The selectivity index values for this compound were superior compared with data obtained using amphotericin B. Furthermore, this cinnamide derivative reduced the infection percentage and number of recovered amastigotes in L. braziliensis-infected macrophages. It also induced an increase in reactive oxygen species production, depolarization of the mitochondrial potential, and disruption of the parasite membrane. Taken together, these findings suggest that this synthetic compound holds potential as an antileishmanial candidate and should be considered for future studies in the treatment of ATL.

Methoxylated Cinnamic Esters with Antiproliferative and Antimetastatic Effects on Human Lung Adenocarcinoma Cells.

Lung cancer is the leading cause of cancer mortality worldwide, and malignant melanomas are highly lethal owing to their elevated metastatic potential. Despite improvements in therapeutic approaches, cancer treatments are not completely effective. Thus, new drug candidates are continuously sought. We synthesized mono- and di-methoxylated cinnamic acid esters and investigated their antitumor potential. A cell viability assay was performed to identify promising substances against A549 (non-small-cell lung cancer) and SK-MEL-147 (melanoma) cells. (E)-2,5-dimethoxybenzyl 3-(4-methoxyphenyl)acrylate (4m), a monomethoxylated cinnamic acid derivative, was identified as the lead antitumor compound, and its antitumor potential was deeply investigated. Various approaches were employed to investigate the antiproliferative (clonogenic assay and cell cycle analysis), proapoptotic (annexin V assay), and antimigratory (wound-healing and adhesion assays) activities of 4m on A549 cells. In addition, western blotting was performed to explore its mechanism of action. We demonstrated that 4m inhibits the proliferation of A549 by promoting cyclin B downregulation and cell cycle arrest at G2/M. Antimigratory and proapoptotic activities of 4m on A549 were also observed. The antitumor potential of 4m involved its ability to modulate the mitogen-activated protein kinases/extracellular signal-regulated kinase (MAPK/ERK) signaling pathway once phosphorylated-ERK expression was considerably reduced in response to treatment. Our findings demonstrate that 4m is a promising anticancer drug candidate.

Synthesis and Fungicide Activity on Asperisporium caricae of Glycerol Derivatives Bearing 1,2,3-Triazole Fragments.

In agriculture, the control of fungal infections is essential to improve crop quality and productivity. This study describes the preparation and fungicidal activity evaluation of 12 glycerol derivatives bearing 1,2,3-triazole fragments. The derivatives were prepared from glycerol in four steps. The key step corresponded to the Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click reaction between the azide 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes (57-91% yield). The compounds were characterized by infrared spectroscopy, nuclear magnetic resonance (1H and 13C), and high-resolution mass spectrometry. The in vitro assessment of the compounds on Asperisporium caricae, that is, the etiological agent of papaya black spot, at 750 mg L-1 showed that the glycerol derivatives significantly inhibited conidial germination with different degrees of efficacy. The most active compound 4-(3-chlorophenyl)-1-((2,2-dimethyl-1,3-dioxolan-4-yl) methyl)-1H-1,2,3-triazole (4c) presented a 91.92% inhibition. In vivo assays revealed that 4c reduced the final severity (70.7%) and area under the disease severity progress curve of black spots on papaya fruits 10 days after inoculation. The glycerol-bearing 1,2,3-triazole derivatives also present agrochemical-likeness properties. Our in silico study using molecular docking calculations show that all triazole derivatives bind favorably to the sterol 14α-demethylase (CYP51) active site at the same region of the substrate lanosterol (LAN) and fungicide propiconazole (PRO). Thus, the mechanism of action of the compounds 4a-4l may be the same as the fungicide PRO, blocking the entrance/approximation of the LAN into the CYP51 active site by steric effects. The reported results point to the fact that the glycerol derivatives may represent a scaffold to be explored for the development of new chemical agents to control papaya black spot.

Synthesis and virucide activity on zika virus of 1,2,3-triazole-containing vanillin derivatives.

