Acibenzolar-S-methyl
(Synonyms: S-甲基苯并[1,2,3]噻二唑-7-硫代羧酸酯,BTH) 目录号 : GC46790
A fungicide inducer of systemic acquired resistance
Cas No.:135158-54-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Acibenzolar-S-methyl is a fungicide that induces systemic acquired resistance (SAR) in a variety of plants leading to infection resistance.1 It induces resistance in wheat concomitant with expression of wheat chemically-induced (WCI) genes when applied at 30 g per hectare.2 Acibenzolar-S-methyl (0.4 g/L) is protective against V. inaequalis in apple trees when used in combination with light integrated pest management (IPM) and increases fruit yield in comparison to the IPM-only group.1
1.Marolleau, B., Gaucher, M., Heintz, C., et al.When a plant resistance inducer leaves the lab for the field: Integrating ASM into routine apple protection practicesFront. Plant Sci.8:1938(2017) 2.GÖrlach, J., Volrath, S., Knauf-Beiter, G., et al.Benzothiadiazole, a novel class of inducers of systemic acquired resistance, activates gene expression and disease resistance in wheatPlant Cell8(4)629-643(1996)
| Cas No. | 135158-54-2 | SDF | |
| 别名 | S-甲基苯并[1,2,3]噻二唑-7-硫代羧酸酯,BTH | ||
| Canonical SMILES | O=C(SC)C1=CC=CC2=C1SN=N2 | ||
| 分子式 | C8H6N2OS2 | 分子量 | 210.3 |
| 溶解度 | DMF: 1 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,Ethanol: slightly soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.7551 mL | 23.7756 mL | 47.5511 mL |
| 5 mM | 0.951 mL | 4.7551 mL | 9.5102 mL |
| 10 mM | 0.4755 mL | 2.3776 mL | 4.7551 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Acibenzolar-S-methyl Activates Stomatal-Based Defense Systemically in Japanese Radish
Front Plant Sci 2020 Oct 30;11:565745.PMID:33193493DOI:10.3389/fpls.2020.565745.
Acibenzolar-S-methyl (ASM) is a well-known plant activator, which is a synthetic analog of salicylic acid (SA). Recently, copper fungicides and antibiotics are major strategies for controlling bacterial diseases. However, resistant strains have already been found. Therefore, there is an increasing demand for sustainable new disease control strategies. We investigated the ASM disease control effect against Pseudomonas cannabina pv. alisalensis (Pcal), which causes bacterial blight on Japanese radish. In this study, we demonstrated that ASM effectively suppressed Pcal disease symptom development associated with reduced bacterial populations on Japanese radish leaves. Interestingly, we also demonstrated that ASM activated systemic acquired resistance (SAR), including stomatal-based defense on ASM-untreated upper and lower leaves. Reactive oxygen species (ROS) are essential second messengers in stomatal-based defense. We found that ASM induced stomatal closure by inducing ROS production through peroxidase. These results indicate that stomatal closure induced by ASM treatment is effective for preventing Pcal pathogen invasion into plants, and in turn reduction of disease development.
Ellman's method-based determination of Acibenzolar-S-methyl in tobacco by transesterification with methanol and SABP2-catalyzed hydrolysis
Anal Sci 2022 May;38(5):749-757.PMID:35298794DOI:10.1007/s44211-022-00091-w.
Acibenzolar-S-methyl (ASM) is the most commercially successful biological antibacterial agent used for crop through systemic acquired resistance (SAR). In this study, a reproducible and accurate procedure, based on the spectrophotometric/microplate reader analysis, has been developed to detect ASM in tobacco leaves. This method involves oxidation of methyl mercaptan by the Ellman's reagent 5,5'-dithio-bis (2-nitrobenzoic acid) (DTNB) to form the yellow derivative 5'-thio-2-nitrobenzoic acid (TNB2-), measurable at 412 nm. Methyl mercaptan can be produced by either the ASM transesterification with methanol or the SA-binding protein 2 (SABP2)-catalyzed ASM hydrolysis. The proportions of methanol, reaction time, temperature, the concentrations of EDTA and DTNB were optimized in a 96-well plate. The calibration curve of ASM was linear over the range of 25.2-315 μg g-1. The results of the intra- and inter-day accuracy and precision data were within the FDA acceptance criteria. With ASM as substrate, the turnover number of SABP2 was determined, with the kcat value of 31.1 min-1 using the Michaelis-Menten equation. In tobacco plants treated with 100 μM ASM, it was decreased as time elapsed in treated tobacco, reaching negligible values 72 h after treatment. The optimized method was applied for the determination of ASM transesterification with methanol and the kinetic data determination of SABP2-catalyzed ASM hydrolysis.
Acibenzolar-S-methyl activates calcium signalling to mediate lignin synthesis in the exocarp of Docteur Jules Guyot pears
Plant Physiol Biochem 2022 Nov 1;190:174-183.PMID:36116226DOI:10.1016/j.plaphy.2022.09.001.
