Tricyclazole
(Synonyms: 三环唑) 目录号 : GC37827
Tricyclazole 是一种五酮类黑色素生物合成抑制剂，也是水稻稻瘟病防治的独特杀菌剂。
Cas No.:41814-78-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Tricyclazole is a pentaketide-derived melanin biosynthesis inhibitor and a unique fungicide for control of Pyricularia oryzae on rice[1][2]. Pentaketide-derived melanin biosynthesis[1]
[1]. Peterson L.G. Tricyclazole for Control of Pyricularia Oryzae on Rice: the Relationship of the Mode of Action and Disease Occurrence and Development. Pest Management in Rice. Springer, Dordrecht. [2]. G.Lazarovits, et al. Tricyclazole induces melanin shunt products and inhibits altersolanol a accumulation by Alternaria solani. Pesticide Biochemistry and Physiology
| Cas No. | 41814-78-2 | SDF | |
| 别名 | 三环唑 | ||
| Canonical SMILES | CC1=C2N3C(SC2=CC=C1)=NN=C3 | ||
| 分子式 | C9H7N3S | 分子量 | 189.24 |
| 溶解度 | DMSO: 125 mg/mL (660.54 mM) | 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 | 5.2843 mL | 26.4215 mL | 52.843 mL |
| 5 mM | 1.0569 mL | 5.2843 mL | 10.5686 mL |
| 10 mM | 0.5284 mL | 2.6421 mL | 5.2843 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。
A critical Assessment of the Genotoxicity Profile of the Fungicide Tricyclazole
Environ Mol Mutagen 2020 Mar;61(3):300-315.PMID:31633836DOI:10.1002/em.22344.
Tricyclazole (8-methyl-[1,2,4]triazolo[3,4-b][1,3]benzothiazole) is a fungicide used globally on rice for treatment of the seasonal rice blast disease. Human exposure to this fungicide can occur via dietary and nondietary routes. In a battery of in vitro assays, Tricyclazole did not induce gene mutations in bacteria (Ames test) or at the Hprt locus of CHO cells. It was also negative for the induction of micronuclei in human lymphocyte cultures and unscheduled DNA synthesis (UDS) in primary rat hepatocyte. Paradoxically, Tricyclazole induced a mutagenic response at the Tk locus of the mouse lymphoma L5178Ycells (MLA), which occurred equally among small/large colony phenotypes. Selection of preexisting mutants leading to a false-positive response in the MLA was ruled out in follow-up experiments. In vivo, Tricyclazole was negative in the rat liver UDS assay, mouse bone micronucleus test and a transgenic (MutaMouse) gene mutation assay in glandular stomach, liver, and kidney. Other supporting evidence for the lack of genotoxicity for Tricyclazole comes from an in vivo study for sister chromatid exchanges in Chinese hamsters, and a dominant lethal test in the male germ cells of mice. The combined evidence from the genotoxicity studies together with the evidence from toxicokinetic, carcinogenicity, developmental, and reproductive toxicity studies confirm that mutagenicity does not occur in relevant in vivo systems. Data were also compared to potential animal and human exposure, mechanistic data on biological targets and data on analogues, confirming adequacy of the available data for hazard identification and risk assessment. Environ. Mol. Mutagen. 61:300-315, 2020. © 2019 Wiley Periodicals, Inc.
Hepatotoxicity of Tricyclazole in zebrafish (Danio rerio)
Chemosphere 2019 Oct;232:171-179.PMID:31154177DOI:10.1016/j.chemosphere.2019.05.159.
Tricyclazole is widely used in agriculture as a pesticide, but its toxicity in vertebrates is currently poorly evaluated. In this study, we used zebrafish to assess the toxicity of Tricyclazole. We found that Tricyclazole induces liver damage, or hepatotoxicity, in zebrafish, during both development and adulthood. In embryos, we found that Tricyclazole affected the liver development rather than other endodermal tissues such as gut and pancreas. In both embryos and adult zebrafish livers, Tricyclazole disrupted the relationship between oxidant and antioxidant system and resulted in reactive oxygen species (ROS) overload. Meanwhile, it triggered hepatocyte apoptosis and disturbed carbohydrate/lipid metabolism and energy demand systems. These results suggested that Tricyclazole could cause severe consequences for vertebrate hepatic development and function.
