三唑类手性杀菌剂苯醚甲环唑的立体选择性生物活性与环境行为研究
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摘要
手性农药对映体在生物过程中存在较大的差异性，使其生物活性、生态毒理及环境行为往往存在很大不同，因而手性农药的使用及环境安全已成为一个新的关注中心。本文利用高效液相色谱手性固定相方法研究了三唑类手性杀菌剂苯醚甲环唑在设施蔬菜和土壤中的立体选择性环境行为，同时开展了苯醚甲环唑光学纯对映体的毒性和活性差异研究。
在正相液相色谱条件下，考察比较了直链淀粉-三[(s)-α-甲基苯基氨基甲酸酯]、直链淀粉-三(3,5-二甲基苯基氨基甲酸酯)、纤维素-三(3,5-二甲基苯基氨基甲酸酯)及纤维素-三(对甲基苯基甲酸酯)等四种手性固定相对苯醚甲环唑及其手性代谢物CGA205375对映体的化学分离与手性分离效果，发现纤维素-三(对甲基苯基甲酸酯)固定相具有最高手性分离能力。通过进一步对醇改性剂种类及含量、分离温度等手性分离因素的优化，成功实现了苯醚甲环唑及其代谢物CGA205375对映体的同时基线分离。
通过模拟实际生产田间茎叶喷雾法开展了苯醚甲环唑对映体在黄瓜与蕃茄植株上的选择性行为研究。数据表明苯醚甲环唑对映体在黄瓜和蕃茄果实内的降解符合一级动力学规律，且四个对映体在黄瓜和蕃茄果实中降解速度不同。在黄瓜果实内，四个对映体降解速度大小顺序为：（-）-苯醚甲环唑-A>（+）-苯醚甲环唑-A，（-）-苯醚甲环唑-B>（+）-苯醚甲环唑-B，随着施药后时间的推移，造成黄瓜果实中（+）-苯醚甲环唑-A和（-）-苯醚甲环唑-B的富集；在蕃茄果实内，四个对映体降解速度均慢于在黄瓜中的降解速度，并且也存在明显差异，在蕃茄内苯醚甲环唑降解速度大小顺序为：（+）-苯醚甲环唑-A>（-）-苯醚甲环唑-A，（-）-苯醚甲环唑-B>（+）-苯醚甲环唑-B，其中（-）-苯醚甲环唑-A和（-）-苯醚甲环唑-B在蕃茄果实中富集。
通过向6种不同类型的农田土壤中添加外消旋苯醚甲环唑进行培养，研究了有氧和无氧条件下苯醚甲环唑在土壤中的降解动态和选择性降解情况。结果表明在有氧或无氧土壤中苯醚甲环唑的降解均符合一级动力学降解规律。在不同土壤及培养条件下，苯醚甲环唑对映体的降解速率差别较大。苯醚甲环唑在弱碱性土壤中降解速率最快，在中性土壤中其次，在酸性土壤中降解速率最慢，研究发现在碱性和酸性土壤中苯醚甲环唑对映体的立体选择性降解比在中性土壤中更加明显。苯醚甲环唑四个对映体在无氧条件下降解速度显著小于其在有氧条件下土壤中的降解速度。在有氧和无氧两种条件下，苯醚甲环唑对映体在供试土壤中均存在不同程度的选择性代谢，（+）-苯醚甲环唑A和（+）-苯醚甲环唑B均被优先降解，但两种条件下苯醚甲环唑对映体降解的立体选择性强度没有显著性差异。通过进一步的光学纯对映体实验，证明了苯醚甲环唑对映体在土壤降解过程中是保持手性稳定的，四个对映体之间没有发生构型转变。
开展了手性三唑类杀菌剂苯醚甲环唑外消旋体及四个光学纯对映体对斜生栅藻、大型溞和斑马鱼三种水生生物的急性毒性差异研究。结果表明苯醚甲环唑四个对映体对三种水生生物的急性毒性存在不同，毒性顺序均为：（-）-苯醚甲环唑A>（+）-苯醚甲环唑B>（+）-苯醚甲环唑A>（-）-苯醚甲环唑B，外消旋苯醚甲环唑毒性处于四个对映体之间。
开展了苯醚甲环唑外消旋体及四个对映体对番茄早疫病菌(Alternaria solani)、蕃茄灰霉病菌(Botrytis cinerea)、蕃茄叶霉病菌（Fulvia fulva (Cooke) Cifferri）、水稻纹枯病菌(Rhizoctonia solani)和西瓜炭疽病菌(Colletotrichum lagenarium)等5种病源真菌的活性差异研究。研究发现，对于试验选定的植物病原菌而言，苯醚甲环唑四个对映体的抑菌活性存在明显差异，活性大小顺序为：（-）-苯醚甲环唑B>（+）-苯醚甲环唑A>（+）-苯醚甲环唑B>（-）-苯醚甲环唑A，外消旋苯醚甲环唑活性处于四个对映体之间。
In gerenal, the enantiomers/diastereoisomers of chiral pesticides are different in some biologicalprocesses and thus pose enantioselective environmental behavior and ecotoxicity to nontarget biology.Consequently, the application and environmental safety of chiral pesticides have been becoming a newpoint of scientific researches. In the present study, the enantioselective degradation