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含两个手性中心的三唑类农药色谱分离研究进展

唐守英 王飞 孟秀柔 张钰萍

唐守英, 王飞, 孟秀柔, 张钰萍. 含两个手性中心的三唑类农药色谱分离研究进展[J]. 农药学学报. doi: 10.16801/j.issn.1008-7303.2021.0065
引用本文: 唐守英, 王飞, 孟秀柔, 张钰萍. 含两个手性中心的三唑类农药色谱分离研究进展[J]. 农药学学报. doi: 10.16801/j.issn.1008-7303.2021.0065
Shouying TANG, Fei WANG, Xiurou MENG, Yuping ZHANG. Research progress in chromatographic separation of triazole pesticides containing two chiral centers[J]. Chinese Journal of Pesticide Science. doi: 10.16801/j.issn.1008-7303.2021.0065
Citation: Shouying TANG, Fei WANG, Xiurou MENG, Yuping ZHANG. Research progress in chromatographic separation of triazole pesticides containing two chiral centers[J]. Chinese Journal of Pesticide Science. doi: 10.16801/j.issn.1008-7303.2021.0065

含两个手性中心的三唑类农药色谱分离研究进展

doi: 10.16801/j.issn.1008-7303.2021.0065
基金项目: 国家重点研发计划子课题 (2016YFD0200206- 3);国家自然科学基金 (21866009和21667007)
详细信息
    作者简介:

    唐守英,女,硕士研究生,E­mail:1261718747@qq.com

    通讯作者:

    张钰萍,通信作者 (Author for correspondence),女,副教授,主要从事农药残留分析与环境行为研究,E­mail:zhangyupinggz@163.com

  • 中图分类号: S482.2;TQ450.2

Research progress in chromatographic separation of triazole pesticides containing two chiral centers

  • 摘要: 三唑类杀菌剂是目前世界上广泛应用的杀菌剂,而绝大多数三唑类杀菌剂属于手性农药,具有1个或2个手性中心,存在2个或4个对映异构体。本文在近年有关三唑类杀菌剂研究成果的基础上,综述了采用高效液相色谱、超临界流体色谱、毛细管电泳、气相色谱和合相色谱法等方法对含两个手性中心的11种三唑类手性农药 (氟环唑、多效唑、三唑醇、联苯三唑醇、丙环唑、苯醚甲环唑、叶菌唑、苄氯三唑醇、环唑醇、糠菌唑和乙环唑) 进行分离测定的研究进展,可为多个手性中心三唑类化合物的分离、分析和深入研究提供参考。
  • 1  11种含两个手性中心的三唑类农药的化学结构式

    1.  Chemical structures of 11 triazole pesticides with two chiral centers

    表  1  11种含两个手性中心的三唑类手性农药基本信息

    Table  1.   Basic information of 11 triazole chiral pesticides with two chiral centers

    农药  
    Pesticide  
    CAS号
    CAS number
    对映体抑菌活性  
    Biological Activity of Enantiomers  
    参考文献
    Reference
    氟环唑 epoxiconazole 135319-73-2 (R, S)-体是 (S, R)-体的1.3~7.25倍
    (R, S)-epoxiconazole is1.3-7.25 times of (S, R)-epoxiconazole.
    [6]
    多效唑 paclobutrazol 76738-62-0 (R, R)-体 > (S, R)-体 > (R, S)-体≈(S, S)-体,(S, S)-体植物生长调节作用最强
    (R, R)- > (S, R)- > (R, S)- ≈ (S, S)-paclobutrazol, (the growth regulation of (S, S)- paclobutrazol was the strongest).
    [7]
    三唑醇 triadimenol 55219-65-3 (S, R)-体是 (R, S)-体、(R, R)-体、(S, S)-体的1000多倍
    (S, R)-triadimenol is more than 1000 times of (R, S)-, (R, R) - and (S, S)- triadimenol.
    [8]
    联苯三唑醇 bitertanol 55179-31-2 (S, R)-体比其他异构体抗真菌生物活性强4.3-314.7倍
    The antifungal activity of (S, R)-bitertanol was 4.3-314.7 times stronger than that of other stereoisomers.
    [9]
    丙环唑 propiconazole 60207-90-1 活性不同靶标活性最大相差23.47倍,(2R-体的植物生长调节作用比2S-体强)
    The activity of different targets was 23.47 times higher than that of 2R-enantiomers (2R-enantiomershas stronger plant growth regulation than 2S-enantiomers).
    [10]
    苯醚甲环唑 difenoconazole 119446-68-3 (R, S)-体 > (R, R)-体 > (S, R)-体 > (S, S)-体
    (R, S)- > (R, R)- > (S, R)- > (S, S)-difenoconazole.
    [11]
    叶菌唑 metconazole 125116-23-6 (S, R)-体为活性体
    (S, R)-metconazole are active bodies.
    [12]
    苄氯三唑醇 diclobutrazol 75736-33-3 (R, R)-体远高于 (R, S)-、(S, R)-、(S, S)-体
    The activity of (R, R)-diclobutrazol was much higher than that of (R, S)-, (S, R)- and (S, S)-diclobutrazol.
    [13]
    环唑醇 cyproconazole 94361-06-5 (S, S)-体 > 立体异构体混合物 > (S, R)-体 > (R, R)-体 > (R, S)-体
    (S, S)- > racemic > (S, R)- > (R, R)- > (R, S)-cyproconazol.
    [14]
    糠菌唑 bromuconazole 116255-48-2 未见报道 Not reported. -
    乙环唑 etaconazole 60207-93-4 (S, R)-体远高于 (R, S)-、(R, R)-、(S, S)-体
    The activity of (S, R)-etaconazole was much higher than that of (R, S)-, (R, R)- and (S, S)- etaconazole.
    [15]
    下载: 导出CSV

