Recebido em 24/6/05; aceito em13/2/06; publicado na web em 28/11/06 ORGANOPHOSPHORUS PENTAVALENT COMPOUNDS: HISTORY, SYNTHETIC METHODS OF PREPARATION AND APPLICATION AS INSECTICIDES AND ANTITUMOR AGENTS. This paper is a review of the history, synthesis and application of organophosphorus compounds, especially of those of pentavalent phosphorus, such as phosphoramidates, phosphorothioates, phosphonates and phosphonic acids with insecticide and anticancer activities. The organophosphorus compounds with agrochemical applications show great structural variety, They include not only insecticides, but also fungicides, herbicides, and others. The large variety of commercially available organophosphorus pesticides is remarkable. Even more interesting is the high efficiency of some organophosphorus compounds as anticancer agents such as cyclophosphamide and its derivatives.Keywords: organophosphorus compounds; insecticides; anticancer agents. ) e as fosforanas ou ilídeos. Os compostos de fósforo trivalentes são bons agentes redutores por causa da forte reatividade dos pares de elétrons não ligantes e da facilidade de formação da ligação P=O e, por isto, os compostos fosforados são rapidamente oxidados por oxigênio, ozônio, peróxidos e outros agentes oxidantes. A força da ligação carbonofósforo é similar à da ligação carbono-carbono e muito resistente para oxidação e hidrólise 5 . As diferentes atividades dos compostos organofosforados estão relacionadas, evidentemente, com características estruturais, tais como o tipo de heteroátomo ou grupo funcional ligado ao átomo de fósforo e seu estado de oxidação. INTRODUÇÃOEstudos a respeito da conversão de compostos carbonílicos em alcenos por Wittig 2,6 e o uso de catálise homogênea abriram novas áreas no uso de compostos de fósforo em síntese orgânica. Mais recentemente, a preparação de compostos pentavalentes de fósforo estáveis e as discussões de processos de pseudorotações por Westheimer e outros conduziram a um maior progresso nesta área 2 . Atualmente, vários compostos de fósforo usados comercialmente são inorgânicos, mas compostos de fósforo orgânicos estão se tornando bastante importantes. Eles são usados como antioxidantes e estabilizantes para plásticos e óleos industriais, e em diversas áreas de aplicação, assim como resistência à corrosão, extração e complexação e como agroquímicos (inseticidas, fungicidas, herbicidas) 7 . Entre as diversas aplicações industriais pode ser citado o uso como reagente de flotação, matéria-prima na sín-tese de plásticos não inflamáveis, antioxidantes, plastificantes, aditivo para óleos lubrificantes e combustíveis hidrocarbônicos, solventes aplicados em extrações seletivas e, principalmente, como inseticidas 1,4,5 e agentes antitumorais 8,9 . As aplicações industriais, junto com o aumento do uso de compostos de fósforo em síntese orgânica e na química de compostos organometálicos, têm adquirido um rápido aumento na literatura da química de organofosforados.Os compostos de fósforo estão entre os precursores necessários à vida e estão pres...
Direct infusion electrospray ionization mass spectrometry (ESI-MS) of aqueous/methanolic extracts of biodiesel samples is shown to permit simple and fast fingerprinting typification, identification of the alcohol used in the trans-esterification process, monitoring of degradation and adulteration, and screening of residual glycerin and mono-, di-, and tri-glycerides. As proof-of-principle cases, ESI-MS fingerprints in both the positive and the negative ion modes were acquired for biodiesel samples derived from soybean oil, sunflower oil, canola oil, olive oil, castor oil, jatropha curcas oil, palm oil, lard, and tallow. In the negative ion mode, characteristic sets of ions corresponding to de-protonated fatty acids were detected for each type of biodiesel, thus allowing their reliable typification via these taxonomic markers. Biodiesel degradation was also monitored by ESI(-)-MS with the detection of degradation markers, mainly oxidized fatty acids. When using ESI(+)-MS, the main diagnostic ions detected were the protonated fatty esters, which reveal therefore both the oil source and the alcohol (methanol or ethanol, or other heavier alcohols) used for trans-esterification. Residual glycerin and mono-, di-, and tri-glycerides are also detected, which makes ESI-MS also applicable for laboratory and on-site screening of biodiesel quality.
Recebido em 19/1/11; aceito em 21/5/11; publicado na web em 22/7/11 A method using LC/ESI-MS/MS for the quantitative analysis of Ochratoxin A in roasted coffee was described. Linearity was demonstrated (r = 0.9175). The limits of detection and quantification were 1.0 and 3.0 ng g -1 , respectively. Trueness, repeatability and intermediate precision values were 89.0-108.8%; 2.4-13.7%; 12.5-17.8%, respectively. To the best of our knowledge, this is the first report in which Ochratoxin A in roasted coffee is analysed by LC/ESI-MS/MS, contributing to the field of mycotoxin analysis, and it will be used for future production of Certified Reference Material.
