The control of fungal species in agriculture is mainly conducted with the use of contact or systemic fungicides. However, environmental and human health concerns and increased resistance of fungal species to existing fungicides have increased the pressure on researchers to find new active ingredients for fungal control which present low toxicity to non-target organisms, are environmentally safe, and can be applied at very low concentrations. It is herein described the synthesis of eleven glycerol triazole containing compounds (ten of them fluorinated derivatives) and evaluation of their fungicidal activity. Eight out of eleven synthesized compounds are novel and all of the glycerol derivatives were characterized using infrared (IR), nuclear magnetic ressonance (NMR), and mass spectrometry (MS) techniques. Theoretical calculations were also carried out and the results are discussed. Starting from glycerol, the triazole derivatives were prepared in four steps. Evaluation of them against Colletrotricum gloesporioides showed that compound 1-((2,2-dimethyl-1,3 dioxolan-4-yl)methyl)-4-(2-fluorophenyl)-1H-1,2,3-triazole (4d) (ED50 = 59.14 µg mL-1) was slightly more active than commercial fungicide tebuconazole (61.35 µg mL-1). Compound 4d presented attractive physicochemical features for agrochemical purposes as revealed by the calculated physicochemical parameters. It is believed that glycerol-fluorinated triazole derivatives can be explored towards the development of new chemicals for the control of fungal species.

It is herein described the synthesis of a series of thirty novel 1,2,3-triazole-1,4 disubstituted compounds inspired on the known SRPKs inhibitor N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)isonicotinamide (SRPIN340) and biological evaluation of them against human glioblastoma multiforme cell line U87MG. Starting with 1-fluoro-2 nitro-4-(trifluoromethyl)benzene (1), the substances were prepared via a five-step synthetic route. The crucial step corresponded to the copper-catalyzed cycloaddition reaction between trifluoromethyl phenyl azides and different alkynes. In general, the compounds were obtained with good yields and they were characterized utilizing spectroscopic (IR and NMR) and spectrometric (HRMS) techniques. The evaluation of the synthesized compounds at three different treatment time (24 h, 48 h, and 72 h) and concentrations (50, 100, and 150 µmol L-1) revealed that five derivatives were capable of reducing cell viability by 50% after 72 h of treatment at the highest concentration. On the contrary, three derivatives significantly increased cell viability being this effect more pronounced after 48 h of treatment. In this regard, it stands out the compound 2-((1-(2-morpholino-5-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)isoindoline-1,3-dione (7) which increased cell viability in approximately 300% after 48 h of treatment at 100 µmol L-1. The substances that increased cell viaiblity present as common structural features the presence of a saturated nitrogen-containing six-membered ring and carbonylated fragments.

The benzophenones are synthetic and natural compounds presenting a variety of activities, including photoprotective, cytotoxic and antiviral. It is herein described the preparation of a series of twenty-seven benzophenone derivatives bearing 1,2,3-triazole functionalities and the evaluation of their photoprotective, cytotoxic and antiviral on Zika Virus (ZIKV) activities. The compounds were prepared in three steps, namely reduction of benzophenone, alkylation of diphenylmethanol and CuAAC reactions. The in vitro evaluation of the photoprotective activity revealed that the most active derivative 4-((benzhydryloxy)methyl)-1-(4-nitrobenzyl)-1H-1,2,3-triazole (4k) displayed UVB sun protection factor equal to 6,9±0,53, which make this compound a possible candidate to be used in formulations for photoprotective applications. In terms of cytotoxicity, the compounds were evaluated against MDA-MB-231 and B16F10 cell lines. It was observed that the compounds were more active against MDA-MB-231 cells and three of them were capable of reducing cell viability by approximately 55% at 100 µmol L-1. In the antiviral screening against ZIKV, compound 4-(3-benzhydryloxy)propyl)-1-(3-methylbenzyl)-1H-1,2,3-triazole (5j) was the most effective in mantaining Vero cell viability.