    表  2  手性色谱柱基本信息

    Table  2.   Basic information about chiral columns

    固定相
    Stationary phase
    类型
    Type
    商品名
    Trade name
    生产公司
    Company
    纤维素-三 (3, 5-二甲基苯基氨基甲酸酯)
    Cellulose tris (3, 5-dimethyl phenyl carbamate), CDMPC
    涂敷型 Coating type Chiralcel OD Daicel
    Enantiopak OD Guangzhou Yanchuang Biotechnology Development Co., Ltd
    键合型 Bond type Chiralpak IB Daicel
    Lux-cellulose-1 Phenomenex
    直链淀粉-三 (3, 5-二甲基苯基氨基甲酸酯)
    Amylose- tris (3, 5-dimethyl phenyl carbamate), ADMPC
    涂敷型 Coating type Chiralcel AD-H Daicel
    Enantiopak AD Guangzhou Yanchuang Biotechnology Development Co., Ltd
    键合型 Bond type Chiralpark IA-3 Daicel
    纤维素-三 (4-甲基苯基甲酸酯)
    Cellulose tri s (4-methyl-phenyl formate), CTMB
    涂敷型Coating type Chiralcel OJ Daicel
    Sino-ChiralOJ Daicel
    键合型 Bond type Lux-cellulose-3 Phenomenex
    直链淀粉-三[S-α-乙苯基氨基甲酸酯]
    Amylose - tris [S-α- ethyl phenyl carbamate], ATEPC
    涂敷型 Coating typ Chiralpak AS-H Daicel
    直链淀粉-三 (3-氯-5-甲基苯基氨基甲酸酯)
    Amylose tris (3-chloro-5-methyl phenyl carbamate), ACMPC
    键合型 Bond type Chiralcel IG Daicel
    纤维素-三 (3-氯-4-甲基苯基氨基甲酸酯)
    Cellulose tris (3-chloro-4-methyl phenyl carbamate), CCMPC
    键合型 Bond type Lux-cellulose-2 Phenomenex
    直链淀粉-三 (5-氯-2-甲基苯基氨基甲酸酯)
    Amylose tris (5-chloro-2-methyl phenyl carbamate)
    键合型 Bond type Lux Amylose-2 Phenomenex
    20%三-丁基二甲基硅烷基-β-环糊精
    20% tris-butyl dimethylsilyl - β-cyclodextrin
    毛细管 Capillary BGB 172 BGB
    下载: 导出CSV

    表  3  正相色谱法分离检测三唑类手性农药

    Table  3.   Separation and detection of chiral triazole pesticides by normal phase chromatography

