MedKoo Cat#: 571245 | Name: Oxamyl oxime

Description:

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

Oxamyl oxime is an agricultural chemical and pesticide.

Chemical Structure

Oxamyl oxime
Oxamyl oxime
CAS#30558-43-1 (oxime)

Theoretical Analysis

MedKoo Cat#: 571245

Name: Oxamyl oxime

CAS#: 30558-43-1 (oxime)

Chemical Formula: C5H10N2O2S

Exact Mass: 162.0463

Molecular Weight: 162.21

Elemental Analysis: C, 37.02; H, 6.21; N, 17.27; O, 19.73; S, 19.76

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Synonym
Oxamyl oxime; A2213; A 2213; A-2213
IUPAC/Chemical Name
Ethanimidothioic acid, 2-(dimethylamino)-N-hydroxy-2-oxo-, methyl ester
InChi Key
KIDWGGCIROEJJW-XQRVVYSFSA-N
InChi Code
InChI=1S/C5H10N2O2S/c1-7(2)5(8)4(6-9)10-3/h9H,1-3H3/b6-4-
SMILES Code
O=C(N(C)C)/C(SC)=N/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
Biological target:
Oxamyl oxime is an agricultural chemical and pesticide.
In vitro activity:
TBD
In vivo activity:
In this study, the developmental toxicity of oxamyl was demonstrated using zebrafish, which is a representative model as it is associated with rapid embryogenesis and a toxic response similar to that of other vertebrates. Analysis of transgenic zebrafish (olig2:dsRED and flk1:eGFP line) and mRNA levels of genes associated with individual organ development revealed that oxamyl exerted toxic effects on the development of neuron, notochord, and vascular system. Next, the adverse effect of oxamyl on the mitochondrial electron transport chain was examined. Treatment with oxamyl altered the PI3K/Akt signaling and p38 Mapk signaling pathways in zebrafish. Reference: Sci Total Environ. 2023 Feb 10;859(Pt 2):160458. https://pubmed.ncbi.nlm.nih.gov/36435248/