The Zika virus (ZIKV) is an arbovirus and belongs to the Flaviviridae family and Flavivirus genus, with dissemination in the Americas. In Brazil, the predominant strain is the Asian, promoting outbreaks that started in 2015 and are directly related to microcephaly in newborns and Guillain-Barré syndrome in adults. Recently, researchers identified a new African strain circulating in Brazil at the mid-end of 2018 and the beginning of 2019, with the potential to originate a new epidemic. To date, there is no approved vaccine or drug for the treatment of Zika syndrome, and the development of therapeutic alternatives to treat it is of relevance. A critical approach is to use natural products when searching for new chemical agents to treat Zika syndrome. The present investigation describes the preparation of a series of 1,2,3-triazoles derived from the natural product vanillin and the evaluation of their virucide activity. A series of fourteen derivatives were prepared via alkylation of vanillin followed by CuAAC (the copper(I)-catalyzed azide-alkyne cycloaddition) reaction. The compounds were fully characterized by infrared (I.R.), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS) techniques. The cytotoxicity of Vero cells and the effect on the Zika Virus of the vanillin derivatives were evaluated. It was found that the most effective compound corresponded to 4-((1-(4-isopropylbenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxybenzaldehyde (8) (EC50 = 27.14 µM, IC50 = 334.9 µM). Subsequent assessments, namely pre and post-treatment assays, internalization and adsorption inhibition assays, kinetic, electronic microscopy analyses, and zeta potential determination, revealed that compound 8 blocks the Zika virus infection in vitro by acting on the viral particle. A molecular docking study was performed, and the results are also discussed.

Synthesis and Phytotoxic Evaluation of Isatin Derivatives Supported by 3D-QSAR Study.

Concerned about weed infestation, a major threat to food production and herbicide resistance that interferes in the mechanism of action of the main herbicides, we have synthesized eight isatin derivatives using the "Click Chemistry" approach through copper-catalyzed azide-alkyne cycloadditions (CuAAC). Sixteen isatin derivatives were evaluated for their phytotoxic activity against the seed culture of the model plants, Lactuca sativa and Allium cepa. Six of them showed phytotoxic activity similar to the positive control, trifluralin. Hypocotyl length measurement analysis in L. sativa revealed that triazole derivative 8 is more active than trifluralin. For A. cepa, root length measurement analyses revealed that 3, 10, 14, 16, and 17 were similar to the positive control trifluralin. Three-dimensional quantitative structure-activity relationship (3D-QSAR) comparative molecular field analysis (CoMFA) model construction using the acetolactate synthase (ALS) crystallographic structure displayed pki values of predicted inhibitory activity and contour maps revealing sterically bulky groups for 11, the CF3 group in ortho, and for 17, Br in ortho, favoring the inhibitory ALS activity.

Eugenol derivatives with 1,2,3-triazole moieties: Oral treatment of cutaneous leishmaniasis and a quantitative structure-activity relationship model for their leishmanicidal activity.

Leishmaniasis is a group of neglected vector-borne tropical diseases caused by protozoan parasites of the genus Leishmania that multiply within phagocytic cells and have a wide range of clinical manifestations. Cutaneous leishmaniasis (CL) is a serious public health that affects more than 98 countries, putting 350 million people at risk. There are no vaccines that have been proven to prevent CL, and the treatment relies on drugs that often have severe side effects, justifying the search for new antileishmanial treatments. In the present investigation, it is demonstrated that 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-(4-methylbenzyl)-1H-1,2,3-triazole (7k) presents significant antileishmanial activity (IC50 of 7.4 µmol L-1 and 1.6 µmol L-1 for promastigote and amastigote forms, respectively), low cytotoxicity against macrophage cells (IC50 of 211.9 µmol L-1), and a selective index of 132.5. Under similar conditions, compound 7k outperformed glucantime and pentamidine, two commonly used drugs in clinics. In vivo assays on CL-infected female BALB/c mice demonstrated that compound 7k had activity similar to intralesional glucantime when administered orally, with decreased lesion and parasitic load, and a low systemic toxic effect. Given the importance of understanding the relationship between compound structure and biological activity in the research and development of new drugs, the development of a quantitative structure-activity relationship (QSAR) model for the leishmanicidal activity presented by the eugenol derivatives with 1,2,3-triazole functionalities is also described herein. This study demonstrates the therapeutic potential of orally active eugenol derivatives against CL and provides useful insights into the relationship between the chemical structures of triazolic eugenol derivatives and their biological profile.

