精噁唑禾草灵和解草唑的水解、光解及对大型溞的急性毒性变化
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摘要
研究污染物的环境转化所导致的生态毒理学效应的变化,对于化学污染物的环境风险性评价具有重要意义。精噁唑禾草灵(FE)是一种芳氧苯氧丙酸类高效茎叶选择性除草剂,解草唑(FCE)是FE的安全剂;由于优良的除草性能,FE和FCE得到了广泛应用。本文研究了FE和FCE的水解和光解动力学、影响因素和降解机理,并以大型溞为实验生物研究了FE水解和光解过程的毒性变化。
FE和FCE在不同温度和pH值条件下的水解遵循一级动力学。随着助溶剂乙腈含量的降低和温度的升高,FE和FCE的水解速率逐渐增大。FE在pH=6.0时水解速率最小,随着pH值的增加或降低,水解速率均变大。不同pH值条件下,FE的水解产物不同。酸性条件下(pH=4.0,5.1),FE水解生成了6-氯苯并噁唑酮和2-(4-羟基苯氧基)丙酸乙酯;碱性条件下(pH=8.0,9.0,10.0),FE水解生成了精噁唑禾草灵酸;中性条件下(pH=6.0,7.0),同时生成了以上3种降解产物。FCE在酸性条件下水解很慢,随着pH值的升高,水解速率逐渐增大。碱性条件下(pH=8.0,9.0,10.0),FCE水解生成了解草唑酸。建立的温度和pH值的联合等式,能够用于预测FE和FCE在缓冲溶液中的水解半减期。结果表明,当水的温度范围在10～15℃,pH值范围在6～8之间时,FE的水解半减期介于390 d和24.5 d之间,FCE的半减期介于192 d和1.7 d之间。利用Bronsted酸碱催化理论推导了所用缓冲溶液对FE和FCE水解速率的影响,结果表明缓冲溶液对它们的水解存在明显的催化作用,加快了它们的水解速率。在pH值为4.0和9.0的条件下,FE和FCE对彼此的水解速率没有影响。
实验室研究中,在λ＞200 nm和λ＞290 nm的光照条件下,FE和FCE的光化学转化符合一级动力学,在λ＞200 nm光照条件下光解更快。太阳光照射下,FE能够发生光解,并且丙酮的存在显著加快了其光解。不同波长光照条件下,FE的光化学转化产物相同,但不同产物生成量不同。FE通过酯键断裂、酯键断裂后脱羧、光致异构化、异构化后脱醇、光致水解、脱氯和醚键断裂等途径生成了至少15种光解产物。在λ＞200nm光照条件下,主要光解产物能够进一步光解。噁唑酚作为FE的光转化产物,在λ＞200 nm光照条件下的光解半减期大于母体化合物,而在λ＞290 nm光照条件下几乎不光解,说明FE光解生成了比自身光解更稳定的产物。FCE在λ＞200 nm光照条件下的主要光化学转化途径为光致水解和-CCl_3基团脱落;同时还发生了-CCl_3基团被-OH取代;苯环与三唑环相联的C-N键断裂和三唑环开环等反应。在λ＞290 nm的光照条件下,由于光竞争作用,硝酸盐对FE和FCE的光降解起抑制作用,浓度越大抑制作用越明显。由于光解与水解的共同作用,碳酸氢盐对FE和FCE的降解起促进作用,且浓度越大促进作用越明显,并且光解对FE和FCE在碳酸氢盐溶液中的降解贡献更大。在λ＞290 nm的光照条件下,FE和FCE共存时对彼此的光解速率没有影响。
FCE在最大可测试浓度范围内,没有对大型溞表现出急性毒性。对苯二酚和噁唑酚作为FE的降解产物,对大型溞48 h急性毒性高于母体化合物,其他测试的FE降解产物的急性毒性小于母体化合物,说明FE水解后对大型溞的急性毒性降低了,而光解不完全是解毒过程。由于噁唑酚在λ＞290 nm条件下不光解,因此,FE光解生成了比自身光解更稳定和毒性更大的产物。FE水解和光解的共同产物6-氯苯并噁唑酮和R-2-(4-羟基苯氧基)丙酸乙酯以等毒性比方式混合时,对大型溞的联合毒性是独立作用。
Assessing the hazard of a pesticide requires an understanding of its degradation and toxicity of the products.Fenoxaprop-p-ethyl(FE),an aryloxyphenoxypropionate herbicide,is used to selectively control annual grass weeds in broadleaf crops.Fenchlorazole-ethyl(FCE) is the safener of FE,and they have been widely used in many countries.The purpose of this study was to elucidate the hydrolysis and photolysis behaviors of FE and FCE.The effects of different influential factors on the rate constants and the pathways of hydrolysis and photolysis of them were studied.Besides,evolution of acute toxicity upon hydrolysis and photolysis of FE was assessed using Daphnia magna.