Preparing Stock Solutions

The following data is based on the product molecular weight 162.21 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:
An G, Hong T, Park H, Lim W, Song G. Oxamyl exerts developmental toxic effects in zebrafish by disrupting the mitochondrial electron transport chain and modulating PI3K/Akt and p38 Mapk signaling. Sci Total Environ. 2023 Feb 10;859(Pt 2):160458. doi: 10.1016/j.scitotenv.2022.160458. Epub 2022 Nov 24. PMID: 36435248.
In vitro protocol:
TBD
In vivo protocol:
An G, Hong T, Park H, Lim W, Song G. Oxamyl exerts developmental toxic effects in zebrafish by disrupting the mitochondrial electron transport chain and modulating PI3K/Akt and p38 Mapk signaling. Sci Total Environ. 2023 Feb 10;859(Pt 2):160458. doi: 10.1016/j.scitotenv.2022.160458. Epub 2022 Nov 24. PMID: 36435248.
1: Chapman RA, Harris CR. Determination of residues of methomyl and oxamyl and their oximes in crops by gas-liquid chromatography of oxime trimethylsilyl ethers. J Chromatogr. 1979 Apr 1;171:249-62. PubMed PMID: 546852. 2: Rousidou K, Chanika E, Georgiadou D, Soueref E, Katsarou D, Kolovos P, Ntougias S, Tourna M, Tzortzakakis EA, Karpouzas DG. Isolation of Oxamyl-degrading Bacteria and Identification of cehA as a Novel Oxamyl Hydrolase Gene. Front Microbiol. 2016 Apr 29;7:616. doi: 10.3389/fmicb.2016.00616. eCollection 2016. PubMed PMID: 27199945; PubMed Central PMCID: PMC4850150. 3: McGarvey BD, Potter JW, Chiba M. Nematostatic Activity of Oxamyl and N,N-Dimethyl-1-cyanoformamide (DMCF) on Meloidogyne incognita Juveniles. J Nematol. 1984 Jul;16(3):328-32. PubMed PMID: 19294031; PubMed Central PMCID: PMC2618382. 4: Timmer LW, French JV. Control of Tylenchulus semipenetrans on Citrus With Aldicarb, Oxamyl, and DBCP. J Nematol. 1979 Oct;11(4):387-94. PubMed PMID: 19300660; PubMed Central PMCID: PMC2617976. 5: Strathmann TJ, Stone AT. Reduction of the pesticides oxamyl and methomyl by FeII: effect of pH and inorganic ligands. Environ Sci Technol. 2002 Feb 15;36(4):653-61. PubMed PMID: 11878379. 6: Strathmann TJ, Stone AT. Reduction of the carbamate pesticides oxamyl and methomyl by dissolved FeII and CuI. Environ Sci Technol. 2001 Jun 15;35(12):2461-9. PubMed PMID: 11432549. 7: Strathmann TJ, Stone AT. Reduction of oxamyl and related pesticides by FeII: influence of organic ligands and natural organic matter. Environ Sci Technol. 2002 Dec 1;36(23):5172-83. PubMed PMID: 12523435. 8: Kwon E, Park KM, Park H, Kim TH. Crystal structure of oxam-yl. Acta Crystallogr E Crystallogr Commun. 2016 Nov 18;72(Pt 12):1816-1818. eCollection 2016 Dec 1. PubMed PMID: 27980838; PubMed Central PMCID: PMC5137616. 9: Öztürk B, Ghequire M, Nguyen TP, De Mot R, Wattiez R, Springael D. Expanded insecticide catabolic activity gained by a single nucleotide substitution in a bacterial carbamate hydrolase gene. Environ Microbiol. 2016 Dec;18(12):4878-4887. doi: 10.1111/1462-2920.13409. Epub 2016 Jul 15. PubMed PMID: 27312345. 10: Nano GV, Strathmann TJ. Application of surface complexation modeling to the reactivity of iron(II) with nitroaromatic and oxime carbamate contaminants in aqueous TiO2 suspensions. J Colloid Interface Sci. 2008 May 15;321(2):350-9. doi: 10.1016/j.jcis.2008.02.017. Epub 2008 Mar 14. PubMed PMID: 18342323. 11: Steele AE. Effects of oxime carbamate nematicides on development of Heterodera schachtii on sugarbeet. J Nematol. 1976 Apr;8(2):137-41. PubMed PMID: 19308211; PubMed Central PMCID: PMC2620171. 12: Chapman RA, Cole CM. Observations on the influence of water and soil pH on the persistence of insecticides. J Environ Sci Health B. 1982;17(5):487-504. PubMed PMID: 7175098. 13: Dekker A, Houx NW. Simple determination of oxime carbamates in soil and environmental water by high pressure liquid chromatography. J Environ Sci Health B. 1983;18(3):379-92. PubMed PMID: 6875217. 14: Lu H, Lin Y, Wilson PC. Organic-solvent-free extraction method for determination of carbamate and carbamoyloxime pesticides in soil and sediment samples. Bull Environ Contam Toxicol. 2009 Nov;83(5):621-5. doi: 10.1007/s00128-009-9873-7. PubMed PMID: 19771381. 15: Steele AE. Effects of selected carbamate and organophosphate nematicides on hatching and emergence of Heterodera schachtii. J Nematol. 1977 Apr;9(2):149-54. PubMed PMID: 19305582; PubMed Central PMCID: PMC2620221. 16: Krause RT. Liquid chromatographic determination of N-methylcarbamate insecticides and metabolites in crops. II. Analytical characteristics and residue findings. J Assoc Off Anal Chem. 1985 Jul-Aug;68(4):734-41. PubMed PMID: 4030646. 17: Heinemann B. Prophage induction in lysogenic Escherichia coli with simple hydroxylamine and hydrazine compounds. Appl Microbiol. 1971 Apr;21(4):726-31. PubMed PMID: 4930282; PubMed Central PMCID: PMC377264.