四种三唑类手性农药的环境行为研究
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摘要
三唑类农药是农业生产中应用最广泛的一类杀菌剂,同时一部分三唑类杀菌剂还具有一定的植物生长调节作用。几乎所有的三唑类农药都具有手性中心,具有两个或者多个对映异构体。研究表明手性三唑类杀菌剂对映体的毒性和活性存在巨大的差异,但是大部分该类手性农药目前仍以外消旋体形式生产和销售,这有可能对环境产生较大的负担,并且对人类的健康造成一定的损害。
本文利用高效液相色谱手性固定相方法拆分制备了多效唑,烯唑醇,腈菌唑,戊唑醇四种三唑类农药光学纯异构体,结合旋光检测仪对其对映体旋光性进行分析,确定了其绝对构型。
首先测定了四种手性三唑类农药对于对大型溞24h和48h的急性毒性。结果表明对映体毒性之间存在很大差异。多效唑的毒性大小顺序为：2S,3S-多效唑>Rac-多效唑>2R,3R-多效唑,其48h LC50分别为12.80,16.70,20.50μg/mL。对于烯唑醇,其R-体,外消旋体和S-体的48h LC50分别为2.11,2.22,2.82μg/mL。R-烯唑醇的毒性是S-烯唑醇的1.33倍,外消旋体介于两者之间。腈菌唑及其对映体对大型溞的急性毒性大小为：(+)-体>R外消旋体>(-)-体,并且随着暴露时间的增加,其毒性也逐渐增大,(+)-腈菌唑的毒性是(-)-腈菌唑的1.42-1.85倍。R-戊唑醇的毒性略微大于S-戊唑醇,其48h LC50分别为R-体3.00μg/mL,外消旋体3.54,S-体3.57μg/mL,对映体之间的差异并不明显。
其次考察了四种手性三唑类农药对芒果炭疽,苹果炭疽,番茄早疫,黄瓜炭疽,小麦赤霉,蔬菜菌核和番茄灰霉等病原菌的杀菌活性。结果表明：R-多效唑的杀菌活性远远高于S-体,其外消旋体,R-体和S-体对番茄早疫96h EC50分别为0.87,0.51和9473.58μg/mL,两对映体活性差异高达18575倍；R-烯唑醇和R-戊唑醇杀菌活性也优于对应的外消旋体和S-体；腈菌唑生物活性大小为(+)-腈菌唑>外消旋体>(-)-腈菌唑。除了杀菌活性不同,三唑类农药对植物的生长调节作用也具有一定的选择性。通过考察多效唑和烯唑醇对映体对油菜和玉米幼苗生长的作用发现：多效唑和烯唑醇能够显著抑制植物茎的生长；低浓度的对映体能促进植物根的生长,随着浓度增加,其抑制作用增强。对于不用的对映体,其生长调节存在明显的选择性,S-体是主要活性体,R-体作用不明显。进一步测定了多效唑和烯唑醇处理后的玉米幼苗中抗氧化酶活性的脂质过氧化物(MDA)的含量,结果表明其对映体对植物体内抗氧化酶活性的影响具有选择性,并且都能提高超氧化物歧化酶(SOD),过氧化物酶(POD)和过氧化氢酶(CAT)的活性,同时能够显著降低MDA的含量,这在一定程度上提高了植物的抗逆性,延缓了植物的衰老。
最后考察了三唑类手性农药在环境和动物体内的选择性降解代谢行为。结果表明多效唑两对映体在番茄和油菜体内的的降解存在着明显的立体选择性,R-多效唑降解速率快于S-体。同时发现戊唑醇对映体在苹果中降解存在立体选择性,R-戊唑醇的降解速率快于S-戊唑醇。在供试土壤中,戊唑醇两对映体并无明显的选择性差异。在家兔耳静脉外消旋体给药后,发现腈菌唑对映体在家兔体内的药代动力学是立体选择性的,其杀菌活性体(+)-腈菌唑比(-)-腈菌唑降解快；两对映体在家兔各组织中的降解也存在差异。
Triazole pesticides in agricultural production is the most widely used class of fungicides and plant growth regulators. Most of the triazole pesticides are chiral characteristics, studies have shown that the activity and toxicity of chiral triazole fungicide enantiomers are often very different, but the vast majority of such chiral pesticides are still sold in racemic form and may cause a lot of human and environmental safety risks.