The hydrolysis of FE and FCE follow first-order kinetics at different pH levels and temperatures.FE and FCE hydrolysis rates decreased with the increasing of the ratio of acetonitrile and were greatly increased at elevated temperatures at pH=9.0.FE was relatively stable at pH=6.0,whereas it degraded rapidly with decreasing or increasing pH values.In acidic conditions(pH=4.0,5.1),the benzoxazolyl-oxy-phenyl ether linkage of FE was cleaved to form ethyl 2-(4-hydroxyphenoxy) propanoate(EHPP) and 6-chloro-2,3-dihydrobenzoxazol -2-one(CDHB).While in basic conditions(pH=8.0,9.0,10.0), fenoxaprop-p was formed via breakdown of the ester bond of the herbicide.Both the two pathways were concurrent in near neutral conditions(pH=6.0,7.0).For FCE,half-lives were greatly reduced at elevated pH levels at 30℃.In basic conditions(pH=8.0,9.0,10.0), fenchlorazole was formed via the breakdown of the ester bond of the safener.The hydrolysis rate constants of FE and FCE as a function of temperature and pH were mathematically combined to predict the hydrolytic dissipation of them.The equations suggested that the hydrolysis half-lives of FE ranged from 390 d to 24.5 d and that of FCE ranged from 192 d to 1.7 d when temperature between 10℃and 15℃and pH between 6 and 8.The maximum contribution of buffer catalysis to the hydrolysis of FE and FCE was assessed based on application of the Bronsted equations for general acid-base catalysis.The results suggested that the buffer solutions played an obvious catalysis role in hydrolysis of FE and FCE and the hydrolysis rate of them was quickened by the buffer solutions.The existence of FCE did not have significant effects on FE hydrolysis at pH 4.0 and 9.0.And FE did not impact the hydrolysis rates of FCE too.
Under the irradiation atλ＞200 nm andλ＞290 nm,the photolysis of FE and FCE followed the first-order kinetics,and photodegraded rapidly atλ＞200 nm.Under solar irradiation,FE can undergo photodegradation and acetone enhanced the photolysis rates significantly.The same photoproducts of FE were formed under both high and low wavelengths irradiation experiments but relative proportions of the photoproducts were different.FE was phototransformed to at least 15 products through de-esterification,loss of carboxyl after de-esterification,rearrangement,loss of ethanol after rearrangement, dechlorination,photohydrolysis,and the breakdown of the ether linkages.The main photolysis products were photodegraded under irradiation atλ＞200 nm.4-[(6-chloro-2-benzoxazolyl)oxy] phenol(CBOP) as one of the photolysis products of FE,had a slower photolysis rate than FE atλ＞200 nm irradiation and was almost resistant to photolysis atλ＞290 nm irradiation.Therefore,photolysis of FE resulted in a more persistent product.The major degradation pathways of FCE under irradiation atλ＞200 nm were hydroxylated process and loss of trichloromethyl fragment.The trichloromethyl fragment substituted by -OH,C-N cleavage and triazole ring-opening also occurred.Under irradiation atλ＞290 nm, increasing nitrate concentrations increased the half-lives of FE and FCE due to screen of the incident light.The photolysis rates of FE and FCE increased with increasing concentrations of bicarbonate due to the degradation by both photolysis and hydrolysis,and photolysis played a more important role than hydrolysis.Under irradiation atλ＞290 nm,FCE did not have significant effects on FE degradation rate,and FE neither has significant effects on FCE photolysis.
It was not possible to obtain EC_(50) value of FCE since it is higher than its solubility in water.FE transformed products,1,4-dihydroxybenzene and CBOP were more toxic to Daphnia magna than the parent FE.Other tested products of FE were less toxic to Daphnia magna than the parent,which suggested toxicity of FE to Daphnia magna decreased due to its hydrolysis but increased due to its photodegradation.Since CBOP was resistant to photolysis atλ＞290 nm irradiation,FE resulted in a product more photochemically stable and toxic than itself.The binary mixture toxicity of CDHB and EHPP,which were both hydrolysis and photolysis products of FE,mixed in the ratio of their individual EC_(50) values can be predicted by independent action model.