Bioactivity of Meliaceae, Amaryllidaceae, Solanaceae and Amaranthaceae plant aqueous extracts against the cattle tick Rhipicephalus microplus.

Commercial synthetic acaricides have selected resistant populations of Rhipicephalus microplus, and generate residues in the environment or in milk/cattle products. In this study, aqueous extracts (AE) from Melia azedarach (Maz), Allium sativum, Capsicum chinense, Nicotiana tabacum (Nta) and Dysphania ambrosioides were evaluated for the bioactivity against the cattle tick. The treatment using Nta or Maz AE resulted in the lowest egg hatching rate (34.0 ± 11% and 25.0 ± 19%), and in the values of reproduction inhibition ranging from 89.0% to 85.3%. Phytochemical screening associated to RP-HPLC/DAD analysis suggested the presence of alkaloids for Nta and gallic acid derivatives and catechins, for Maz. Such results highlighted that the use of Nta and Maz AE can be a promising source of bioactive compounds for the control of infections caused by the cattle tick.

Chemical composition and effect of Dysphania ambrosioides (L.) mosyakin & clemants essential oil on Biomphalaria tenagophila (D'Orbigny, 1835).

Dysphania ambrosioides (L.) Mosyakin & Clemants, known as santa maria herb, is a medicinal plant used on pest control and to treat parasitic diseases. Due to its potential for pest control, the aim of this work was to determine the chemical composition of D. ambrosioides essential oil and evaluate its molluscicidal effect on Biomphalaria tenagophila, which is an intermediate host for the Schistosoma mansoni trematode, that is responsible for causing human schistosomiasis. The essential oil extracted from its leaves showed 87% of (Z)-ascaridole and 100% of mortality against B. tenagophila at 10 ppm after 24 h of experiment. LC50 and LC90 values were, respectively, 2.40 (1.90-2.99) ppm and 8.75 (6.39-14.12) ppm. D. ambrosioides essential oil proved to be a promising natural molluscicide against schistosomiasis when compared with commercial products.

Evaluation of genetic divergence of coffee genotypes using the volatile compounds and sensory attributes profile.

The quality of the coffee beverage is related to the chemical, physical, and sensory attributes of the coffee beans that vary with the geographic location of the crop, genetic factors, and post-harvest processing. So, the objective of this study was to evaluate the genetic divergence of 27 genotypes of Coffea canephora using the volatile compounds and sensory attributes profile to select genotypes that produce a coffee beverage with high sensory quality. This genetic diversity was estimated from the Euclidean distance matrix using non-standard data and the Unweighted Pair-Group Method Using Arithmetic Averages (UPGMA). The 2-furyl-methanol, 4-ethenyl-2-methoxyphenol, furfural, 5-methylfurfural, methylpyrazine, and 2,6-dimethylpyrazine were predominating volatile compounds in the genotypes. The sensory attributes had a positive Pearson's correlation with the total score. The volatile compounds had a different relative contribution to the genetic divergence between the genotypes of C. canephora. The 4-ethenyl-2-methoxyphenol, 2-furyl-methanol, and furfural were volatile compounds that most contributed to the formation of the groups in the UPGMA dendrogram. The relative contribution of sensory attributes to dissimilarity among genotypes was 6.42% to 20.20%. Therefore, this study verified the relative contribution of volatile compounds, in specially 4-ethenyl-2-methoxyphenol, 2-furyl-methanol, and furfural, and sensory attributes (flavor, mouthfeel, and bitterness/sweetness) to the genetic divergence between the genotypes of the three clonal varieties. Thus, this work points out compounds that positively contribute to the sensory quality of the Conilon coffee beverage.