    农药  
    Pesticide  
    手性柱
    Chiral column
    流动相 (体积比) 
    Mobile phase (V/V) 
    流速
    Fliw rate/
    (mL/min)
    柱温
    Temperature/
    检测波长
    Wavelength/
    nm
    分离度
    Resolution
    RS12, RS23, RS34
    参考文献
    Reference
    氟环唑a
    epoxiconazole
    Chiralcel OD-H 正己烷/异丙醇 (80 : 20)
    n-hexane/isopropanol (80 : 20)
    0.5 室温 (Room) 254 5.88 [16]
    Chiralcel OJ-H 正己烷/异丙醇 (60 : 40)
    n-hexane/isopropanol (60 : 40)
    0.5 室温 (Room) 254 1.98 [17]
    Chiralcel AD-H 正己烷/乙醇 (70 : 30)
    n-hexane/ethanol (70 : 30)
    0.5 室温 (Room) 254 4.52 [18]
    多效唑a
    paclobutrazol
    Chiralcel OD-H 正己烷/异丙醇 (100 : 2)
    n-hexane/isopropanol (100 : 2)
    0.8 20 225 1.84 [19]
    Chiralcel OJ-H 正己烷/异丙醇 (10 : 1)
    n-hexane/isopropanol (10 : 1)
    0.8 20 225 4.05 [19]
    三唑醇
    triadimenol
    Chiralpak AS-H 正己烷/乙醇 (95 : 5)
    n-hexane/ethanol (95 : 5)
    1.0 25 225 2.28, < 1.5, 1.88 [20]
    三唑醇
    atriadimenol a
    Chiralcel OD-H 正己烷/异丙醇 (100 : 3)
    n-hexane/isopropanol (100 : 3)
    1.0 30 225 3.25 [21]
    Chiralcel OJ-H 正己烷/异丙醇 (100 : 3)
    n-hexane/isopropanol (100 : 3)
    1.0 30 225 3.79 [21]
    三唑醇
    btriadimenol b
    Chiralcel OD-H 正己烷/异丙醇 (100 : 3)
    n-hexane/isopropanol (100 : 3)
    1.0 30 225 0.79 [21]
    Chiralcel OJ-H 正己烷/异丙醇 (100 : 3)
    n-hexane/isopropanol (100 : 3)
    1.0 30 225 2.08 [21]
    联苯三唑醇b
    bitertanol
    Chiralcel OD-H 正己烷/异丙醇 (100 : 3)
    n-hexane/isopropanol (100 : 3)
    0.8 20 254 1.52 [19]
    Chiralcel OJ-H 正己烷/异丙醇 (10 : 1)
    n-hexane/isopropanol (10 : 1)
    0.8 20 254 3.70 [19]
    丙环唑
    propiconazole
    Chiralcel OD-H 正己烷/乙醇 (95 : 5)
    n-hexane/ethanol (95 : 5)
    0.6 25 220 6.67, 4.06, 2.05 [10]
    Chiralcel AD-H 正己烷/乙醇 (95 : 5)
    n-hexane/ethanol (95 : 5)
    0.6 25 220 4.97, 2.94, 2.24 [10]
    Chiralcel OD 正己烷/异丙醇 (90 : 10)
    n-hexane/isopropanol (90 : 10)
    0.4 10 230 5.25, 3.98, 2.40 [24]
    苯醚甲环唑
    difenoconazole
    Chiralcel OJ 正己烷/乙醇 (90 : 10)
    n-hexane/ethanol (90 : 10)
    0.5 10 230 1.32, 0.88, 4.30 [24]
    Chiralpak IB-3 甲醇和正己烷梯度
    methanol and n-hexane gradient
    - - - 1.62, 1.59, 1.56 [4]
    苯醚甲环唑及代谢物
    difenoconazole and metabolin
    Chiralcel OJ-H 正己烷/乙醇 (90 : 10)
    n-hexane/ethanol (90 : 10)
    0.8 20 220 2.01, 1.66, 2.21, 1.76, 7.07 [11]
    叶菌唑
    metconazole
    Enantiopak AD 正己烷/乙醇 (97 : 3)
    n-hexane/ethanol (97 : 3)
    1.0 25 220 3.91, 2.05, 1.51 [12]
    Enantiopak OD 正己烷/乙醇 (97 : 3)
    n-hexane/ethanol (97 : 3)
    1.0 25 220 2.37, 2.43, 4.55 [12]
    注:a商品药只含一对对映异构体,b 4个对映异构体只能拆分成两对对映异构体。Note : a Commercial drugs contained only one pair of enantiomers, b the four enantiomers could only be separated into two pairs.
    下载: 导出CSV

    表  4  反相色谱法分离检测三唑类手性农药

    Table  4.   Separation and detection of triazole chiral pesticides by reversed-phase chromatography