of chiral triazolefungicide difenoconazole in greenhouse vegetables and agriculture soils based on the high-performanceliquid chromatography (HPLC) with chiral stationary phases (CSPs) technology were investigated. Andthe optical pure diastereoisomers of difenoconazole were also selected to investigate theirenantioselective ecotoxicologies to three aquatic organisms and their enantioselective fungitoxicities to anumber of fungi.
The separation of difenoconazole and its major metabolite CGA-205375including theirsimultaneous enantioseparation was studied using four different polysaccharide-type chiral stationaryphases inculding Amylose tris-[(S)–α-methylbenzylcarbamate](AS-H), Amylose tris(3,5-dimethylphenyl carbamate)(AD-H), Cellulose tris-(3,5-dimethylphenyl-carbamate)](OD-H) andcellulose tris-(4-methylbenzoate)(OJ-H) in combination with n-hexane-polar organic alcohols mobilephase. Compared with other three CSPs, cellulose tris-(4-methylbenzoate)(OJ-H) exhibited higherresolving ability for difenoconazole and CGA205375. And after the optimization of otherchromatographic conditions such as the mobile phase composition and column temperature, a baselinechemoseparation and enantioseparation of two enantiomers of CGA205375and four stereoisomers ofdifenoconazole was successfylly afforded.
The greenhouse experiment was used to investigate the stereoselective behavior of difenoconazolestereoisomers in cucumber and tomato plants. The results indicated that the degradation of four isomersof difenoconazole followed first-order kinetics and significantly stereoselective behavior was observedin both cucumber and tomato fruits. Preferential dissipation of (-)-difenoconazole-A and(-)-difenoconazole-B were determined in cucumber fruits after foliar treatment, which resulted in plantsenriched with (+)-difenoconazole-A and (+)-difenoconazole-B. Results also showed that(+)-difenoconazole-A and (-)-difenoconazole-B degraded faster than their optical antipode in tomatofruits, which resulted in tomato enriched with stereoisomers of (-)-difenoconazole-A and(-)-difenoconazole-B.
