Exploring the degradation and soil enzyme impact of pyroxasulfone and its main metabolites in soils

doi:10.3969/j.issn.1004-1524.20240254

Acta Agriculturae Zhejiangensis ›› 2025, Vol. 37 ›› Issue (4): 847-857.DOI: 10.3969/j.issn.1004-1524.20240254

• Plant Protection • Previous Articles Next Articles

Exploring the degradation and soil enzyme impact of pyroxasulfone and its main metabolites in soils

DU Song¹^,²(), TANG Tao², CHENG Xi², ZHAO Xueping², ZHANG Chunrong², LIANG Xiaoyu³, WANG Meng³, ZHANG Zhen⁴, LI Yongcheng¹, ZHANG Chenghui¹^,^*()

1. College of Food Science and Engineering, Hainan University, Haikou 570228, China
2. Institute of Agro-Product Safety and Nutrition, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, China
3. College of Tropical Agriculture and Forestry, Hainan University, Haikou 570228, China
4. Key Laboratory of Quality and Safety Control for Subtropical Fruit and Vegetable, Ministry of Agriculture and Rural Affairs, Analysis and Test Center, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China

Received:2024-03-19 Online:2025-04-25 Published:2025-05-09

Abstract

Abstract:

Pyroxasulfone, a new isoxazole pre-emergence herbicide, is registered for use on wheat, but the risk of its main metabolites, M-1 and M-3, to the soil environment is not known. In this study, the effects of different physicochemical conditions on the elimination of pyroxasulfone and its major metabolites, as well as the effects of pyroxasulfone and its major metabolites on soil enzyme activities were investigated using three types of soils with different physicochemical properties, namely, black soil, brown soil, and red soil. The results showed that M-1 and M-3 were eliminated at lower rates than the parent in different soils, after 120 d of incubation in three soils, the elimination rates of pyroxasulfone ranged from 12.3% to 38.0%; those of M-1 ranged from 3.8% to 4.6%; and those of M-3 ranged from 4.6% to 21.0%. Pyroxasulfone is readily dissipated in soils with high pH value and high organic matter content (black soils), M-1 is readily dissipated in soils with high cation exchange (black soils), and M-3 is readily degraded in soils with low pH value and low organic matter content (red soils). Soil cation exchange and pH value were the main factors affecting the dissolution of M-1 and M-3. And both M-1 and M-3 gradually accumulated during the parent elimination process. The effect on soil enzyme activities was found that pyroxasulfone and its metabolites, M-1 and M-3, inhibited soil acid phosphatase, β-glucosidase, urease, and dehydrogenase activities, and the metabolites inhibited them more strongly than pyroxasulfone. Therefore, the ecological risks of pyroxasulfone and its metabolites need to be considered comprehensively when assessing the potential risk of pyroxasulfone to soil, so as to provide a scientific basis for the rational use of pesticides.

Key words: pyroxasulfone, metabolites, elimination dynamics, soil enzyme activity

CLC Number:

X131.3

DU Song, TANG Tao, CHENG Xi, ZHAO Xueping, ZHANG Chunrong, LIANG Xiaoyu, WANG Meng, ZHANG Zhen, LI Yongcheng, ZHANG Chenghui. Exploring the degradation and soil enzyme impact of pyroxasulfone and its main metabolites in soils[J]. Acta Agriculturae Zhejiangensis, 2025, 37(4): 847-857.

