几种典型手性三唑类杀菌剂对映体的分析、环境行为及其生物毒性研究
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摘要
三唑类杀菌剂是农业生产中应用最广泛的一类杀菌剂，而绝大多数该类杀菌剂都是手性农药。实践证明，当外消旋体手性农药进入生态环境后，其对靶标生物的活性或非靶标生物的毒性及其在生态环境中的降解代谢都可能存在着明显的立体选择性差异。在传统的安全评价研究中，通常不区分手性农药的对映体之间的这种差别，正因如此，目前对手性农药的风险评估的数据往往是不准确的，给人类和环境带来了诸多安全隐患。研究表明手性三唑类杀菌剂的对映体活性往往差异很大，然而绝大多数该类手性农药目前仍以外消旋体形式大量销售和使用。
首先，本文首次以高效液相色谱串联质谱与反相手性固定相结合为基础，建立了一系列手性三唑类杀菌剂及其手性代谢产物（戊唑醇、四氟醚唑、氟环唑、烯唑醇、己唑醇、多效唑、腈菌唑、三唑酮及其代谢产物三唑醇、腈苯唑及其手性代谢产物）在植物和（或）环境样品中的残留分析方法。方法的准确度、精密度及灵敏度均符合农药残留分析的要求。该方法的优点是很好的解决了传统分析方法的灵敏度低、基质干扰大、很难实现多个对映体同时分离的难题。
然后，利用所建立的手性残留分析方法，探讨了几种典型手性三唑类杀菌剂的立体选择性环境行为。首先，研究了己唑醇和三唑酮在设施环境下的选择性降解行为。结果表明：（1）己唑醇在设施黄瓜果实、番茄果实内和土壤中均存在着明显的立体选择性降解行为，且对映体选择降解规律与其所在基质有关：（+）-己唑醇在黄瓜和番茄果实中被优先降解，而在土壤中则是（-）-己唑醇降解速率较快，造成了相应的对映体被相对累积。（2）无论是在茎叶喷雾施药还是土壤灌根施药条件下，三唑酮在黄瓜、番茄和土壤中均存在着一致的选择性降解规律，即S-（+）-三唑酮被优先降解，造成R-（-）-三唑酮被累积；三唑酮转化成其手性代谢产物三唑醇4对映体规律为：叶面喷雾施药条件下，RS-（+）-三唑醇在番茄中转化累积量最大，而在黄瓜和土壤中RR-（+）-三唑醇的累积最多；在土壤灌根施药的条件下，三唑醇对映体在黄瓜和番茄中生成的浓度大小顺序与其在茎叶喷雾施药条件下结果一致，而在番茄中的生成规律则不相同。
此外，还研究了腈苯唑及其手性代谢产物（RH-9129和RH-9130）在室内有氧和无氧条件下两种不同土壤中的降解代谢规律。结果表明无论是有氧还是无氧条件下，（-）-腈苯唑均被优先降解。腈苯唑转化成其手性代谢产物RH-9129和RH-9130的基本规律为：在廊坊碱性土中，转化成4个对映体浓度的大小顺序依次为（-）-RH-9129＞（+）-RH-9129＞（-）-RH-9130＞（+）-RH-9130；而在长沙酸性土中，其浓度大小顺序则为（-）-RH-9129＞（+）-RH-9129＞（+）-RH-9130＞（-）-RH-9130。RH-9129和RH-9130对映体在两种不同性质土壤中也存在着明显的立体选择性降解规律，（+）-RH-9130和（+）-RH-9129被优先降解，导致（-）-RH-9130和（-）-RH-9129在土壤中被累积。
最后，进行了三唑酮、三唑醇、戊唑醇和腈菌唑及其对映体对三种水生生物（斜生栅藻、大型溞和斑马鱼）的急性毒性的研究。结果显示，供试手性三唑类杀菌剂对映体之间的毒性均存在差异：对于斜生栅藻来说，SR-（-）-三唑醇的毒性约为SS-（-）-三唑醇的8.2倍；R-（-）-戊唑醇的毒性约为S-（+）-戊唑醇的5.9倍；外消旋体腈菌唑的毒性分别是两个对映体的（+）-腈菌唑的7.3倍和（-）-腈菌唑6.1倍。对于大型溞来说，RS-（-）-三唑醇的毒性约为SS-（-）-三唑醇的3.2倍；R-（-）-戊唑醇的毒性约为S-（+）-戊唑醇的1.6倍；外消旋体腈菌唑的毒性分别是两个对映体的（+）-腈菌唑的2.5倍和（-）-腈菌唑2.1倍。而对于斑马鱼来说，对映体之间的毒性差别非常微小：R-（-）-戊唑醇的毒性仅约为S-（+）-戊唑醇的1.4倍；外消旋体腈菌唑的毒性分别是两个对映体的（+）-腈菌唑的1.4倍和（-）-腈菌唑1.3倍。实验数据表明，沿着水生食物链由低到高，供试手性三唑类杀菌剂对映体之间的急性毒性差异也越来越小，说明低营养级水生生物对三唑类杀菌剂手性结构的差异更敏感。
Triazole fungicides is one of the most widely used in the agricultural crops, and most of themhave stereogenic centers and they consist of one or two pairs of enantiomers. Once introduced inthe ecological environmet, chiral pesticide enantiomers often show different bioactivity to thetarget organisms and toxicity non-target organisms; however, this property is usually ignoredwhen evaluating their environmental and public health risks in the traditional studies. Thus, whentraditional risk assessment are unreliable if the enantioselective behaviors occur. The establisheddata indicated that the enantiomers of chiral triazol fungicides often different bioactivity, however,most triazole pesticides still sold and widely used in the racemic form.
