Review on the Analysis and Testing Method of Typical Plant Growth Regulators in Environment
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摘要:
近年来，植物生长调节剂被广泛应用于农业领域，主要有加速或延缓种子萌发、打破植物休眠、刺激或减少芽伸长、诱导开花结果以及影响衰老过程等功效，对植物的生长有着重要作用。但是，由于其施用量不断增加，导致植物生长调节剂在环境介质中被多次检出，且经过一系列环境行为产生的中间产物可能具有更强的毒性，严重威胁环境安全乃至人体健康。通过总结植物生长调节剂分析测试相关国内外研究文献发现，果蔬、肥料和土壤等固态基质样品的前处理多采用固相萃取方法，而水体、食用油和营养液等液态基质样品的前处理则多以液液萃取方法为主。同时，大多数植物生长调节剂的辛醇水分配系数在0~4之间，具有极强的亲水性，而高效液相色谱-串联质谱法(HPLC-MS/MS)具有较低检出限和较高准确度等优点，使其成为目前使用最多的植物生长调节剂分析测试技术。其次，部分植物生长调节剂沸点低、易挥发，也可以采用气相色谱法或气相色谱-质谱联用法(GC-MS)进行检测。几种常用分析测试技术检出限的大小顺序大致为：气相色谱法>液相色谱法>色谱-质谱联用法，其中，色谱-质谱联用法的仪器检出限可低至10-5mg/kg。但是，由于大部分植物生长调节剂溶解度高、自然衰减速率快，导致其在土壤和水体等复杂环境基质中的检出浓度偏低，关于土壤和水体中痕量植物生长调节剂及其中间产物的分析测试问题仍亟待解决。未来，相关研究应聚焦于植物生长调节剂中间产物的分析测试，并开发基于新材料、新技术的植物生长调节剂分析测试方法。
Abstract:Plant growth regulators (PGRs) are defined as naturally occurring or artificially synthesized compounds. The functions of PGRs mainly include accelerating or delaying seed germination, breaking plant dormancy, stimulating or reducing bud elongation, inducing flowering and fruiting, and affecting the aging process. The application of PGRs has effectively promoted the growth of plants. However, the application concentration of PGRs is more than one millionth. The large amount of abuse and misuse of PGRs in the process of use not only reduces the yield of crops, but also exacerbates their residues in the environment, especially in agricultural products such as fruits and vegetables. So, they are detected in many environmental media like fruits, vegetables, and water. In addition, most PGRs are toxic, and some of them will undergo adsorption, desorption, hydrolysis, photolysis, microbial degradation, and other environmental behaviors after entering the soil. The decomposition products produced by this process are more toxic.In order to comprehensively understand the current status of PGRs pretreatment, analysis and test method, the common pretreatment methods of solid phase extraction and liquid-liquid extraction for typical PGRs in solid substrates such as fruits and vegetables, fertilizers and soil, and in liquid substrates such as water, edible oil and nutrient solution are summarized in this paper, as well as the analysis and testing techniques such as high-performance liquid chromatography (HPLC) and ultra-high performance liquid chromatography (UPLC). Moreover, to reduce the detection limit, high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) is also frequently used. At the same time, considering the strong natural attenuation ability of PGRs and the high toxicity of their intermediates, the advantages, disadvantages and applicability of different testing techniques are systematically summarized, taking into account the special structure and nature of PGRs, in order to fully understand the current status of pretreatment and analytical testing of PGRs and provide literature support for subsequent research on analytical testing, migration transformation, pollution evaluation and treatment of PGRs.
Due to many impurities in the sample that can interfere with the detection, the appropriate pretreatment method can improve the accuracy of the test results. However, the sample pretreatment process accounts for more than 70% of the total analysis and test work, and about 50% of the error in the final test results comes from pretreatment. Therefore, establishing a fast, simple, and stable pretreatment method can effectively improve the efficiency and accuracy of analysis and detection. At present, the forms of environmental media detected for PGRs are mainly divided into two types: solid matrix samples (such as fruits, vegetables, fertilizers and soil, etc.) and liquid matrix samples (water, oil and nutrient solution, etc.). The related pretreatment methods are also mostly targeted at these two different forms of environmental media.