FE和FCE在不同温度和pH值条件下的水解遵循一级动力学。随着助溶剂乙腈含量的降低和温度的升高,FE和FCE的水解速率逐渐增大。FE在pH=6.0时水解速率最小,随着pH值的增加或降低,水解速率均变大。不同pH值条件下,FE的水解产物不同。酸性条件下(pH=4.0,5.1),FE水解生成了6-氯苯并噁唑酮和2-(4-羟基苯氧基)丙酸乙酯;碱性条件下(pH=8.0,9.0,10.0),FE水解生成了精噁唑禾草灵酸;中性条件下(pH=6.0,7.0),同时生成了以上3种降解产物。FCE在酸性条件下水解很慢,随着pH值的升高,水解速率逐渐增大。碱性条件下(pH=8.0,9.0,10.0),FCE水解生成了解草唑酸。建立的温度和pH值的联合等式,能够用于预测FE和FCE在缓冲溶液中的水解半减期。结果表明,当水的温度范围在10～15℃,pH值范围在6～8之间时,FE的水解半减期介于390 d和24.5 d之间,FCE的半减期介于192 d和1.7 d之间。利用Bronsted酸碱催化理论推导了所用缓冲溶液对FE和FCE水解速率的影响,结果表明缓冲溶液对它们的水解存在明显的催化作用,加快了它们的水解速率。在pH值为4.0和9.0的条件下,FE和FCE对彼此的水解速率没有影响。
实验室研究中,在λ＞200 nm和λ＞290 nm的光照条件下,FE和FCE的光化学转化符合一级动力学,在λ＞200 nm光照条件下光解更快。太阳光照射下,FE能够发生光解,并且丙酮的存在显著加快了其光解。不同波长光照条件下,FE的光化学转化产物相同,但不同产物生成量不同。FE通过酯键断裂、酯键断裂后脱羧、光致异构化、异构化后脱醇、光致水解、脱氯和醚键断裂等途径生成了至少15种光解产物。在λ＞200nm光照条件下,主要光解产物能够进一步光解。噁唑酚作为FE的光转化产物,在λ＞200 nm光照条件下的光解半减期大于母体化合物,而在λ＞290 nm光照条件下几乎不光解,说明FE光解生成了比自身光解更稳定的产物。FCE在λ＞200 nm光照条件下的主要光化学转化途径为光致水解和-CCl_3基团脱落;同时还发生了-CCl_3基团被-OH取代;苯环与三唑环相联的C-N键断裂和三唑环开环等反应。在λ＞290 nm的光照条件下,由于光竞争作用,硝酸盐对FE和FCE的光降解起抑制作用,浓度越大抑制作用越明显。由于光解与水解的共同作用,碳酸氢盐对FE和FCE的降解起促进作用,且浓度越大促进作用越明显,并且光解对FE和FCE在碳酸氢盐溶液中的降解贡献更大。在λ＞290 nm的光照条件下,FE和FCE共存时对彼此的光解速率没有影响。
FCE在最大可测试浓度范围内,没有对大型溞表现出急性毒性。对苯二酚和噁唑酚作为FE的降解产物,对大型溞48 h急性毒性高于母体化合物,其他测试的FE降解产物的急性毒性小于母体化合物,说明FE水解后对大型溞的急性毒性降低了,而光解不完全是解毒过程。由于噁唑酚在λ＞290 nm条件下不光解,因此,FE光解生成了比自身光解更稳定和毒性更大的产物。FE水解和光解的共同产物6-氯苯并噁唑酮和R-2-(4-羟基苯氧基)丙酸乙酯以等毒性比方式混合时,对大型溞的联合毒性是独立作用。
Assessing the hazard of a pesticide requires an understanding of its degradation and toxicity of the products.Fenoxaprop-p-ethyl(FE),an aryloxyphenoxypropionate herbicide,is used to selectively control annual grass weeds in broadleaf crops.Fenchlorazole-ethyl(FCE) is the safener of FE,and they have been widely used in many countries.The purpose of this study was to elucidate the hydrolysis and photolysis behaviors of FE and FCE.The effects of different influential factors on the rate constants and the pathways of hydrolysis and photolysis of them were studied.Besides,evolution of acute toxicity upon hydrolysis and photolysis of FE was assessed using Daphnia magna.