Functionalized silver nanoparticles as colorimetric probes for sensing Tricyclazole
Food Chem 2021 Jun 15;347:129044.PMID:33472118DOI:10.1016/j.foodchem.2021.129044.
A colorimetric assay for highly selective and sensitive detection of Tricyclazole using fluorescein-functionalized silver nanoparticles (F-AgNPs) as sensing probes was investigated. As the addition of Tricyclazole to F-AgNPs, a drastic decrease in the absorbance at 394 nm was detected, which was accompanied with a noticeable color change from yellow to gray. The sensing mechanism involved an interaction between Tricyclazole and F-AgNPs, which led to aggregation of the latter, inducing a color change from yellow to gray. An excellent linear calibration curve (R2 = 0.9994) was achieved between absorbance at 394 nm and the Tricyclazole concentration in the range between 0.06 and 1.0 ppm. Moreover, the detection limit was estimated at 0.051 ppm. The developed colorimetric assay also showed good selectivity and was successfully utilized to quantify Tricyclazole in rice samples with satisfactory recoveries. The proposed assay has been successfully applied for monitoring Tricyclazole in rice samples.
The ADME profile of the fungicide Tricyclazole in rodent via the oral route: A critical review for human health safety assessment
Regul Toxicol Pharmacol 2019 Nov;108:104438.PMID:31461669DOI:10.1016/j.yrtph.2019.104438.
Herein, we publish data from regulatory studies investigating the oral ADME (absorption, distribution, metabolism, excretion) of Tricyclazole in vivo, in silico and in vitro. The oral route is relevant to human dietary exposure assessment. Tricyclazole is readily absorbed and highly bioavailable in rodents (>86%) with indication of saturation of absorption at high doses. Enterohepatic recirculation is evident. Excretion occurs quickly both via urinary (31-64%) and faecal routes (39-65%), with substantial biliary elimination in the rat (≥58%). The tricyclazole-derived radioactivity is distributed to major organs, including those investigated in in vivo genotoxicity studies (liver, kidney, gastrointestinal tract and bone marrow). There is no evidence of bioaccumulation. Metabolism is extensive (approximately 30 metabolites), with the liver being identified as the primary metabolism organ with Phase I and II enzymes involved. Several metabolites are formed following an initial cleavage of the central thiazole ring, with no loss of free triazole from the remaining phenyl ring. A group of 4 metabolites derive from an initial oxidation step with the formation of the tricyclazole-alcohol, a relevant crop metabolite, and account for up to 13% of the administered dose. In vitro metabolism, investigated with liver microsomes, confirmed that humans do not form unique metabolites.
Evidence of Pyricularia oryzae adaptability to Tricyclazole
J Environ Sci Health B 2021;56(10):869-876.PMID:34459365DOI:10.1080/03601234.2021.1971913.
Pyricularia oryzae is the etiological agent of rice blast, the most destructive disease in rice crops and chemical control based on fungicide is the main method used in its management. The aim of this study was characterize pathogenicity and identify P. oryzae isolates adapted to Tricyclazole. P. oryzae monosporic isolates were collected in the state of Tocantins and inoculated in international differentiating series of rice cultivars for determination of pathotypes. After, the same isolates were inoculated in the rice cultivar IRGA 424 to evaluate resistance to fungicide Bim® 750 BR (Tricyclazole - 250 g/ha) that was applied 24 and 48 hours after pathogen inoculation (hai). Leaf blast severity and infection efficiency were evaluated 9 days after inoculation (dai), latency period (2 dai) and sporulation intensity (7 dai). Nine different pathotypes were identified, predominantly as IA group. The latent period of isolates occurred between from 48 to 120 h. The application of Tricyclazole, 24 hai reduced disease severity with the exception of the isolate Py 7.1. The great variability of the pathogen allowed for adaptation to this molecule and can increase its aggressiveness and should be considered to guide the integrated management of the disease.