Metalaxyl
(Synonyms: 甲霜灵) 目录号 : GC47632
A fungicide
Cas No.:57837-19-1
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
Metalaxyl is a fungicide that inhibits protein synthesis in fungi.1,2 It inhibits the growth of potato blight (P. infestans) fungal isolates from Serbian potato fields (EC50s = 0.3-3.9 μg/ml).1 Metalaxyl (300 and 1,000 μg/ml) induces formation of chromosomal aberrations in human lymphocytes.3 It exhibits aquatic toxicity against S. quadricanda, D. magna, and D. rerio (IC50s = 222.89, 471.95, and 241.98 mg/L, respectively).4 Metalaxyl also induces tremors, twitches, tonic extension, ataxia, and hypnosis, symptoms of CNS poisoning, and lethality in rats (LD50s = 265 and 288.8 mg/kg for female and male rats, respectively).2
1.Rekanovi?, E., Poto?nik, I., Milijaševi?-Mar?i?, S., et al.Toxicity of metalaxyl, azoxystrobin, dimethomorph, cymoxanil, zoxamide and mancozeb to Phytophthora infestans isolates from SerbiaJ. Environ. Sci. Health B.47(5)403-409(2012) 2.Naidu, K.A., and Radhakrishnamurty, R.Metalaxyl-induced bradycardia in rats: Mediated by α-adrenoreceptorsJ. Toxicol. Environ. Health23(4)495-498(1988) 3.Hrelia, P., Maffei, F., Fimognari, C., et al.Cytogenetic effects of metalaxyl on human and animal chromosomesMutat. Res.369(1-2)81-86(1996) 4.Yao, K., Zhu, L., Duan, Z., et al.Comparison of R-metalaxyl and rac-metalaxyl in acute, chronic, and sublethal effect on aquatic organisms: Daphnia magna, Scenedesmus quadricanda, and Danio rerioEnviron. Toxicol.24(2)148-156(2009)
| Cas No. | 57837-19-1 | SDF | |
| 别名 | 甲霜灵 | ||
| Canonical SMILES | CC1=CC=CC(C)=C1N(C(COC)=O)C(C(OC)=O)C | ||
| 分子式 | C15H21NO4 | 分子量 | 279.3 |
| 溶解度 | Chloroform: Soluble,Methanol: Soluble | 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 | 3.5804 mL | 17.9019 mL | 35.8038 mL |
| 5 mM | 0.7161 mL | 3.5804 mL | 7.1608 mL |
| 10 mM | 0.358 mL | 1.7902 mL | 3.5804 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 different toxic effects of Metalaxyl and metalaxyl-M on Tubifex tubifex
Ecotoxicol Environ Saf 2021 Jan 15;208:111587.PMID:33396110DOI:10.1016/j.ecoenv.2020.111587.
Metalaxyl and Metalaxyl-M are the fungicides that widely used in many countries. In this study, the environmental behaviors between Metalaxyl and metalaxyl-M in Tubifex tubifex (T. tubifex) were quantitative analyzed by using a high performance liquid chromatography with photo-diode-array-detector (HPLC-DAD). Results demonstrated that there was no significant difference (p > 0.05) in the concentration of Metalaxyl and metalaxyl-M in T. tubifex during the exposure process. However, the dissipation behaviors of Metalaxyl and metalaxyl-M in T. tubifex were different (p < 0.05) during the non-exposure culture process. Meanwhile, the toxic effects were also evaluated by comparing the different influences of these two compounds on related physiological indicators, and functional enzyme activities. The survival rates of T. tubifex were 63.33 ± 15.28% (20 mg L-1), 63.33 ± 5.77% (200 mg L-1) treated with Metalaxyl and were 50.00 ± 10.00% (20 mg L-1), 46.67 ± 11.55 (200 mg L-1) treated with metalaxyl-M at the non-exposure culture process. The autotomy rates were increased significantly compared with the initial in all treatments. Besides, the activities of CAT, SOD, and GST in T. tubifex were also inhibited by Metalaxyl and metalaxyl-M treatments. Finally, the high-throughput transcriptome sequencing technology was applied to investigate the metabolic pathways of target analytes in T. tubifex, and results proved that the metabolic pathways associated with human diseases (such as viral myocarditis) were up-regulated expression for Metalaxyl and metalaxyl-M treatments, and metalaxyl-M up-regulated more significantly. All the results demonstrated that metalaxyl-M had a higher toxicity than Metalaxyl on T. tubifex.