Thymol as an Interesting Building Block for Promising Fungicides against Fusarium solani.

The semisynthesis of 15 new thymol derivatives was achieved through Williamson synthesis and copper-catalyzed azide-alkyne cycloaddition (CuAAC) approaches. The reaction of CuAAC using the "Click Chemistry" strategy, in the presence of an alkynyl thymol derivative and commercial or prepared azides, provided nine thymol derivatives under microwave irradiation. This procedure reduces reaction time and cost. All molecular entities were elucidated by 1H and 13C NMR, IR, and HRMS data. These derivatives were evaluated in vitro for their fungicidal activity against Fusarium solani sp. Among the nine triazolic thymol derivatives obtained, seven of them were found to have moderated antifungal activity. In contrast, naphthoquinone/thymol hybrid ether 2b displayed activity comparable with that of the commercial fungicide thiabendazole. The structure-activity relationship for the most active compound 2b was discussed, and the mode of action was predicted by a possible binding to the fungic ergosterol and interference of osmotic balance of K+ into the extracellular medium.

Environmental risk assessment for sustainable pesticide use in coffee production.

The extensive use of pesticides in agricultural practices has been associated with human health problems and environmental contamination worldwide. Brazil is the largest consumer of pesticides in the world and Espírito Santo State stands out as the second Brazilian producer of coffee. However, there is no information about environmental impact of coffee producing at Itapemirim River Basin (IRB) region, Espírito Santo State, Brazil; hence a simple and quick method using open access softwares (AGROSCRE and ARAquá Web) to estimate surface entrainment and pesticide leaching potential was carried out. AGROSCRE evaluates the contamination risk of superficial and groundwater by Active Ingredients (AIs), using GOSS Method, GUS index and US EPA criteria, while ARAquá Web estimates AI concentrations in water resources, indicating their suitability based on water quality requirements for different uses. Regarding pesticides used in coffee plantations, there is 44.7% chance of surface water and 23.7% chance of groundwater contamination. Results showed that ametryne, cyproconazole, diuron, epoxiconazole, flutriafol, triadimenol and triazophos pose contamination risk to both surface water and groundwater in the IRB region. Of these, 10.5% of the total AIs are triazoles and fall under environmental classes II and III (Product Very/Dangerous to the Environment). The AIs ametryne, thiamethoxam, iprodione, flutriafol, triazophos, endosulfan, triadimenol, cyproconazole, diuron, pendimethalin, chlorpyrifos, copper II hydroxide, etion, epoxiconazole and paraquat dichloride, were found to be potentially toxic, presenting environmental concentrations ranging from 123.40 µg L-1 to 0.14 µg L-1, which are higher than the safety standard for potable water (0.1 µg L-1). With respect to these AIs, chlorpyrifos, ethion and triazophos showed concentrations higher than EC50 values for aquatic invertebrates and ametryne and diuron for algae. Thus, local residents and environment may be at high risk of pesticide exposure, when these AIs are used in coffee plantations next to surface water or groundwater.

Semisynthetic Phenol Derivatives Obtained from Natural Phenols: Antimicrobial Activity and Molecular Properties.

Semisynthetic phenol derivatives were obtained from the natural phenols: thymol, carvacrol, eugenol, and guaiacol through catalytic oxychlorination, Williamson synthesis, and aromatic Claisen rearrangement. The compounds characterization was carried out by 1H NMR, 13C NMR, and mass spectrometry. The natural phenols and their semisynthetic derivatives were tested for their antimicrobial activity against the bacteria: Staphylococcus aureus, Escherichia coli, Listeria innocua, Pseudomonas aeruginosa, Salmonella enterica Typhimurium, Salmonella enterica ssp. enterica, and Bacillus cereus. Minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) values were determined using concentrations from 220 to 3.44 µg mL-1. Most of the tested compounds presented MIC values ≤220 µg mL-1 for all the bacteria used in the assays. The molecular properties of the compounds were computed with the PM6 method. Through principle components analysis, the natural phenols and their semisynthetic derivatives with higher antimicrobial potential were grouped.

Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities.

The synthesis of a series of 1,2,3-triazoles using glycerol as starting material is described. The key step in the preparation of these triazolic derivatives is the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), also known as click reaction, between 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes. The eight prepared derivatives were evaluated with regard to their fungicide, phytotoxic and cytotoxic activities. The fungicidal activity was assessed in vitro against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. It was found that the compounds 1-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazol-4-yl)-cyclo-hexanol (4g) and 2-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazol-4-yl)propan-2-ol (4h) demonstrated high efficiency in controlling C. gloeosporioides when compared to the commercial fungicide tebuconazole. The triazoles did not present any phytotoxic effect when evaluated against Lactuca sativa. However, five derivatives were mitodepressive, inducing cell death detected by the presence of condensed nuclei and acted as aneugenic agents in the cell cycle of L. sativa. It is believed that glycerol derivatives bearing 1,2,3-triazole functionalities may represent a promising scaffold to be explored for the development of new agents to control C. gloeosporioides.

Spatial and temporal distribution of urban heat islands.

The formation of an urban heat island (UHI) is one of the most common impacts of the urbanization process. To mitigate the effects of UHI, the planning of urban forests (e.g., creation of parks, forests and afforestation streets) has been the major tool applied in this context. Thus, the aim of this study is to evaluate the spatial and temporal distribution of heat islands in Vila Velha, ES, Brazil using the mono-window algorithm. The study followed these methodological steps: 1) mapping of urban green areas through a photointerpretation screen; 2) application of the mono-window algorithm to obtain the spatial and temporal patterns of land surface temperature (LST); 3) correlation between LST and the normalized difference vegetation index (NDVI) and normalized difference build-up index (NDBI); 4) application of ecological evaluation index. The results showed that the mean values of LST in urban areas were at least 2.34 to 7.19°C higher than undeveloped areas. Moreover, the positive correlation between LST and NDBI showed an amplifying effect of the developed areas for UHI, while areas with a predominance of vegetation attenuated the effect of UHI. Urban centers, clustered in some parts of the city, received the worst ecological assessment index. Finally, the adoption of measures to guide the urban forest planning within urban centers is necessary to mitigate the effect of heat islands and provide thermal comfort in urban areas.

Phytotoxicity and Cytotoxicity of Essential Oil from Leaves of Plectranthus amboinicus, Carvacrol, and Thymol in Plant Bioassays.

The essential oil of Plectranthus amboinicus and its chemotypes, carvacrol and thymol, were evaluated on the germination and root and aerial growth of Lactuca sativa and Sorghum bicolor and in acting on the cell cycle of meristematic root cells of L. sativa. The main component found in the oil by analysis in gas chromatography-mass spectrometry and gas chromatography flame ionization detection was carvacrol (88.61% in area). At a concentration of 0.120% (w v(-1)), the oil and its chemotypes retarded or inhibited the germination and decreased root and aerial growth in monocot and dicot species used in the bioassays. In addition, all substances caused changes in the cell cycle of the meristematic cells of L. sativa, with chromosomal alterations occurring from the 0.015% (w v(-1)) concentration. The essential oil of P. amboinicus, carvacrol, and thymol have potential for use as bioherbicides.