Solid substrates involving PGRs mainly include fruits and vegetables, fertilizers and soil. Among them, fruits and vegetables are the most frequently detected solid substrates of PGRs, and some PGRs have also been detected in fertilizers, soil and other substrates. The pretreatment process of solid matrix samples can be divided into two parts: extraction and purification. Among them, solid phase extraction is the most commonly used extraction technology, and QuEChERS method is the most widely used purification method.
Water, edible oil, and nutrient solution are the most frequently detected liquid substrates of PGRs. At present, liquid-liquid extraction is the most commonly used extraction method for liquid matrix. For the selection of extractants, the octanol-water partition coefficient of PGRs such as gibberellic acid and ethephon is less than 1, which is a strong polar compound and can be extracted by hydrophilic organic solvents such as methanol, ethanol and acetone; the polarity of most other PGRs such as forchlorfenuron and paclobutrazol is relatively weak, but it still belongs to the category of strong polarity compared with other kinds of compounds such as benzene and chloroethane (n-octanol-water partition coefficient>10). Therefore, the extractant can not only use methanol, but also use polar organic solvents such as ethyl acetate and chloroform that are insoluble in water. Although liquid-liquid extraction requires a lot of extractants, the high-water solubility of most PGRs makes them often directly detected by HPLC-MS/MS, which eliminates the complex pretreatment steps such as extraction and purification. In addition, because some PGRs have poor chromatographic characteristics or are not easily detected, the derivatization is also required to convert the components into derivatives suitable for analysis.
Analytical and testing technologies mainly include gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS), HPLC/UPLC, HPLC-MS/MS, ion chromatography (IC), spectrophotometry (SP), capillary electrophoresis (CE), enzyme-linked immunosorbent assay (ELISA) and electrochemical sensor method.
At present, the solubility of most PGRs in water (20℃) is 0.50-10g/L, and the octanol-water partition coefficient of most PGRs is 0-4, with strong hydrophilicity. Therefore, HPLC-MS/MS are applicable to the detection of almost all PGRs. However, HPLC-MS/MS are often used to detect the residues of PGRs in fruits and vegetables, followed by soil and fertilizer, while there are few related studies in natural water. This may be due to the rapid natural decay rate of PGRs in the natural environment, resulting in extremely small amounts of residues in natural water bodies such as surface water and groundwater that cannot be directly detected.
GC has the advantages of low cost and easy maintenance, and GC-MS has become a conventional testing technology. However, GC-MS are greatly affected by sample matrix interference and require high pretreatment methods. In addition, due to the influence of the physical and chemical properties of different PGRs (such as abscisic acid and indole acetic acid with a boiling point over 400℃, or forchlorfenuron and cinnamic acid with hydroxyl and carboxyl groups), most PGRs have poor gas chromatographic characteristics and are not easily detected.
The order of detection limits of PGRs is GC>HPLC>chromatography-mass spectrometry, and the lowest instrumental detection limit of chromatography-mass spectrometry is 10-5mg/kg. However, the higher solubility and the larger natural attenuation rate of most PGRs lead to the lower detection concentrations in complex environmental substrates such as soil and water, so there is still an urgent need to solve the problem of analytical testing of trace PGRs and its intermediates.
In future, PGRs analysis and test method will focus on the analysis and detection of trace PGRs and their intermediates, as well as the development of new materials and technology-based methodologies.