Figures/Tables 12

References 34

[1]	TANETANI Y, KAKU K, KAWAI K, et al. Action mechanism of a novel herbicide, pyroxasulfone[J]. Pesticide Biochemistry and Physiology, 2009, 95(1): 47-55.
[2]	KHALIL Y, FLOWER K, SIDDIQUE K H M, et al. Effect of crop residues on interception and activity of prosulfocarb, pyroxasulfone, and trifluralin[J]. PLoS One, 2018, 13(12): e0208274.
[3]	JHALA A J, SINGH M, SHERGILL L, et al. Very long chain fatty acid-inhibiting herbicides: Current uses, site of action, herbicide-resistant weeds, and future[J]. Weed Technology, 2024, 38: e1.
[4]	曲明静, 曲春娟, 高兴祥, 等. 40%砜吡草唑悬浮剂的除草活性及对花生的安全性评价[J]. 植物保护, 2024, 50(1): 295-303.
	QU M J, QU C J, GAO X X, et al. Herbicidal activity of pyroxasulfone 40% SC on weeds and its safety evaluation on peanuts[J]. Plant Protection, 2024, 50(1): 295-303. (in Chinese with English abstract)
[5]	ZHANG J J, NIU Y J, MA C, et al. Accumulation and metabolism of pyroxasulfone in tomato seedlings[J]. Ecotoxicology and Environmental Safety, 2023, 254: 114765.
[6]	WANG Y H, MEN J N, ZHENG T, et al. Impact of pyroxasulfone on sugarcane rhizosphere microbiome and functioning during field degradation[J]. Journal of Hazardous Materials, 2023, 455: 131608.
[7]	顾闻. 砜吡草唑在土壤和水环境中的环境行为特性研究[D]. 南京: 南京农业大学, 2017.
	GU W. Study on environmental behavior characteristics of fenpyrad in soil and water environment[D]. Nanjing: Nanjing Agricultural University, 2017. (in Chinese with English abstract)
[8]	Minnesota Department of Agriculture. Pyroxasulfone[R/OL]. Minnesota: Minnesota Department, 2012. (2013-03-26). https://www.mda.state.mn.us/sites/default/files/inline-files/nair-pyroxasulfone.pdf
[9]	Australian Pesticides and Veterinary Medicines Authority. Public Release Summary on the Evaluation of the New Active PYROXASULFONE in the Product SAKURA^® 850 WG HERBICIDE[R]. Canberra: Australian Government. 2011. https://www.apvma.gov.au/node/13976.
[10]	CHAI T T, ZHAO H L, YANG S M, et al. Different transformation of carbosulfan to its higher toxic metabolites in pakchoi (Brassica campestris ssp.) and cucumber (Cucumissativus L.) after field application[J]. International Journal of Environmental Analytical Chemistry, 2015, 95(12): 1124-1133.
[11]	WU M, LI G L, LI P F, et al. Assessing the ecological risk of pesticides should not ignore the impact of their transformation byproducts-The case of chlorantraniliprole[J]. Journal of Hazardous Materials, 2021, 418: 126270.
[12]	SINCLAIR C J, BOXALL A B A. Assessing the ecotoxicity of pesticide transformation products[J]. Environmental Science & Technology, 2003, 37(20): 4617-4625.
[13]	LI Z J. Improving screening model of pesticide risk assessment in surface soils: Considering degradation metabolites[J]. Ecotoxicology and Environmental Safety, 2021, 222: 112490.
[14]	FERNANDES G, APARICIO V C, DE GERÓNIMO E, et al. Epilithic biofilms as a discriminating matrix for long-term and growing season pesticide contamination in the aquatic environment: Emphasis on glyphosate and metabolite AMPA[J]. Science of the Total Environment, 2023, 900: 166315.
[15]	TAN X P, NIE Y X, MA X M, et al. Soil chemical properties rather than the abundance of active and potentially active microorganisms control soil enzyme kinetics[J]. Science of the Total Environment, 2021, 770: 144500.
[16]	闫雷, 李晓亮, 秦智伟, 等. 农药对土壤酶活性影响的研究进展[J]. 农机化研究, 2009, 31(11): 223-226.
	YAN L, LI X L, QIN Z W, et al. Research advance of influence of pesticides on enzyme activities in soil[J]. Journal of Agricultural Mechanization Research, 2009, 31(11): 223-226. (in Chinese with English abstract)
[17]	DU Z K, ZHU Y Y, ZHU L S, et al. Effects of the herbicide mesotrione on soil enzyme activity and microbial communities[J]. Ecotoxicology and Environmental Safety, 2018, 164: 571-578.
[18]	马爱军, 何任红, 蒋新宇, 等. 毒死蜱与乙草胺单一污染和复合污染对土壤酶活性及微生物生物量碳的影响[J]. 生态与农村环境学报, 2008, 24(2): 57-60.
	MA A J, HE R H, JIANG X Y, et al. Effects of single and combined pollution of chlorpyrifos and acetochlor on soil enzyme activity and microbial biomass carbon[J]. Journal of Ecology and Rural Environment, 2008, 24(2): 57-60. (in Chinese with English abstract)