Ethanol extract of Cymbopogon winterianus on mortality and number of eggs of Tetranychus urticae / Extrato etanólico de Cymbopogon winterianus na mortalidade e no número de ovos de Tetranychus urticae

Plant extracts have been studied as a promising source of natural insecticides. This study assessed the effect of the ethanol extract of Cymbopogon winterianus Jowitt (citronella grass) in comparison with an insecticide containing azadirachtin (ICA) on mortality and number of eggs of Tetranychus urticae Koch (Acari: Tetranychidae) in laboratory conditions. For the tests, the mites were sprayed with the aid of a Potter spray tower. To assess the mortality of females, LC50 value for extract of citronella grass and ICA was, respectively, 2.63 and 2.83%. With respect to the number of eggs, the greatest reduction was observed at a concentration of 5% for the evaluation period of 120h, both for the extract of citronella grass (86%) and for ICA (81%). These results suggest the potential of the ethanol extract of citronella grass to control of T. urticae. However, experiments, under field conditions, involving other populations of T. urticae should be performed to verify the efficacy of this extract as an alternative to be used in pest management programs.

Extratos vegetais têm sido estudados como uma fonte promissora de inseticidas naturais. Neste trabalho, foi avaliado o efeito do extrato etanólico de Cymbopogon winterianus Jowitt (capim-citronela) em comparação com um inseticida contendo azadiractina (ICA) sobre a mortalidade e o número de ovos de Tetranychus urticae Koch (Acari: Tetranychidae), em condições de laboratório. Para a realização dos ensaios, os ácaros foram pulverizados com o auxílio da torre de Potter. Para o teste de avaliação da mortalidade de fêmeas, a CL50, para o extrato de capim-citronela e ICA, foi, respectivamente, 2,63 e 2,83%. Em relação ao número de ovos, a maior redução foi observada na concentração de 5% no intervalo de avaliação de 120h, tanto para o extrato de capim-citronela (86%) quanto para o ICA (81%). Estes resultados sugerem que o extrato etanólico de capim-citronela apresenta potencial para ser utilizado no controle de T. urticae. Entretanto, ainda devem ser realizados experimentos em condições de campo, envolvendo outras populações de T. urticae, para averiguar a eficácia deste extrato como alternativa a ser utilizada em programas de manejo da praga.

Atividade fungicida do óleo essencial de Cymbopogon winterianus jowit (Citronela) contra Fusarium solani / Fungicide activity of essential oil Cymbopogon winterianus jowit (Citronella) against Fusarium solani

O declínio é a principal doença da goiabeira causada pelo parasitismo de Meloidogyne enterolobii e pelo fungo Fusarium solani, tem sido responsável pela erradicação de muitos pomares em âmbito nacional, o que resulta em elevada perda econômica aos produtores. Devido à crescente pressão da sociedade por produtos naturais e com o aumento da importância dos óleos essenciais no manejo de doenças de plantas, o objetivo deste trabalho foi identificar os principais componentes e avaliar o efeito fungitóxico do óleo essencial de Cymbopogon winterianus (citronela) sobre três isolados de Fusarium solani (UENF/CF163, UENF/CF241 e UENF/CF295). O óleo essencial foi obtido por hidrodestilação, utilizando o aparelho tipo Clevenger. Os compostos foram identificados por cromatografia gasosa e cromatografia gasosa com detector de massas do óleo essencial. Para avaliar o efeito dos óleos essenciais no crescimento micelial, esporulação e germinação de esporos do fungo, foram utilizadas alíquotas de 5, 10, 15, 20, 25 e 30 µL do óleo essencial que foram distribuídas na superfície do meio de cultura BDA contido em placas de Petri antes da repicagem do fungo. O delineamento experimental foi inteiramente casualizado num esquema fatorial 1 x 6 + 1, (um óleo, seis alíquotas e uma testemunha adicional), com 5 repetições. Os principais componentes encontrados no óleo de C. winterianus foram o geranial (28,62%), citronelol (23,62%) e neral (17,10%). A menor alíquota do óleo essencial de citronela (5µL) inibiu em mais de 90% a germinação de esporos dos isolados UENF/CF241 e UENF/CF295 e reduziu a produção de esporos em mais de 95% nos três isolados, indicando que esse óleo possui uma boa atividade fungitoxica para esses isolados.

