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MedKoo Cat#: 592543 | Name: Phoxim

Description:

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

Phoxim is a biochemical.

Chemical Structure

Phoxim
Phoxim
CAS#14816-18-3

Theoretical Analysis

MedKoo Cat#: 592543

Name: Phoxim

CAS#: 14816-18-3

Chemical Formula: C12H15N2O3PS

Exact Mass: 298.0541

Molecular Weight: 298.30

Elemental Analysis: C, 48.32; H, 5.07; N, 9.39; O, 16.09; P, 10.38; S, 10.75

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Synonym
Phoxim
IUPAC/Chemical Name
3,5-Dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile, 4-ethoxy-7-phenyl-, 4-sulfide
InChi Key
ATROHALUCMTWTB-OWBHPGMISA-N
InChi Code
InChI=1S/C12H15N2O3PS/c1-3-15-18(19,16-4-2)17-14-12(10-13)11-8-6-5-7-9-11/h5-9H,3-4H2,1-2H3/b14-12-
SMILES Code
CCOP(O/N=C(C1=CC=CC=C1)/C#N)(OCC)=S
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phoxim is an organic phosphorus pesticide and widely applies worldwide for agricultural purposes.
In vitro activity:
TBD
In vivo activity:
Phoxim was given by gavage administration once a day for 28 days. The results showed that phoxim significantly reduced jejunum villus height in rats (P < 0.05), and decreased the mRNA expression of junction protein genes of rats, including Occlidin and Claudin-4 (P < 0.05). Phoxim reduced GSH content and T-AOC level in the intestinal mucosa (P < 0.05). The mRNA expression levels of oxidative stress-related genes (Nrf2 and GPx2) were decreased. The mRNA expression of SOD was significantly increased. In addition, phoxim increased the level of interleukin-6 (IL-6) in jejunum mucosa and significantly reduced the level of IL-8 in ileum mucosas, while significantly increased TNF-α secretion. Reference: Environ Sci Pollut Res Int. 2018 Sep;25(26):26682-26692. https://pubmed.ncbi.nlm.nih.gov/30003487/