In this study, a series of novel and sensitive single or multi-residue methods for enantiomericanalysis of triazole fungicides and their chiral metabolites (tebuconazole, tetraconazole,epoxiconazole, diniconazole, hexaconazole, paclobutrazol, myclobutanil, triadimefon andtriadimenol, fenbuconazole and its chiral metabolites) in plants and (or) environmental samplesusing chiral liquid chromatography coupled with tandem mass spectrometry combined withreversed chiral columns. Validation of the methods included precisions, linearity and limit ofdetection (LOD). The results indicated that the developed methods were effective enough fordetecting the residual enantiomers in the matrix and could be used for studying theenantioselective environmental behaviors.
Based on the established chiral analytical methods, Stereoselective environmental behaviors ofthe some triazole fungicides enantiomers were investigated. Firstly, the proposed method wassuccessfully applied to investigate the possible enantioselective environmental behaviors ofrac-hexaconazole and rac-triadimefon in plants (tomato and cucumber) and soil under greenhouseconditions. The results shows that:(1) The degradation of the two enantiomers of hexaconazoleproved to be enantioselective and dependent on the media: The (+)-enantiomer showed a fasterdegradation in plants, while the (-)-enantiomer dissipated faster than the (+)-form in field soil,resulting in relative enrichment of the opposite enantiomer.(2) Under foliage application or soilirrigation application, the S-(+)-triadimefon was preferentially degraded, resulting in relativeenrichment of the more toxic R-(-)-enantiomer in two vegetables and soil. Further enantioselectiveanalysis of converted triadimenol showed that the composition of four product stereoisomers weredifferent from each other and closely depend on environmental conditions as well as applicationmodes: the most toxic RS-(+)-triadimenol was the most preferentially produced isomer in tomatounder foliage treatment, while the RR-(+)-triadimenol was proved to be the highest amount ofmetabolite isomer in cucumber and soil under both treatment modes and in tomato under soiltreatment.
