Pirimiphos-methyl
(Synonyms: 甲基嘧啶磷) 目录号 : GC60291
Pirimiphos-methyl 是一种快速作用的有机磷杀虫剂和杀螨剂，可抑制目标生物体中的乙酰胆碱酯酶 (AChE)。Pirimiphos-methyl 经常在农业谷物的储存过程中用于预防和控制甲虫，鼻子甲虫，飞蛾和埃氏小球藻。
Cas No.:29232-93-7
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
Pirimiphos-methyl is a rapid-acting organophosphorus insecticide and acaricide, causing inhibition of AChE in target organisms. Pirimiphos-methyl is often used for prevention and control of beetles, snout beetles, moths and Ephestia cautella during storage of agricultural grains[1][2][3].
[1]. Shizhuang Weng, et al. Detection of Pirimiphos-Methyl in Wheat Using Surface-Enhanced Raman Spectroscopy and Chemometric Methods. Molecules. 2019 Apr 30;24(9):1691. [2]. PÅl A Olsvik, et al. In Vitro Toxicity of Pirimiphos-Methyl in Atlantic Salmon Hepatocytes. Toxicol In Vitro. 2017 Mar;39:1-14. [3]. Esther BorrÁs, et al. Atmospheric Degradation of the Organothiophosphate Insecticide - Pirimiphos-methyl. Sci Total Environ. 2017 Feb 1;579:1-9.
| Cas No. | 29232-93-7 | SDF | |
| 别名 | 甲基嘧啶磷 | ||
| Canonical SMILES | S=P(OC)(OC)OC1=NC(N(CC)CC)=NC(C)=C1 | ||
| 分子式 | C11H20N3O3PS | 分子量 | 305.33 |
| 溶解度 | DMSO : 50 mg/mL (163.76 mM; Need ultrasonic) | 储存条件 | 4°C, away from moisture and 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 | 3.2751 mL | 16.3757 mL | 32.7514 mL |
| 5 mM | 0.655 mL | 3.2751 mL | 6.5503 mL |
| 10 mM | 0.3275 mL | 1.6376 mL | 3.2751 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。
[Chlorpyrifos-Methyl, Pirimiphos-methyl and Fenitrothion Residues in Commercial Wheat Products]
Shokuhin Eiseigaku Zasshi 2018;59(5):228-233.PMID:30429422DOI:10.3358/shokueishi.59.228.
We measured the concentrations of organophosphorus pesticide （chlorpyrifos-methyl, Pirimiphos-methyl and fenitrothion） residues in domestic and imported commercial wheat products （flour, noodles, cookies） collected from 2008 to 2016. Chlorpyrifos-methyl and fenitrothion in domestic flour samples were detected in 16 out of 34 samples at levels of ＜0.001 to 0.016 ppm, and in 14 out of 34 samples at levels of ＜0.001 to 0.004 ppm. Chlorpyrifos-methyl was detected in 22 out of 38 domestic cookies at levels of ＜0.001 to 0.054 ppm （median: 0.001 ppm）. Relatively high concentrations of chlorpyrifos-methyl （0.005 to 0.054 ppm） were found in six domestic cookies containing wheat bran. Pirimiphos-methyl was detected in 32 out of 68 cookies from foreign countries at levels of ＜0.001 to 0.11 ppm. Pirimiphos-methyl was detected frequently in products imported from Europe.
Detection of Pirimiphos-methyl in Wheat Using Surface-Enhanced Raman Spectroscopy and Chemometric Methods
Molecules 2019 Apr 30;24(9):1691.PMID:31052245DOI:10.3390/molecules24091691.
Pesticide residue detection is a hot issue in the quality and safety of agricultural grains. A novel method for accurate detection of Pirimiphos-methyl residues in wheat was developed using surface-enhanced Raman spectroscopy (SERS) and chemometric methods. A simple pretreatment method was conducted to extract Pirimiphos-methyl residue from wheat samples, and highly effective gold nanorods were prepared for SERS measurement. Raman peaks assignment was calculated using density functional theory. The Raman signal of Pirimiphos-methyl can be detected when the concentrations of residue in wheat extraction solution and contaminated wheat is as low as 0.2 mg/L and 0.25 mg/L, respectively. Quantification of Pirimiphos-methyl was performed by applying regression models developed by partial least squares regression, support vector machine regression and random forest with principal component analysis using different preprocessed methods. As for the contaminated wheat samples, the relative deviation between gas chromatography-mass spectrometry value and predicted value is in the range of 0.10%-6.63%, and predicted recovery is 94.12%-106.63%, ranging from 23.93 mg/L to 0.25 mg/L. Results demonstrated that the proposed SERS method is an effective and efficient analytical tool for detecting Pirimiphos-methyl in wheat with high accuracy and excellent sensitivity.
