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MedKoo Cat#: 596227 | Name: Metalaxyl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metalaxyl is an acylalanine fungicide with systemic function. Its chemical name is methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate. It can be used to control Pythium in a number of vegetable crops, and Phytophthora in peas. Metalaxyl-M or Ridomil Gold are trade names for the optically pure (-) / D / R active stereoisomer, which is also known as Mefenoxam.

Chemical Structure

Metalaxyl
CAS#57837-19-1

Theoretical Analysis

MedKoo Cat#: 596227

Name: Metalaxyl

CAS#: 57837-19-1

Chemical Formula: C15H21NO4

Exact Mass: 279.1471

Molecular Weight: 279.34

Elemental Analysis: C, 64.50; H, 7.58; N, 5.01; O, 22.91

Price and Availability

Size Price Availability Quantity
100mg USD 285.00 2 weeks
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Synonym
Metalaxyl; CGA 48988; CGA-48988; CGA48988; Allegiance; Metalaxil; Ridomil 72WP;
IUPAC/Chemical Name
methyl N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate
InChi Key
ZQEIXNIJLIKNTD-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3
SMILES Code
CC(C(OC)=O)N(C1=C(C)C=CC=C1C)C(COC)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Metalaxyl is a fungicide agent that inhibits the protein synthesis in fungi.
In vitro activity:
Therefore, growth, physiological and biochemical responses in leaves and roots of Solanum nigrum L. exposed to the commonly used fungicide metalaxyl were investigated. Metalaxyl inhibits growth by reducing photosynthesis and inducing photorespiration. Elevated antioxidant defenses protect metalaxyl-treated plants from oxidative damage. Reference: Front Plant Sci. 2017 Nov 30;8:1967. https://pubmed.ncbi.nlm.nih.gov/29250085/
In vivo activity:
The effect of the fungicide metalaxyl [methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaniate] on cardiac activity was investigated in albino rats anesthetized with phentobarbitone. Metalaxyl caused dose-dependent bradycardia, and at higher doses (250 and 300 mg/kg body weight) the sustained bradycardia led to cardiac arrest. Reference: J Toxicol Environ Health. 1988;23(4):495-8. https://pubmed.ncbi.nlm.nih.gov/2834560/
Solvent mg/mL mM comments
Solubility
DMSO 100.0 357.99
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 279.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. de Sousa A, AbdElgawad H, Asard H, Pinto A, Soares C, Branco-Neves S, Braga T, Azenha M, Selim S, Al Jaouni S, Fidalgo F, Teixeira J. Metalaxyl Effects on Antioxidant Defenses in Leaves and Roots of Solanum nigrum L. Front Plant Sci. 2017 Nov 30;8:1967. doi: 10.3389/fpls.2017.01967. PMID: 29250085; PMCID: PMC5715272. 2. Hrelia P, Maffei F, Fimognari C, Vigagni F, Cantelli-Forti G. Cytogenetic effects of Metalaxyl on human and animal chromosomes. Mutat Res. 1996 Jul 10;369(1-2):81-6. doi: 10.1016/s0165-1218(96)90051-8. PMID: 8700187. 3. Zeng S, Peng Y, Ma J, Ge Y, Huang Y, Xie S, Yuan W, Lu C, Zhang H, Luo Q, Liao X, Lu H. Hematopoietic stem cell and immunotoxicity in zebrafish embryos induced by exposure to Metalaxyl-M. Sci Total Environ. 2022 Feb 25;809:152102. doi: 10.1016/j.scitotenv.2021.152102. Epub 2021 Dec 2. PMID: 34863748. 4. Naidu KA, Radhakrishnamurty R. Metalaxyl-induced bradycardia in rats: mediated by alpha-adrenoreceptors. J Toxicol Environ Health. 1988;23(4):495-8. doi: 10.1080/15287398809531130. PMID: 2834560.
In vitro protocol:
1. de Sousa A, AbdElgawad H, Asard H, Pinto A, Soares C, Branco-Neves S, Braga T, Azenha M, Selim S, Al Jaouni S, Fidalgo F, Teixeira J. Metalaxyl Effects on Antioxidant Defenses in Leaves and Roots of Solanum nigrum L. Front Plant Sci. 2017 Nov 30;8:1967. doi: 10.3389/fpls.2017.01967. PMID: 29250085; PMCID: PMC5715272. 2. Hrelia P, Maffei F, Fimognari C, Vigagni F, Cantelli-Forti G. Cytogenetic effects of Metalaxyl on human and animal chromosomes. Mutat Res. 1996 Jul 10;369(1-2):81-6. doi: 10.1016/s0165-1218(96)90051-8. PMID: 8700187.
In vivo protocol:
1. Zeng S, Peng Y, Ma J, Ge Y, Huang Y, Xie S, Yuan W, Lu C, Zhang H, Luo Q, Liao X, Lu H. Hematopoietic stem cell and immunotoxicity in zebrafish embryos induced by exposure to Metalaxyl-M. Sci Total Environ. 2022 Feb 25;809:152102. doi: 10.1016/j.scitotenv.2021.152102. Epub 2021 Dec 2. PMID: 34863748. 2. Naidu KA, Radhakrishnamurty R. Metalaxyl-induced bradycardia in rats: mediated by alpha-adrenoreceptors. J Toxicol Environ Health. 1988;23(4):495-8. doi: 10.1080/15287398809531130. PMID: 2834560.
1: Yu W, Luo X, Qin X, Huang M, Li J, Zeng S, Zhang K, Hu D. Simultaneous determination and risk assessment of metalaxyl and azoxystrobin in potato by liquid chromatography with tandem mass spectrometry. Environ Monit Assess. 2018 May 9;190(6):335. doi: 10.1007/s10661-018-6717-0. PubMed PMID: 29744742. 2: Staveley JP, Green JW, Nusz J, Edwards D, Henry K, Kern M, Deines AM, Brain R, Glenn B, Ehresman N, Kung T, Ralston-Hooper K, Kee F, McMaster S. Variability in Non-Target Terrestrial Plant Studies Should Inform Endpoint Selection. Integr Environ Assess Manag. 2018 May 4. doi: 10.1002/ieam.4055. [Epub ahead of print] PubMed PMID: 29729081. 3: Zhang Y, Fan Y, Zhang W, Wu G, Wang J, Cheng F, Zheng J, Wang Z. Bio-preparation of (R)-DMPM using whole cells of Pseudochrobactrum asaccharolyticum WZZ003 and its application on kilogram-scale synthesis of fungicide (R)-metalaxyl. Biotechnol Prog. 2018 Apr 25. doi: 10.1002/btpr.2638. [Epub ahead of print] PubMed PMID: 29694734. 4: Gu J, Ji C, Yue S, Shu D, Su F, Zhang Y, Xie Y, Zhang Y, Liu W, Zhao M. Enantioselective Effects of Metalaxyl Enantiomers in Adolescent Rat Metabolic Profiles Using NMR-Based Metabolomics. Environ Sci Technol. 2018 May 1;52(9):5438-5447. doi: 10.1021/acs.est.7b06540. Epub 2018 Apr 23. PubMed PMID: 29683314. 5: Zhao P, Zhao J, Lei S, Guo X, Zhao L. Simultaneous enantiomeric analysis of eight pesticides in soils and river sediments by chiral liquid chromatography-tandem mass spectrometry. Chemosphere. 2018 Aug;204:210-219. doi: 10.1016/j.chemosphere.2018.03.204. Epub 2018 Apr 3. PubMed PMID: 29656157. 6: Masbou J, Meite F, Guyot B, Imfeld G. Enantiomer-specific stable carbon isotope analysis (ESIA) to evaluate degradation of the chiral fungicide Metalaxyl in soils. J Hazard Mater. 2018 Mar 29;353:99-107. doi: 10.1016/j.jhazmat.2018.03.047. [Epub ahead of print] PubMed PMID: 29649698. 7: Barchanska H, Danek M, Sajdak M, Turek M. Review of Sample Preparation Techniques for the Analysis of Selected Classes of Pesticides in Plant Matrices. Crit Rev Anal Chem. 2018 Apr 5:1-25. doi: 10.1080/10408347.2018.1451297. [Epub ahead of print] PubMed PMID: 29621408. 8: Atmaca N, Arikan S, Essiz D, Kalender H, Simsek O, Bilmen FS, Kabakci R. Effects of mancozeb, metalaxyl and tebuconazole on steroid production by bovine luteal cells in vitro. Environ Toxicol Pharmacol. 2018 Apr;59:114-118. doi: 10.1016/j.etap.2018.03.009. Epub 2018 Mar 13. PubMed PMID: 29558666. 