[19]	ZHANG Y, HU Y, AN N, et al. Short-term response of soil enzyme activities and bacterial communities in black soil to a herbicide mixture: Atrazine and Acetochlor[J]. Applied Soil Ecology, 2023, 181: 104652.
[20]	国家质量监督检验检疫总局, 中国国家标准化管理委员会.化学农药环境安全评价试验准则第1部分:土壤降解试验: GB/T 31270.1—2014[S]. 北京: 中国标准出版社, 2015.
[21]	李娜, 黄金, 耿玉清, 等. 青海湖湖滨不同土地类型土壤酶活性的研究[J]. 北京林业大学学报, 2019, 41(10): 49-56.
	LI N, HUANG J, GENG Y Q, et al. Research on soil enzyme activities of different land types in lakeside of Qinghai Lake, northwestern China[J]. Journal of Beijing Forestry University, 2019, 41(10): 49-56. (in Chinese with English abstract)
[22]	李旭, 焉莉, 王继岩, 等. 吉林省水稻种植区不同土壤类型的微生物多样性差异及影响因子研究[J/OL]. 四川农业大学学报.(2022-11-24). https://kns.cnki.net/kcms2/article/abstract?v=uQzRnDzoTXEZX3o8QxbCyUcAUShnN-tVsZEKwIJhDAxzuUzr4dYNVv3dCgKQo7Ea9AC-cugUlZ-lFhwrePgAl71CASF_vEmRZHnCmCDQXl5CB8XTYX2-rHGGXwiW1eFBmryEid5l4cP86i2egQVQk6Lf-1r35DaYoPFwD4_nJPeEVGLV8btTp87c-wpU1mKbs&uniplatform=NZKPT&language=CHS
	LI X, YIAN L, WANG J Y, et al. Study on microbial diversity differences and influencing factors of different soil types in rice growing areas of Jilin Province[J/OL]. Journal of Sichuan Agricultural College. (2022-11-24). https://kns.cnki.net/kcms2/article/abstract?v=uQzRnDzoTXEZX3o8-QxbCyUcAUShnNtVsZEKwIJhDAxzuUzr4dYNVv3dCgKQo7-Ea9AC-cugUlZ-lFhwrePgAl71CASF_vEmRZHnCmCDQXl5-CB8XTYX2-rHGGXwiW1eFBmryEid5l4cP86i2egQVQk6Lf-1r35DaYoPFwD4_nJPeEVGLV8btTp87c-wpU1mKbs&uniplatform=NZKPT&language=CHS (in Chinese with English abstract)
[23]	中华人民共和国农业农村部. 农作物中农药残留试验准则:NY·T788—2018[S].北京: 中国农业出版社, 2018.
[24]	SANCHEZ W, BURGEOT T, PORCHER J M. A novel “Integrated Biomarker Response” calculation based on reference deviation concept[J]. Environmental Science and Pollution Research, 2013, 20(5): 2721-2725.
[25]	程超. 两种农药单独及与纳米TiO₂复合暴露对土壤微生物的毒性效应[D]. 泰安: 山东农业大学, 2022.
	CHENG C. Toxic effects of two pesticides alone and combined with nano-TiO₂ on soil microorganisms[D]. Taian: Shandong Agricultural University, 2022. (in Chinese with English abstract)
[26]	王宇轩. 添加生物质炭对苯磺隆胁迫下土壤养分和酶活性的影响[D]. 太谷: 山西农业大学, 2020.
	WANG Y X. Effects of adding biomass charcoal on soil nutrients and enzyme activities under tribenuron-methyl stress[D]. Taigu: Shanxi Agricultural University, 2020. (in Chinese with English abstract)
[27]	LIU Y F, FAN X X, ZHANG T, et al. Effects of the long-term application of atrazine on soil enzyme activity and bacterial community structure in farmlands in China[J]. Environmental Pollution, 2020, 262: 114264.
[28]	ZHANG Y Q, ZHANG J W, SHI B H, et al. Effects of cloransulam-methyl and diclosulam on soil nitrogen and carbon cycle-related microorganisms[J]. Journal of Hazardous Materials, 2021, 418: 126395.
[29]	GODIN A M, LIDHER K K, WHITESIDE M D, et al. Control of soil phosphatase activities at millimeter scales in a mixed paper birch-Douglas-fir forest: The importance of carbon and nitrogen[J]. Soil Biology and Biochemistry, 2015, 80: 62-69.
[30]	LIU K H, LI C M, TANG S Q, et al. Heavy metal concentration, potential ecological risk assessment and enzyme activity in soils affected by a lead-zinc tailing spill in Guangxi, China[J]. Chemosphere, 2020, 251: 126415.
[31]	BELIAEFF B, BURGEOT T. Integrated biomarker response: a useful tool for ecological risk assessment[J]. Environmental Toxicology and Chemistry, 2002, 21(6): 1316-1322.
[32]	ZHANG C, ZHANG J W, ZHU L S, et al. Fluoxastrobin-induced effects on acute toxicity, development toxicity, oxidative stress, and DNA damage in Danio rerio embryos[J]. Science of the Total Environment, 2020, 715: 137069.
[33]	YANG R, XIA X M, WANG J H, et al. Dose and time-dependent response of single and combined artificial contamination of sulfamethazine and copper on soil enzymatic activities[J]. Chemosphere, 2020, 250: 126161.
[34]	CHENG Y L, SONG W H, TIAN H M, et al. The effects of high-density polyethylene and polypropylene microplastics on the soil and earthworm Metaphire guillelmi gut microbiota[J]. Chemosphere, 2021, 267: 129219.

