Bitertanol
(Synonyms: 联苯三唑醇) 目录号 : GC46933
A triazole fungicide
Cas No.:55179-31-2
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
Bitertanol is a broad-spectrum triazole fungicide that is active against a variety of fungi, including V. inaequalis and V. pirina, which are responsible for apple and pear scab, respectively, as well as S. mors-uvae and P. ribis, which are responsible for American gooseberry mildew and leaf spot in black currants, respectively.1 It is active against isolates of V. inaequalis (MICs = 0.6 and 1 µg/ml) but repeated use leads to resistance and cross-resistance (MICs = 9.8-13 µg/ml for bitertanol-resistant isolates).2 Bitertanol inhibits the cytochrome P450 (CYP450) isoform CYP3A4 (IC50 = 2.74 µM) and inhibits androgenic activity induced by the androgen receptor agonist DHT in a yeast two-hybrid assay (IC50 = 79.85 µM).3 In rats, bitertanol (10-300 mg/kg, i.p.) increases operant responding on one- and five-minute fixed interval schedules with no effect on motor activity.4
1.Birch, P.A., Rose, P.W., and Wainwright, A.A broad spectrum fungicide of the triazole group for use in pome and bush fruitBrit. Crop Prot. Conf. - Pests and Dis., Proc.11(2)545-554(1981) 2.Hildebrand, P.D., Lockhart, C.L., Newberry, R.J., et al.Resistance of Venturia inaequalis to bitertanol and other demethylation-inhibiting fungicidesCan. J. Plant Path.10(4)311-316(1988) 3.Lv, X., Pan, L., Wang, J., et al.Effects of triazole fungicides on androgenic disruption and CYP3A4 enzyme activityEnviron. Pollut.222(2016)504-512(2017) 4.Allen, A.R., and MacPhail, R.C.Bitertanol, a triazole fungicide, increases operant responding but not motor activityNeurotoxicol. Teratol.15(4)237-242(1993)
| Cas No. | 55179-31-2 | SDF | |
| 别名 | 联苯三唑醇 | ||
| Canonical SMILES | OC(C(C)(C)C)C(N1N=CN=C1)OC(C=C2)=CC=C2C3=CC=CC=C3 | ||
| 分子式 | C20H23N3O2 | 分子量 | 337.4 |
| 溶解度 | Chloroform: slightl soluble,DMSO: Slightly Soluble,Methanol: 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 | 2.9638 mL | 14.8192 mL | 29.6384 mL |
| 5 mM | 0.5928 mL | 2.9638 mL | 5.9277 mL |
| 10 mM | 0.2964 mL | 1.4819 mL | 2.9638 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。
Stereoselective environmental behavior and biological effects of the chiral Bitertanol
Sci Total Environ 2020 Aug 1;728:138867.PMID:32570326DOI:10.1016/j.scitotenv.2020.138867.
Bitertanol is a widely used chiral triazole fungicide. The stereoselective environmental behavior and biological effects of Bitertanol are not clear. The present study evaluated the stereoselectivity of Bitertanol, including its degradation in five typical soils (under laboratory controlled aerobic, anaerobic and sterilization conditions), metabolism in rat liver microsomes (RLM; in vitro), and the endocrine disruption effects on the estrogen receptor (ER) and thyroid hormone receptor (TR) using reporter gene assays. The results indicated that (1S,2R)-bitertanol and (1R,2S)-bitertanol had faster degradation rates in soil than the other stereoisomers. The half-lives of four Bitertanol stereoisomers ranged from 9.1 d to 86.6 d in different soils under different conditions. (1S,2R)-bitertanol was preferentially metabolized in RLM. The molecular docking results confirmed the in vitro experiments that (1S,2R)-bitertanol had shortest binding distances and lowest energies with cytochrome P450 enzymes (CYPs). Four Bitertanol stereoisomers showed stereoselective antagonistic effects on ER. Additionally, (1S,2R)-bitertanol and (1R,2S)-bitertanol exhibited antagonistic effects on TR. These results suggest that the use of pure (1S,2R)-bitertanol instead of the commercial stereoisomer mix, may help reduce environmental pollution and biological toxicity.
Stereoselective bioactivity, toxicity and degradation of the chiral triazole fungicide Bitertanol
Pest Manag Sci 2020 Jan;76(1):343-349.PMID:31207141DOI:10.1002/ps.5520.
Background: The chiral pesticide Bitertanol has been widely used in the prevention and treatment of fungal diseases on many crops. However, research on Bitertanol at the stereoisomer level has not been reported. Here, we study the stereoselective bioactivity, toxicity, and degradation of this pesticide under laboratory and field conditions. Result: (1S,2R)-Bitertanol was the most effective stereoisomer, showing 4.3-314.7 times more potent bioactivity than other stereoisomers against eight target pathogenic fungi. (1S,2R)-Bitertanol showed 10.2 times greater inhibition of Botrytis cinerea spore germination than (1R,2S)-bitertanol. According to the receptor-drug docking results, the distances from the nitrogen atom in the heterocycle of (1S,2R)-, (1R,2S)-, (1R,2R)-, and (1S,2S)-bitertanol to the central Fe + atoms in the ferriporphyrin were 2.5, 3.8, 2.6, and 3.8 Å, respectively. (1S,2S)-Bitertanol was 1.6-2.7 times more toxic than (1R,2R)-bitertanol to Chlorella pyrenoidosa. The half-lives of (1R,2S)-, (1S,2R)-, (1R,2R)-, and (1S,2S)-bitertanol were 3.7, 4.1, 4.1, and 4.8 d, respectively, in tomato. Conclusion: The stereoselective bioactivity, toxicity, and degradation for Bitertanol were first studied here. (1S,2R)-Bitertanol was a high efficiency and low toxicity stereoisomer. Moreover, the stereoselective bioactivity among all stereoisomers correlated with the binding distances and calculated energy differences between stereoisomers and the target protein. This study also provides a foundation for a systematic evaluation of Bitertanol at the stereoisomer level. © 2019 Society of Chemical Industry.