Six soils with a wide range of soil properties were selected to investiate the stereoselective behaviorof difenoconazole stereoisomers. Racemic-and enantiopure stereoisomers of difenoconazole wereincubated under aerobic and anaerobic conditions. Results indicated that both aerobic and anaerobicdegradation of stereoisomers of difenconazole in the test soils during incubation period generallycomplied with the first-order kinetics. It could be proved that the dissipation rates of difenoconazoleisomers were greatly influenced by pH value. The results revealed that the dissipation rates of fourstereoisomers of difenoconazole in soils were different, the orders were alkali soil>normal soil>acid soil. Moreover, data showed that the stereoselective degradation of the stereoisomes of difenoconaozle inalkali soil and acid soil was more obivious than that in normal soil. All four stereoisomers ofdifenoconazole in test soils were more slowly degraded under anaerobic conditons as comparison of thatunder aerobic conditions, but anaerobic condition has no more significant enantioselectivity than aerobiccondition. The degradation of difenoconazole stereoisomers in all test soils is enantioselective underboth aerobic and anaerobic conditions, and the (+)-difenoconazole-A and (+)-difenoconazole-B werepreferentially degraded, resulting in relative enrichment of (-)-difenoconazole-A and(-)-difenoconazole-B. The enantiopure stereoisomers of difenoconazole were incubated under bothaerobic and anaerobic conditions, and it revealed that difenoconazole was configurationally stable in soil,showing no interconversion among the stereoisomers.
Herein is reported, for the first time, the enantioselectivities of individual stereoisomers of triazolefungicide difenoconazole in acute aquatic toxicity to three aquatic orgnisms including S. obliquus, D.magna and Danio rerio. For the above three aquatic organisms, significant differences were observed inthe acute toxicity among the stereoisomers of difenoconazole. The order of the toxicity to three aquaticorganisms for the stereoisomers of difenoconazole was (-)-difenoconazole-A>(+)-difenoconazole-B>(+)-difenoconazole-A>(-)-difenoconazole-B, rac-difenoconazole had an intermediate potency oftoxicity as compared to its respective individual stereoisomers.
It was also the first report about the enantioselectivities of individual stereoisomers of triazolefungicide difenoconazole in the fungitoxicity against a number of fungi including Alternaria solani,Botrytis cinerea, Fulvia fulva (Cooke) Cifferri, Rhizoctonia solani and Colletotrichum lagenarium.Significant differences were observed in the fungicidal activities among the stereoisomers ofdifenoconazole on the test fungi. The fungitoxicity for the stereoisomers of difenoconazole has beenfound to be (-)-difenoconazole-B>(+)-difenoconazole-A>(+)-difenoconazole-B>(-)-difenoconazole-A,rac-difenoconazole had an intermediate potency of fungitoxicity as compared to its respective individualstereoisomers.
