Flupyradifurone
(Synonyms: 氟吡呋喃酮) 目录号 : GC66073
Flupyradifurone 是一种 nAChR 激动剂，可干扰害虫中枢神经系统的信号转导，可用作杀虫剂。
Cas No.:951659-40-8
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
Flupyradifurone is a systemic nAChR agonist that interferes with signal transduction in the central nervous system of sucking pests. Flupyradifurone can be used as a butenolide insecticide[1].
Flupyradifurone is a butenolide insecticide that activates insect nAChRs. Flupyradifurone is a butenolide insecticide and is considered friendly to honey bee fitness[1].
Flupyradifurone (FLF), an insecticide, compete with imidacloprid (IMI) for the same high affinity-binding site at the insect nAChR, the modulation of which leads to the toxic end point[2].
The half-life of Flupyradifurone in peppers is 2.6-3.8 days. The national estimated daily intake of Flupyradifurone is 0.00094 mg/kg[3].
| Cas No. | 951659-40-8 | SDF | Download SDF |
| 别名 | 氟吡呋喃酮 | ||
| 分子式 | C12H11ClF2N2O2 | 分子量 | 288.68 |
| 溶解度 | DMSO : 100 mg/mL (346.40 mM; Need ultrasonic) | 储存条件 | 4°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 | 3.464 mL | 17.3202 mL | 34.6404 mL |
| 5 mM | 0.6928 mL | 3.464 mL | 6.9281 mL |
| 10 mM | 0.3464 mL | 1.732 mL | 3.464 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。
Flupyradifurone induces transgenerational hormesis effects in the cowpea aphid, Aphis craccivora
Ecotoxicology 2022 Aug;31(6):909-918.PMID:35616792DOI:10.1007/s10646-022-02556-0.
With low-dose stimulation and high-dose inhibition, insecticide-induced hormesis, a biphasic phenomenon, can contribute to pest resurgence. The cowpea aphid, Aphis craccivora (Koch) (Homoptera: Aphididae), is a vital insect that infests legume crops. Its hormesis of Flupyradifurone has not been previously established. Age-stage two-sex life analysis is used to investigate the sublethal and transgenerational effects of Flupyradifurone on two successive generations of A. craccivora. A leaf-dip bioassay method revealed high toxicity of Flupyradifurone against A. craccivora, with lethal concentration 50% value (LC50) of 1.82 mg L-1 after 48 h exposure. Treatment of parent generation (F0) with LC10 and LC25 of Flupyradifurone significantly increased the longevity and fecundity of the directly exposed adults. The results of transgenerational effects showed that the treatment of (F0) with LC25 induced significant hormetic effects in progeny generation (F1). Furthermore, Flupyradifurone at LC25 significantly enhanced the biological traits, such as intrinsic rate of increase (r), finite rate of increase (λ), and net reproductive rate (R0) compared with the control. Similarly, both LC10 and LC25 induced a significant increase in the mean generation time T (d). Conversely, both treatments caused a significant decrease in the doubling time (DT). Data in the present study demonstrate that the exposure of (F0) to Flupyradifurone at LC10 and LC25 enhanced longevity and fecundity in the directly exposed adults of A. craccivora, and induced transgenerational hormesis across the subsequent (F1) generation. These results should be taken into consideration when using Flupyradifurone for controlling cowpea aphid.
Statement on the active substance Flupyradifurone
EFSA J 2022 Jan 24;20(1):e07030.PMID:35106089DOI:10.2903/j.efsa.2022.7030.
Flupyradifurone is a novel butenolide insecticide, first approved as an active substance for use in plant protection products by Commission Implementing Regulation (EU) 2015/2084. Following concerns that this substance may pose high risks to humans and the environment, the French authorities, in November 2020, asked the Commission to restrict its uses under Article 69 of Regulation (EC) No 1107/2009. To support this request, competent Authorities from France cited a series of literature papers investigating its hazards and/or exposure to humans and the environment. In addition, in June 2020, the Dutch Authorities notified the Commission, under Article 56 of Regulation (EC) No 1107/2009, of new information on Flupyradifurone on the wild bee species Megachile rotundata. This notification is also referred to in the French notification on Flupyradifurone. Consequently, the EFSA PPR Panel was mandated to quantify the likelihood of this body of evidence constituting proof of serious risks to humans or the environment. Therefore, the EFSA PPR Panel evaluated the likelihood of these studies indicating new or higher hazards and exposure to humans and the environment compared to previous EU assessments. A stepwise methodology was designed, including: (i) the initial screening; (ii) data extraction and critical appraisal based on the principles of OHAT/NTP; (iii) weight of evidence, including consideration of the previous EU assessments; (iv) uncertainty analysis, followed, whenever relevant, by an expert knowledge elicitation process. For the human health, only one study was considered relevant for the genotoxic potential of Flupyradifurone in vitro. These data did not provide sufficient information to overrule the EU assessment, as in vivo studies already addressed the genotoxic potential of Flupyradifurone. Environment: All available data investigated hazards in bee species. For honey bees, the likelihood of the new data indicating higher hazards than the previous EU assessment was considered low or moderate, with some uncertainties. However, among solitary bee species - which were not addressed in the previous EU assessment - there was evidence that Megachile rotundata may be disproportionately sensitive to Flupyradifurone. This sensitivity, which may partially be explained by the low bodyweight of this species, was mechanistically linked to inadequate bodily metabolisation processes.