Preparing Stock Solutions

The following data is based on the product molecular weight 298.30 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. Li F, Li M, Mao T, Wang H, Chen J, Lu Z, Qu J, Fang Y, Gu Z, Li B. Effects of phoxim exposure on gut microbial composition in the silkworm, Bombyx mori. Ecotoxicol Environ Saf. 2020 Feb;189:110011. doi: 10.1016/j.ecoenv.2019.110011. Epub 2019 Nov 30. PMID: 31796255. 2. Sun Y, Zhang J, Song W, Shan A. Vitamin E alleviates phoxim-induced toxic effects on intestinal oxidative stress, barrier function, and morphological changes in rats. Environ Sci Pollut Res Int. 2018 Sep;25(26):26682-26692. doi: 10.1007/s11356-018-2666-y. Epub 2018 Jul 12. PMID: 30003487.
In vitro protocol:
TBD
In vivo protocol:
1. Li F, Li M, Mao T, Wang H, Chen J, Lu Z, Qu J, Fang Y, Gu Z, Li B. Effects of phoxim exposure on gut microbial composition in the silkworm, Bombyx mori. Ecotoxicol Environ Saf. 2020 Feb;189:110011. doi: 10.1016/j.ecoenv.2019.110011. Epub 2019 Nov 30. PMID: 31796255. 2. Sun Y, Zhang J, Song W, Shan A. Vitamin E alleviates phoxim-induced toxic effects on intestinal oxidative stress, barrier function, and morphological changes in rats. Environ Sci Pollut Res Int. 2018 Sep;25(26):26682-26692. doi: 10.1007/s11356-018-2666-y. Epub 2018 Jul 12. PMID: 30003487.
1: Liénard E, Nabuco A, Vandenabeele S, Losson B, Tosi I, Bouhsira É, Prévot F, Sharif S, Franc M, Vanvinckenroye C, Caron Y. First evidence of Besnoitia bennetti infection (Protozoa: Apicomplexa) in donkeys (Equus asinus) in Belgium. Parasit Vectors. 2018 Jul 18;11(1):427. doi: 10.1186/s13071-018-2993-3. PubMed PMID: 30021659. 2: Sun Y, Zhang J, Song W, Shan A. Vitamin E alleviates phoxim-induced toxic effects on intestinal oxidative stress, barrier function, and morphological changes in rats. Environ Sci Pollut Res Int. 2018 Jul 12. doi: 10.1007/s11356-018-2666-y. [Epub ahead of print] PubMed PMID: 30003487. 3: Thomas E, Zoller H, Liebisch G, Alves LFA, Vettorato L, Chiummo RM, Sigognault-Flochlay A. In vitro activity of fluralaner and commonly used acaricides against Dermanyssus gallinae isolates from Europe and Brazil. Parasit Vectors. 2018 Jun 25;11(1):361. doi: 10.1186/s13071-018-2956-8. PubMed PMID: 29941050; PubMed Central PMCID: PMC6019301. 4: Zhang S, Luo J, Wang L, Zhang L, Zhu X, Jiang W, Cui J. Bacterial communities in natural versus pesticide-treated Aphis gossypii populations in North China. Microbiologyopen. 2018 Jun 7:e00652. doi: 10.1002/mbo3.652. [Epub ahead of print] PubMed PMID: 29877631. 5: Zheng M, Wang C, Wang Y, Wei W, Ma S, Sun X, He J. Green synthesis of carbon dots functionalized silver nanoparticles for the colorimetric detection of phoxim. Talanta. 2018 Aug 1;185:309-315. doi: 10.1016/j.talanta.2018.03.066. Epub 2018 Mar 23. PubMed PMID: 29759205. 6: Chen M, Zhai J, Liu Y, Xue B, Hu J, Cheng X, Li J, Hu J, Li B. Molecular cloning and characterization of C(1) tetrahydrofolate (C(1)-THF) synthase in Bombyx mori, silkworm. Gene. 2018 Jul 15;663:25-33. doi: 10.1016/j.gene.2018.04.037. Epub 2018 Apr 14. PubMed PMID: 29660516. 7: Hu J, Chen J, Wang H, Mao T, Li J, Cheng X, Hu J, Xue B, Li B. Cloning and Functional Analysis of CncC and Keap1 Genes in Silkworm. J Agric Food Chem. 2018 Mar 21;66(11):2630-2636. doi: 10.1021/acs.jafc.7b05820. Epub 2018 Mar 2. PubMed PMID: 29482325. 8: Ranjan A, Chauhan A, Jindal T. In-silico and in-vitro evaluation of human acetylcholinesterase inhibition by organophosphates. Environ Toxicol Pharmacol. 2018 Jan;57:131-140. doi: 10.1016/j.etap.2017.12.014. Epub 2017 Dec 17. PubMed PMID: 29272792. 