在正相液相色谱条件下，考察比较了直链淀粉-三[(s)-α-甲基苯基氨基甲酸酯]、直链淀粉-三(3,5-二甲基苯基氨基甲酸酯)、纤维素-三(3,5-二甲基苯基氨基甲酸酯)及纤维素-三(对甲基苯基甲酸酯)等四种手性固定相对苯醚甲环唑及其手性代谢物CGA205375对映体的化学分离与手性分离效果，发现纤维素-三(对甲基苯基甲酸酯)固定相具有最高手性分离能力。通过进一步对醇改性剂种类及含量、分离温度等手性分离因素的优化，成功实现了苯醚甲环唑及其代谢物CGA205375对映体的同时基线分离。
通过模拟实际生产田间茎叶喷雾法开展了苯醚甲环唑对映体在黄瓜与蕃茄植株上的选择性行为研究。数据表明苯醚甲环唑对映体在黄瓜和蕃茄果实内的降解符合一级动力学规律，且四个对映体在黄瓜和蕃茄果实中降解速度不同。在黄瓜果实内，四个对映体降解速度大小顺序为：（-）-苯醚甲环唑-A>（+）-苯醚甲环唑-A，（-）-苯醚甲环唑-B>（+）-苯醚甲环唑-B，随着施药后时间的推移，造成黄瓜果实中（+）-苯醚甲环唑-A和（-）-苯醚甲环唑-B的富集；在蕃茄果实内，四个对映体降解速度均慢于在黄瓜中的降解速度，并且也存在明显差异，在蕃茄内苯醚甲环唑降解速度大小顺序为：（+）-苯醚甲环唑-A>（-）-苯醚甲环唑-A，（-）-苯醚甲环唑-B>（+）-苯醚甲环唑-B，其中（-）-苯醚甲环唑-A和（-）-苯醚甲环唑-B在蕃茄果实中富集。
通过向6种不同类型的农田土壤中添加外消旋苯醚甲环唑进行培养，研究了有氧和无氧条件下苯醚甲环唑在土壤中的降解动态和选择性降解情况。结果表明在有氧或无氧土壤中苯醚甲环唑的降解均符合一级动力学降解规律。在不同土壤及培养条件下，苯醚甲环唑对映体的降解速率差别较大。苯醚甲环唑在弱碱性土壤中降解速率最快，在中性土壤中其次，在酸性土壤中降解速率最慢，研究发现在碱性和酸性土壤中苯醚甲环唑对映体的立体选择性降解比在中性土壤中更加明显。苯醚甲环唑四个对映体在无氧条件下降解速度显著小于其在有氧条件下土壤中的降解速度。在有氧和无氧两种条件下，苯醚甲环唑对映体在供试土壤中均存在不同程度的选择性代谢，（+）-苯醚甲环唑A和（+）-苯醚甲环唑B均被优先降解，但两种条件下苯醚甲环唑对映体降解的立体选择性强度没有显著性差异。通过进一步的光学纯对映体实验，证明了苯醚甲环唑对映体在土壤降解过程中是保持手性稳定的，四个对映体之间没有发生构型转变。
开展了手性三唑类杀菌剂苯醚甲环唑外消旋体及四个光学纯对映体对斜生栅藻、大型溞和斑马鱼三种水生生物的急性毒性差异研究。结果表明苯醚甲环唑四个对映体对三种水生生物的急性毒性存在不同，毒性顺序均为：（-）-苯醚甲环唑A>（+）-苯醚甲环唑B>（+）-苯醚甲环唑A>（-）-苯醚甲环唑B，外消旋苯醚甲环唑毒性处于四个对映体之间。
开展了苯醚甲环唑外消旋体及四个对映体对番茄早疫病菌(Alternaria solani)、蕃茄灰霉病菌(Botrytis cinerea)、蕃茄叶霉病菌（Fulvia fulva (Cooke) Cifferri）、水稻纹枯病菌(Rhizoctonia solani)和西瓜炭疽病菌(Colletotrichum lagenarium)等5种病源真菌的活性差异研究。研究发现，对于试验选定的植物病原菌而言，苯醚甲环唑四个对映体的抑菌活性存在明显差异，活性大小顺序为：（-）-苯醚甲环唑B>（+）-苯醚甲环唑A>（+）-苯醚甲环唑B>（-）-苯醚甲环唑A，外消旋苯醚甲环唑活性处于四个对映体之间。
In gerenal, the enantiomers/diastereoisomers of chiral pesticides are different in some biologicalprocesses and thus pose enantioselective environmental behavior and ecotoxicity to nontarget biology.Consequently, the application and environmental safety of chiral pesticides have been becoming a newpoint of scientific researches. In the present study, the enantioselective degradation of chiral triazolefungicide difenoconazole in greenhouse vegetables and agriculture soils based on the high-performanceliquid chromatography (HPLC) with chiral stationary phases (CSPs) technology were investigated. Andthe optical pure diastereoisomers of difenoconazole were also selected to investigate theirenantioselective ecotoxicologies to three aquatic organisms and their enantioselective fungitoxicities to anumber of fungi.
The separation of difenoconazole and its major metabolite CGA-205375including theirsimultaneous enantioseparation was studied using four different polysaccharide-type chiral stationaryphases inculding Amylose tris-[(S)–α-methylbenzylcarbamate](AS-H), Amylose tris(3,5-dimethylphenyl carbamate)(AD-H), Cellulose tris-(3,5-dimethylphenyl-carbamate)](OD-H) andcellulose tris-(4-methylbenzoate)(OJ-H) in combination with n-hexane-polar organic alcohols mobilephase. Compared with other three CSPs, cellulose tris-(4-methylbenzoate)(OJ-H) exhibited higherresolving ability for difenoconazole and CGA205375. And after the optimization of otherchromatographic conditions such as the mobile phase composition and column temperature, a baselinechemoseparation and enantioseparation of two enantiomers of CGA205375and four stereoisomers ofdifenoconazole was successfylly afforded.
