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Structural characterization of photoproducts of pyrimethanil

机译：嘧啶酮光产物的结构表征

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Introduction Pyrimethanil is an anilino-pyrimidine fungicide particularly active against gray mold (Botrytis cinerea) and pear scab (Venturia inaequalis and Venturia pirina) on grapes, strawberries, tomatoes, fruits, vegetables and ornamental plants in greenhouses and open field situation. According to the European Food Safety Authority, pyrimethanil has no evident mutagenic, genotoxic or carcinogenic potential, but a short-term toxicity study on rats and mice has shown an increase in liver weight accompanied by changes in the histopathology of the liver and thyroid. To avoid these side effects, the concentration of pyrimethanil has been limited by legislation. The European Commission set the Maximum Residue Level of pyrimethanil at 10 mg/l in citrus fruits, 5 mg/l in pome fruits, strawberries, table and wine grapes and 0.05 mg/l in tree nuts (EC/600/2010). It is thus important to increase our knowledge regarding the concentration of pyrimethanil in environmental matrices, its degradability and the factors affecting it. One of these factors is the photo alteration by sunlight, which is known to play a significant role in the degradation of this compound, due to the prolonged half-life (77 days approximately) of pyrimethanil in the environment. Previous studies on the degradation of pyrimethanil were carried out mainly in a waste water treatment context and focused on the photo catalytic degradation using various salts as catalysts. Agüera et al. used TiO2, Vanni et al. and Anfossi et al. added iron III, Navarro et al. added ZnO and Gomis et al. used thiopyrylium. Irradiation was carried out using a mercury or xenon lamp or direct sunlight. These studies have showed that a long irradiation time (between 150 and 1400 min, depending on the conditions and catalyst) is required for total disappearance of pyrimethanil. Degradation of pyrimethanil in water using the technique of photo-Fenton was investigated by Sirtori et al. They reported that the addition of sodium chloride accelerated the reaction and characterized four chlorinated photo-Fenton by-products. The aim of the present study was the identification of UV-visible photo transformation products of pyrimethanil in water. Liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) and gas chromatography coupled with multi stage mass spectrometry (GC-MS~n) were used for analysis, with the aim of covering a large range of polarities for the detection of the potential transformation products. Elucidation of the structures of photoproducts was carried out performing high-resolution measurements and collision-induced dissociation (CID) experiments. Photolysis mechanisms have also been proposed to explain the formation of photo products of pyrimethanil in water.
机译：简介嘧霉胺是一种苯胺-嘧啶类杀菌剂，对温室，空地大棚中的葡萄，草莓，西红柿，水果，蔬菜和观赏植物上的灰霉病（灰葡萄孢）和梨结ab（文氏不动杆菌和维纳图里亚pirina）特别有效。根据欧洲食品安全局的说法，嘧菌胺没有明显的诱变，遗传毒性或致癌性，但对大鼠和小鼠的短期毒性研究显示，肝脏重量增加，同时肝脏和甲状腺的组织病理学改变。为了避免这些副作用，立法已限制了嘧菌胺的浓度。欧盟委员会将柑橘类水果中嘧菌胺的最大残留量定为10 mg / l，石榴果，草莓，鲜食和酿酒葡萄中的嘧啶腈的最大残留量为5 mg / l，而坚果中的0.05 mg / l（EC / 600/2010）。因此，重要的是增加我们对环境基质中嘧霉胺浓度，其可降解性及其影响因素的认识。这些因素之一是由于阳光引起的光变，由于在环境中嘧啶醇的半衰期延长（约77天），已知在该化合物的降解中起重要作用。先前关于嘧霉胺降解的研究主要是在废水处理的背景下进行的，并且集中于使用各种盐作为催化剂的光催化降解。 Agüera等。使用TiO2，Vanni等。和Anfossi等。 Navarro等人添加了铁III。添加ZnO和Gomis等。用过的硫代吡啶鎓。使用汞或氙气灯或直射阳光进行辐照。这些研究表明，嘧啶酮的全部消失需要较长的照射时间（150至1400分钟，具体取决于条件和催化剂）。 Sirtori等人研究了使用光芬顿技术降解水中的嘧霉胺。他们报告说，添加氯化钠可加速反应，并表征了四种氯化光芬顿副产物。本研究的目的是鉴定水中嘧菌胺的紫外可见光转化产物。液相色谱-串联质谱（LC-MS / MS）和气相色谱-多级质谱（GC-MS〜n）用于分析，目的是覆盖大范围的极性以检测潜在的转型产品。进行了高分辨率测量和碰撞诱导解离（CID）实验，从而阐明了光产物的结构。还提出了光解机理来解释嘧啶酮在水中的光产物的形成。

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