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植物生长调节剂分类 作用 典型产品 植物生长促进剂 促进机体细胞分裂和新生器官分化 生长素、细胞分裂素、赤霉素、胺鲜酯、乙烯利及油菜素甾醇类化合物等 植物生长抑制剂 导致茎伸长，从而抑制植物的顶端优势，促进植物侧叶增多 肉桂酸、香豆素和脱落酸等 植物生长延缓剂 抑制植株节间伸长，使得植株变矮 矮壮素、多效唑、烯效唑、氟节胺和吡啶醇等 
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表 2 部分典型植物生长调节剂的化学式、结构式和常用理化性质
Table 2. Chemical formula, structural formula and common physical and chemical properties of the typical plant growth regulators
植物生长调节剂分类 典型代表 化学式 熔点(℃) 沸点(℃) 密度(g/cm3) 水中溶解度(g/L) 正辛醇-水分配系数 结构式 植物生长促进剂 赤霉酸 C19H22O6 227 628.60±55 1.50±0.10 20℃：5.00 0.01 
吲哚乙酸 C10H9NO2 165~169 415 1.36 20℃：8.00 1.43 
氯吡脲 C12H10ClN3O 170 308.40 1.42 22℃：0.04 3.83 
乙烯利 C2H6ClO3P 70~72 333.40 1.57 23℃：1000 -1.42 
2，4-二氯苯氧乙酸 C8H6Cl2O3 140.5 160 1.56 20℃：0.89 2.59 
植物生长抑制剂 脱落酸 C15H20O4 163 458.70 1.19 20℃：3~5 1.70 
肉桂酸 C9H8O2 133 300 1.25 20℃：0.40 2.41 
香豆素 C9H6O2 68~73 298 0.94 25℃：2.50100℃：20 1.39 
植物生长延缓剂 矮壮素 C5H13Cl2N 239~243 260.30 1.22 20℃：0.74 0.93 
多效唑 C15H20ClN3O 165~166 460.90 1.19 20℃：0.03 2.99 
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表 3 植物生长调节剂分析测试时固态基质样品和液态基质样品常用的前处理方法
Table 3. Common pretreatment methods of solid matrix samples and liquid matrix samples for the analysis and test of the plant growth regulators
介质类型 测定物质 样品前处理方法 提取剂 回收率(%) 参考文献 固态基质 肥料 茉莉酸、多效唑、水杨酸、反式玉米素、赤霉素、吲哚乙酸、脱落酸、芸苔素内酯、胺鲜酯 液液萃取 甲醇 92.00~104.70 [41] 果蔬 赤霉酸、脱落酸、吲哚丙酸、对氯苯氧乙酸、噻苯隆、4-苯氧基乙酸、调果酸、2，4-二氯苯氧乙酸、氯吡脲、抗倒胺、环丙酸酰胺、吲哚乙酸、6-氨基嘌呤、吲哚丁酸、抗倒酯、多效唑、烯效唑、抑芽唑 QuEChERS 乙酸-乙腈溶液 70.10~116.20 [42] 大米 五氟磺草胺、哌草丹、乙草胺、多效唑、烯效唑、矮壮素、脱落酸、2，4-二氯苯氧乙酸 QuEChERS 乙腈-水-甲酸溶液 75.10~115.00 [43] 黄瓜番茄 4-氯苯氧乙酸、6-糖基氨基嘌呤、吲哚丁酸、α-萘乙酸、氯吡脲等 分散固相萃取 乙腈-二氯甲烷(含0.5%甲酸) 71.90~113.80 [44] 豆芽 4-氯苯氧乙酸、2-萘乙酸、吲哚乙酸、吲哚丁酸、4-氟苯氧乙酸、2，3，5-三碘苯甲酸、4-溴苯氧乙酸、2，4-二氯苯氧乙酸、2，4，5-三氯苯氧乙酸、2，6-二甲基苯氧乙酸 超声-固相萃取 乙腈 96.30~102.10 [20] 液态基质 植物营养剂 赤霉酸、多效唑、异戊烯腺嘌呤、5-硝基邻甲氧苯酚钠、6-苄基腺嘌呤、4-氯苯氧乙酸、吲哚丁酸、烯效唑、4-氟苯氧乙酸、氯吡脲、噻苯隆 超声-固相萃取 甲醇 92.50~103.50 [45] 食用油 赤霉酸、吲哚乙酸、吲哚丙酸、吲哚丁酸、1-萘乙酸、2-萘乙酸 微波辅助萃取 甲醇 96.10~104.40 [26]
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表 4 高效液相色谱/超高效液相色谱及液相色谱-串联质谱法分析条件及部分植物生长调节剂检出情况
