Dinotefuran (MTI-446)
(Synonyms: 呋虫胺; MTI-446) 目录号 : GC32185
A neonicotinoid insecticide
Cas No.:165252-70-0
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
Dinotefuran is a neonicotinoid insecticide.1 It is an agonist of nicotinic acetylcholine receptors (nAChRs), inducing inward currents in isolated American cockroach (P. americana) neurons with an EC50 value of 7.6 ?M. Dinotefuran, alone or in combination with the metabolic inhibitors piperonyl butoxide or propargyl propyl benzenephosphonate (NIA), induces mortality in adult P. americana.2 It is lethal to insecticide-sensitive or -resistant strains of A. gambiae, C. quinquefasciatus, and A. aegypti in larval (LC50s = 0.14-0.44 mg/L) and adult (LD50s = 0.18-31.16 ng/mg) bioassays.3 Dinotefuran has been found in a variety of commercial foodstuffs, including rice, cucumber, milk, egg, and pork samples, as well as in water samples from freshwater streams.4,5 Formulations containing dinotefuran have been used in the agricultural and veterinary control of insect infestations.
1.Tan, J., Galligan, J.J., and Hollingworth, R.M.Agonist actions of neonicotinoids on nicotinic acetylcholine receptors expressed by cockroach neuronsNeurotoxicology28(4)829-842(2007) 2.Kiriyama, K., and Nishimura, K.Structural effects of dinotefuran and analogues in insecticidal and neural activitiesPest Manag. Sci.58(7)669-676(2002) 3.Corbel, V., Duchon, S., Zaim, M., et al.Dinotefuran: A potential neonicotinoid insecticide against resistant mosquitoesJ. Med. Entomol.41(4)712-717(2004) 4.Zhang, Y., Wu, X., Duan, T., et al.Ultra high performance liquid chromatography with tandem mass spectrometry method for determining dinotefuran and its main metabolites in samples of plants, animal-derived foods, soil, and waterJ. Sep. Sci.41(14)2913-2923(2018) 5.Hladik, M.L., and Kolpin, D.W.First national-scale reconnaissance of neonicotinoid insecticides in streams across the USAEnviron. Chem.1312-20(2016)
| Cas No. | 165252-70-0 | SDF | |
| 别名 | 呋虫胺; MTI-446 | ||
| Canonical SMILES | O=[N+](N/C(NC)=N/CC1COCC1)[O-] | ||
| 分子式 | C7H14N4O3 | 分子量 | 202.21 |
| 溶解度 | Water : 50 mg/mL (247.27 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 | 4.9454 mL | 24.7268 mL | 49.4535 mL |
| 5 mM | 0.9891 mL | 4.9454 mL | 9.8907 mL |
| 10 mM | 0.4945 mL | 2.4727 mL | 4.9454 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。
The enantioselective toxicity and oxidative stress of Dinotefuran on zebrafish (Danio rerio)
Ecotoxicol Environ Saf 2021 Dec 15;226:112809.PMID:34592523DOI:10.1016/j.ecoenv.2021.112809.
Dinotefuran is a widely used neonicotinoid pesticides in agriculture and it has certain ecological toxicity to aquatic organisms. Studies on the potential toxicological effects of Dinotefuran on fish are limited. In the present study, 96 h acute toxicity test indicated that enantiomers of R-(-)-dinotefuran had a greater toxic effect than Rac-dinotefuran on zebrafish, and S-(+)-dinotefuran was the least. In chronic assay, R-(-)-dinotefuran exerted more effects on the development of zebrafish than S-(+)-dinotefuran, and Dinotefuran also had enantioselective effect on oxidative stress. Significant changes were observed in the superoxide dismutase (SOD), glutathione S-transferase (GST) and acetylcholinesterase (AChE) activities and malondialdehyde (MDA) contents, which demonstrated Dinotefuran induced oxidative stress in zebrafish. Besides, through an ultra-performance liquid chromatography quadrupole-TOF mass spectrometry (UPLC-Q-TOF-MS)-based metabolomics method was used to evaluate the enantioselectivity of Dinotefuran enantiomers in zebrafish. The results indicated that R-(-)-dinotefuran caused greater disturbances of endogenous metabolites. Phenylalanine metabolic pathways, glycine, serine and threonine metabolic pathways are only involved in zebrafish exposed to R-(-)-dinotefuran; whereas phenylalanine, tyrosine and tryptophan biosynthesis was only involved in zebrafish exposed to S-(+)-dinotefuran. This study provides a certain reference value for assessing the environmental risks of Dinotefuran enantiomers to aquatic organisms, and has practical significance for guiding the ecologically and environmentally safety use of Dinotefuran.