实验基质 Experimental soil	来源 Source	pH值 pH value	有机质含量 Organic matter content/(g·kg^-1)	阳离子交换量 Cation exchange capacity (CEC)/(cmol·kg^-1)	土壤质地 Soil texture
褐土Brown soil (S1)	河北Hebei	6.58	12.0	12.8	壤土Loam
红土Red soil (S2)	湖南Hunan	4.60	5.51	13.4	黏壤土Clay loam
黑土Black soil (S3)	吉林Jilin	7.90	35.7	28.9	粉黏壤土Powdery clay loam

实验基质 Experimental soil	来源 Source	pH值 pH value	有机质含量 Organic matter content/(g·kg^-1)	阳离子交换量 Cation exchange capacity (CEC)/(cmol·kg^-1)	土壤质地 Soil texture
褐土Brown soil (S1)	河北Hebei	6.58	12.0	12.8	壤土Loam
红土Red soil (S2)	湖南Hunan	4.60	5.51	13.4	黏壤土Clay loam
黑土Black soil (S3)	吉林Jilin	7.90	35.7	28.9	粉黏壤土Powdery clay loam

时间 Time/min	甲醇 Methanol/%	0.1%甲酸水 0.1% formic acid water/%	流速 Flow velocity/ (mL·min^-1)
0.01	40	60	0.25
0.5	65	35	0.25
1.5	95	5	0.25
3.4	95	5	0.25
3.5	40	60	0.25
6.0	40	60	0.25

时间 Time/min	甲醇 Methanol/%	0.1%甲酸水 0.1% formic acid water/%	流速 Flow velocity/ (mL·min^-1)
0.01	40	60	0.25
0.5	65	35	0.25
1.5	95	5	0.25
3.4	95	5	0.25
3.5	40	60	0.25
6.0	40	60	0.25

农药 Pesticide	母离子 Parent ion (m/z)	定量离子对 Quantitative ion pair(m/z)	定性离子对 Qualitative ion pair(m/s)	Q1偏转电压 Q1 deflection voltage/V	碰撞气能量 Collision gas energy/eV	Q3偏转电压 Q3 deflection voltage/V
砜吡草唑Pyroxasulfone	392.1	229.1	179.1	-11;-11	-17;-32	-17;-13
代谢物M-1 Metabolite-1	309	259	195	23; 12	21; 17	22; 12
代谢物M-3 Metabolite-3	258.9	165.05	214.95	13; 10	16; 8	17; 14

Exploring the degradation and soil enzyme impact of pyroxasulfone and its main metabolites in soils