Flupyradifurone (Sivanto™) and its novel butenolide pharmacophore: Structural considerations
Pestic Biochem Physiol 2015 Jun;121:31-8.PMID:26047109DOI:10.1016/j.pestbp.2014.10.011.
Flupyradifurone (4-[(2,2-difluoroethyl)amino]-2(5H)-furanone), a member of the new class of butenolide insecticides, contains a novel bioactive scaffold as pharmacophore. It is very versatile in terms of application methods to a variety of crops, exhibits excellent and fast action against a broad spectrum of sucking pest insects including selected neonicotinoid resistant pest populations such as whiteflies and aphids expressing metabolic resistance mechanisms. As a partial agonist Flupyradifurone reversibly binds to insect nicotinic acetylcholine receptors (nAChRs) and lacks metabolization by CYP6CM1, a cytochrome P450 over-expressed in cotton whiteflies resistant to imidacloprid and pymetrozine. The butenolide insecticides exhibit structure-activity relationships (SAR) that are different from other nAChR agonists such as the classes of neonicotinoids and sulfoximines. The paper briefly reviews the discovery of the butenolide insecticide Flupyradifurone, its SAR differentiating it from established nAChR agonists and a molecular docking approach using the binding site model of CYP6CM1vQ of Bemisia tabaci known to confer metabolic resistance to neonicotinoid insecticides.
Effect of Flupyradifurone on zebrafish embryonic development
Environ Pollut 2021 Sep 15;285:117323.PMID:34091267DOI:10.1016/j.envpol.2021.117323.
Evaluation of the toxicity of pesticide residues on non-target organisms in the ecosystem is an important part of pesticide environmental risk assessment. Flupyradifurone is a new type of butenolide insecticide produced by Bayer, who claims it to be "low toxic" to non-target organisms in the environment. However, there is little evidence in the literature to show how Flupyradifurone affects aquatic organism development. In the current study, zebrafish embryos were treated with 0.1, 0.15, and 0.2 mg/mL of Flupyradifurone within 6.0-72 h past fertilization (hpf). We found that the half-lethal concentration (LC50) of Flupyradifurone for zebrafish embryos at 96 hpf was 0.21 mg/mL. Flupyradifurone decreases the heart rate, survival rate, and body length of zebrafish embryos. The Flupyradifurone treatment also led to the failure of heart looping, and pericardial edema. Moreover, Flupyradifurone increased the level of reactive oxygen species (ROS) and decreased the enzymatic catalysis of catalase (CAT) and superoxide dismutase (SOD). Alterations were induced in the transcription of apoptosis-related genes (bcl-2, bax, bax/bcl-2, p53 and caspase-9) and the heart development-related genes (gata4, myh6, nkx2.5, nppa, tbx2b, tbx5 and vmhc). In the current study, new evidences have been provided regarding the toxic effects of Flupyradifurone and the risk of its residues in agricultural products and the environment.
Flupyradifurone resistance in Myzus persicae populations from peach and tobacco in Greece
Pest Manag Sci 2022 Jan;78(1):304-312.PMID:34498376DOI:10.1002/ps.6637.
Background: Myzus persicae has evolved resistance to various insecticides in Greece. Here we examine the effectiveness of the insecticide Flupyradifurone against aphid clones collected from tobacco and peach in Greece during 2017-2020. Furthermore, we monitored the frequency of the neonicotinoid resistance mutation R81T in the sampled clones, and the association between the responses to Flupyradifurone and acetamiprid. Results: Of 43 clones tested with Flupyradifurone, 6.977%, 60.465% and 32.558% showed low (10-14), moderate (19-89) and high (104-1914) resistance factor (RF) values, respectively. Resistance was higher in clones from peach than from tobacco with 42.308% and 17.647% of clones (respectively) failing into the high RF category (median RF values 67.5 and 36.4 for clones from peach and tobacco, respectively). Acetamiprid resistance was detected in clones collected in 2019-2020, in line with our previous study in Greece. The analysis of the whole dataset (54 clones collected during 2017-2020) revealed that all tobacco clones had RF < 7.5, whereas 55.263%, 18.421% and 26.316% of the peach clones exhibited low (<12), moderate (20-48) and high (100-145) RF values, respectively. A significant but moderate association between Flupyradifurone and acetamiprid responses was detected (r = 0.513, P < 0.001). The R81T mutation was detected in aphids from peach (5.6% and 32.6% as homozygotes and heterozygotes, respectively) and in one aphid specimen (heterozygote) from tobacco. R81T was partially associated with the resistance to both insecticides, but many highly resistant clones did not possess the mutation, indicating the possible operation of one or more alternative underlying resistance mechanisms. Conclusions: The use of Flupyradifurone and acetamiprid in IPM/IRM should be based on further ongoing susceptibility monitoring. © 2021 Society of Chemical Industry.