Secondly, the enantioselective degradation of fenbuconazole and its chiral metabolites,RH-9129and RH-9130, in two soils under aerobic and anaerobic conditions were investigated.Under aerobic or anaerobic conditions, the results showed the occurrence of enantioselectivity with (-)-fenbuconazole preferentially degraded in both soils. Further enantioselective analysis ofconverted products showed that the concentrations of four RH-9129and RH-9130stereoisomerswere different from each other under both aerobic and anaerobic conditions. The four stereoisomerconcentrations followed the order (-)-RH-9129>(+)-RH-9129>(-)-RH-9130>(+)-RH-9130inLangfang alkaline soil. However, in the case of Changsha acidic soil, different RH-9129and RH-9130stereoisomer patterns were produced in the order (-)-RH-9129>(+)-RH-9129>(+)-RH-9130>(-)-RH-9130. The degradation of RH-9129and RH-9130in the two soils is alsostereoselective under both aerobic and anaerobic conditions, the results indicating that the(+)-RH-9130enantiomer degraded faster than the (-)-RH-9130enantiomer and the (+)-RH-9129enantiomer degraded faster than the (-)-RH-9129enantiomer.
Lastly, in present study, triadimefon, triadimenol, tebuconazole, and myclobutanil as well astheir enantiomers in acute toxicity to three aquatic organisms (S. obliquus, D. magna and Daniorerio) were studied. The results indicated there were significant differences between (among)stereoisomers of the same compound: as for the S. obliquus, the SR-(-)-triadimenol was about8.2times more toxic than the SS-(+)-form, the R-(-)-tebuconazole was about5.9times more toxicthan the S-(+)-form, and the rac-myclobutanil about7.3and6.1times more toxic than the(+)-myclobutanil and (-)-myclobutanil, respectively; for the D. magna, the RS-(-)-triadimenol wasabout3.2times more toxic than the SS-(+)-form, the R-(-)-tebuconazole was about1.6times moretoxic than the S-(+)-form, and the rac-myclobutanil about2.5and2.1times more toxic than the(+)-myclobutanil and (-)-myclobutanil, respectively. However, in the case of Danio rerio, thedifferences between the enantiomers were slightly: the R-(-)-tebuconazole was about1.4timesmore toxic than the S-(+)-form, and the rac-myclobutanil about1.4and1.3times more toxic thanthe (+)-myclobutanil and (-)-myclobutanil, respectively. The results show that the distancebetween (among) the stereoisomers of chiral fungicides to aquatic organism gets shorter at highernutrition level.
首先，本文首次以高效液相色谱串联质谱与反相手性固定相结合为基础，建立了一系列手性三唑类杀菌剂及其手性代谢产物（戊唑醇、四氟醚唑、氟环唑、烯唑醇、己唑醇、多效唑、腈菌唑、三唑酮及其代谢产物三唑醇、腈苯唑及其手性代谢产物）在植物和（或）环境样品中的残留分析方法。方法的准确度、精密度及灵敏度均符合农药残留分析的要求。该方法的优点是很好的解决了传统分析方法的灵敏度低、基质干扰大、很难实现多个对映体同时分离的难题。