Resistance to Dinotefuran in Bemisia tabaci in China: status and characteristics
Pest Manag Sci 2023 Feb;79(2):833-844.PMID:36264629DOI:10.1002/ps.7251.
Background: Bemisia tabaci (Gennadius) is a serious agricultural pest worldwide. Neonicotinoids are the most important new class of synthetic insecticides used in the management of B. tabaci. However, B. tabaci populations have developed resistance to various active ingredients in neonicotinoids following long-term and widespread application. Results: Dinotefuran exhibited high toxicity against most B. tabaci field populations. One population (Din-R) with a high level of resistance to Dinotefuran (255.6-fold) was first identified in the field. The Din-R population exhibited medium to high levels of resistance to all the tested neonicotinoid insecticides and a high level of resistance to spinetoram. Genetic inheritance analysis revealed that resistance to Dinotefuran was incompletely recessive and polygenic. The synergist piperonyl butoxide significantly increased the toxicity of Dinotefuran to Din-R. P450 activity in the Din-R population was 2.19-fold higher than in the susceptible population. RNA-sequencing analysis showed that 12 P450 genes were significantly upregulated in the Din-R population, of which CYP6DW5, CYP6JM1 and CYP306A1 were found to exhibit more than 3.00-fold higher expression in Din-R when using a reverse transcription quantitative real-time polymerase chain reaction. Expression of eight P450 genes was obviously induced by Dinotefuran, and CYP6DW5 showed the highest expression level. After knockdown of CYP6DW5 in Din-R, the toxicity of Dinotefuran increased significantly. Conclusion: P450 had a crucial role in Dinotefuran resistance in B. tabaci, and CYP6DW5 was involved in the resistance. These results provide important information for the management of resistance in B. tabaci and improve our understanding of the resistance mechanism of Dinotefuran. 漏 2022 Society of Chemical Industry.
Enantioselective Bioaccumulation and Toxicity of the Neonicotinoid Insecticide Dinotefuran in Earthworms ( Eisenia fetida)
J Agric Food Chem 2018 May 2;66(17):4531-4540.PMID:29652142DOI:10.1021/acs.jafc.8b00285.
The enantioselective bioaccumulation and toxicity of Dinotefuran in earthworms were studied in this study. The results showed that S-dinotefuran accumulated faster than Rac-dinotefuran and R-dinotefuran in earthworms. The acute toxicity of S-dinotefuran was 1.49 and 2.67 times that of the Rac-dinotefuran and R-dinotefuran in artificial soil during 14 days of exposure. At 1.0 mg/kg, the three tested chemicals inhibited the growth and reproduction as well as induced oxidative stress effects in earthworms; however, the toxic effects induced by S-dinotefuran were the most serious. The transcriptome sequencing results showed that S-dinotefuran had stronger interactions to biomacromolecules and influences on the endoplasmic reticulum (ER) than R-dinotefuran, which may be the main reason for enantioselectivities between the two enantiomers. The present results indicated that the risk of S-dinotefuran was higher than that of Rac-dinotefuran and R-dinotefuran in the soil environment to earthworms. Risk assessment of Dinotefuran should be evaluated at the enantiomer level.
Low-dose cadmium stress increases the bioaccumulation and toxicity of Dinotefuran enantiomers in zebrafish (Danio rerio)?
Environ Pollut 2021 Jan 15;269:116191.PMID:33316505DOI:10.1016/j.envpol.2020.116191.