In this study, chiral separation and prepare of paclobutrazol, diniconazole, myclobutanil and tebuconazole enantiomers was achieved on a chiral HPLC column, and their absolute configurations were confirmed by optical rotatory dispersion (ORD) to determine absolute configuration.
Acute toxicity of four chiral triazole pesticides to Daphnia magna were determined. The results showed great differences between enantiomers. For the two enantiomers of paclobutrazol:2S,3S> Raceme>2R,3R, where the size of S-isomer is1.4.60more toxic than R-isomer. For diniconazole R-isomer is1.33-2.23times toxic than S-isomer and racema. The toxicit myclobutanil is (+)-isomer> Raceme>(-)-isomer and with increasing exposure time. R-tebuconazole toxic is slightly larger than the S-form, but the difference was not significant.
The bactericidal activity of four chiral triazole pesticides against several pathogens were investigated. The results showed:R-paclobutrazol fungicidal is much more activity than the S-form, the difference up to18575times; R-diniconazole and R-tebuconazole were more activity than racemic and S-isomer; myclobutanil bioactive is:(+)-isomer> racemic>(-)-isomer.
Apart from the different bactericidal activity, triazole pesticides for plant growth regulating effects are also steroselective. Our study showed that paclobutrazol and diniconazole can significantly inhibit the growth of plant stems; low concentration of enantiomers can promote the growth of plant roots, with the concentration increases, the inhibition enhanced. For their enantiomers, S-enantiomers were more effective than R-enantiomers. The effects of paclobutrazol and diniconazole to antioxidant enzyme activity and lipid peroxides were determined and found racemate and both enantiomers all can improve SOD, POD and CAT activity, decreased MDA content, which enhaced the resistance of plants.
The environmental behavior of chiral triazole pesticides were investigated. Results showed that the degradation of paclobutrazol in tomato and rape were steroselectivty:R-form degradated faster than S-isomer. Tebuconazole enantiomer also showed the enatioslectivty behavior:the degradation of R-tebuconazole is faster than S-tebuconazole; in the soil tested, the two enantiomers showed no significant differences in degradation. The metabolism of myclobutanil enantiomers in rabbits was investigated:results indicated the high bioactive (+)-enantiomer being preferentially metabolized and eliminated in plasma; the drgadation rates in diffirent tissues were also stereoselectivity.
本文利用高效液相色谱手性固定相方法拆分制备了多效唑,烯唑醇,腈菌唑,戊唑醇四种三唑类农药光学纯异构体,结合旋光检测仪对其对映体旋光性进行分析,确定了其绝对构型。
首先测定了四种手性三唑类农药对于对大型溞24h和48h的急性毒性。结果表明对映体毒性之间存在很大差异。多效唑的毒性大小顺序为：2S,3S-多效唑>Rac-多效唑>2R,3R-多效唑,其48h LC50分别为12.80,16.70,20.50μg/mL。对于烯唑醇,其R-体,外消旋体和S-体的48h LC50分别为2.11,2.22,2.82μg/mL。R-烯唑醇的毒性是S-烯唑醇的1.33倍,外消旋体介于两者之间。腈菌唑及其对映体对大型溞的急性毒性大小为：(+)-体>R外消旋体>(-)-体,并且随着暴露时间的增加,其毒性也逐渐增大,(+)-腈菌唑的毒性是(-)-腈菌唑的1.42-1.85倍。R-戊唑醇的毒性略微大于S-戊唑醇,其48h LC50分别为R-体3.00μg/mL,外消旋体3.54,S-体3.57μg/mL,对映体之间的差异并不明显。
其次考察了四种手性三唑类农药对芒果炭疽,苹果炭疽,番茄早疫,黄瓜炭疽,小麦赤霉,蔬菜菌核和番茄灰霉等病原菌的杀菌活性。结果表明：R-多效唑的杀菌活性远远高于S-体,其外消旋体,R-体和S-体对番茄早疫96h EC50分别为0.87,0.51和9473.58μg/mL,两对映体活性差异高达18575倍；R-烯唑醇和R-戊唑醇杀菌活性也优于对应的外消旋体和S-体；腈菌唑生物活性大小为(+)-腈菌唑>外消旋体>(-)-腈菌唑。除了杀菌活性不同,三唑类农药对植物的生长调节作用也具有一定的选择性。通过考察多效唑和烯唑醇对映体对油菜和玉米幼苗生长的作用发现：多效唑和烯唑醇能够显著抑制植物茎的生长；低浓度的对映体能促进植物根的生长,随着浓度增加,其抑制作用增强。对于不用的对映体,其生长调节存在明显的选择性,S-体是主要活性体,R-体作用不明显。进一步测定了多效唑和烯唑醇处理后的玉米幼苗中抗氧化酶活性的脂质过氧化物(MDA)的含量,结果表明其对映体对植物体内抗氧化酶活性的影响具有选择性,并且都能提高超氧化物歧化酶(SOD),过氧化物酶(POD)和过氧化氢酶(CAT)的活性,同时能够显著降低MDA的含量,这在一定程度上提高了植物的抗逆性,延缓了植物的衰老。
