Hydrolysis of a neonicotinoid: a theoretical study on the reaction mechanism of dinotefuran

Chen, Rong; Yin, Hui; Zhang, Chaoqing; Liang, Guangchao

doi:10.1007/s11224-017-1030-z

Cited by 9 publications

(2 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reductions in p-NEOs in the boiled tap water sample might directly reveal the stabilities of different p-NEOs, but the studies on NEOs reductions in tap water are still limited. A previous study suggested that the hydrolysis rate of THM in water is much higher than those of IMI, ACE, and CLO at 21.5 °C [ 44 ], and DIN could also experience hydrolysis through different pathways in the water phase [ 45 ]. Therefore, THM and DIN might present fewer stabilities in tap water than ACE, IMI, CLO, and THD, especially during the heating process, which might promote hydrolysis and pyrolysis.…”

Section: Resultsmentioning

confidence: 99%

Changing on the Concentrations of Neonicotinoids in Rice and Drinking Water through Heat Treatment Process

Wei

Zhang

et al. 2023

Molecules

View full text Add to dashboard Cite

Neonicotinoids (NEOs) have become the most widely used insecticides in the world since the mid-1990s. According to Chinese dietary habits, rice and water are usually heated before being consumed, but the information about the alteration through the heat treatment process is very limited. In this study, NEOs in rice samples were extracted by acetonitrile (ACN) and in tap water, samples were extracted through an HLB cartridge, then, a high-performance liquid chromatography system and a triple quadrupole mass spectrometry (HPLC-MS/MS) were applied for target chemical analysis. The parents of NEOs (p-NEOs) accounted for >99% of the total NEOs mass (∑NEOs) in both uncooked (median: 66.8 ng/g) and cooked (median: 41.4 ng/g) rice samples from Guangdong Province, China, while the metabolites of NEOs (m-NEOs) involved in this study accounted for less than 1%. We aimed to reveal the concentration changes of NEOs through heat treatment process, thus, several groups of rice and water samples from Guangdong were cooked and boiled, respectively. Significant (p < 0.05) reductions in acetamiprid, imidacloprid (IMI), thiacloprid, and thiamethoxam (THM) have been observed after the heat treatment of the rice samples. In water samples, the concentrations of THM and dinotefuran decreased significantly (p < 0.05) after the heat treatment. These results indicate the degradation of p-NEOs and m-NEOs during the heat treatment process. However, the concentrations of IMI increased significantly in tap water samples (p < 0.05) after heat treatment process, which might be caused by the potential IMI precursors in those industrial pesticide products. The concentrations of NEOs in rice and water can be shifted by the heat treatment process, so this process should be considered in relevant human exposure studies.

show abstract

Section: Resultsmentioning

confidence: 99%

Changing on the Concentrations of Neonicotinoids in Rice and Drinking Water through Heat Treatment Process

Wei

Zhang

et al. 2023

Molecules

View full text Add to dashboard Cite

show abstract

“…Biotic degradation also contributes to the environmental behavior and transformation of NEOs [ 14 , 15 ]. Hydrolysis processes of NEOs essentially involve a nucleophilic substitution reaction in which nucleophiles (i.e., H2O and OH − ) attack the electrophilic groups (i.e., C, S, and P) in the NEO molecules [ 16 ]. The extent of hydrolysis depends on pH, temperature, dissolved organic carbon concentration, and humic acid content [ 13 , 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

The Degradation Process of Typical Neonicotinoid Insecticides in Tidal Streams in Subtropical Cities: A Case Study of the Wuchong Stream, South China

Jia

Cai

Xiao

et al. 2023

Toxics

View full text Add to dashboard Cite

Neonicotinoid insecticides (NEOs) are commonly used to prevent unwanted insects in urban fields. Degradation processes have been one of the important environmental behaviors of NEOs in an aquatic environment. In this research, hydrolysis, biodegradation, and photolysis processes of four typical NEOs (i.e., thiacloprid (THA), clothianidin (CLO), acetamiprid (ACE), and imidacloprid (IMI)) were examined through the adoption of response surface methodology–central composite design (RSM-CCD) for an urban tidal stream in South China. The influences of multiple environmental parameters and concentration levels on the three degradation processes of these NEOs were then evaluated. The results indicated that the three degradation processes of the typical NEOs followed a pseudo-first-order reaction kinetics model. The primary degradation process of the NEOs were hydrolysis and photolysis processes in the urban stream. The hydrolysis degradation rate of THA was the highest (1.97 × 10−5 s−1), and that of CLO was the lowest (1.28 × 10−5 s−1). The temperature of water samples was the main environmental factor influencing the degradation processes of these NEOs in the urban tidal stream. Salinity and humic acids could inhibit the degradation processes of the NEOs. Under the influence of extreme climate events, the biodegradation processes of these typical NEOs could be suppressed, and other degradation processes could be further accelerated. In addition, extreme climate events could pose severe challenges to the migration and degradation process simulation of NEOs.

show abstract

Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and Their Derivatives

Bedford¹

2023

Organic Reaction Mechanisms Series

View full text Add to dashboard Cite

Hydrolysis of a neonicotinoid: a theoretical study on the reaction mechanism of dinotefuran

Cited by 9 publications

References 35 publications

Changing on the Concentrations of Neonicotinoids in Rice and Drinking Water through Heat Treatment Process

Changing on the Concentrations of Neonicotinoids in Rice and Drinking Water through Heat Treatment Process

The Degradation Process of Typical Neonicotinoid Insecticides in Tidal Streams in Subtropical Cities: A Case Study of the Wuchong Stream, South China

Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and Their Derivatives

Contact Info

Product

Resources

About