The present work describes the development of a certified reference material (CRM) composed of solutions of ethanol in water in five different concentrations, and all stages necessary for the development of an CRM, according to the guidelines of ISO GUIDES 30, 31, 32, 33, 34 and 35
There are numerous Calibration and Measurement Capability Claims (CMCs) on PAH analysis in various matrices published in the BIPM key comparison database, Appendix C. By July 2007 such CMCs were released in Category 10 Biological fluids and materials, Subcategory 10.4 Tissues, Category 11 Food, Subcategory 11.2 Contaminants and Category 13 Sediments, soils, ores and particulates, Subcategories 13.1 Sediments, 13.2 Soils and 13.4 Particulates. CCQM comparisons are needed to underpin these claims.A pilot study CCQM-P69 'PAHs in soil' was successfully conducted in 2004. After review of the results at the OAWG meeting in September 2005 it was decided to proceed with a key comparison and a concurrent second pilot study CCQM-K50/P69.1. CENAM and BAM agreed to coordinate the intercomparison. The measurand of the study was specified as amount of specific PAHs in solid matrices as extracted under exhaustive extraction conditions. As for the preceding pilot study and two studies for PAHs in solution (CCQM-P31a and CCQM-K38), five target analytes, phenanthrene, fluoranthene, benz[a]anthracene, benzo[a]pyrene and benzo[ghi]perylene, were selected as representative of the measurement of individual compounds.The CCQM-K50 study utilized a soil sample from BAM and an air particulate sample from NIST. Both materials were naturally contaminated, not enriched or spiked. The mass fraction of target analytes in the samples ranged from 2 mg/kg to 15 mg/kg. NIST SRM 1649a Urban Dust was provided as a control material. Participants were requested to determine the mass fraction of the selected PAHs on a dry mass basis and submit a complete uncertainty budget for their measurements.Ten NMIs participated in the study. All participants applied Soxhlet or Accelerated Solvent extraction (ASE) and GC-MS with either deuterated or 13C labelled internal standards. Results demonstrate a good level of equivalence in capabilities of the participating NMIs to identify and measure PAHs in highly contaminated environmental samples. With a few exceptions, data agree within the range ±5% from the Key Comparison Reference Value (KCRV) for the soil and ±10% from the KCRV for the particulate. Relative expanded uncertainties of the KCRV range from 2% to 5% for the soil and from 4% to 13% for the particulate matter. The KCRV was agreed upon during the OAWG meeting in November 2008 as the arithmetic mean of participants' results. Data of laboratories who did not take part in the preceding pilot study or whose results were not fully traceable to an NMI were excluded from the calculation of KCRVs. Degree of equivalence statements were given for all participants.Main text. To reach the main text of this paper, click on Final Report. Note that this text is that which appears in Appendix B of the BIPM key comparison database kcdb.bipm.org/.The final report has been peer-reviewed and approved for publication by the CCQM, according to the provisions of the CIPM Mutual Recognition Arrangement (MRA).
This chapter aims to present the developments performed by the Brazilian Metrology Institute (NMI) – Inmetro, considering the environmental demand. Inmetro addresses a great part of its activities to the study of the traceability transference based on production and dissemination of certified reference material (CRM) of different areas in chemistry. The chapter presents results from certification of the following reference materials developed: BTEX and PAH in solution, besides automotive emission gas mixtures and bioethanol. So, the achievements made are the growth in developing CRM in order to support the needs of the national industry and to disseminate traceability among the society.
Dezenove dialquilfosforilidrazonas com diferentes substituintes no anel aromático foram avaliadas como inibidores potenciais de tirosinase, que poderiam ser usadas como agentes eficientes no controle de desordens de pigmentação. A atividade inibitória foi medida através de uma modificação do método de UV-Vis de Patil e Zucker. Os ensaios foram realizados com soluções contendo tampão fosfato, L-3,4-diidroxifenilalanina (L-DOPA), EDTA, tirosinase e diferentes concentrações de compostos organofosforados e a formação de dopacromona foi determinada através do monitoramento da absorvância a 475 nm. Três compostos foram os mais ativos da série (CI 50 = 105 ± 20 mmol L-1), (CI 50 = 127 ± 16 mmol L-1) e (CI 50 = 188 ± 27 mmol L-1), sendo de 3 a 7 vezes mais ativos do que o ácido ascórbico (CI 50 = 730 mmol L-1), utilizado como controle. O composto mais ativo é apenas 1,5 vezes menos ativo do que o ácido kójico (IC 50 = 69,4 mmol L-1), que é utilizado comercialmente. Esta investigação pode levar à descoberta de agentes potentes contra importantes desordens de pigmentação inclusive a hiperpigmentação. Nineteen dialkylphosphorylhydrazones with different substituents at the aromatic ring were evaluated as potential tyrosinase inhibitors, which could then be used as efficient agents in the control of pigmentation disorders. The inhibition activity was measured by a modified Patil and Zucker UV-Vis method. Briefly, the assays were carried out with solutions containing phosphate buffer, L-3,4-dihidroxyphenylalanine (L-DOPA), (EDTA), tyrosinase and varying concentrations of organophosphorus compounds. The formation of dopachromone was determined by monitoring the absorbance at 475 nm. Three compounds were found to be the most active compounds of the series (IC 50 = 105 ± 20 mmol L-1), (IC 50 = 127 ± 16 mmol L-1) and (IC 50 = 188 ± 27 mmol L-1), being three to seven times more active than ascorbic acid (IC 50 = 730 mmol L-1), used as a standard. The most active compound is only 1.5 times less potent than the commercial kojic acid (IC 50 = 69.4 mmol L-1). This study may lead to the discovery of potent agents against very important pigmentation disorders including hyperpigmentation.
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