    农药
    Pesticide
    手性柱
    Chiral column
    流动相
    Mobile phase/(v/v)
    流速
    Fliw rate/
    (mL/min)
    柱温
    Temperature/
    分离度
    Resolution
    RS12RS23RS34
    参考文献
    Reference
    氟环唑b
    epoxiconazole
    Chiralcel OD-H 甲醇/水 (80 : 20)
    Methanol/water (80 : 20)
    0.5 室温 (Room) 6.50 [16]
    Lux Cellulose-1 乙腈/0.1%甲酸水 (60 : 40)
    Acetonitrile/0.1% formic acid water (60 : 40)
    0.2 25 9.05 [26]
    Lux Cellulose-2 甲醇/0.1%甲酸水 (70 : 30)
    Methanol/0.1% formic acid water (70 : 30)
    0.2 25 14.00 [26]
    Lux Cellulose-2 乙腈/0.1%甲酸水 (60 : 40)
    Acetonitrile/0.1% formic acid water (60 : 40)
    0.2 25 17.6 [26]
    Chiralcel OD-3R 乙腈/0.05%甲酸水 (60 : 40)
    Acetonitrile/0.05% formic acid water (60 : 40)
    0.25 30 10.96 [29]
    Lux-Cellulose-1 乙腈/水 (70 : 30)
    Acetonitrile/water (70 : 30)
    0.3 20 10.45 [28]
    Chiralpak IG 乙腈/0.05%甲酸水5 mM醋酸铵 (53 : 47)
    Acetonitrile/0.05% formic acid water and 5 mM ammonium acetate (53 : 47)
    0.25 30 3.21 [31]
    Chiralpak IG-3 乙腈/0.1%二乙胺和1.1%三氟乙酸水 (80 : 20)
    Acetonitrile/0.1% diethylamine and 1.1% trifluoroacetic acid water (80 : 20)
    1.0 20 3.25 [33]
    Lux Cellulose-1 乙腈/水 (55 : 45)
    Acetonitrile/water (55 : 45)
    0.6 30 12.03 [35]
    Chiralcel OD 乙腈/水 (50 : 50)
    Acetonitrile/water (50 : 50)
    0.8 25 9.23 [36]
    多效唑b
    paclobutrazol
    Lux Cellulose-1 甲醇/0.1%甲酸水 (70 : 30)
    Methanol/0.1% formic acid water (70 : 30)
    0.2 25 1.77 [26]
    Lux Cellulose-2 乙腈/0.1%甲酸水 (50 : 50)
    Acetonitrile/0.1% formic acid water (50 : 50)
    0.2 25 1.80 [26]
    Lux Amylose-2 乙腈/0.1%甲酸水 (60 : 40)
    Acetonitrile/0.1% formic acid water (60 : 40)
    0.2 25 1.54 [26]
    Chiralpak AD-RH 甲醇/水 (70 : 30)
    Methanol/water (70 : 30)
    0.45 25 2.48 [27]
    Lux Amylose-2 乙腈/水 (55 : 45)
    Acetonitrile/water (55 : 45)
    0.25 25 2.23 [27]
    三唑醇
    triadimenol
    Lux Cellulose-1 甲醇/0.1%甲酸水 (50 : 50)
    Methanol/0.1% formic acid water (50 : 50)
    0.2 35 1.52, 3.02, 1.51 [26]
    Lux Cellulose-1 甲醇/水 (75 : 25)
    Methanol/water (75 : 25)
    0.5 室温 (Room) 1.26, 1.44, 2.41 [29]
    Lux Cellulose-1 甲醇/水 (60 : 40)
    Methanol/water (60 : 40)
    0.5 室温 (Room) 1.45, 2.73, 2.16 [29]
    联苯三唑醇
    bitertanol
    Lux Cellulose-1 乙腈/0.1%甲酸水 (45 : 55)
    Acetonitrile/0.1% formic acid water (60 : 40)
    0.2 25 1.54, 4.33, 9.08 [26]
    丙环唑
    propiconazole
    Lux Cellulose-2 甲醇/0.1%甲酸水 (60 : 40)
    Methanol/0.1% formic acid water (60 : 40)
    0.2 40 2.00, 2.20, 1.55 [26]
    苯醚甲环唑
    difenoconazole
    Lux Cellulose-3 乙腈/0.1%甲酸水 (30 : 70)
    Acetonitrile/0.1% formic acid water (30 : 70)
    0.2 25 1.48, 1.18, 1.25 [26]
    Chiralpak IG-3 甲醇/三氟乙酸/二乙胺 (100 : 0.1 : 0.3)
    Methanol/trifluoroacetic acid /diethylamine (100 : 0.1 : 0.3)
    1 20 < 1.00, 2.95, 3.95 [33]
    苄氯三唑醇a
    diclobutrazol
    Lux Cellulose-1 甲醇/0.1%甲酸水 (70 : 30)
    Methanol/0.1% formic acid water (70 : 30)
    0.2 25 2.02 [26]
    Lux Cellulose-1 乙腈/0.1%甲酸水 (50 : 50)
    Acetonitrile/0.1% formic acid water (50 : 50)
    0.2 25 1.93 [26]
    Lux Amylose-2 乙腈/0.1%甲酸水 (70 : 30)
    Acetonitrile/0.1% formic acid water (70 : 30)
    0.2 25 2.69 [26]
    环唑醇
    cyproconazole
    Lux Cellulose-1 乙腈/0.1%甲酸水 (45 : 55)
    Acetonitrile/0.1% formic acid water (45 : 55)
    0.2 25 3.10, 1.97, 17.4 [26]
    Lux Cellulose-2 甲醇/0.1%甲酸水 (60 : 40)
    Methanol/0.1% formic acid water (60 : 40)
    0.2 25 3.54, 1.77, 6.61 [26]
    糠菌唑
    bromuconazole
    Lux Cellulose-2 乙腈/0.1%甲酸水 (60 : 40)
    Acetonitrile/0.1% formic acid water (60 : 40)
    0.2 25 5.24, 2.12, 1.82 [26]
    Lux Amylose-2 乙腈/0.1%甲酸水 (40 : 60)
    Acetonitrile/0.1% formic acid water (40 : 60)
    0.2 25 1.69, 3.28, 5.15 [26]
    注:a苄氯三唑醇拆分成两对对映异构体,b商品药只含一对对映异构体。Note : aDiclobutrazol could be separated into two pairs of enantiomers, bCommercial drugs contained only one pair of enantiomers.
    下载: 导出CSV