Metalaxyl: persistence, degradation, metabolism, and analytical methods
Rev Environ Contam Toxicol 2000;164:1-26.PMID:12587832doi
Metalaxyl is a systemic fungicide used to control plant diseases caused by Oomycete fungi. Its formulations include granules, wettable powders, dusts, and emulsifiable concentrates. Application may be by foliar or soil incorporation, surface spraying (broadcast or band), drenching, and seed treatment. Metalaxyl registered products either contain Metalaxyl as the sole active ingredient or are combined with other active ingredients (e.g., captan, mancozeb, copper compounds, carboxin). Due to its broad-spectrum activity, Metalaxyl is used world-wide on a variety of fruit and vegetable crops. Its effectiveness results from inhibition of uridine incorporation into RNA and specific inhibition of RNA polymerase-1. Metalaxyl has both curative and systemic properties. Its mammalian toxicity is classified as EPA toxicity class III and it is also relatively non-toxic to most nontarget arthropod and vertebrate species. Adequate analytical methods of TLC, GLC, HPLC, MS, and other techniques are available for identification and determination of Metalaxyl residues and its metabolites. Available laboratory and field studies indicate that Metalaxyl is stable to hydrolysis under normal environmental pH values, It is also photolytically stable in water and soil when exposed to natural sunlight. Its tolerance to a wide range of pH, light, and temperature leads to its continued use in agriculture. Metalaxyl is photodecomposed in UV light, and photoproducts are formed by rearrangement of the N-acyl group to the aromatic ring, demethoxylation, N-deacylation, and elimination of the methoxycarbonyl group from the molecule. Photosensitizers such as humic acid, TiO2, H2O2, acetone, and riboflavin accelerate its photodecomposition. Information is provided on the fate of Metalaxyl in plant, soil, water, and animals. Major metabolic routes include hydrolysis of the methyl ester and methyl ether oxidation of the ring-methyl groups. The latter are precursors of conjugates in plants and animals. In soils the most relevant metabolite is the Metalaxyl acid, which is formed predominantly by soil microorganisms. Plant uptake, microbial degradation, photodecomposition, and leaching are the major route of Metalaxyl dissipation. It has a tendency to migrate to deeper soil horizons with a potential to contaminate groundwater, particularly in soils with low organic matter and clay content. Therefore, precautions should be taken for the continuous application of Metalaxyl to crops. If use of Metalaxyl is greately increased, the risk of occurrence in groundwater must be reassessed, as by monitoring studies in the most vulnerable areas in main use regions. The R-isomer of Metalaxyl (mefenoxam) has recently been registered as the only active compound. Therefore, quantitative studies on the fate of this specific isomer are needed, including appropriate analytical methods. As the use rates of mefenoxam are approximately one-half those recommended for Metalaxyl and mefenoxam dissipates more rapidly, concerns for mefenoxam reaching groundwater are even less justified.
Enantioselective Degradation and Chiral Stability of Metalaxyl-M in Tomato Fruits
Chirality 2016 May;28(5):382-6.PMID:27008381DOI:10.1002/chir.22585.
