苯脲系除草劑常被大量使用於農業中，而其汙染水源的案例已被過去許多研究文獻所提及，顯示此類除草劑在許多水源水質惡化的案例中扮演著重要角色，若苯脲系除草劑本身可經由水處理過程消毒氧化學反應產生具更強毒性之消毒副產物，將更進一步增加此類除草劑對下游水使用者可能產生的健康危害與風險。本研究利用六種常見苯脲系除草劑作為測試前驅物，其中包括Diuron、Fluometuron、Linuron、Metobromuron、Propanil 和Isouron，模擬實廠加氯消毒程序，並量測六種新興消毒副產物亞硝胺化合物包括N-Nitrosodiethylamine (NDMA) 、N-Nitrosomethylethylamine (NMEA) 、N-Nitrosodiethylamine (NDEA) 、N-Nitrosodipropylamine (NDPA) 、N-Nitrosodibutylamine (NDBA) 和N-Nitrosopyrrolidine (NPYR)的生成潛勢，並針對不同的消毒機制（如自由氯、添加氨氮後加氯、一氯胺和二氯胺）與不同氮化物來源種類（如氨氮、亞硝酸鹽和硝酸鹽）對消毒過程中生成亞硝胺的可能影響進行探討。
研究過程以實驗室規模反應槽進行模擬試驗，實驗前添加定量苯脲系除草劑後加入不同消毒劑如氯及氯胺，配合特定待研究之操作及水質條件，包含不同水質pH及水中額外氮化物種類影響，在接觸時間結束後以固相萃取進行前處理，後續分析使用氣相層析質譜或液相層析或超高效能液相層析三重串聯四極桿質譜分析反應生成之亞硝胺物種及其濃度。
結果顯示，苯脲系除草劑可經由加氯消毒過程生成NDMA，且在16小時後NDMA生成漸趨穩定並於24小時達到最大生成量，生成機制屬於一皆反應模型，除NDMA外，NPYR為另一主要生成之物種。在不同加氯方式間氯胺消毒為具有較強亞硝胺生成潛勢之消毒劑，且在pH 8的中性水質條件下可觀察到較高的NDMA生成量，若水體中存在額外氮化物與氯參與反應後，可顯著增加NDMA在消毒過程的生成量。另外結果顯示，由於NPYR其生成路徑與NDMA不同，因此在許多影響因子的結果上，如消毒劑種類、水質pH、及水中氮化物種類，皆與以NDMA為研究對象之結論有所差異。除了亞硝胺物種間的差異，藉由觀察使用不同苯脲系除草劑進行實驗之結果除了消毒機制及氮化物來源種類，亞硝胺的生成亦受到苯脲系除草劑自身是否特定化學結構式特徵或官能基之影響。
由本研究結果可知苯脲系除草劑在亞硝胺生成上可能產生之危害與關鍵因素以及亞硝胺生成途徑的複雜性，未來若欲控制飲用水中亞硝胺生成所產生之健康風險，除改變消毒機制、去除水中氮化物和調整水質條件如水中pH，前驅物（如本研究中探討之苯脲系除草劑）的種類及其結構特徵亦將是重要的考慮環節之一。