Co-occurrence of pesticides and heavy metals has attracted extensive attention. The enantioselective behaviors of Dinotefuran to aquatic organisms have not been reported, and the effects of cadmium (Cd) was absent, which were investigated in this study at environmentally relevant concentrations. The enantioselective accumulation and elimination of Dinotefuran enantiomers were observed in zebrafish, and it had tissue specificity. The S-dinotefuran concentrations were higher than R-dinotefuran in heads and viscera, but it was opposite in muscles. There existed competition between S-dinotefuran and R-dinotefuran, and the existence of S-dinotefuran might decrease the accumulation and elimination of the R-dinotefuran in zebrafish. When co-exposure to Cd and Dinotefuran, the accumulation concentrations of Dinotefuran enantiomers increased in zebrafish at the initial stage, which were opposite latterly. The accumulation concentrations of R-dinotefuran in R + Cd treatment in fish were 3.4 times higher than those in R-dinotefuran treatment, and the enantiomer fraction (EF) values changed from 0.484 to 0.195. The oxidative stress of S-dinotefuran on zebrafish was highest, followed by rac- and R-dinotefuran. Co-exposure to Cd led to toxicity increase for R-dinotefuran, the malonaldehyde (MDA) content decreased significantly in R + Cd treatment during 7-28 days, while obvious declination of MDA contents was found on the 28th day in R-dinotefuran treatment. Furthermore, compared to R-dinotefuran treatment, Cd increased the relative expression of cz-sod (3.4 times), cas3 (1.6 times) and p53 (5.7 times) in R + Cd treatment. The co-exposure of Cd might alter the environmental behaviors and toxicity effects of Dinotefuran enantiomers in zebrafish, including the enantioselectivity. The effects of Cd on accumulation and toxicity of R-dinotefuran were greater than those on S-dinotefuran. Thus, it is necessary to consider the effects of coexistent metals to chiral pesticides in ecological risk. SUMMARIZES: The enantioselective accumulation and elimination of Dinotefuran enantiomers had tissue specificity. Cd increased the accumulation and toxicity of R-dinotefuran in zebrafish.
Urinary neonicotinoid concentrations and pubertal development in Chinese adolescents: A cross-sectional study
Environ Int 2022 May;163:107186.PMID:35325769DOI:10.1016/j.envint.2022.107186.
Background: Animal studies suggest that exposure to certain neonicotinoids may interfere with the normal function of endocrine system in mammals. However, evidence from human studies is limited. Objectives: This study conducted a cross-sectional analysis to examine urinary neonicotinoids concentrations in Chinese adolescents and its association with pubertal development. Methods: 774 urine samples from 439 boys (median age: 13.7 years; 25th-75th percentile: 12.7-14.5 years) and 335 girls (median age: 13.7 years; 25th-75th percentile: 12.7-14.5 years) were collected for determination of ten neonicotinoids (imidacloprid, nitenpyram, acetamiprid, thiacloprid, imidaclothiz, thiamethoxam, clothianidin, Dinotefuran, flonicamid, sulfoxaflor) and one metabolite (N-desmethyl-acetamiprid). Urinary creatinine was detected for concentration adjustment. Pubertal development including pubic hair, axillary hair, genitalia (boys), testicular volume (boys) and breast (girls) assessed by Tanner stages and others (spermarche, facial hair for boys and menarche for girls) were obtained by physical examination and questionnaire. Logistic and bayesian kernel machine regression were used to investigate the association between neonicotinoids concentrations and pubertal developments. Results: High detection rates ranged from 72.0% to 100.0% for all neonicotinoids. Boys and girls with thiacloprid concentration at the >75th percentile had lower stage of genitalia development (OR: 0.83, 95% CI: 0.33-0.93) and higher stage of axillary hair development (OR: 1.46, 95% CI: 1.12-3.41), respectively, compared with those at the <25th percentile. The estimate change in genitalia stage was significantly different at or above the 75th percentile concentration of neonicotinoids mixture compared to the 50th percentile concentration. No associations were found between other urinary neonicotinoids and other indicators of puberty. Conclusions: Higher thiacloprid concentration was associated with delayed genitalia development in boys and early axillary hair development in girls. Neonicotinoids mixture was negatively associated with genitalia stage in the joint effect. Given the characteristic of the cross-sectional study, our results need further confirmation of the causal relationship.