新农药三氟苯嘧啶在土壤中的吸附
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摘要
为杀虫剂三氟苯嘧啶合理使用准则的制定和环境安全性评价,本文选择湖南红壤、北京潮土和吉林黑土等3种代表性土壤,采用批量平衡法研究了三氟苯嘧啶在土壤中的吸附。试验结果表明:三氟苯嘧啶在土壤中的吸附可用Freundlich吸附等温方程很好地拟合,其在湖南红壤、北京潮土和吉林黑土中的吸附系数KF值分别为1.24、2.02和6.63,其ΔG变化绝对值分别为0.093、1.642和4.438,均小于10 kJ·mol~(-1),说明三氟苯嘧啶在土壤中的吸附以物理作用为主。三氟苯嘧啶在土壤中的吸附与土壤理化性质和药剂本身结构有关,其中以土壤有机质含量和黏粒含量对吸附的影响最显著,沙粒的影响次之,而土壤pH值和粉粒含量对吸附的影响最小,说明有机质含量和黏粒含量是三氟苯嘧啶在土壤中吸附的主导支配因素。
Triflumezopyrim is a novel class of mesoionic insecticides discovered by DuPont Crop Protection, and registered for use on rice,vegetables, and fruits for control of insect pests. In order to provide a reference for setting of reasonable application guidelines and ecological risk assessment of the insecticide, adsorption of triflumezopyrim on three soils, the laterite from Hunan Province, fluvo-aquic soil from Beijing, and terra preta from Jilin Province was studied in the laboratory using high performance liquid chromatography(HPLC)with diode array detector(DAD)according to batch equilibrium method. The experimental results showed that there was a weak sorption of triflumezopyrim on soils. The adsorption isotherms of triflumezopyrim on soils can be described very well by Freudlich equation, and the adsorption coefficient(KF)of triflumezopyrim on the laterite, fluvo-aquic soil, and terra preta was 1.24, 2.02, and 6.63, respectively, and the adsorption free energy(ΔG)was 0.093, 1.642, and 4.438, respectively, indicating that the adsorption largely resulted from the physical adsorption, according to the pesticide environmental test guidelines of China. The adsorption coefficient KF value of triflumezopyrim was influenced by physicochemical properties of soils, and the chemical structure and water solubility of the insecticide itself. Most significant correlation was observed between the KF value of triflumezopyrim and the organic matter and clay content of soils; slight correlation between the KFvalue of triflumezopyrim and the sand content of soils, and very poor correlation between the KF value of triflumezopyrim and pH value and silt content of soils, suggesting that the organic matter and clay content of soils are important factors affecting the adsorption of triflumezopyrim in water-soil environment system.
Triflumezopyrim is a novel class of mesoionic insecticides discovered by DuPont Crop Protection, and registered for use on rice,vegetables, and fruits for control of insect pests. In order to provide a reference for setting of reasonable application guidelines and ecological risk assessment of the insecticide, adsorption of triflumezopyrim on three soils, the laterite from Hunan Province, fluvo-aquic soil from Beijing, and terra preta from Jilin Province was studied in the laboratory using high performance liquid chromatography(HPLC)with diode array detector(DAD)according to batch equilibrium method. The experimental results showed that there was a weak sorption of triflumezopyrim on soils. The adsorption isotherms of triflumezopyrim on soils can be described very well by Freudlich equation, and the adsorption coefficient(KF)of triflumezopyrim on the laterite, fluvo-aquic soil, and terra preta was 1.24, 2.02, and 6.63, respectively, and the adsorption free energy(ΔG)was 0.093, 1.642, and 4.438, respectively, indicating that the adsorption largely resulted from the physical adsorption, according to the pesticide environmental test guidelines of China. The adsorption coefficient KF value of triflumezopyrim was influenced by physicochemical properties of soils, and the chemical structure and water solubility of the insecticide itself. Most significant correlation was observed between the KF value of triflumezopyrim and the organic matter and clay content of soils; slight correlation between the KFvalue of triflumezopyrim and the sand content of soils, and very poor correlation between the KF value of triflumezopyrim and pH value and silt content of soils, suggesting that the organic matter and clay content of soils are important factors affecting the adsorption of triflumezopyrim in water-soil environment system.
引文
[1]刘维屏,季谨.农药在土壤-水环境中归宿的主要支配因素：吸附和脱附[J].中国环境科学, 1996, 16(1):25-30.LIU Wei-ping, JI Jin. One of the most important factors affecting the fate of pesticides in soil-water environmental:Sorption and desorption[J]. China Environmental Sciences, 1996, 16(1):25-30.