    表  5  超临界流体色谱法分离检测含两个手性中心的三唑类农药

    Table  5.   Separation and detection of ten triazole pesticides with two chiral centers by supercritical fluid chromatography

    农药
    Pesticide
    手性柱
    Chiral column
    流速
    Fliw rate/
    (mL/min)
    柱温
    Temperature/
    系统背压
    System back
    pressure/
    Mpa
    改性剂
    (体积分数)
    Modifier
    分离度
    Resolution
    RS12, RS23, RS34
    参考文献
    Reference
    氟环唑a epoxiconazole Chiralcel OD-H 2 34 15 15%异丙醇15% isopropanol 23.37 [39]
    多效唑a paclobutrazol Chiralcel OD-H 2 34 15 5%甲醇5% methanol 1.87 [37]
    Chiralcel OD-H 2 34 15 9%乙醇9% ethanol 1.85 [39]
    三唑醇b triadimenol Chiralpak AD 2 35 20 3%甲醇3% methanol 8.53 [40]
    Chiralpak AD 2 35 20 3%乙醇3% ethanol 7.25 [40]
    联苯三唑醇 bitertanol Sino-Chiral OJ 2 34 15 13%乙醇13% ethanol 2.08, 7.41, 13.55 [38-39]
    丙环唑 propiconazole Chiralpak AD 2 35 20 5%异丙醇5% isopropanol 4.26, 2.59, 3.24 [41]
    苯醚甲环唑 difenoconazole Chiralcel OD-H 2 34 15 5%乙醇5% ethanol 4.19, 1.52, 1.33 [38-39]
    叶菌唑 metconazole Chiralpak IB 2 34 15 6%甲醇6% methanol 2.74, 5.83, 5.50 [38-39]
    苄氯三唑醇 diclobutrazol Chiralcel OD-H 2 34 15 3%乙醇3% ethanol 1.55, 3.97, 3.88 [38-39]
    环唑醇 cyproconazole Chiralpak AD 2 35 20 5%甲醇5% methanol 1.49, 1.01, 2.83 [41]
    糠菌唑 bromuconazole Sino-Chiral OJ 2 34 15 7%乙醇7% ethanol 5.24, 1.80, 1.71 [38-39]
    乙环唑 etaconazole Chiralcel OD-H 2 35 15 7%乙醇7% ethanol 1.11, 1.55, - [38-39]
    注:a商品药只含一对对映异构体,b三唑醇只能拆分成两对对映异构体。Note: aCommercial drugs contained only one pair of enantiomers, btriadimenol could only be split into two pairs of enantiomers.
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  • 收稿日期:  2020-10-16
  • 录用日期:  2021-01-16
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