Influence of Chiral Difference on the Degradation of Fenvalerate in Aquaculture Sediment Environment

doi:10.11924/j.issn.1000-6850.casb2020-0727

Abstract

Abstract:

To study the dynamic degradation regulation of fenvalerate (FV) and its chiral isomers (trans-isomer: FV1 and FV2; cis-isomer: FV3 and FV4) in aquaculture sediment, the degradation regulation of FV and chiral isomers were studied through laboratory simulation. The degradation of FV in sediment followed the first-order degradation kinetics. The half-lives of FV in the sediment ranged from 19.47 to 38.73 days. There was no significant difference in the degradation half-lives of FV. Nevertheless, the half-lives of different chiral isomers in the sediment were different. The degradation half-life of FV1 was substantially longer than those of other isomers, and the degradation half-life of FV3 was significantly longer than those of FV2 and FV4. FV underwent α-C isomerization in the sediment. When the conversion was carried out for 21 d, the conversion rate was slowing down and the changes in conversion products decreased. Because FV had a long accumulation period in sediments, the direct exposure of sediment to FV should be minimized. To effectively conduct environmental and ecological risk assessments of FV, the different chiral isomers should be distinguished in sediment FV residues.

Key words: fenvalerate, sediment environment, chiral isomer, half-life, conversion

CLC Number:

Song Chao, Zou Jianmin, Wang Qian, Chen Xi, Fang Longxiang, Qiu Liping, Chen Jiazhang. Influence of Chiral Difference on the Degradation of Fenvalerate in Aquaculture Sediment Environment[J]. Chinese Agricultural Science Bulletin, 2021, 37(28): 153-158.

Figures/Tables 9

References 28

[1]	朱薇薇. 太湖底泥沉积物中菌群落数量和种类分布及藻菌关系研究[D]. 南京:南京大学, 2011.
[2]	Lu S, Liao M, Xie C, et al. Seasonal dynamics of ammonia-oxidizing microorganisms in freshwater aquaculture ponds[J]. Annals of Microbiology, 2015, 65(2):651-657. doi: 10.1007/s13213-014-0903-2 URL
[3]	Weston D P, You J, Lydy M J. Distribution and toxicity of sediment-associated pesticides in agriculture-dominated water bodies of California's Central Valley[J]. Environmental science & technology, 2004, 38(10):2752-2759. doi: 10.1021/es0352193 URL
[4]	Tang W, Wang D, Wang J, et al. Pyrethroid pesticide residues in the global environment: An overview[J]. Chemosphere, 2018, 191(Supplement C):990-1007. doi: 10.1016/j.chemosphere.2017.10.115 URL
[5]	徐春娟. 拟除虫菊酯在鄂、皖、川、渝淡水养殖水体及水产品中的残留状况及来源分析研究[D]. 上海:上海海洋大学, 2017.
[6]	Wang J Z, Bai Y S, Wu Y, et al. Occurrence, compositional distribution, and toxicity assessment of pyrethroid insecticides in sediments from the fluvial systems of Chaohu Lake, Eastern China[J]. Environmental Science and Pollution Research, 2016, 23(11):10406-10414. doi: 10.1007/s11356-015-5831-6 URL
[7]	Reddy P S, Bhagyalakshmi A. Modulation of Protein Metabolism in Selected Tissues of the Crab (Oziotelphusa senex) under Fenvalerate-Induced Stress[J]. Ecotoxicology and Environmental Safety, 1994, 27(2):214-219. pmid: 7516287
[8]	Li H, Cheng F, Wei Y, et al. Global occurrence of pyrethroid insecticides in sediment and the associated toxicological effects on benthic invertebrates: An overview[J]. Journal of Hazardous Materials, 2017, 324:258-271. doi: 10.1016/j.jhazmat.2016.10.056 URL
[9]	Sobha K, Tilak K. Toxicity and histopathological changes in the three Indian major carps, Labeo rohita (Hamilton), Catla catla (Hamilton) and Cirrhinus mrigala (Hamilton) exposed to fenvalerate[J]. Czech Academy of Agriculture Sciences, 2012(6):232-238.
[10]	陈莉, 章钢娅, 胡锋. 氰戊菊酯在土壤中的降解及其影响因子研究[J]. 土壤学报, 2008, 45(1):90-97.
[11]	Ma Y, Chen L, Lu X, et al. Enantioselectivity in aquatic toxicity of synthetic pyrethroid insecticide fenvalerate[J]. Ecotoxicology and Environmental Safety, 2009, 72(7):1913-1918. doi: 10.1016/j.ecoenv.2009.07.005 URL
[12]	Li Z, Zhang Z, Zhang L, et al. Isomer- and enantioselective degradation and chiral stability of fenpropathrin and fenvalerate in soils[J]. Chemosphere, 2009, 76(4):509-516. doi: 10.1016/j.chemosphere.2009.03.015 URL
[13]	Chapman R A, Harris C R. Persistence of four pyrethroid insecticides in a mineral and an organic soil[J]. Journal of Environmental Science & Health Part B: Pesticides Food Contaminants & Agricultural Wastes, 1981, 16(5):605-615.
[14]	赵晨, 彭书传, 陈天虎, 等. 巢湖流域和太湖流域沉积物中苄氯菊酯和高效氰戊菊酯的生态风险评价[J]. 环境科学学报, 2016, 36(3):1080-1091.
[15]	张敬卫, 宋超, 张聪, 等. 水产养殖常规管理活动对农药氰戊菊酯及其顺反异构体消除规律影响的研究[J]. 中国农学通报, 2018, 34(35):143-150.
[16]	Kabir M H, Abd El-Aty A M, Rahman M M, et al. Dissipation kinetics, pre-harvest residue limits, and dietary risk assessment of the systemic fungicide metalaxyl in Swiss chard grown under greenhouse conditions[J]. Regulatory Toxicology and Pharmacology, 2018, 92:201-206. doi: 10.1016/j.yrtph.2017.12.003 URL
[17]	Liu W, Qin S, Gan J. Chiral stability of synthetic pyrethroid insecticides[J]. Journal of Agricultural Food and Chemistry, 2005, 53(10):3814-3820. doi: 10.1021/jf048425i URL
[18]	Nillos M G, Qin S, Larive C, et al. Epimerization of Cypermethrin Stereoisomers in Alcohols[J]. Journal of Agricultural & Food Chemistry, 2009, 57(15):6938-6943.
[19]	Birolli W G, Borges E M, Nitschke M, et al. Biodegradation Pathway of the Pyrethroid Pesticide Esfenvalerate by Bacteria from Different Biomes[J]. Water, Air, & Soil Pollution, 2016, 227(8):1-11.
[20]	Zhang J, Song C, Zhang C, et al. Effects of multiple environmental factors on elimination of fenvalerate and its cis-trans isomers in aquaculture water[J]. Environmental Science and Pollution Research, 2018, 26(4):3795-3802. doi: 10.1007/s11356-018-3916-8 URL
[21]	Cotham W E, Bidleman T F. Degradation of malathion, endosulfan, and fenvalerate in seawater and seawater/sediment microcosms[J]. Journal of Agricultural and Food Chemistry, 1989, 37(3):824-828. doi: 10.1021/jf00087a055 URL
[22]	Wang C, Wang L, Wang G. Adsorption regularity of fenvalerate in sediments[A]. Proceedings of the National Environmental Chemistry Conference[C]. 2008.
[23]	Corcellas C, Eljarrat E, Barceló D. First report of pyrethroid bioaccumulation in wild river fish: A case study in Iberian river basins (Spain)[J]. Environment International, 2015, 75:110-116. doi: 10.1016/j.envint.2014.11.007 URL
[24]	Rosa R, Bordalo M D, Soares A M, et al. Effects of the Pyrethroid Esfenvalerate on the Oligochaete, Lumbriculus variegatus[J]. Bull Environ Contam Toxicol, 2016, 96(4):438-442. doi: 10.1007/s00128-015-1718-y URL
[25]	胡志强, 许良忠, 任雪景, 等. 拟除虫菊酯类杀虫剂的研究进展[J]. 青岛科技大学学报:自然科学版, 2002, 23(1):48-51.
[26]	You J, Lydy M J. A solution for isomerization of pyrethroid insecticides in gas chromatography[J]. Journal of Chromatography A, 2007, 1166(1-2):181-190. doi: 10.1016/j.chroma.2007.08.014 URL
[27]	李朝阳, 张智超, 张玲, 等. 土壤中高效氟氯氰菊酯对映体选择性降解的研究[J]. 农业环境科学学报, 2006, 25(6):1640-1643.
[28]	李劭彤. 拟除虫菊酯类农药的微生物手性降解特征[D]. 石家庄:河北科技大学, 2016.