Bitertanol, a triazole fungicide, increases operant responding but not motor activity
Neurotoxicol Teratol 1993 Jul-Aug;15(4):237-42.PMID:8413077DOI:10.1016/0892-0362(93)90004-8.
Several recent reports indicate that triadimefon, a triazole fungicide, has effects on behavior that are similar to those of psychomotor stimulants. For example, triadimefon increases overall fixed-interval (FI) response rate, disrupts FI response patterning, increases motor activity, and produces stereotypies at high doses. The present study was designed to determine whether similar behavioral effects on FI performance and motor activity could be produced by another triazole fungicide, Bitertanol. The effects of Bitertanol (10-300 mg/kg, IP) were determined in rats on performance maintained under a multiple FI 1-min FI 5-min schedule of reinforcement. Intermediate doses of Bitertanol increased response rates and disrupted response patterning in both FI components. A second experiment determined the effects of the same doses of Bitertanol on motor activity. In contrast to its effects on operant responding, Bitertanol did not increase motor activity at any of the doses tested. These findings indicate that the behavioral similarities between Bitertanol and triadimefon are limited and that a dissociation exists between biteranol's effects on operant performance and motor activity.
Stereoselective Separation of the Fungicide Bitertanol Stereoisomers by High-Performance Liquid Chromatography and Their Degradation in Cucumber
J Agric Food Chem 2018 Dec 19;66(50):13303-13309.PMID:30495953DOI:10.1021/acs.jafc.8b04594.
Bitertanol is a widely used triazole fungicide and consists of four stereoisomers. A new high-performance liquid chromatography (HPLC) method was developed for simultaneous analysis of the four stereoisomers in apple, pear, tomato, cucumber, and soil. The mechanism of separation was explained with molecular docking and effects of thermodynamic parameters on the resolution. The absolute configuration and optical rotation of four stereoisomers were confirmed by X-ray diffraction and HPLC tandem circular dichroism, respectively. A good linearity ( R2 ≥ 0.999) was obtained for four stereoisomers in all matrix-matched calibration curves in the range of 0.02-10 mg/L. The mean recoveries of four stereoisomers in five matrices ranged from 74.6% to 101.0% with an intraday and interday relative standard deviation from 0.6% to 9.9%. Stereoselective degradation of Bitertanol in cucumber was observed: (1 R,2 S)-bitertanol and (1 R,2 R)-bitertanol were preferentially degraded with enantiomeric fraction values from 0.5 to 0.43 at 7 d and 0.42 at 5 d, respectively. This research provides a useful tool for the analysis of Bitertanol stereoisomers.
Induction and inhibition of cytochrome P450-dependent monooxygenases of rats by fungicide Bitertanol
Food Chem Toxicol 2006 Dec;44(12):2047-57.PMID:16971034DOI:10.1016/j.fct.2006.07.005.
The effects of fungicide Bitertanol on cytochrome P450-dependent monooxygenases were studied using rats treated intraperitoneally with the N-substituted triazole for 4 days. Treatment with 10, 25, and 100 mg/kg Bitertanol produced 2-, 4-, and 14-fold increases of 7-ethoxyresorufin O-deethylation activity in liver microsomes, respectively. Immunoblot analysis of microsomal proteins revealed that 25 mg/kg Bitertanol increased CYP1A1 protein in the liver, kidney, and lung by 10-, 13-, and 17-fold, respectively. Bitertanol produced smaller increases of CYP2B and CYP3A catalytic activity and protein than that of CYP1A1 in liver. RT-PCR analysis of total RNA indicated that bitertanol-induced CYP1A1, CYP2B, and CYP3A mRNA. Additions of 0.01-100 microM Bitertanol to liver microsomes from rats treated with 25 mg/kg Bitertanol or 3-methylcholanthrene inhibited microsomal 7-ethoxyresorufin O-deethylation activity (IC(50)=0.8 or 0.9 microM). Bitertanol at 100 mg/kg increased liver UDP-glucuronosyltransferase and glutathione S-transferase activities by 2-fold. Bitertanol at 25 mg/kg produced a minor increase in metabolic activation of benzo[a]pyrene by liver S-9 fraction in the Ames mutagenicity test while the increase was blocked by addition of 100 microM Bitertanol. These findings show that Bitertanol is an inducer of CYP1A1, CYP2B, and CYP3A in vivo and an inhibitor of CYP1A catalytic activity in vitro.