Photochemical Transformations of Dichloroacetamide Safeners

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

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Photochemical Transformations of Dichloroacetamide Safeners

机译：二氯乙酰胺安全剂的光化学转化

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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被添加到商业氯乙酰胺除草剂配方中，并在世界范围内广泛使用，但是由于其被归类为“惰性”成分，因此其环境命运受到严格审查。在这里，我们研究了二氯乙酰胺安全剂的光解作用，以更好地了解其在地表水中的持久性及其转化产物的性质。高分辨率质谱（HRMS）和核磁共振（NMR）光谱用于表征光产物。在四种常用的二氯乙酰胺安全剂中，只有苯氧沙星在模拟的自然阳光下（t（1/2）类似于10分钟）进行直接光解。通过光引发的闭环反应，贝诺沙克最初产生了一种单氯化的中间体，该中间体在较长的照射时间内会降解，这是两个完全脱氯的非对映异构体和一个互变异构体，它们在数天内进一步光降解为通过NMR证实的结构相关的醛。在存在硝酸盐，亚硝酸盐和腐殖酸的光敏剂的情况下，间接光解法可更缓慢地降解二氯草胺，AD-67和呋喃唑。基于使用选择性淬灭剂，这些反应中涉及的反应性实体可能是羟基自由基和单线态氧。这些安全剂还可以在较高能量的紫外线（UV）下直接光解，表明它们在使用紫外线进行消毒的工程系统中具有潜在的转化能力。二氯乙酰胺安全剂可以在相关时间范围内在环境系统中进行光解的发现表明，评估这类“惰性”农用化学品的命运至关重要。

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《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.;
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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;

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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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1. Photochemical Transformations of Dichloroacetamide Safeners [J] . Kral Andrew E., Pflug Nicholas C., McFadden Monica E., Environmental Science & Technology . 2019,第12期

机译：二氯乙酰胺安全性的光化学转化
2. Reductive transformations of dichloroacetamide safeners: effects of agrochemical co-formulants and iron oxide plus manganese oxide binary-mineral systems [J] . Ricko Allison N., Psoras Andrew W., Sivey John D. Environmental Science: Processes & Impacts . 2020,第10期

机译：二氯甲酰胺安全性的还原转化：农用化学型共配方和氧化铁加锰氧化物二元矿物系统的影响
3. Abiotic Reduction Reactions of Dichloroacetamide Safeners:Transformations of 'Inert' Agrochemical Constituents [J] . John D. Sivey, A. Lynn Roberts Environmental Science & Technology . 2012,第4期

机译：二氯乙酰胺安全剂的非生物还原反应：“惰性”农用化学成分的转化
4. Mechanisms of Tryptophan Transformations Involving the Photochemical Formation of Silver Nanoparticles [C] . O. Smirnova, A. Grebenyuk, Iu. Mukha, International Conference Nanotechnology and Nanomaterials . 2020

机译：涉及银纳米粒子光化学形成的色氨酸转化机制
5. Photochemical Transformations of Dichloroacetamide Safeners [D] . Kral, Andrew. 2018

机译：二氯乙酰胺安全剂的光化学转化
6. Specific binding of a dichloroacetamide herbicide safener in maize at a site that also binds thiocarbamate and chloroacetanilide herbicides. [O] . J D Walton, J E Casida 2019

机译：二氯乙酰胺除草剂在玉米中的安全结合位点也与硫代氨基甲酸酯和氯乙苯胺除草剂结合。
7. Specific binding of a dichloroacetamide herbicide safener in maize at a site that also binds thiocarbamate and chloroacetanilide herbicides. [O] . Walton, J D, Casida, J E 1995

机译：二氯乙酰胺除草剂在玉米中的安全结合位点也与硫代氨基甲酸酯和氯乙苯胺除草剂结合。
8. Relating Ocean Optics to Photochemical Transformations of Chromophoric Dissolved Organic Matter (CDOM) in Coastal Waters. [R] . Miller, W. L. 2003

机译：海洋光学与沿海水域发色溶解有机物（CDOm）光化学转化的关系。

Photochemical Transformations of Dichloroacetamide Safeners

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