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首页> 外文期刊>Environmental Science & Technology >Photochemical Transformations of Dichloroacetamide Safeners
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Photochemical Transformations of Dichloroacetamide Safeners

机译：二氯乙酰胺安全性的光化学转化

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摘要

Dichloroacetamide safeners are commonly added to commercial chloroacetamide herbicide formulations and widely used worldwide, but their environmental fate has garnered little scrutiny as a result of their classification as "inert" ingredients. Here, we investigated the photolysis of dichloroacetamide safeners to better understand their persistence and the nature of their transformation products in surface waters. High-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy were used to characterize photoproducts. Of the four commonly used dichloroacetamide safeners, only benoxacor undergoes direct photolysis under simulated natural sunlight (t(1/2) similar to 10 min). Via a photoinitiated ring closure, benoxacor initially yields a monochlorinated intermediate that degrades over longer irradiation time two fully dechlorinated diastereomers and a tautomer, which further photodegrade over several days to a structurally related aldehyde confirmed via NMR. Dichlormid, AD-67, and furilazole were more slowly degraded by indirect photolysis in the presence of the photosensitizers nitrate, nitrite, and humic acid. Reactive entities involved in these reactions are likely hydroxyl radical and singlet oxygen based on the use of selective quenchers. These safeners also directly photolyzed under higher energy ultraviolet (UV) light, suggesting their potential transformation in engineered systems using UV for disinfection. The finding that dichloroacetamide safeners can undergo photolysis in environmental systems over relevant time scales demonstrates the importance of evaluating the fate of this class of "inert" agrochemicals.
机译：二氯乙酰胺安全剂通常为商业氯乙酰胺除草剂配方中加入并广泛应用于全球，但由于其分类为“惰性”成分，它们的环境命运已经获得了很小的审查。在这里，我们研究了二氯乙酰胺安全性的光解，以更好地了解其在地表水中转化产物的持久性和性质。高分辨率质谱（HRMS）和核磁共振（NMR）光谱用于表征光POPRODUCTS。在四种常用的二氯乙酰胺安全性的中，只有苯氧霍夫在模拟的自然阳光下经历直接光解（T（1/2）类似于10分钟）。通过光灭绝的环闭合，苯氧霍醇最初产生一氯化的中间体，其降低过较长的照射时间两次完全脱氯的非对映异构体和互变异构体，其进一步光降低几天以通过NMR证实的结构相关的醛。在光敏剂，亚硝酸盐和腐殖酸存在下间接光解更缓慢地降解Dichlormid，Ad-67和呋喃唑。参与这些反应的反应实体可能基于使用选择性猝灭剂的羟基自由基和单线氧。这些安全剂还在更高的能量紫外（UV）光下直接光解，表明使用UV用于消毒的工程系统中的潜在转化。发现二氯乙酰胺安全性可以通过相关的时间尺度进行环境系统中的光解，证明了评估这类“惰性”农用化学品的命运的重要性。

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  • 来源
    《Environmental Science & Technology》 |2019年第12期|6738-6746|共9页
  • 作者

    Kral Andrew E.; Pflug Nicholas C.; McFadden Monica E.; LeFevre Gregory H.; Sivey John D.; Cwiertny David M.;

  • 作者单位

    Univ Iowa Dept Civil & Environm Engn Seamans Ctr Engn Arts & Sci 4105 Iowa City IA 52242 USA;

    Univ Iowa Dept Chem E331 Chem Bldg Iowa City IA 52242 USA;

    Univ Iowa Dept Civil & Environm Engn Seamans Ctr Engn Arts & Sci 4105 Iowa City IA 52242 USA;

    Univ Iowa Dept Civil & Environm Engn Seamans Ctr Engn Arts & Sci 4105 Iowa City IA 52242 USA|Univ Iowa IIHR Hydrosci & Engn C Maxwell Stanley Hydraul Lab 100 Iowa City IA 52242 USA;

    Towson Univ Dept Chem 543 Smith Hall Towson MD 21252 USA;

    Univ Iowa Dept Civil & Environm Engn Seamans Ctr Engn Arts & Sci 4105 Iowa City IA 52242 USA|Univ Iowa Dept Chem & Biochem Engn Seamans Ctr Engn Arts & Sci 4133 Iowa City IA 52242 USA|Univ Iowa IIHR Hydrosci & Engn C Maxwell Stanley Hydraul Lab 100 Iowa City IA 52242 USA|Univ Iowa Ctr Hlth Effects Environm Contaminat 251 North Capitol St Chem Bldg Room W195 Iowa City IA 52242 USA|Univ Iowa Publ Policy Ctr 310 South Grand Ave 209 South Quadrangle Iowa City IA 52242 USA;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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