The greenhouse experiment was used to investigate the stereoselective behavior of difenoconazolestereoisomers in cucumber and tomato plants. The results indicated that the degradation of four isomersof difenoconazole followed first-order kinetics and significantly stereoselective behavior was observedin both cucumber and tomato fruits. Preferential dissipation of (-)-difenoconazole-A and(-)-difenoconazole-B were determined in cucumber fruits after foliar treatment, which resulted in plantsenriched with (+)-difenoconazole-A and (+)-difenoconazole-B. Results also showed that(+)-difenoconazole-A and (-)-difenoconazole-B degraded faster than their optical antipode in tomatofruits, which resulted in tomato enriched with stereoisomers of (-)-difenoconazole-A and(-)-difenoconazole-B.
Six soils with a wide range of soil properties were selected to investiate the stereoselective behaviorof difenoconazole stereoisomers. Racemic-and enantiopure stereoisomers of difenoconazole wereincubated under aerobic and anaerobic conditions. Results indicated that both aerobic and anaerobicdegradation of stereoisomers of difenconazole in the test soils during incubation period generallycomplied with the first-order kinetics. It could be proved that the dissipation rates of difenoconazoleisomers were greatly influenced by pH value. The results revealed that the dissipation rates of fourstereoisomers of difenoconazole in soils were different, the orders were alkali soil>normal soil>acid soil. Moreover, data showed that the stereoselective degradation of the stereoisomes of difenoconaozle inalkali soil and acid soil was more obivious than that in normal soil. All four stereoisomers ofdifenoconazole in test soils were more slowly degraded under anaerobic conditons as comparison of thatunder aerobic conditions, but anaerobic condition has no more significant enantioselectivity than aerobiccondition. The degradation of difenoconazole stereoisomers in all test soils is enantioselective underboth aerobic and anaerobic conditions, and the (+)-difenoconazole-A and (+)-difenoconazole-B werepreferentially degraded, resulting in relative enrichment of (-)-difenoconazole-A and(-)-difenoconazole-B. The enantiopure stereoisomers of difenoconazole were incubated under bothaerobic and anaerobic conditions, and it revealed that difenoconazole was configurationally stable in soil,showing no interconversion among the stereoisomers.
Herein is reported, for the first time, the enantioselectivities of individual stereoisomers of triazolefungicide difenoconazole in acute aquatic toxicity to three aquatic orgnisms including S. obliquus, D.magna and Danio rerio. For the above three aquatic organisms, significant differences were observed inthe acute toxicity among the stereoisomers of difenoconazole. The order of the toxicity to three aquaticorganisms for the stereoisomers of difenoconazole was (-)-difenoconazole-A>(+)-difenoconazole-B>(+)-difenoconazole-A>(-)-difenoconazole-B, rac-difenoconazole had an intermediate potency oftoxicity as compared to its respective individual stereoisomers.
It was also the first report about the enantioselectivities of individual stereoisomers of triazolefungicide difenoconazole in the fungitoxicity against a number of fungi including Alternaria solani,Botrytis cinerea, Fulvia fulva (Cooke) Cifferri, Rhizoctonia solani and Colletotrichum lagenarium.Significant differences were observed in the fungicidal activities among the stereoisomers ofdifenoconazole on the test fungi. The fungitoxicity for the stereoisomers of difenoconazole has beenfound to be (-)-difenoconazole-B>(+)-difenoconazole-A>(+)-difenoconazole-B>(-)-difenoconazole-A,rac-difenoconazole had an intermediate potency of fungitoxicity as compared to its respective individualstereoisomers.
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