Source water pollutions by the presences of urea herbicides have been widely reported. As urea herbicides in source waters have the potentials to be collected by drinking water treatment processes, these compounds may react with disinfectants/oxidants during the processes to form disinfection byproducts, which could be more potent and toxic than the parent compounds for downstream water users. In this study, six widely used urea herbicides, including diuron, fluometuron, linuron, metobromuron, propanil and isouron, were examined as model precursors to understand their potentials to form nitrosamine compounds during chlorine-employed disinfection. The nitrosamines of interest included N-nitrosodimethylamine (NDMA), N-nitrosomethylethylamine (NMEA), N-nitrosodiethylamine (NDEA), N-nitrosodipropylamine (NDPA), N-nitrosodibutylamine (NDBA), and N-nitrosopyrrolidine (NPYR). Lab-scale batch reactors containing pre-determined amounts of urea herbicides were prepared, followed by the addition of chlorine or chloramines and reactions for certain contact times to simulate disinfection in conventional drinking water treatment plants. The solutions were thus pre-treated by solid-phase extraction and analyzed by gas chromatography coupled with mass spectrometry and ultra-high pressure lquid chromatography coupled with triple quadruple mass spectrometry. Besides the investigation of nitrosamie formation from urea herbicies, these experiments were conducted under different operational and water quality circumstances to investigate the effects of different methods of adding chlorine and the presence of excess nitrogen sources on the formation of nitorsamines. In the results, it is indicated that more than one single type of nitrosamines including NPYR less reported in the early studies were produced by the reactions between urea herbicides and different disinfectants. When dichloramine was used for disinfection or ammonia is present, the formation of nitrosamine, particularly NDMA, was significantly enhanced during disinfection of urea herbiceds. Besides the types of additional nitrogen sources and disinfection mechanisms, the nitrosamine formation was also affected by the chemical structures of urea herbicides. The findings suggest the potential hazards of urea herbicides with respect to the formation of nitrosamines during disinfection and provide the information that may be of help to develop management strategies that minimize the adverse health risks of nitrosamines in drinking water by controlling their possible precursors in source waters.

論文審定書 i
致謝 ii
摘要 iii
Abstract v
目錄 vii
圖目錄 x
表目錄 xiii
第一章 前言 1
1.1 研究緣起 1
1.2 研究目的 4
第二章 文獻回顧 7
2.1 新興含氮消毒副產物 8
2.2 亞硝胺類化合物介紹 10
2.2.1 亞硝胺類化合物物化特性 11
2.2.2亞硝胺類化合物規範 15
2.2.3亞硝胺類化合物可能前驅物及生成機制 16
2.2.4亞硝胺類化合物之汙染流佈 24
2.2.5亞硝胺類化合物之處理方式 28
2.3苯脲系除草劑介紹 29
2.3.1苯脲系除草劑物化特性 30
2.3.2 苯脲系除草劑反應機制及副產物 32
2.3.3苯脲系除草劑之使用 37
2.3.4苯脲系除草劑之流佈 40
2.3.5苯脲系除草劑之處理方式 41
第三章 研究設備與方法 43
3.1實驗材料與設備 43
3.1.1材料與試劑 43
3.1.2儀器分析 46
3.2實驗方法 47
3.2.1完全混合消毒程序模擬系統 48
3.2.2消毒劑的製備 49
3.2.3亞硝胺類化合物樣品前處理 50
3.2.4亞硝胺類化合物樣品分析 51
3.3動力曲線預測模式 52
第四章 結果與討論 54
4.1苯脲系除草劑Fluometuron生成NDMA 54
4.1.1 反應速率常數估算 55
4.1.2 NDMA生成模式預測驗證 58
4.2Fluometuron在消毒過程生成多種亞硝胺的可能性 61
4.3前驅物改變後不同消毒機制對亞硝胺生成的影響 65
4.4水體pH值對不同前驅物生成亞硝胺反應的影響 68
4.5水體中存在額外氮化物來源對亞硝胺生成的影響 77
4.6前驅物改變後氮化物對亞硝胺生成的影響 79
4.7苯脲系除草劑生成亞硝胺類化合物的莫爾轉換率 84
4.8不同操作及水質條件下對亞硝胺生成之整體影響 88
4.8.1環境中存在之苯脲系除草劑其亞硝胺生成濃度範圍 88
4.8.2不同加氯消毒劑對總亞硝胺生成之影響 90
4.8.3不同苯脲系除草劑對總亞硝胺生成之影響 91
4.8.4在不同苯脲系除草劑及加氯消毒條件下個別亞硝胺生成莫爾轉換率範圍 92
第五章 結論與建議 94
5.1 結論 94
5.2 建議 96
參考文獻 98
附錄 113

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