RESUMO O inseto Dysmicoccus brevipes (Hemiptera: Pseudococcidae) tem sido relatado como uma praga de importância para diversas culturas, em especial a cafeicultura. Os óleos essenciais cítricos podem ser obtidos como subprodutos da indústria de sucos e vem sendo testados como alternativa no controle de diferentes grupos de insetos. Logo, objetivou-se neste trabalho determinar a composição química e avaliar a toxicidade de óleos essenciais comerciais de laranja doce (Citrus sinensis), laranja amarga (Citrus aurantium), limão Siciliano (Citrus limon) e do monoterpeno D-limoneno sobre a D. brevipes. Os óleos essenciais foram analisados por cromatografia gasosa. Foram realizados dois bioensaios. O primeiro para avaliar a mortalidade em todos os óleos e o segundo para avaliar as concentrações letais (CL50 e CL95) dos óleos mais efetivos. Os constituintes majoritários do óleo de laranja doce foram o D-limoneno (83,33%); linalol (8,91%), do óleo de laranja amarga foram o D-limoneno (78,53%); γ-terpineno (12,65%), do óleo de limão Siciliano foram o D-limoneno (59,78%); beta-pineno (14,71%); γ-terpineno (10,19%) e o composto D-limoneno (97% de pureza). O óleo de limão Siciliano e laranja doce foram os que apresentaram maior percentual de mortalidade, sendo 98,68%, 94,11%.As CL50 e CL95, para o óleo de laranja doce foram de 2,21% e 3,55% e para o óleo de limão Siciliano foram de 0,72% e 2,91%, respectivamente. Portanto, o composto majoritário presente na composição química do óleo essencial de laranja doce e do limão Siciliano foi o D-limoneno e o mais efetivo sobre D. brevipes foio óleo de limão Siciliano.

ABSTRACT The insect Dysmicoccus brevipes (Hemiptera: Pseudococcidae) has been reported as an important pest for several crops, especially coffee. The citrus essential oils can be obtained as by-products of the citrus-processing industry and have been tested as an alternative to control different insect groups. Therefore, the objective of this work was to determine the chemical composition and evaluate the toxicity of commercial sweet orange (Citrus sinensis), bitter orange (Citrus aurantium) and Sicilian lemon (Citrus limon) essential oils and pure monoterpene D-limonene on D. brevipes. The essential oils were analyzed by gas chromatography. Two bioassays were conducted; the first assessing the insect mortality in all oils and the second assessing the lethal concentrations (LC50 and LC95) of the most effective oils. The main components of the oils were D-limonene (83.33%) and Linalool (8.91%) (sweet orange); D-limonene (78.53%) and γ-terpinene (12.65%) (bitter orange); D-limonene (59.78%), beta-pinene (14.71%) and γ-terpinene (10.19%) (Sicilian lemon) and the compound D-limonene had 97% of purity. The highest mortalities were found with the use of the Sicilian lemon (98.68%) and sweet orange (94.11%)oils. The sweet orange oil presented lethal concentrations at 2.21% (LC50) and 3.55% (LC95), and the Sicilian lemon oil at 0.72% (LC50) and 2.91% (LC95). The main component of the sweet orange and Sicilian lemon essential oils was the D-limonene, and the Sicilian lemon oil was most effective oil to control D. brevipes.

ResumenLepidaploa rufogrisea es una candidata prometedora en la búsqueda de herbicidas naturales, con compuestos (lactano sesquiterpeno- glaucolíde B) los cuales han sido reportados por presentar un potencial fitotóxico contra las malas hierbas. Por lo tanto, este trabajo tuvo como objetivo lograr la investigación fitoquímica de L. rufogrisea, así como también la evaluación de sus efectos biológicos sobre el modelo de planta Lactuca sativa L. Para esto, diferentes extractos (acuosos, hidroalcohólicos y hexanos) de L. rufogrisea fueron evaluados. El porcentaje de semillas germinadas, el índice de velocidad de germinación y la longitud de raíz de plántulas de L. sativa var. Cristina fueron evaluadas, así como también la citotoxicidad de los extractos en las células meristemáticas. Los extractos disminuyeron el índice de velocidad de germinación y también el crecimiento de las raíces de las plántulas de L. sativa. La proliferación celular no se vio significativamente afectada por los extractos. Sin embargo, se observaron alteraciones cromosómicas y nucleares, debido a la interferencia de los aleloquímicos presentes en L. rufogrisea en el huso mitótico. Además, el modelo de planta L. sativa demostró ser eficiente para tales estudios.

AbstractLepidaploa rufogrisea is a promising candidate in the search of natural herbicides, with compounds (sesquiterpene lactones-glaucolide B) which have been reported to present phytotoxic potential against weeds. Thus, this work aimed to accomplish the phytochemical investigation of L. rufogrisea as well as the evaluation of its biological effects on the plant model Lactuca sativa. To this end, different extracts (aqueous, hydroalcoholic and hexane) of L. rufogrisea at different concentrations [0.25, 0.5, 1.0, 2.0 and 4.0 % (m/v)] were evaluated from macroscopic (percentage of germinated seeds, germination speed index and root length) and microscopic analysis (mitotic index and cell cycle alterations) in plantlets (150 per treatment) and meristematic cells (10 000 per treatment) of L. sativa var. Cristina. The extracts decreased the germination speed index and also the root growth of L. sativa plantlets. Cell proliferation was not significantly affected by the extracts. However, some chromosome and nuclear alterations in the mitotic spindle were observed, due to the interference of allelochemicals present in L. rufogrisea. Moreover, the plant model L. sativa demonstrated to be efficient for this kind of studies.