分组		浓度/(μg/L)	药品
1	TL	20	FV（4类异构体混合）
2	AL		FV1 (αR,2S- FV)
3	BL		FV2 (αS,2R- FV)
4	CL		FV3 (αR,2R- FV)
5	DL		FV4 (αS,2S- FV)
6	TH	200	FV（4类异构体混合）
7	AH		FV1 (αR,2S- FV)
8	BH		FV2 (αS,2R- FV)
9	CH		FV3 (αR,2R- FV)
10	DH		FV4 (αS,2S- FV)

分组		浓度/(μg/L)	药品
1	TL	20	FV（4类异构体混合）
2	AL		FV1 (αR,2S- FV)
3	BL		FV2 (αS,2R- FV)
4	CL		FV3 (αR,2R- FV)
5	DL		FV4 (αS,2S- FV)
6	TH	200	FV（4类异构体混合）
7	AH		FV1 (αR,2S- FV)
8	BH		FV2 (αS,2R- FV)
9	CH		FV3 (αR,2R- FV)
10	DH		FV4 (αS,2S- FV)

出峰顺序	药品	保留时间/min	面积	面积比/%
1	FV1	11.074	7547326	25.13
2	FV2	15.48	8490729	28.27
3	FV3	17.34	6582565	21.92
4	FV4	21.225	7416057	24.69

出峰顺序	药品	保留时间/min	面积	面积比/%
1	FV1	11.074	7547326	25.13
2	FV2	15.48	8490729	28.27
3	FV3	17.34	6582565	21.92
4	FV4	21.225	7416057	24.69

试验组	降解动力学方程	相关性系数	降解速率常数
FV-低	C_t=37.659e^-0.024^t	0.916	0.024±0.001
FV1-低	C_t=41.185e^-0.018^t	0.979	0.018±0.001
FV2-低	C_t=40.199e^-0.036^t	0.971	0.036±0.002
FV3-低	C_t=38.406e^-0.022^t	0.936	0.022±0.001
FV4-低	C_t=38.458e^-0.029^t	0.986	0.028±0.001
FV-高	C_t=362.090e^-0.026^t	0.969	0.026±0.002
FV1-高	C_t=390.700e^-0.02^t	0.965	0.019±0.002
FV2-高	C_t=365.680e^-0.035^t	0.991	0.036±0.001
FV3-高	C_t=369.040e^-0.022^t	0.927	0.022±0.001
FV4-高	C_t=362.780e^-0.029^t	0.957	0.030±0.004