Resistance to Pirimiphos-methyl in West African Anopheles is spreading via duplication and introgression of the Ace1 locus
PLoS Genet 2021 Jan 21;17(1):e1009253.PMID:33476334DOI:10.1371/journal.pgen.1009253.
Vector population control using insecticides is a key element of current strategies to prevent malaria transmission in Africa. The introduction of effective insecticides, such as the organophosphate Pirimiphos-methyl, is essential to overcome the recurrent emergence of resistance driven by the highly diverse Anopheles genomes. Here, we use a population genomic approach to investigate the basis of Pirimiphos-methyl resistance in the major malaria vectors Anopheles gambiae and A. coluzzii. A combination of copy number variation and a single non-synonymous substitution in the acetylcholinesterase gene, Ace1, provides the key resistance diagnostic in an A. coluzzii population from Côte d'Ivoire that we used for sequence-based association mapping, with replication in other West African populations. The Ace1 substitution and duplications occur on a unique resistance haplotype that evolved in A. gambiae and introgressed into A. coluzzii, and is now common in West Africa primarily due to selection imposed by other organophosphate or carbamate insecticides. Our findings highlight the predictive value of this complex resistance haplotype for phenotypic resistance and clarify its evolutionary history, providing tools to for molecular surveillance of the current and future effectiveness of Pirimiphos-methyl based interventions.
Atmospheric degradation of the organothiophosphate insecticide - Pirimiphos-methyl
Sci Total Environ 2017 Feb 1;579:1-9.PMID:27881242DOI:10.1016/j.scitotenv.2016.11.009.
The gas phase atmospheric degradation of Pirimiphos-methyl (a widely used organophosphate insecticide and acaricide in many European regions) has been investigated at the large outdoor European Photoreactor (EUPHORE) in Valencia, Spain. Its photolysis has been studied under sunlight conditions and its reaction rate constant with OH radicals was measured by the relative rate method. The reaction with ozone was also investigated. The tropospheric degradation of Pirimiphos-methyl is controlled mainly by the OH radical reaction. The rate coefficient of the OH reaction with Pirimiphos-methyl, k, was measured by a conventional relative rate technique, where aniline was taken as a reference. The resulting value of the OH reaction rate constant with Pirimiphos-methyl was k=(1.14±0.2)×10-10cm3molecule-1s-1. The tropospheric lifetime of Pirimiphos-methyl with respect to the reaction with OH radicals was estimated to be around 1.6h (283±10) K and atmospheric pressure. Significant aerosol formation was observed in the OH reaction with yields that ranged from 25 to 37%, and with particle diameters below 550nm. This therefore reveals a high human risk due to PM<1, without taking into account the chemical composition of the degradation products. SO2, glyoxal and other oxygenated and nitrogenated compounds were the main degradation products detected.
In vitro toxicity of Pirimiphos-methyl in Atlantic salmon hepatocytes
Toxicol In Vitro 2017 Mar;39:1-14.PMID:27845199DOI:10.1016/j.tiv.2016.11.008.
Recent screening of Atlantic salmon feeds has uncovered residues of several pesticides, including Pirimiphos-methyl. Pirimiphos-methyl is an organophosphate (OP) insecticide, causing inhibition of acetylcholinesterase in target organisms. The aim of this study was to examine Pirimiphos-methyl non-targeted mode of action toxicity in Atlantic salmon using in vitro exposure. Hepatocyte cells were exposed to Pirimiphos-methyl (control-0.1-1.0-10-100-1000μM) for 48h. Transcriptomics (RNA-seq) and non-targeted metabolomics were used to screen for effects of the pesticide. The results showed that the compound acts cytotoxic and impacts accumulation of lipids (steatosis) at 1000μM. Metabolomics screening revealed effects on lipid metabolism (diHOME fatty acids, cholesterol and lysophospholipids), glutathione (depletion), glycolysis and tryptophan metabolism, as well as on several vitamins. At 1000μM, vitamin E levels increased, while folate and thiamine derivate levels decreased. Surprisingly few transcripts were affected by the treatment, with only 64 differentially expressed genes (DEGs) showing a clear dose-dependent response. Several DEGs encoding proteins in cholesterol biosynthesis showed negative correlations with Pirimiphos-methyl exposure. Other affected DEGs indicate an estrogenic effect, and points to mitochondrial dysfunction at the highest dose. The finding suggests that glutathione and glycine conjugation reactions are involved in the detoxification process. In conclusion, this study shows that Pirimiphos-methyl is a relatively potent toxicant in Atlantic salmon hepatocytes affecting lipid and vitamin metabolism as well as glutathione turn-over.