Table 4. Analysis conditions of high performance liquid chromatography/ultra-high performance liquid chromatography and liquid chromatography-tandem mass spectrometry and detection limits of some plant growth regulators
测试技术 固态/液态介质 PGRs种类 色谱仪 检测器 检出限(土壤、肥料、果蔬mg/kg；水ng/L) 回收率(%) 参考文献 型号 色谱柱 HPLC 肥料 赤霉酸 Agilent 1260 Waters Atlantis T3 UV 0.60 70.40~107.20 [74] 脱落酸 0.20 萘乙酸 0.20 氯吡脲 1.90 烯效唑 5.10 土壤 多效唑 Waters Alliance 2695 Capcell PAK C18 MGⅡ 0.80×10-2 98.30~102.10 [75] 水体 氯吡脲 Shimadzu LC6A Li-Chrospher 100 RP-8 0.40 90.00~92.00 [76] UPLC 黄瓜 噻苯隆 Agilent 1290-infinity Poroshell 120 EC-C18 DAD 1.90×10-2 86.20~95. 00 [44] 西瓜 氯吡脲 0.50×10-2 85.00~90.50 番茄 脱落酸 1.90×10-2 101.20~110.00 葡萄 2, 4-二氯苯氧乙酸 7.60×10-2 96.60~103.80 HPLC-MS/MS 苹果 丁酰肼 Waters Alliance 2690 Hypersil APS-2 质谱 0.80×10-2 98.0~102.0 [77] 叶子 0.02 112.0~116.0 土壤 烯效唑 LC-20A Agilent Poroshell 120 SB-C18 10-5 84.00~87.00 [78] UPLC-MS/MS 麦冬 多效唑 Waters Corp Acquity HSS T3 column 质谱 30 86.90~115.40 [79] 土壤 烯效唑 50 81.30~108.20 水产品 水杨酸 Waters TQ-S C18 0.26×10-2 69.10~97.30 [80] 肥料 嘧啶醇 Agilent 1290 Waters Acquity UPLC BEH C18 0.09~2.51 85.40~95.30 [81] 调节膦 三唑醇 缩节胺 土壤 胺鲜酯 Agilent 1200 VarianVF-5ms 三重四极杆质谱 0.80×10-2 89.40~103.30 [82] UPLC-HRMS 水体 青霉素 Agilent 1290 ZORB-AX RRHD SB-C18 高分辨质谱 1~10 91.20~106.40 [9]
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表 5 气相色谱法及气相色谱-质谱联用法分析条件及部分植物生长调节剂检出情况
Table 5. Analysis conditions of gas chromatography and gas chromatography-mass spectrometry and detection limits of some plant growth regulators
测试技术 固态/液态介质 PGRs种类 色谱仪 检测器 检出限(mg/kg) 回收率(%) 参考文献 型号 色谱柱 GC 肥料 胺鲜酯多效唑烯效唑 Agilent 7890B HP-5毛细管柱 FID 10.0 80.60~97.10 [23] 杨梅
苹果
枣树
卷心菜
西兰花2，4-二氯苯氧乙酸
1-萘乙酸
吲哚乙酸
吲哚丁酸Agilent 7890A HP-5毛细管柱 12.0
23.0
15.0
18.083.00~96.00 [83] 水体 胺鲜酯 Varian CP-3800 CP 7625 / 79.00~107.00 [84] 土壤 多效唑 Agilent 7890A HP-5毛细管柱 NPD 0.03 72.50~108.80 [85] GC-MS 豆芽番茄 对氯苯氧乙酸
2，4-二氯苯氧乙酸
1-萘乙酸
吲哚乙酸
吲哚丁酸Agilent 7890A/5975C HP-5MS 质谱 1.50×10-2 70.00~127.00 [86] 土壤 胺鲜酯 Agilent 6890-5975B HP-5MS 0.10×10-2 83.00~98.50 [87] 多效唑 GCMS-QP2010 VF-1701毛细管柱 0.42×10-2 106.0~124.0 [88]
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