Photochemical behavior and photo-induced toxicity of chiral pesticides and their chiral monomers in aqueous environment
The photochemical behaviors of chiral pollutants in aqueous solutions are rarely studied using chiral monomers, which may hamper their precise risk assessment and lead to suspicious conclusions. In this study, we systematically investigated the phototransformation behavior and toxicity evolution of...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-07-01
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| Series: | Environment International |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S0160412023002696 |
| _version_ | 1797801834831675392 |
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| author | Jia Wang Shaochen Li Yandong Yang Lingyun Fan Weichao Qin Limin Su Yuanhui Zhao Chao Li |
| author_facet | Jia Wang Shaochen Li Yandong Yang Lingyun Fan Weichao Qin Limin Su Yuanhui Zhao Chao Li |
| author_sort | Jia Wang |
| collection | DOAJ |
| description | The photochemical behaviors of chiral pollutants in aqueous solutions are rarely studied using chiral monomers, which may hamper their precise risk assessment and lead to suspicious conclusions. In this study, we systematically investigated the phototransformation behavior and toxicity evolution of two widely used chiral pesticides (triadimefon (TF) and triadimenol (TN)) at enantiomer and diastereomer levels, and proposed a calculation method of total photolysis rate constants of chiral mixture. Results show that TF and TN could be photodegraded faster in pure water than in natural waters, and the observed photolysis rate constants (kobs) of TN with two chiral centers exhibit enantioselectivity, i.e., kobs(TN-RS) = kobs(TN-SR) > kobs(TN-RR) = kobs(TN-SS). The photolysis of TF and TN mainly occurs through their excited singlet and triplet states, respectively. Their photodegradation pathways mainly include dechlorination and elimination of triazole ring. TF could also undergo ether bond cleavage. It is also found that, both TF and TN exhibit photo-induced toxicity to V. fischeri, due to the generation of more toxic products than parent compounds. Furthermore, TN exhibits enantioselective photo-induced toxicity after 240-min irradiation, which could be ascribed to the formation of chiral products. These results could benefit the understanding of enantioselective environmental behavior of chiral pollutants. |
| first_indexed | 2024-03-13T04:56:35Z |
| format | Article |
| id | doaj.art-4858d7e27e8a4fdcaf3adcc19d2ebb8c |
| institution | Directory Open Access Journal |
| issn | 0160-4120 |
| language | English |
| last_indexed | 2024-03-13T04:56:35Z |
| publishDate | 2023-07-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Environment International |
| spelling | doaj.art-4858d7e27e8a4fdcaf3adcc19d2ebb8c2023-06-18T05:00:20ZengElsevierEnvironment International0160-41202023-07-01177107996Photochemical behavior and photo-induced toxicity of chiral pesticides and their chiral monomers in aqueous environmentJia Wang0Shaochen Li1Yandong Yang2Lingyun Fan3Weichao Qin4Limin Su5Yuanhui Zhao6Chao Li7State Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, Engineering Lab for Water Pollution Control and Resources Recovery, School of Environment, Northeast Normal University, Changchun, Jilin 130117, PR ChinaState Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, Engineering Lab for Water Pollution Control and Resources Recovery, School of Environment, Northeast Normal University, Changchun, Jilin 130117, PR ChinaState Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, Engineering Lab for Water Pollution Control and Resources Recovery, School of Environment, Northeast Normal University, Changchun, Jilin 130117, PR ChinaState Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, Engineering Lab for Water Pollution Control and Resources Recovery, School of Environment, Northeast Normal University, Changchun, Jilin 130117, PR ChinaState Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, Engineering Lab for Water Pollution Control and Resources Recovery, School of Environment, Northeast Normal University, Changchun, Jilin 130117, PR ChinaState Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, Engineering Lab for Water Pollution Control and Resources Recovery, School of Environment, Northeast Normal University, Changchun, Jilin 130117, PR ChinaCorresponding authors.; State Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, Engineering Lab for Water Pollution Control and Resources Recovery, School of Environment, Northeast Normal University, Changchun, Jilin 130117, PR ChinaCorresponding authors.; State Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, Engineering Lab for Water Pollution Control and Resources Recovery, School of Environment, Northeast Normal University, Changchun, Jilin 130117, PR ChinaThe photochemical behaviors of chiral pollutants in aqueous solutions are rarely studied using chiral monomers, which may hamper their precise risk assessment and lead to suspicious conclusions. In this study, we systematically investigated the phototransformation behavior and toxicity evolution of two widely used chiral pesticides (triadimefon (TF) and triadimenol (TN)) at enantiomer and diastereomer levels, and proposed a calculation method of total photolysis rate constants of chiral mixture. Results show that TF and TN could be photodegraded faster in pure water than in natural waters, and the observed photolysis rate constants (kobs) of TN with two chiral centers exhibit enantioselectivity, i.e., kobs(TN-RS) = kobs(TN-SR) > kobs(TN-RR) = kobs(TN-SS). The photolysis of TF and TN mainly occurs through their excited singlet and triplet states, respectively. Their photodegradation pathways mainly include dechlorination and elimination of triazole ring. TF could also undergo ether bond cleavage. It is also found that, both TF and TN exhibit photo-induced toxicity to V. fischeri, due to the generation of more toxic products than parent compounds. Furthermore, TN exhibits enantioselective photo-induced toxicity after 240-min irradiation, which could be ascribed to the formation of chiral products. These results could benefit the understanding of enantioselective environmental behavior of chiral pollutants.http://www.sciencedirect.com/science/article/pii/S0160412023002696Chiral pesticidesPhotolysis mechanismKineticsPhoto-induced toxicity |
| spellingShingle | Jia Wang Shaochen Li Yandong Yang Lingyun Fan Weichao Qin Limin Su Yuanhui Zhao Chao Li Photochemical behavior and photo-induced toxicity of chiral pesticides and their chiral monomers in aqueous environment Environment International Chiral pesticides Photolysis mechanism Kinetics Photo-induced toxicity |
| title | Photochemical behavior and photo-induced toxicity of chiral pesticides and their chiral monomers in aqueous environment |
| title_full | Photochemical behavior and photo-induced toxicity of chiral pesticides and their chiral monomers in aqueous environment |
| title_fullStr | Photochemical behavior and photo-induced toxicity of chiral pesticides and their chiral monomers in aqueous environment |
| title_full_unstemmed | Photochemical behavior and photo-induced toxicity of chiral pesticides and their chiral monomers in aqueous environment |
| title_short | Photochemical behavior and photo-induced toxicity of chiral pesticides and their chiral monomers in aqueous environment |
| title_sort | photochemical behavior and photo induced toxicity of chiral pesticides and their chiral monomers in aqueous environment |
| topic | Chiral pesticides Photolysis mechanism Kinetics Photo-induced toxicity |
| url | http://www.sciencedirect.com/science/article/pii/S0160412023002696 |
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