Fenobucarb
(Synonyms: 仲丁威) 目录号 : GC60836
Fenobucarb是一种广泛使用的氨基甲酸酯杀虫剂。Fenobucarb通过炎症、氧化应激、变性和凋亡等途径诱导斑马鱼发育神经毒性。Fenobucarb可能对动物心脑血管系统有危害。
Cas No.:3766-81-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Fenobucarb is an extensively used carbamate insecticide. Fenobucarb induces zebrafish developmental neurotoxicity through pathways involved in inflammation, oxidative stress, degeneration and apoptosis. Fenobucarb is a possible risk factor to cardiovascular and cerebrovascular systems in animals[1][2].
[1]. Xiao-Yu Zhu, et al. Fenobucarb-induced developmental neurotoxicity and mechanisms in zebrafish. Neurotoxicology. 2020 Jul;79:11-19. [2]. Xiao-Yu Zhu, et al. Fenobucarb induces heart failure and cerebral hemorrhage in zebrafish. Aquat Toxicol. 2019 Apr;209:34-41.
| Cas No. | 3766-81-2 | SDF | |
| 别名 | 仲丁威 | ||
| Canonical SMILES | CCC(C1=CC=CC=C1OC(NC)=O)C | ||
| 分子式 | C12H17NO2 | 分子量 | 207.27 |
| 溶解度 | DMSO: 100 mg/mL (482.46 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 | 4.8246 mL | 24.1231 mL | 48.2462 mL |
| 5 mM | 0.9649 mL | 4.8246 mL | 9.6492 mL |
| 10 mM | 0.4825 mL | 2.4123 mL | 4.8246 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。
Fenobucarb-induced developmental neurotoxicity and mechanisms in zebrafish
Neurotoxicology 2020 Jul;79:11-19.PMID:32247646DOI:10.1016/j.neuro.2020.03.013.
Fenobucarb (2-sec-butylphenyl methylcarbamate, BPMC) is an extensively used carbamate insecticide. Its developmental neurotoxicity and the underlying mechanisms have not been well investigated. In this study, zebrafish embryos were exposed to various concentrations of BPMC from 6 hpf (hours post fertilization, hpf) to 120 hpf. BPMC induced developmental toxicity with reduced motility in larval zebrafish. The spinal cord neutrophil infiltration, increased ROS production, caspase 3 and 9 activation, central nerve and peripheral motor neuron damage, axon and myelin degeneration were observed in zebrafish treated with BPMC generally in a dose-dependent manner. The expression of eight marker genes for nervous system function or development, namely, a1-tubulin, shha, elavl3, gap43, syn2a, gfap, mbp and manf, was significantly downregulated following BPMC exposure. AChE activity reduction and ache gene expression suppression was also found significantly in BPMC-treated zebrafish. These results indicate that BPMC is highly toxic to zebrafish and that BPMC induces zebrafish developmental neurotoxicity through pathways involved in inflammation, oxidative stress, degeneration and apoptosis.
Fenobucarb induces heart failure and cerebral hemorrhage in zebrafish
Aquat Toxicol 2019 Apr;209:34-41.PMID:30685545DOI:10.1016/j.aquatox.2018.12.020.
The potential risk and toxic mechanisms of Fenobucarb (2-sec-butylphenyl methylcarbamate, BPMC) to animals and humans have not been fully elucidated. In this study, zebrafish embryos were exposed to various concentrations of BPMC from 48 hpf (hour post fertilization, hpf) to 72 hpf. We found that BPMC induced severe heart failure with bradycardia, reduced heart contractions, cardiac output and blood flow dynamics；and myocardial apoptosis. BPMC also induced cerebral hemorrhages and blood erythrocyte reduction in a dose-dependent manner. Also observed were increased ROS production and capase 9 and 3/7 activation. The mRNA levels of the ATPase-related gene (atp2a1l), calcium channel-related gene (cacna1ab), sodium channel-related gene (scn5Lab), potassium channel-related gene (kcnq1), the regulatory gene (tnnc1a) for cardiac troponin C, and several apoptosis-related genes were significantly downregulated in zebrafish following BPMC exposure. These results suggest that exposure to BPMC is a possible risk factor to cardiovascular and cerebrovascular systems in animals.
