Buprofezin
(Synonyms: 噻嗪酮) 目录号 : GC46960
An insecticide
Cas No.:69327-76-0
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
Buprofezin is an insecticide that acts by inhibiting chitin synthesis.1 It inhibits chitin synthesis by 35% in N. lugens nymphs when used at a concentration of 10 ppm. Buprofezin (500 ppm) decreases the lifespan of adult T. vaporariorum with 17.9% mortality after 24 hours.2 It inhibits mitochondrial respiration when used at concentrations of 10 and 30 µM, reduces the expression of enzymes involved in the tricarboxylic acid (TCA) cycle, and stimulates glycolysis in HepG2 cells.3 It also dose-dependently increases the production of reactive oxygen species (ROS) in vitro. Buprofezin accumulates in mouse liver following oral administration of doses ranging from 46.3 to 417 mg/kg. It is not mutagenic and has LD50 values of 6,810 and 5,010 mg/kg in male and female rats, respectively.4 Formulations containing buprofezin have been used as insecticides.
1.Izawa, Y., Uchida, M., Sugimoto, T., et al.Inhibition of chitin biosynthesis by buprofezin analogs in relation to their activity controlling Nilaparvata lugens StÅlPest. Biochem. Phys.24(3)343-347(1985) 2.Yasui, M., Fukada, M., and Maekawa, S.Effects of buprofezin on different developmental stages of the greenhouse whitefly, Trialeurodes vaporariorum (WESTWOOD) (Homoptera : Aleyrodidae)Appl. Ent. Zool.20(3)340-347(1985) 3.Ji, X., Ku, T., Zhu, N., et al.Potential hepatic toxicity of buprofezin at sublethal concentrations: ROS-mediated conversion of energy metabolismJ. Hazard. Mater.320176-186(2016) 4.Xiao, H., Yang, Y., Tang, L., et al.Observation of toxicity and mutagenesis of insect growth regulator buprofezinNanj. Yixuey. Xue.12(1)23-26(1992)
| Cas No. | 69327-76-0 | SDF | |
| 别名 | 噻嗪酮 | ||
| Canonical SMILES | O=C1N(C(C)C)/C(SCN1C2=CC=CC=C2)=N/C(C)(C)C | ||
| 分子式 | C16H23N3OS | 分子量 | 305.4 |
| 溶解度 | Chloroform: Slightly Soluble,Methanol: Slightly Soluble | 储存条件 | Store at -20°C,protect from light |
| 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 | 3.2744 mL | 16.372 mL | 32.7439 mL |
| 5 mM | 0.6549 mL | 3.2744 mL | 6.5488 mL |
| 10 mM | 0.3274 mL | 1.6372 mL | 3.2744 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。
Molecular Mechanism and Genetic Determinants of Buprofezin Degradation
Appl Environ Microbiol 2017 Aug 31;83(18):e00868-17.PMID:28710269DOI:10.1128/AEM.00868-17.
Buprofezin is a widely used insect growth regulator whose residue has been frequently detected in the environment, posing a threat to aquatic organisms and nontarget insects. Microorganisms play an important role in the degradation of Buprofezin in the natural environment. However, the relevant catabolic pathway has not been fully characterized, and the molecular mechanism of catabolism is still completely unknown. Rhodococcus qingshengii YL-1 can utilize Buprofezin as a sole source of carbon and energy for growth. In this study, the upstream catabolic pathway in strain YL-1 was identified using tandem mass spectrometry. Buprofezin is composed of a benzene ring and a heterocyclic ring. The degradation is initiated by the dihydroxylation of the benzene ring and continues via dehydrogenation, aromatic ring cleavage, breaking of an amide bond, and the release of the heterocyclic ring 2-tert-butylimino-3-isopropyl-1,3,5-thiadiazinan-4-one (2-BI). A Buprofezin degradation-deficient mutant strain YL-0 was isolated. A comparative genomic analysis combined with gene deletion and complementation experiments revealed that the gene cluster bfzBA3A4A1A2C is responsible for the upstream catabolic pathway of Buprofezin. The bfzA3A4A1A2 cluster encodes a novel Rieske nonheme iron oxygenase (RHO) system that is responsible for the dihydroxylation of Buprofezin at the benzene ring; bfzB is involved in dehydrogenation, and bfzC is in charge of benzene ring cleavage. Furthermore, the products of bfzBA3A4A1A2C can also catalyze dihydroxylation, dehydrogenation, and aromatic ring cleavage of biphenyl, flavanone, flavone, and bifenthrin. In addition, a transcriptional study revealed that bfzBA3A4A1A2C is organized in one transcriptional unit that is constitutively expressed in strain YL-1.IMPORTANCE There is an increasing concern about the residue and environmental fate of Buprofezin. Microbial metabolism is an important mechanism responsible for the Buprofezin degradation in the natural environment. However, the molecular mechanism and genetic determinants of microbial degradation of Buprofezin have not been well identified. This work revealed that gene cluster bfzBA3A4A1A2C is responsible for the upstream catabolic pathway of Buprofezin in Rhodococcus qingshengii YL-1. The products of bfzBA3A4A1A2C could also degrade bifenthrin, a widely used pyrethroid insecticide. These findings enhance our understanding of the microbial degradation mechanism of Buprofezin and benefit the application of strain YL-1 and bfzBA3A4A1A2C in the bioremediation of Buprofezin contamination.
Effect of Processing on Residual Buprofezin Levels in Ginseng Products
Int J Environ Res Public Health 2021 Jan 8;18(2):471.PMID:33430085DOI:10.3390/ijerph18020471.