The decline is the main disease of guava caused by parasitism of Meloidogyne enterolobii and the fungus Fusarium solani, has been responsible for the eradication of many orchards nationwide, resulting in high economic loss to producers. Due to increasing pressure from society for more natural products and to increase the importance of essential oils in the management of plant diseases, the aim of this study was to determine the chemical composition and evaluate the antifungal effect of the essential oil of Cymbopogon winterianus (citronella) on three isolates of Fusarium solani (UENF/CF 163, and UENF/CF241 UENF/CF295). The essential oil was obtained by hydrodistillation using the Clevenger type apparatus. The compounds were identified by gas chromatography and gas chromatography with mass detector essential oil. To evaluate the effect of essential oils on mycelial growth, sporulation and germination of spores of the fungus were used aliquots of 5, 10, 15, 20, 25 and 30 µl essential oil which were distributed on the surface of PDA culture medium contained in Petri dishes before subculturing the fungus. The experimental design was completely randomized with a 1 x 6 + 1, (an oil, six aliquots and an additional control) with 5 repetitions. The major components found in the oil of C. winterianus were geranial (28.62%), citronellol (23.62%) and neral (17.10%). The lowest essential oil of citronella (5µL) inhibited more than 90% spore germination of isolates UENF/CF241 and UENF/CF295 and reduced the production of spores in over 95% in three isolates.

Potencial acaricida do extrato etanólico de Sapindus saponaria e de solução sabão sobre Tetranychus urticae / Acaricidal potential of ethanolic extract from Sapindus saponaria and soap solution against Tetranychus urticae

Tetranychus urticae Koch (1836) (Acari: Tetranychidae), conhecido como ácaro rajado, é uma praga que pode reduzir a produção de frutos do morangueiro em até 80%. O controle desta praga por meio de acaricidas sintéticos tem proporcionado à destruição de organismos benéficos e o desenvolvimento de populações resistentes. Como alternativa ao controle tradicional, este trabalho teve como objetivo avaliar os efeitos do extrato de Sapindus saponaria e de solução sabão sobre a oviposição e mortalidade de fêmeas de T. urticae. Os ácaros foram pulverizados, com auxílio da Torre de Potter, usando formulações do extrato/solução sabão a 1, 2, 3, 4, 5% (m/v) e avaliados em 24, 72 e 120h. Verificou-se que o extrato de S. saponaria apresentou maior eficiência (CL50, 1,18%) do que a solução sabão (CL50, 1,31%). Em relação à atividade ovicida, o maior efeito foi observado com a formulação a 5% (m/v) após 120h, tanto para o extrato de S. saponaria (60,9%) quanto para solução sabão (84%). Os resultados observados, em condições de laboratório, são favoráveis à utilização do extrato de S. saponaria e de solução sabão no controle de T. urticae em programas de manejo fitossanitário para a cultura do morango.

Tetranychus urticae Koch (1836) (Acari: Tetranychidae), known as spider mite is a pest that can reduce fruit production in strawberry up to 80%. The control of the pest by synthetic acaricides has provided the destruction of beneficial organisms and development of resistant populations. As an alternative to traditional control, this study aimed to evaluate the effects of the extract from Sapindus saponaria and soap solution on the oviposition and mortality of females of T. urticae. The mites were sprayed with the aid of a Potter Tower, using formulations of extract/soap solution at 1, 2, 3, 4, 5% (w / v) and assessed at 24, 72 and 120h. It was found that the extract efficiency (LC50, 1.18%) than the soap solution (LC50, 1.31%). Regarding the ovicidal activity, the greatest effect was observed with the formulation at 5% (w / v) after 120 hours for both the extract (60.9%) as for soap solution (84%). The results observed in laboratory conditions are favorable to the use of the extract and soap solution to control T. urticae in pest management programs for the strawberry crop.