然后，利用所建立的手性残留分析方法，探讨了几种典型手性三唑类杀菌剂的立体选择性环境行为。首先，研究了己唑醇和三唑酮在设施环境下的选择性降解行为。结果表明：（1）己唑醇在设施黄瓜果实、番茄果实内和土壤中均存在着明显的立体选择性降解行为，且对映体选择降解规律与其所在基质有关：（+）-己唑醇在黄瓜和番茄果实中被优先降解，而在土壤中则是（-）-己唑醇降解速率较快，造成了相应的对映体被相对累积。（2）无论是在茎叶喷雾施药还是土壤灌根施药条件下，三唑酮在黄瓜、番茄和土壤中均存在着一致的选择性降解规律，即S-（+）-三唑酮被优先降解，造成R-（-）-三唑酮被累积；三唑酮转化成其手性代谢产物三唑醇4对映体规律为：叶面喷雾施药条件下，RS-（+）-三唑醇在番茄中转化累积量最大，而在黄瓜和土壤中RR-（+）-三唑醇的累积最多；在土壤灌根施药的条件下，三唑醇对映体在黄瓜和番茄中生成的浓度大小顺序与其在茎叶喷雾施药条件下结果一致，而在番茄中的生成规律则不相同。
此外，还研究了腈苯唑及其手性代谢产物（RH-9129和RH-9130）在室内有氧和无氧条件下两种不同土壤中的降解代谢规律。结果表明无论是有氧还是无氧条件下，（-）-腈苯唑均被优先降解。腈苯唑转化成其手性代谢产物RH-9129和RH-9130的基本规律为：在廊坊碱性土中，转化成4个对映体浓度的大小顺序依次为（-）-RH-9129＞（+）-RH-9129＞（-）-RH-9130＞（+）-RH-9130；而在长沙酸性土中，其浓度大小顺序则为（-）-RH-9129＞（+）-RH-9129＞（+）-RH-9130＞（-）-RH-9130。RH-9129和RH-9130对映体在两种不同性质土壤中也存在着明显的立体选择性降解规律，（+）-RH-9130和（+）-RH-9129被优先降解，导致（-）-RH-9130和（-）-RH-9129在土壤中被累积。
最后，进行了三唑酮、三唑醇、戊唑醇和腈菌唑及其对映体对三种水生生物（斜生栅藻、大型溞和斑马鱼）的急性毒性的研究。结果显示，供试手性三唑类杀菌剂对映体之间的毒性均存在差异：对于斜生栅藻来说，SR-（-）-三唑醇的毒性约为SS-（-）-三唑醇的8.2倍；R-（-）-戊唑醇的毒性约为S-（+）-戊唑醇的5.9倍；外消旋体腈菌唑的毒性分别是两个对映体的（+）-腈菌唑的7.3倍和（-）-腈菌唑6.1倍。对于大型溞来说，RS-（-）-三唑醇的毒性约为SS-（-）-三唑醇的3.2倍；R-（-）-戊唑醇的毒性约为S-（+）-戊唑醇的1.6倍；外消旋体腈菌唑的毒性分别是两个对映体的（+）-腈菌唑的2.5倍和（-）-腈菌唑2.1倍。而对于斑马鱼来说，对映体之间的毒性差别非常微小：R-（-）-戊唑醇的毒性仅约为S-（+）-戊唑醇的1.4倍；外消旋体腈菌唑的毒性分别是两个对映体的（+）-腈菌唑的1.4倍和（-）-腈菌唑1.3倍。实验数据表明，沿着水生食物链由低到高，供试手性三唑类杀菌剂对映体之间的急性毒性差异也越来越小，说明低营养级水生生物对三唑类杀菌剂手性结构的差异更敏感。
Triazole fungicides is one of the most widely used in the agricultural crops, and most of themhave stereogenic centers and they consist of one or two pairs of enantiomers. Once introduced inthe ecological environmet, chiral pesticide enantiomers often show different bioactivity to thetarget organisms and toxicity non-target organisms; however, this property is usually ignoredwhen evaluating their environmental and public health risks in the traditional studies. Thus, whentraditional risk assessment are unreliable if the enantioselective behaviors occur. The establisheddata indicated that the enantiomers of chiral triazol fungicides often different bioactivity, however,most triazole pesticides still sold and widely used in the racemic form.
In this study, a series of novel and sensitive single or multi-residue methods for enantiomericanalysis of triazole fungicides and their chiral metabolites (tebuconazole, tetraconazole,epoxiconazole, diniconazole, hexaconazole, paclobutrazol, myclobutanil, triadimefon andtriadimenol, fenbuconazole and its chiral metabolites) in plants and (or) environmental samplesusing chiral liquid chromatography coupled with tandem mass spectrometry combined withreversed chiral columns. Validation of the methods included precisions, linearity and limit ofdetection (LOD). The results indicated that the developed methods were effective enough fordetecting the residual enantiomers in the matrix and could be used for studying theenantioselective environmental behaviors.