Metalaxyl is an important chiral acetanilide fungicide, and the activity almost entirely originates from the R-enantiomer. Racemic Metalaxyl has been gradually replaced by the enantiopure R-enantiomer (metalaxyl-M). In this study a chiral residue analysis method for Metalaxyl and the metabolite Metalaxyl acid was set up based on high-performance liquid chromatography tandem mass spectroscopy (HPLC-MS/MS). The enantioselective degradation and chiral stability of metalaxyl-M in tomato fruits in two geographically distinct regions of China (Heilongjiang and Hunan Province) were evaluated and the enantioselectivity of Metalaxyl acid was also investigated. Tomato plants grew under field conditions with a one-time spray application of metalaxyl-M wettable powder. It was found that R-metalaxyl was not chirally stable and the inactive S-metalaxyl was detected in tomato fruits. At day 40, S-metalaxyl derived from R-metalaxyl accounted for 32% and 26% of the total amount of Metalaxyl, respectively. The metabolites R-metalaxyl acid and S-metalaxyl acid were both observed in tomato, and the ratio of S-metalaxyl acid to the sum of S- and R-metalaxyl acid was 36% and 28% at day 40, respectively. For both Metalaxyl and Metalaxyl acid, the half-life of the S-enantiomer was longer than the R-enantiomer. The results indicated that the enantiomeric conversion should be considered in the bioactivity evaluation and environmental pollution assessment. Chirality 28:382-386, 2016. © 2016 Wiley Periodicals, Inc.
Characterizing the Mechanisms of Metalaxyl, Bronopol and Copper Sulfate against Saprolegnia parasitica Using Modern Transcriptomics
Genes (Basel) 2022 Aug 25;13(9):1524.PMID:36140692DOI:10.3390/genes13091524.
Saprolegniasis, which is caused by Saprolegnia parasitica, leads to considerable economic losses. Recently, we showed that Metalaxyl, bronopol and copper sulfate are good antimicrobial agents for aquaculture. In the current study, the efficacies of Metalaxyl, bronopol and copper sulfate are evaluated by in vitro antimicrobial experiments, and the mechanism of action of these three antimicrobials on S. parasitica is explored using transcriptome technology. Finally, the potential target genes of antimicrobials on S. parasitica are identified by protein-protein interaction network analysis. Copper sulfate had the best inhibitory effect on S. parasitica, followed by bronopol. A total of 1771, 723 and 2118 DEGs upregulated and 1416, 319 and 2161 DEGs downregulated S. parasitica after three drug treatments (Metalaxyl, bronopol and copper sulfate), separately. Additionally, KEGG pathway analysis also determined that there were 17, 19 and 13 significantly enriched metabolic pathways. PPI network analysis screened out three important proteins, and their corresponding genes were SPRG_08456, SPRG_03679 and SPRG_10775. Our results indicate that three antimicrobials inhibit S. parasitica growth by affecting multiple biological functions, including protein synthesis, oxidative stress, lipid metabolism and energy metabolism. Additionally, the screened key genes can be used as potential target genes of chemical antimicrobial drugs for S. parasitica.
Metalaxyl Degradation by Mucorales Strains Gongronella sp. and Rhizopus oryzae
Molecules 2017 Dec 14;22(12):2225.PMID:29240696DOI:10.3390/molecules22122225.
In this study, the degradation of Metalaxyl was investigated in the presence of two Mucorales strains, previously isolated from soil subjected to repeated treatments with this fungicide and selected after enrichment technique. Fungal strains were characterised by a polyphasic approach using phylogenetic analysis of the Internal Transcribed Spacer (ITS) gene region, phenotypic characterisation by Matrix-Assisted Laser Desorption Ionization Time-Of-Flight Mass Spectrometry (MALDI-TOF MS) spectral analysis, and growth kinetics experiments. The strains were identified as Gongronella sp. and Rhizopus oryzae. The fungal growth kinetics in liquid cultures containing Metalaxyl fits with Haldane model. Under laboratory conditions, the ability of Gongronella sp. and R. oryzae cultures to degrade Metalaxyl was evaluated in liquid cultures and soil experiments. Both species were able to: (a) use Metalaxyl as the main carbon and energy source; and (b) degrade Metalaxyl in polluted soils, with rates around 1.0 mg kg-¹ d-¹. This suggests these strains could degrade Metalaxyl in soils contaminated with this fungicide.