9: Sun L, Liu H, Gao X, Chen W, Huang K, Zhang S. Isolation of monocrotophos-degrading strain Sphingobiumsp. YW16 and cloning of its TnopdA. Environ Sci Pollut Res Int. 2018 Feb;25(5):4942-4950. doi: 10.1007/s11356-017-0718-3. Epub 2017 Dec 4. PubMed PMID: 29204940. 10: He L, Cui W, Wang Y, Zhao W, Xiang G, Jiang X, Mao P, He J, Zhang S. Polymeric ionic liquid based on magnetic materials fabricated through layer-by-layer assembly as adsorbents for extraction of pesticides. J Chromatogr A. 2017 Nov 3;1522:9-15. doi: 10.1016/j.chroma.2017.09.047. Epub 2017 Sep 22. PubMed PMID: 28965990. 11: Zhang J, Song W, Sun Y, Shan A. Effects of phoxim-induced hepatotoxicity on SD rats and the protection of vitamin E. Environ Sci Pollut Res Int. 2017 Nov;24(32):24916-24927. doi: 10.1007/s11356-017-0104-1. Epub 2017 Sep 16. PubMed PMID: 28918601. 12: Mullens BA, Murillo AC, Zoller H, Heckeroth AR, Jirjis F, Flochlay-Sigognault A. Comparative in vitro evaluation of contact activity of fluralaner, spinosad, phoxim, propoxur, permethrin and deltamethrin against the northern fowl mite, Ornithonyssus sylviarum. Parasit Vectors. 2017 Aug 3;10(1):358. doi: 10.1186/s13071-017-2289-z. PubMed PMID: 28768553; PubMed Central PMCID: PMC5541702. 13: Zuo YY, Huang JL, Wang J, Feng Y, Han TT, Wu YD, Yang YH. Knockout of a P-glycoprotein gene increases susceptibility to abamectin and emamectin benzoate in Spodoptera exigua. Insect Mol Biol. 2018 Feb;27(1):36-45. doi: 10.1111/imb.12338. Epub 2017 Jul 28. PubMed PMID: 28753233. 14: Zhao Y, Wang Q, Wang Y, Zhang Z, Wei Y, Liu F, Zhou C, Mu W. Chlorfenapyr, a Potent Alternative Insecticide of Phoxim To Control Bradysia odoriphaga (Diptera: Sciaridae). J Agric Food Chem. 2017 Jul 26;65(29):5908-5915. doi: 10.1021/acs.jafc.7b02098. Epub 2017 Jul 17. PubMed PMID: 28672113. 15: Chen C, Shi X, Desneux N, Han P, Gao X. Detection of insecticide resistance in Bradysia odoriphaga Yang et Zhang (Diptera: Sciaridae) in China. Ecotoxicology. 2017 Sep;26(7):868-875. doi: 10.1007/s10646-017-1817-0. Epub 2017 May 23. PubMed PMID: 28536793. 16: Zhang D, He S, Ming T, Lu C, Zhou J, Su X. A metabonomic analysis on the response of Enterobacter cloacae from coastal outfall for land-based pollutant under phoxim stress. Arch Microbiol. 2017 Oct;199(8):1165-1173. doi: 10.1007/s00203-017-1383-0. Epub 2017 May 15. PubMed PMID: 28508092. 17: Han Y, Song S, Wu H, Zhang J, Ma E. Antioxidant enzymes and their role in phoxim and carbaryl stress in Caenorhabditis elegans. Pestic Biochem Physiol. 2017 May;138:43-50. doi: 10.1016/j.pestbp.2017.02.005. Epub 2017 Feb 24. PubMed PMID: 28456303. 18: Cang T, Dai D, Yang G, Yu Y, Lv L, Cai L, Wang Q, Wang Y. Combined toxicity of imidacloprid and three insecticides to the earthworm, Eisenia fetida (Annelida, Oligochaeta). Environ Sci Pollut Res Int. 2017 Mar;24(9):8722-8730. doi: 10.1007/s11356-017-8627-z. Epub 2017 Feb 16. PubMed PMID: 28210953. 19: Hu J, Tian J, Li F, Xue B, Hu J, Cheng X, Li J, Shen W, Li B. Clone and functional analysis of Seryl-tRNA synthetase and Tyrosyl-tRNA synthetase from silkworm, Bombyx mori. Sci Rep. 2017 Jan 30;7:41563. doi: 10.1038/srep41563. PubMed PMID: 28134300; PubMed Central PMCID: PMC5278501. 20: Tian JH, Xue B, Hu JH, Li JX, Cheng XY, Hu JS, Li FC, Chen YH, Li B. Exogenous substances regulate silkworm fat body protein synthesis through MAPK and PI3K/Akt signaling pathways. Chemosphere. 2017 Mar;171:202-207. doi: 10.1016/j.chemosphere.2016.12.080. Epub 2016 Dec 19. PubMed PMID: 28024205.