'Docteur Jules Guyot' pears were immersed in Acibenzolar-S-methyl (ASM) and 0.01 mol L-1 ethyl glycol tetra acetic acid (EGTA) to investigate the changes of Ca2+ receptor proteins and phenylpropanoid pathway. Results showed that ASM treatment increased the activities of phenylalanine ammonia-lyase (PAL), cinnamate-4-hydroxylase (C4H), 4-coumarate coenzyme A ligase (4CL), polyphenol oxidase (PPO), and cinnamyl alcohol dehydrogenase (CAD) in the exocarp of pears, whereas EGTA pre-treatment inhibited the activities of these enzymes. ASM treatment also enhanced the transcription of PcPAL, PcC4H, Pc4CL, PcC3H, PcCOMT, PcCCoAOMT, PcCCR, PcPOD, PcCDPK1, PcCDPK2, PcCDPK5, PcCDPK11, PcCDPK13, PcCBL1, PcCBL9, PcCIPK14, and PcCML27 in pears. EGTA + ASM treatments inhibited the transcription of PcPAL, PcC4H, Pc4CL, PcC3H, PcCCR, PcF5H, PcCAD, PcCDPK11, PcCDPK26, PcCDPK32, PcCBL1, PcCIPK14, PcCIPK23, and PcCaM in the fruit. All these results indicated that ASM induced the gene expressions of Ca2+ receptor proteins, the key enzyme activities and gene expressions in phenylpropanoid pathway; Ca2+ mediated phenylpropane metabolism in pears after ASM treatment.
Peer review of the pesticide risk assessment for the active substance Acibenzolar-S-methyl in light of confirmatory data submitted
EFSA J 2021 Jul 8;19(7):e06687.PMID:34262627DOI:10.2903/j.efsa.2021.6687.
The conclusions of the EFSA following the peer review of the initial risk assessment carried out by the competent authority of the rapporteur Member State, France, for the pesticide active substance Acibenzolar-S-methyl are reported. The context of the peer review was that requested by the European Commission following the submission and evaluation of confirmatory information with regard to the endocrine disruption potential of the substance. The conclusions were reached on the basis of the evaluation of the representative uses of Acibenzolar-S-methyl as a plant activator on pome fruit, tomato and tobacco. The reliable endpoints concluded as being appropriate for use in regulatory risk assessment, derived from the available studies and literature in the dossier peer reviewed, are presented. Assessments not finalised together with the missing information identified as being required by the regulatory framework are listed.
Acibenzolar-S-methyl activates mitogen-activated protein kinase cascade to mediate chlorophyll and carotenoid metabolisms in the exocarp of Docteur Jules Guyot pears
J Sci Food Agric 2022 Aug 30;102(11):4435-4445.PMID:35092628DOI:10.1002/jsfa.11797.
Background: Acibenzolar-S-methyl (ASM), a well-known plant activator, has been used to protect fruit and vegetable from fungal invasion and maintain quality. However, little is known about the molecular mechanism of ASM in regulating chlorophyll and carotenoid metabolisms. Therefore, Docteur Jules Guyot pears were used as the materials to study the changes of hydrogen peroxide (H2 O2 ) production, mitogen-activated protein kinase (MAPK) cascade, transcription factors, chlorophyll, and carotenoid metabolisms after ASM and PD98059 (a MAPK cascade blocker) treatments. Results: ASM increased NADPH oxidase (NOX) and superoxide dismutase (SOD) activities, and H2 O2 content, promoted PcMAPKKK1, PcMAPKK3, and PcMAPK6 expressions, and down-regulated PcMYC2, PcPIF1, PcPIF3, and PcPIF4 expressions in exocarp of pears. ASM also delayed the decrease of chlorophyll a and b contents, and inhibited the accumulation of β-carotene, lycopene and lutein, PcNYC1, PcHCAR, PcPPH, PcSGR1/2, PcPAO, PcPSY, PcLCYB, PcCRTZ2, PcCCS1 expressions, and promoted PcLCYE expression. PD98059 + ASM treatments depressed SOD and NOX activities and H2 O2 content, inhibited PcMAPKKK1, PcMAPKK3, PcMAPK6, PcPIF1, and PcPIF3 expressions, and promoted PcMYC2 and PcPIF4 expressions in exocarp of pears. Additionally, PD98059 + ASM accelerated PcNYC1, PcHCAR, PcPPH, PcSGR1/2, PcPAO, PcPSY, PcCYB, PcCRTZ2, and PcCCS1 expressions, thereby reducing chlorophyll a and b contents, and promoting β-carotene, lycopene and lutein contents. Conclusions: Postharvest ASM treatment promoted the production of H2 O2 to activate the MAPK cascade, then phosphorylated/dephosphorylated transcription factors expression, and delayed chlorophyll decomposition and carotenoid synthesis in pears. © 2022 Society of Chemical Industry.