The hydrolysis of FE and FCE follow first-order kinetics at different pH levels and temperatures.FE and FCE hydrolysis rates decreased with the increasing of the ratio of acetonitrile and were greatly increased at elevated temperatures at pH=9.0.FE was relatively stable at pH=6.0,whereas it degraded rapidly with decreasing or increasing pH values.In acidic conditions(pH=4.0,5.1),the benzoxazolyl-oxy-phenyl ether linkage of FE was cleaved to form ethyl 2-(4-hydroxyphenoxy) propanoate(EHPP) and 6-chloro-2,3-dihydrobenzoxazol -2-one(CDHB).While in basic conditions(pH=8.0,9.0,10.0), fenoxaprop-p was formed via breakdown of the ester bond of the herbicide.Both the two pathways were concurrent in near neutral conditions(pH=6.0,7.0).For FCE,half-lives were greatly reduced at elevated pH levels at 30℃.In basic conditions(pH=8.0,9.0,10.0), fenchlorazole was formed via the breakdown of the ester bond of the safener.The hydrolysis rate constants of FE and FCE as a function of temperature and pH were mathematically combined to predict the hydrolytic dissipation of them.The equations suggested that the hydrolysis half-lives of FE ranged from 390 d to 24.5 d and that of FCE ranged from 192 d to 1.7 d when temperature between 10℃and 15℃and pH between 6 and 8.The maximum contribution of buffer catalysis to the hydrolysis of FE and FCE was assessed based on application of the Bronsted equations for general acid-base catalysis.The results suggested that the buffer solutions played an obvious catalysis role in hydrolysis of FE and FCE and the hydrolysis rate of them was quickened by the buffer solutions.The existence of FCE did not have significant effects on FE hydrolysis at pH 4.0 and 9.0.And FE did not impact the hydrolysis rates of FCE too.
Under the irradiation atλ＞200 nm andλ＞290 nm,the photolysis of FE and FCE followed the first-order kinetics,and photodegraded rapidly atλ＞200 nm.Under solar irradiation,FE can undergo photodegradation and acetone enhanced the photolysis rates significantly.The same photoproducts of FE were formed under both high and low wavelengths irradiation experiments but relative proportions of the photoproducts were different.FE was phototransformed to at least 15 products through de-esterification,loss of carboxyl after de-esterification,rearrangement,loss of ethanol after rearrangement, dechlorination,photohydrolysis,and the breakdown of the ether linkages.The main photolysis products were photodegraded under irradiation atλ＞200 nm.4-[(6-chloro-2-benzoxazolyl)oxy] phenol(CBOP) as one of the photolysis products of FE,had a slower photolysis rate than FE atλ＞200 nm irradiation and was almost resistant to photolysis atλ＞290 nm irradiation.Therefore,photolysis of FE resulted in a more persistent product.The major degradation pathways of FCE under irradiation atλ＞200 nm were hydroxylated process and loss of trichloromethyl fragment.The trichloromethyl fragment substituted by -OH,C-N cleavage and triazole ring-opening also occurred.Under irradiation atλ＞290 nm, increasing nitrate concentrations increased the half-lives of FE and FCE due to screen of the incident light.The photolysis rates of FE and FCE increased with increasing concentrations of bicarbonate due to the degradation by both photolysis and hydrolysis,and photolysis played a more important role than hydrolysis.Under irradiation atλ＞290 nm,FCE did not have significant effects on FE degradation rate,and FE neither has significant effects on FCE photolysis.
It was not possible to obtain EC_(50) value of FCE since it is higher than its solubility in water.FE transformed products,1,4-dihydroxybenzene and CBOP were more toxic to Daphnia magna than the parent FE.Other tested products of FE were less toxic to Daphnia magna than the parent,which suggested toxicity of FE to Daphnia magna decreased due to its hydrolysis but increased due to its photodegradation.Since CBOP was resistant to photolysis atλ＞290 nm irradiation,FE resulted in a product more photochemically stable and toxic than itself.The binary mixture toxicity of CDHB and EHPP,which were both hydrolysis and photolysis products of FE,mixed in the ratio of their individual EC_(50) values can be predicted by independent action model.
引文
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