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[3] Holyoke C W, Cordova D, Zhang W M. Mesoionic insecticides:A novel class of insecticides that modulate nicotinic acetylcholine receptors[J].Pest Management Science, 2017, 73(4):796-806.
[4] US EPA. Triflumezopyrim:Human health risk assessment to establish tolerances for rice without U. S. Registration[EB/OL].(2017-08-17)[2019-05-18]. https：//www. regulations. gov/document?D=EPA-HQOPP-2016-0142-0003.
[5] Zhang W M, Holyoke Jr C W, Pahutskia T F, et al. Mesoionic pyrido[1,2-a] pyrimidinones:Discovery of triflumezopyrim as a potent hopper insecticide[J]. Bioorganic&Medicinal Chemistry Letters, 2017, 27(1):16-20.
[6]朱友理,何东兵,曹书培,等.三氟苯嘧啶对稻飞虱的防效及对天敌的安全性[J].中国植保导刊, 2018, 39(8):71-74.ZHU You-li, HE Dong-bing, CAO Shu-pei, et al. Controlling efficiency of trifluorobenzidine against rice plant hopper and its safety to natural enemies[J]. Bulletin of China Plant Protection, 2018, 39(8):71-74.
[7]英君伍,雷光月,宋玉泉,等.三氟苯嘧啶的合成与杀虫活性研究[J].现代农药, 2017, 16(2):14-16,20.YING Jun-wu, LEI Guang-yue, SONG Yu-quan, et al. Synthesis and bioactivity of triflumesopyrim[J]. Modern Agrochemicals, 2017, 16(2):14-16,20.
[8]欧晓明,余淑英,罗玲,等.新农药硫肟醚在土壤上的吸附[J].农业环境科学学报, 2007, 26(2):577-582.OU Xiao-ming, YU Shu-ying, LUO Ling, et al. Adsorption of novel oxime insecticide IINPC-A9908 on soils[J]. Journal of Agro-Environment Science, 2007, 26(2):577-582.
[9] OECD. Adsorption-desorption using a batch equilibrium method[EB/OL].(2000-01-21)[2019-05-18]. https：//www. oecd-ilibrary. org/docserver/9789264069602-en. pdf?expires=1546505398&id=id&accname=guest&checksum=BB55104BD56A6662742D9B8118C95B77.
[10]彭家慧,廖丽萍,聂思桥,等.三氟苯嘧啶在水稻、土壤和田水中的残留分析方法[J].农药, 2018, 57(1):50-53.PENG Jia-hui, LIAO Li-ping, NIE Si-qiao, et al. Analysis of triflumezopyrim residues in rice, soil and field water[J]. Chinese Agrochemicals, 2018, 57(1):50-53.
[11]唐启义,冯明光.实用统计分析及其DPS数据处理系统[M].北京：科学出版社, 2002:648.TANG Qi-yi, FENG Ming-guang. Practical statistical analysis and DPS data processing system[M]. Beijing:Secientic Press, 2002:648.
[12]近藤精一,石川达雄,安部郁夫.吸附科学[M].二版.北京：化学工业出版社, 2006.Kondo S, Ishikawa T, Abe I. Sorption science[M]. 2th Edition. Beijing:Chemical Industrial Press, 2006.
[13] Boivin A, Cherrier R, Schiavon M. A comparison of five pesticides adsorption and desorption processes in thirteen contrasting field soils[J].Chemosphere, 2005, 61(5):668-676.
[14] Pionke H B, Glotfelty D E, Lucas A D, et al. Pesticide contamination of groundwaters in the mahantango creek watershed[J]. Journal of Environmental Quality, 1988, 17(1):76-84.
[15] Swann R L, Laskowski D A, Mccall P J, et al. A rapid method for the estimation of the environmental parameters octanol/water partition coefficient, soil sorption constant, water to air ratio, and water solubility[J]. Residue Reviews, 1983, 85:17-28.
[16] Singh A, Srivastava A, Srivastava P C. Sorption-desorption of fipronil in some soils, as influenced by ionic strength, pH and temperature[J].Pest Management Science, 2016, 72(8):1491-1499.
[17] Senesi N. Binding mechanisms of pesticides to soil humic substances[J]. Sci Total Environ, 1992, 123/124:347–377.
[18]王连生.有机污染化学[M].北京：高等教育出版社, 2004.WANG Lian-sheng. Chemistry of organic pollution[M]. Beijing:Higher Education Press, 2004.