9: Dey T, Saville A, Myers K, Tewari S, Cooke DEL, Tripathy S, Fry WE, Ristaino JB, Guha Roy S. Large sub-clonal variation in Phytophthora infestans from recent severe late blight epidemics in India. Sci Rep. 2018 Mar 13;8(1):4429. doi: 10.1038/s41598-018-22192-1. PubMed PMID: 29535313; PubMed Central PMCID: PMC5849725. 10: Chen F, Zhou Q, Xi J, Li DL, Schnabel G, Zhan J. Analysis of RPA190 revealed multiple positively selected mutations associated with metalaxyl resistance in Phytophthora infestans. Pest Manag Sci. 2018 Feb 19. doi: 10.1002/ps.4893. [Epub ahead of print] PubMed PMID: 29457681. 11: Castro-Gutiérrez V, Masís-Mora M, Carazo-Rojas E, Mora-López M, Rodríguez-Rodríguez CE. Impact of oxytetracycline and bacterial bioaugmentation on the efficiency and microbial community structure of a pesticide-degrading biomixture. Environ Sci Pollut Res Int. 2018 Apr;25(12):11787-11799. doi: 10.1007/s11356-018-1436-1. Epub 2018 Feb 14. PubMed PMID: 29442313. 12: Huang J, Zhang X, Liang C, Hu J. Impact of TiO(2) on the chemical and biological transformation of formulated chiral-metalaxyl in agricultural soils. J Hazard Mater. 2018 Apr 15;348:67-74. doi: 10.1016/j.jhazmat.2018.01.035. Epub 2018 Jan 31. PubMed PMID: 29367134. 13: Sonchieu J, Akono EN, Ngwamitang CT, Ngassoum BM. Heath risk among pesticide sellers in Bamenda (Cameroon) and peripheral areas. Environ Sci Pollut Res Int. 2018 Apr;25(10):9454-9460. doi: 10.1007/s11356-018-1243-8. Epub 2018 Jan 20. PubMed PMID: 29353357. 14: Fang S, Tao Y, Zhang Y, Kong F, Wang Y. Effects of metalaxyl enantiomers stress on root activity and leaf antioxidant enzyme activities in tobacco seedlings. Chirality. 2018 Apr;30(4):469-474. doi: 10.1002/chir.22810. Epub 2018 Jan 15. PubMed PMID: 29334408. 15: Smalling KL, Hladik ML, Sanders CJ, Kuivila KM. Leaching and sorption of neonicotinoid insecticides and fungicides from seed coatings. J Environ Sci Health B. 2018 Mar 4;53(3):176-183. doi: 10.1080/03601234.2017.1405619. Epub 2017 Dec 29. PubMed PMID: 29286873. 16: Zhao P, Lei S, Xing M, Xiong S, Guo X. Simultaneous enantioselective determination of six pesticides in aqueous environmental samples by chiral liquid chromatography with tandem mass spectrometry. J Sep Sci. 2018 Mar;41(6):1287-1297. doi: 10.1002/jssc.201701259. Epub 2018 Jan 25. PubMed PMID: 29274257. 17: de Sousa A, AbdElgawad H, Asard H, Pinto A, Soares C, Branco-Neves S, Braga T, Azenha M, Selim S, Al Jaouni S, Fidalgo F, Teixeira J. Metalaxyl Effects on Antioxidant Defenses in Leaves and Roots of Solanum nigrum L. Front Plant Sci. 2017 Nov 30;8:1967. doi: 10.3389/fpls.2017.01967. eCollection 2017. PubMed PMID: 29250085; PubMed Central PMCID: PMC5715272. 18: Martins MR, Santos C, Pereira P, Cruz-Morais J, Lima N. Metalaxyl Degradation by Mucorales Strains Gongronella sp. and Rhizopus oryzae. Molecules. 2017 Dec 14;22(12). pii: E2225. doi: 10.3390/molecules22122225. PubMed PMID: 29240696. 19: Kabir MH, Abd El-Aty AM, Rahman MM, Chung HS, Lee HS, Jeong JH, Wang J, Shin S, Shin HC, Shim JH. Dissipation kinetics, pre-harvest residue limits, and dietary risk assessment of the systemic fungicide metalaxyl in Swiss chard grown under greenhouse conditions. Regul Toxicol Pharmacol. 2018 Feb;92:201-206. doi: 10.1016/j.yrtph.2017.12.003. Epub 2017 Dec 9. PubMed PMID: 29233770. 20: Wu S, Yu W, Sun C, Zheng K, Zhang H, Huang M, Hu D, Zhang K. Simultaneous determination of residues of metalaxyl, cyazofamid and a cyazofamid metabolite in tobacco leaves and soil by liquid chromatography with tandem mass spectrometry. Biomed Chromatogr. 2018 Apr;32(4). doi: 10.1002/bmc.4161. Epub 2018 Jan 5. PubMed PMID: 29226978.