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

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

O ácaro-rajado, Tetranychus urticae Koch (1836) (Acari: Tetranychidae), é a principal praga na cultura do morangueiro. O objetivo deste trabalho foi a caracterização química do óleo essencial de Chenopodium ambrosioides L. e a avaliação de seus efeitos sobre o ácaro-rajado. Os compostos do óleo essencial foram identificados pelasanálises de CG-DIC e CG-EM. A mortalidade e a oviposição foram avaliadas após a pulverização do óleo (2,5; 5,0; 7,5 e 10,0% v v-1) sobre fêmeas do ácaro-rajado. O rendimento do óleo essencial foi de 0,3%, e os compostos identificados foram (Z)-ascaridol (87%), (E)-ascaridol (5,04%), p-cimeno (4,83%), a- terpineno (1,24%) e piperitona (0,7%). Os maiores valores para mortalidade e redução de oviposição observados foram 85% e 69%, respectivamente. O óleo essencial de C. ambrosioidesé uma opção promissora para o manejo do ácaro-rajado.

The twospotted spider mite, Tetranychus urticae Koch (1836)(Acari: Tetranychidae), is the major pest in strawberry. The objective of this study was the chemical characterization of the essential oil of Chenopodium ambrosioides L. and the evaluation of their effects on twospotted spider mite. The compounds of the essential oil were identified by GC/FID and GC/MS analysis. The mortality and oviposition were evaluated after spraying the oil (2.5, 5.0, 7.5 and 10.0% v v-1) on twospotted spider mite females. The yield of the essential oil was of 0.3% and the compounds identified were (Z)-ascaridol (87%), (E)-ascaridol (5.04%), p-cymeno (4.83%), a-terpinene (1.24%) and piperitone (0.7%). The highest values for mortality and reduction of oviposition observed were 85% and 69%, respectively. C. ambrosioides essential oil is a promising option for the management of twospotted spider mite.

O tripes, Frankliniella schultzei, e o pulgão-verde, Myzus persicae, além de causarem danos diretos a plantas de importância econômica, também são importantes transmissores de fitoviroses, acarretando grandes perdas econômicas. Os constituintes químicos dos óleos essenciais têm sido cada vez mais estudados, pois apresentam uma ampla gama de atividades biológicas. Neste trabalho, objetivou-se avaliar a atividade inseticida do óleo essencial de capim-citronela, Cymbopogon winterianus, sobre F. schultzei e M. persicae. O óleo essencial foi obtido por hidrodestilação e a identificação dos seus componentes foi realizada por CG/DIC e CG/EM. Uma torre de Potter foi utilizada para pulverizar os insetos com óleo essencial. Os componentes majoritários encontrados são geraniol (28,62%), citronelal (23,62%) e citronelol (17,10%). O óleo essencial de C. winterianus a 1% (m v-1) causa mortalidade de F. schultzei e M. persicae em 34,3% e 96,9%, respectivamente. O valor estimado de CL50 para M. persicae foi 0,36% e CL90 de 0,66%. Assim, o óleo essencial de capim-citronela a 1% (m v-1) é mais tóxico para M. persicae do que para F. schultzei. Este óleo essencial mostra-se promissor para o desenvolvimento de inseticidas para o manejo de M. persicae.

The thrips, Frankliniella schultzei, and green peach aphid, Myzus persicae, cause direct damage to plants of economic importance and transmit phytoviruses, causing large economic losses. Chemical constituents of essential oils present a wide range of biological activities. The aim of this work was to evaluate insecticidal activity of essential oil from citronella grass, Cymbopogon winterianus, on F. schultzei and M. persicae. This essential oil was obtained by steam distillation and components were identified by GC/FID and GC/MS. A Potter spray tower was used to spray insects with the essential oil. The major constituents are geraniol (28.62%), citronellal (23.62%) and citronellol (17.10%). Essential oil of C. winterianus at 1% (w v-1) causes mortality in F. schultzei and M. persicae at 34.3% and 96.9%, respectively. The LC50 value for M. persicae was 0.36% and LC90 0.66%. Thus, citronella grass essential oil at 1% (w v-1) is more toxic to M. persicae than F. schultzei. This essential oil shows promise for developing pesticides to manage M. persicae.