This study determined residual Buprofezin levels in fresh ginseng and evaluated their changes during processing. Supervised field trials were conducted at Yeongju, Geumsan, and Goesan, Korea. Buprofezin 12.5% EC was applied to 5-y ginseng in accordance with the Korean good agriculture practice (GAP). Samples were collected at 0, 7, 14, 21, and 30 d after the final application. On day 14 (GAP-equivalent preharvest date), the ginseng was processed to obtain dried and red ginseng. The average Buprofezin concentrations on day 0 were 0.076 (Yeongju), 0.055 (Geumsan), and 0.078 mg kg-1 (Goesan). Residual concentrations increased as ginseng was processed into dried and red ginseng. Residue levels in dried ginseng manufactured by hot air drying were higher than in red ginseng obtained by steaming, hot air, and sunlight drying. However, the absolute amount of pesticides decreased by approximately 20-30% as a result of calculating the reduction factor considering the dry yield and moisture content. Therefore, the residual concentration in processed products may vary depending on the processing method, and it is deemed necessary to consider the processing yield and moisture content when evaluating the safety of residual pesticides in dried processed products.
Potential hepatic toxicity of Buprofezin at sublethal concentrations: ROS-mediated conversion of energy metabolism
J Hazard Mater 2016 Dec 15;320:176-186.PMID:27544730DOI:10.1016/j.jhazmat.2016.08.027.
Buprofezin is known for its broad-spectrum action and environmental safety. The popularity of Buprofezin has raised concerns about its potentially adverse effects on human health and risk to the environment. In this study, we first identified the liver as one of the major organs in which Buprofezin accumulated, and we detected a severe oxidative stress response. Next, we demonstrated that sublethal concentrations of Buprofezin promoted the conversion of energy metabolism from the aerobic tricarboxylic acid (TCA) cycle and oxidative phosphorylation to anaerobic glycolysis. Importantly, reactive oxygen species (ROS) generation partially accounted for the shunting of the energy metabolism through the buprofezin-mediated inhibition of cytochrome c oxidase activity. ROS directly perturbed the activities of several key TCA cycle enzymes, stimulated glycolysis, and indirectly disturbed the activity of the respiratory chain complex by altering mitochondrial DNA (mtDNA). These findings clarify the potential mechanisms of Buprofezin toxicity and provide biomarkers for buprofezin-mediated hepatotoxicity at sublethal concentrations.
Buprofezin susceptibility survey, resistance selection and preliminary determination of the resistance mechanism in Nilaparvata lugens (Homoptera: Delphacidae)
Pest Manag Sci 2008 Oct;64(10):1050-6.PMID:18506673DOI:10.1002/ps.1606.
Background: Buprofezin has been used for many years to control Nilaparvata lugens (Stål). Assessment of susceptibility change in the insect is essential for maintaining control efficiency and resistance management. Results: Eleven-year surveys showed that most field populations were susceptible before 2004. However, substantially higher levels of resistance (up to 28-fold) were found in most of the rice fields in China after 2004. A field population was collected and periodically selected for Buprofezin resistance in the laboratory. After 65 generations (56 were selected), the colony successfully obtained 3599-fold resistance to Buprofezin. Synergism tests showed that O,O-diethyl-O-phenyl phosphorothioate (SV1), piperonyl butoxide (PBO) and diethyl maleate (DEM) increased Buprofezin toxicity in the resistant strain by only 1.5-1.6 fold, suggesting that esterases, P450-monooxygenases and glutathione S-transferases had no substantial effect on Buprofezin resistance development. Conclusion: The results from this study indicate that N. lugens has the potential to develop high resistance to Buprofezin. A resistance management program with rotation of Buprofezin and other pesticides may efficiently delay or slow down resistance development in the insect. Further investigation is also necessary to understand the resistance mechanisms in N. lugens.
Variations in Endosymbiont Infection Between Buprofezin-Resistant and Susceptible Strains of Laodelphax striatellus (Fallén)
Curr Microbiol 2018 Jun;75(6):709-715.PMID:29569154DOI:10.1007/s00284-018-1436-x.
The endosymbionts Wolbachia and Rickettsia have been shown to be correlated with the insecticide resistance of mosquito and whitefly. The small brown planthopper (SBPH), Laodelphax striatellus, harbours many species of endosymbionts, and has developed a high resistance to Buprofezin in China. In this study, we examined the species and the infection incidences of endosymbionts in a buprofezin-resistant (BR) strain, a buprofezin-susceptible (BS) strain, and the BR strain after exposure to Buprofezin, and we also investigated the change in Buprofezin susceptibility after removal of Wolbachia from the BR strain. The results showed that Wolbachia infection incidences were 100% in both the BR and BS strains, but the Wolbachia density in the BR strain was significantly higher than that in the BS strain. There were no significant differences in Arsenophonus infection incidence between the two strains. However, the infection incidence of Serratia and double infection incidence of Serratia + Wolbachia in the BR strain were significantly higher than that in the BS strain. After the BR strain was exposed to 1200 mg/L Buprofezin, the infection incidence of Arsenophonus in the surviving individuals increased, and the infection rate of Serratia did not differ, but the double infection incidence of Serratia + Wolbachia decreased. And when a Wolbachia-infected line originating from the BR strain was cleared of Wolbachia, its susceptibility to Buprofezin increased. The results suggest that Serratia and Wolbachia infection might improve the Buprofezin resistance of SBPH.