Photolysis and photo-enhanced toxicity of three novel designed neonicotinoids: Impact of novel modifying groups

Lingyun Fan; Chen Wang; Jia Wang; Xujia Zhang; Qi Li; Hanxi Wang; Yuan Hui Zhao

doi:10.1016/j.jhazmat.2023.132132

Photolysis and photo-enhanced toxicity of three novel designed neonicotinoids: Impact of novel modifying groups

J Hazard Mater. 2023 Oct 5:459:132132. doi: 10.1016/j.jhazmat.2023.132132. Epub 2023 Jul 23.

Authors

Lingyun Fan¹, Chen Wang², Jia Wang², Xujia Zhang³, Qi Li⁴, Hanxi Wang⁵, Yuan Hui Zhao⁶

Affiliations

¹ State Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, School of Environment, Northeast Normal University, Changchun 130117, China; Heilongjiang Province Key Laboratory of Geographical Environment Monitoring and Spatial Information Service in Cold Regions, Heilongjiang Province Collaborative Innovation Center of Cold Region Ecological Safety, School of Geographical Sciences, Harbin Normal University, Harbin 150025, China.
² State Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, School of Environment, Northeast Normal University, Changchun 130117, China.
³ Heilongjiang Province Key Laboratory of Geographical Environment Monitoring and Spatial Information Service in Cold Regions, Heilongjiang Province Collaborative Innovation Center of Cold Region Ecological Safety, School of Geographical Sciences, Harbin Normal University, Harbin 150025, China.
⁴ School of Environmental Science & Engineering, Yancheng Institute of Technology, Yancheng 224051, China.
⁵ Heilongjiang Province Key Laboratory of Geographical Environment Monitoring and Spatial Information Service in Cold Regions, Heilongjiang Province Collaborative Innovation Center of Cold Region Ecological Safety, School of Geographical Sciences, Harbin Normal University, Harbin 150025, China. Electronic address: wanghx197@nenu.edu.cn.
⁶ State Environmental Protection Key Laboratory of Wetland Ecology and Vegetation Restoration, School of Environment, Northeast Normal University, Changchun 130117, China. Electronic address: zhaoyh@nenu.edu.cn.

PMID: 37494794
DOI: 10.1016/j.jhazmat.2023.132132

Abstract

Three novel neonicotinoids (cycloxaprid, flupyradifurone and sulfoxaflor) were designed to reduce the biotoxicity for non-target organisms. These neonicotinoids were photolyzed under light radiation, but it was unclear for the photo-enhanced toxicity and influences of the novel modifying group of the three neonicotinoids. The photolysis and photo-enhanced toxicity experiments were performed for the three neonicotinoids, coupled with quantum chemistry calculation, the mechanisms of photolysis, photo-enhanced toxicity and the influences of novel modifying groups were analyzed. The results showed the photolysis pathways were enriched as compared with previous neonicotinoids due to the composition of modifying groups, singlet oxygen and hydroxyl participated the photolysis of cycloxaprid and flupyradifurone. All tested neonicotinoids exhibited photo-enhanced toxicity to Vibrio fischeri. Due to the difference of photolysis mechanism and toxicity to V. fischeri, the photo-enhanced toxicity curves showed diverse variation when histidine, tert-butanol or dissolved organic matters was in presence of the test solutions. The impact of novel modifying groups over photolysis and photo-enhanced toxicity were analyzed based on the comparison with previous neonicotinoids, theoretically predicted UV-Vis spectra and photo-physical/chemical property descriptors. The data showed the composition of novel modifying group increased the light absorption and photo-chemical activities for the three neonicotinoids.

Keywords: Neonicotinoids; Photo-enhanced toxicity; Photolysis; Quantum chemistry calculation; Vibrio fischeri.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone*
Aliivibrio fischeri
Neonicotinoids / chemistry
Photolysis
Water Pollutants, Chemical* / chemistry

Substances

Neonicotinoids
flupyradifurone
4-Butyrolactone
Water Pollutants, Chemical