Systemic Stereoselectivity Study of Fenobucarb: Environmental Behaviors in Greenhouse Vegetables, Fruits, Earthworms, and Soils and Its Cytotoxicity
J Agric Food Chem 2022 Feb 23;70(7):2127-2135.PMID:35138837DOI:10.1021/acs.jafc.1c06420.
Fenobucarb (2-sec-butylphenyl methylcarbamate, BPMC) is a potent carbamate pesticide with high insecticidal activity. In this study, the enantioselective accumulation of BPMC in earthworms (Eisenia foetida) and dissipation in cabbage, Chinese cabbage, strawberry, and soils were investigated. The samples were prepared using the QuEChERS method and analyzed using fast and sensitive chiral high-performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS) analysis. The stereoselective accumulation of BPMC enantiomers revealed that S-(+)-BPMC was preferentially accumulated in earthworms rather than its antipode. However, the dissipation studies showed that S-(+)-BPMC degraded faster than the R-(-)-isomer in cabbage, Chinese cabbage, strawberry, and soils. Furthermore, the cytotoxic effect of BPMC enantiomers toward PC12 and N9 neuronal, A549 lung cancer, and MRC5 lung fibroblast cell lines was evaluated using an 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Compared with R-(-)- and rac-isomers, S-(+)-BPMC exhibited lower cytotoxicity in neuronal cells and a weaker proliferating effect on lung cancer and lung fibroblast cells. Altogether, the findings suggest the use of the pure S-(+)-enantiomer in agricultural management rather than the use of the racemate or the R-(-)-isomer, which might reduce the environmental risk.
Comprehensive Enantioselectivity Evaluation of Insecticidal Activity and Mammalian Toxicity of Fenobucarb
J Agric Food Chem 2022 May 4;70(17):5330-5338.PMID:35451821DOI:10.1021/acs.jafc.2c00093.
To comprehensively evaluate the efficiency and risk of the chiral pesticide Fenobucarb, the bioactivity, toxicity, and environmental behavior of Fenobucarb (FNC) enantiomers were investigated. The results showed that R-FNC possesses 1.8-2.7 times more bioactivity than S-FNC but 1.3-3.0 times lower toxicity than S-FNC against four nontarget organisms: Chlorella pyrenoidosa, HepG2, and Danio rerio and its embryos. The corresponding enzyme inhibitory activity showed consistent results; the acetylcholinesterase inhibitory activity of target organisms was ordered as R-FNC > rac-FNC > S-FNC, while the reduction in catalase activity after exposure to R-FNC was 2.5 times that after exposure to S-FNC in zebrafish. The enantioselective bioactivity mechanism of FNC enantiomers was further explored in silico. No significant enantioselective degradation was found in soils or rat liver microsomes. In sum, R-FNC possesses higher insecticidal activity and lower toxicity. The development of R-FNC as a commercial agrochemical is beneficial for reducing pesticide inputs.
Isolation and characterization of fenobucarb-degrading bacteria from rice paddy soils
Biodegradation 2014 Jun;25(3):383-94.PMID:24197220DOI:10.1007/s10532-013-9667-9.
Forty-five fenobucarb-degrading bacteria were isolated from rice paddy soils, and their genetic and phenotypic characteristics were investigated. The isolates were able to utilize Fenobucarb as a sole source of carbon and energy. Analysis of the 16S rRNA gene sequence indicated that all the isolates were related to members of the genera Sphingobium and Novosphingobium. Among 45 isolates, 21 different chromosomal DNA fingerprinting patterns were obtained. All these strains exhibited similar growth and degradation patterns on Fenobucarb. 2-sec-butylphenol was identified as an intermediate during Fenobucarb degradation by HPLC analysis. All of the isolates were able to degrade another carbamate insecticide, carbaryl, and 2-sec-butylphenol, but not other Fenobucarb related compounds such as aldicarb and fenoxycarb. Representative strains of the different repetitive extragenic palindromic sequence PCR fingerprint types had one to six plasmids. The plasmid-cured strains lost their degradation abilities, suggesting that Fenobucarb degradative genes were on their plasmid DNAs in these strains. When analyzed with PCR amplification using the primers targeting for the previously reported carbamate hydrolase genes, most of the isolates did not exhibit any positive signals for different genes involved in carbamate degradation such as mcd, cahA and cehA genes. This is the first report that microorganisms involved in the degradation of Fenobucarb have been isolated and the intermediate of Fenobucarb biodegradation was identified.