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References 34

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农药 Pesticide	土壤类型 Soil type	标准曲线 Standard curve	R²
砜吡草唑	S1	y=67 112.9x + 7 247.6	0.999 8
Pyroxasulfone	S2	y=66 899.9x + 8 900.6	0.999 7
	S3	y=68 601.5x + 1 637.3	0.999 8
代谢物M-1	S1	y=20 178.3x + 631.1	0.999 9
Metabolite-1	S2	y=20 030.3x-299.4	0.999 8
	S3	y=20 866.0x + 770.6	0.999 9
代谢物M-3	S1	y=84 350.3x + 16 146.0	0.999 8
Metabolite-3	S2	y=82 986.9x + 15 028.5	0.999 8
	S3	y=84 780.0x + 17 830.3	0.999 9

农药 Pesticide	土壤类型 Soil type	回归方程 Regression equation	R²	t_1/2/d
砜吡草唑	S1	C_t=1.783e^{-0.002 54}^t	0.977 8	272.8
Pyroxasulfone	S2	C_t=1.768e^{-0.000 81}^t	0.764 4	855.7
	S3	C_t=1.789e^{-0.004 75}^t	0.925 8	145.9
代谢物M-1	S1	C_t=1.792e^{-0.000 31}^t	0.848 8	2 236.0
Metabolite-1	S2	C_t=1.747e^{-0.000 30}^t	0.961 8	2 310.5
	S3	C_t=1.715e^{-0.000 43}^t	0.873 5	1 612.0
代谢物M-3	S1	C_t=1.844e^{-0.001 11}^t	0.879 3	624.5
Metabolite-3	S2	C_t=1.798e^{-0.001 87}^t	0.981 5	370.7
	S3	C_t=1.793e^{-0.000 34}^t	0.787 8	2 038.7

农药 Pesticide	土壤性质 Soil properties	回归方程 Regression equation	R²
砜吡草唑	pH值pH value	y=0.132 4x+2.165 2	0.996 1
Pyroxasulfone	有机质含量	y=0.012 9x+1.552 5	0.869 0
	Organic matter content
	CEC	y=0.1x+1.523 3	0.206 0
代谢物M-1	pH值pH value	y=0.004 4x+1.691 2	0.083 8
Metabolite-1	有机质含量	y=0.001 1x+1.682	0.441 3
	Organic matter content
	CEC	y=0.025x+1.713 3	0.986 8
代谢物M-3	pH值pH value	y=-0.086 1x+1.032 2	0.983 8
Metabolite-3	有机质含量	y=-0.007 7x+1.443 7	0.717 4
	Organic matter content
	CEC	y=-0.04x+1.5	0.076 9

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农药 Pesticide	土壤类型 Soil type	添加浓度 Additive concentration/ (mg·kg^-1)	平均回收率 Average recovery Rate/%	RSD/%
砜吡草唑	S1	0.2	96	3.5
Pyroxasulfone		2	97	3.3
	S2	0.2	93	2.7
		2	95	1.5
	S3	0.2	95	1.7
		2	98	1.3
代谢物M-1	S1	0.2	95	2.0
Metabolite-1		2	90	0.5
	S2	0.2	86	1.4
		2	87	2.3
	S3	0.2	91	1.8
		2	92	1.0
代谢物M-3	S1	0.2	94	1.6
Metabolite-3		2	87	1.5
	S2	0.2	92	1.0
		2	89	2.3
	S3	0.2	88	1.7
		2	86	2.8

农药 Pesticide	土壤类型 Soil type	添加浓度 Additive concentration/ (mg·kg^-1)	平均回收率 Average recovery Rate/%	RSD/%
砜吡草唑	S1	0.2	96	3.5
Pyroxasulfone		2	97	3.3
	S2	0.2	93	2.7
		2	95	1.5
	S3	0.2	95	1.7
		2	98	1.3
代谢物M-1	S1	0.2	95	2.0
Metabolite-1		2	90	0.5
	S2	0.2	86	1.4
		2	87	2.3
	S3	0.2	91	1.8
		2	92	1.0
代谢物M-3	S1	0.2	94	1.6
Metabolite-3		2	87	1.5
	S2	0.2	92	1.0
		2	89	2.3
	S3	0.2	88	1.7
		2	86	2.8