Based on the established chiral analytical methods, Stereoselective environmental behaviors ofthe some triazole fungicides enantiomers were investigated. Firstly, the proposed method wassuccessfully applied to investigate the possible enantioselective environmental behaviors ofrac-hexaconazole and rac-triadimefon in plants (tomato and cucumber) and soil under greenhouseconditions. The results shows that:(1) The degradation of the two enantiomers of hexaconazoleproved to be enantioselective and dependent on the media: The (+)-enantiomer showed a fasterdegradation in plants, while the (-)-enantiomer dissipated faster than the (+)-form in field soil,resulting in relative enrichment of the opposite enantiomer.(2) Under foliage application or soilirrigation application, the S-(+)-triadimefon was preferentially degraded, resulting in relativeenrichment of the more toxic R-(-)-enantiomer in two vegetables and soil. Further enantioselectiveanalysis of converted triadimenol showed that the composition of four product stereoisomers weredifferent from each other and closely depend on environmental conditions as well as applicationmodes: the most toxic RS-(+)-triadimenol was the most preferentially produced isomer in tomatounder foliage treatment, while the RR-(+)-triadimenol was proved to be the highest amount ofmetabolite isomer in cucumber and soil under both treatment modes and in tomato under soiltreatment.
Secondly, the enantioselective degradation of fenbuconazole and its chiral metabolites,RH-9129and RH-9130, in two soils under aerobic and anaerobic conditions were investigated.Under aerobic or anaerobic conditions, the results showed the occurrence of enantioselectivity with (-)-fenbuconazole preferentially degraded in both soils. Further enantioselective analysis ofconverted products showed that the concentrations of four RH-9129and RH-9130stereoisomerswere different from each other under both aerobic and anaerobic conditions. The four stereoisomerconcentrations followed the order (-)-RH-9129>(+)-RH-9129>(-)-RH-9130>(+)-RH-9130inLangfang alkaline soil. However, in the case of Changsha acidic soil, different RH-9129and RH-9130stereoisomer patterns were produced in the order (-)-RH-9129>(+)-RH-9129>(+)-RH-9130>(-)-RH-9130. The degradation of RH-9129and RH-9130in the two soils is alsostereoselective under both aerobic and anaerobic conditions, the results indicating that the(+)-RH-9130enantiomer degraded faster than the (-)-RH-9130enantiomer and the (+)-RH-9129enantiomer degraded faster than the (-)-RH-9129enantiomer.
Lastly, in present study, triadimefon, triadimenol, tebuconazole, and myclobutanil as well astheir enantiomers in acute toxicity to three aquatic organisms (S. obliquus, D. magna and Daniorerio) were studied. The results indicated there were significant differences between (among)stereoisomers of the same compound: as for the S. obliquus, the SR-(-)-triadimenol was about8.2times more toxic than the SS-(+)-form, the R-(-)-tebuconazole was about5.9times more toxicthan the S-(+)-form, and the rac-myclobutanil about7.3and6.1times more toxic than the(+)-myclobutanil and (-)-myclobutanil, respectively; for the D. magna, the RS-(-)-triadimenol wasabout3.2times more toxic than the SS-(+)-form, the R-(-)-tebuconazole was about1.6times moretoxic than the S-(+)-form, and the rac-myclobutanil about2.5and2.1times more toxic than the(+)-myclobutanil and (-)-myclobutanil, respectively. However, in the case of Danio rerio, thedifferences between the enantiomers were slightly: the R-(-)-tebuconazole was about1.4timesmore toxic than the S-(+)-form, and the rac-myclobutanil about1.4and1.3times more toxic thanthe (+)-myclobutanil and (-)-myclobutanil, respectively. The results show that the distancebetween (among) the stereoisomers of chiral fungicides to aquatic organism gets shorter at highernutrition level.
引文
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