[2]刘维屏.农药环境化学[M].北京：化学工业出版社, 2006.LIU WEI-ping. Pesticide environmental chemistry[M]. Beijing:Chemical Industrial Press, 2006.
[3] Holyoke C W, Cordova D, Zhang W M. Mesoionic insecticides:A novel class of insecticides that modulate nicotinic acetylcholine receptors[J].Pest Management Science, 2017, 73(4):796-806.
[4] US EPA. Triflumezopyrim:Human health risk assessment to establish tolerances for rice without U. S. Registration[EB/OL].(2017-08-17)[2019-05-18]. https：//www. regulations. gov/document?D=EPA-HQOPP-2016-0142-0003.
[5] Zhang W M, Holyoke Jr C W, Pahutskia T F, et al. Mesoionic pyrido[1,2-a] pyrimidinones:Discovery of triflumezopyrim as a potent hopper insecticide[J]. Bioorganic&Medicinal Chemistry Letters, 2017, 27(1):16-20.
[6]朱友理,何东兵,曹书培,等.三氟苯嘧啶对稻飞虱的防效及对天敌的安全性[J].中国植保导刊, 2018, 39(8):71-74.ZHU You-li, HE Dong-bing, CAO Shu-pei, et al. Controlling efficiency of trifluorobenzidine against rice plant hopper and its safety to natural enemies[J]. Bulletin of China Plant Protection, 2018, 39(8):71-74.
[7]英君伍,雷光月,宋玉泉,等.三氟苯嘧啶的合成与杀虫活性研究[J].现代农药, 2017, 16(2):14-16,20.YING Jun-wu, LEI Guang-yue, SONG Yu-quan, et al. Synthesis and bioactivity of triflumesopyrim[J]. Modern Agrochemicals, 2017, 16(2):14-16,20.
[8]欧晓明,余淑英,罗玲,等.新农药硫肟醚在土壤上的吸附[J].农业环境科学学报, 2007, 26(2):577-582.OU Xiao-ming, YU Shu-ying, LUO Ling, et al. Adsorption of novel oxime insecticide IINPC-A9908 on soils[J]. Journal of Agro-Environment Science, 2007, 26(2):577-582.
[9] OECD. Adsorption-desorption using a batch equilibrium method[EB/OL].(2000-01-21)[2019-05-18]. https：//www. oecd-ilibrary. org/docserver/9789264069602-en. pdf?expires=1546505398&id=id&accname=guest&checksum=BB55104BD56A6662742D9B8118C95B77.
[10]彭家慧,廖丽萍,聂思桥,等.三氟苯嘧啶在水稻、土壤和田水中的残留分析方法[J].农药, 2018, 57(1):50-53.PENG Jia-hui, LIAO Li-ping, NIE Si-qiao, et al. Analysis of triflumezopyrim residues in rice, soil and field water[J]. Chinese Agrochemicals, 2018, 57(1):50-53.
[11]唐启义,冯明光.实用统计分析及其DPS数据处理系统[M].北京：科学出版社, 2002:648.TANG Qi-yi, FENG Ming-guang. Practical statistical analysis and DPS data processing system[M]. Beijing:Secientic Press, 2002:648.
[12]近藤精一,石川达雄,安部郁夫.吸附科学[M].二版.北京：化学工业出版社, 2006.Kondo S, Ishikawa T, Abe I. Sorption science[M]. 2th Edition. Beijing:Chemical Industrial Press, 2006.
[13] Boivin A, Cherrier R, Schiavon M. A comparison of five pesticides adsorption and desorption processes in thirteen contrasting field soils[J].Chemosphere, 2005, 61(5):668-676.
[14] Pionke H B, Glotfelty D E, Lucas A D, et al. Pesticide contamination of groundwaters in the mahantango creek watershed[J]. Journal of Environmental Quality, 1988, 17(1):76-84.
[15] Swann R L, Laskowski D A, Mccall P J, et al. A rapid method for the estimation of the environmental parameters octanol/water partition coefficient, soil sorption constant, water to air ratio, and water solubility[J]. Residue Reviews, 1983, 85:17-28.
[16] Singh A, Srivastava A, Srivastava P C. Sorption-desorption of fipronil in some soils, as influenced by ionic strength, pH and temperature[J].Pest Management Science, 2016, 72(8):1491-1499.
[17] Senesi N. Binding mechanisms of pesticides to soil humic substances[J]. Sci Total Environ, 1992, 123/124:347–377.
[18]王连生.有机污染化学[M].北京：高等教育出版社, 2004.WANG Lian-sheng. Chemistry of organic pollution[M]. Beijing:Higher Education Press, 2004.
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