最后考察了三唑类手性农药在环境和动物体内的选择性降解代谢行为。结果表明多效唑两对映体在番茄和油菜体内的的降解存在着明显的立体选择性,R-多效唑降解速率快于S-体。同时发现戊唑醇对映体在苹果中降解存在立体选择性,R-戊唑醇的降解速率快于S-戊唑醇。在供试土壤中,戊唑醇两对映体并无明显的选择性差异。在家兔耳静脉外消旋体给药后,发现腈菌唑对映体在家兔体内的药代动力学是立体选择性的,其杀菌活性体(+)-腈菌唑比(-)-腈菌唑降解快；两对映体在家兔各组织中的降解也存在差异。
Triazole pesticides in agricultural production is the most widely used class of fungicides and plant growth regulators. Most of the triazole pesticides are chiral characteristics, studies have shown that the activity and toxicity of chiral triazole fungicide enantiomers are often very different, but the vast majority of such chiral pesticides are still sold in racemic form and may cause a lot of human and environmental safety risks.
In this study, chiral separation and prepare of paclobutrazol, diniconazole, myclobutanil and tebuconazole enantiomers was achieved on a chiral HPLC column, and their absolute configurations were confirmed by optical rotatory dispersion (ORD) to determine absolute configuration.
Acute toxicity of four chiral triazole pesticides to Daphnia magna were determined. The results showed great differences between enantiomers. For the two enantiomers of paclobutrazol:2S,3S> Raceme>2R,3R, where the size of S-isomer is1.4.60more toxic than R-isomer. For diniconazole R-isomer is1.33-2.23times toxic than S-isomer and racema. The toxicit myclobutanil is (+)-isomer> Raceme>(-)-isomer and with increasing exposure time. R-tebuconazole toxic is slightly larger than the S-form, but the difference was not significant.
The bactericidal activity of four chiral triazole pesticides against several pathogens were investigated. The results showed:R-paclobutrazol fungicidal is much more activity than the S-form, the difference up to18575times; R-diniconazole and R-tebuconazole were more activity than racemic and S-isomer; myclobutanil bioactive is:(+)-isomer> racemic>(-)-isomer.
Apart from the different bactericidal activity, triazole pesticides for plant growth regulating effects are also steroselective. Our study showed that paclobutrazol and diniconazole can significantly inhibit the growth of plant stems; low concentration of enantiomers can promote the growth of plant roots, with the concentration increases, the inhibition enhanced. For their enantiomers, S-enantiomers were more effective than R-enantiomers. The effects of paclobutrazol and diniconazole to antioxidant enzyme activity and lipid peroxides were determined and found racemate and both enantiomers all can improve SOD, POD and CAT activity, decreased MDA content, which enhaced the resistance of plants.
The environmental behavior of chiral triazole pesticides were investigated. Results showed that the degradation of paclobutrazol in tomato and rape were steroselectivty:R-form degradated faster than S-isomer. Tebuconazole enantiomer also showed the enatioslectivty behavior:the degradation of R-tebuconazole is faster than S-tebuconazole; in the soil tested, the two enantiomers showed no significant differences in degradation. The metabolism of myclobutanil enantiomers in rabbits was investigated:results indicated the high bioactive (+)-enantiomer being preferentially metabolized and eliminated in plasma; the drgadation rates in diffirent tissues were also stereoselectivity.
引文
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