tolylfluanid

Synonyms: "tolylfluanide", "N,N-Dimethyl-N-(4-tolyl)-N-(dichlorofluor-methylthio)-sulfamide", "N'-Dichlorofluoromethylthio-N,N-dimethyl-N'-(4-tolyl)sulfamide", "Euparen M", "Tolyfluanid", "Dichlofluanid-methyl".

Source: Tolylfluanid is a member of the phenylsulfamide group of fungicides and it has been applied in agriculture for control of fungal diseases during thinning, pruning, and harvesting fruitsand vegetables.

Identifiers:

IUPAC Name: N-[dichloro(fluoro)methyl]sulfanyl-N-(dimethylsulfamoyl)-4-methylaniline
CAS Number: 731-27-1
PubChem ID: 12898
InChiKey: HYVWIQDYBVKITD-UHFFFAOYSA-N
Canonical SMILES: CC1=CC=C(C=C1)N(SC(F)(Cl)Cl)S(=O)(=O)N(C)C

Structural Properties:

Molecular Formula: C₁₀H₁₃Cl₂FN₂O₂S₂
Molecular Weight: 347.244

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 6
Number of atoms different from hydrogen: 19

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3D structure (.sdf)
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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Johansson M, Johansson N, Lund BO. 2005. Xenobiotics and the glucocorticoid receptor: additive antagonistic effects on tyrosine aminotransferase activity in rat hepatoma cells. Basic Clin Pharmacol Toxicol 96(4):309-315. DOI: 10.1111/j.1742-7843.2005.pto960406.x. URL: https://www.ncbi.nlm.nih.gov/pubmed/15755314.
Neel BA, Brady MJ, Sargis RM. 2013. The Endocrine Disrupting Chemical Tolylfluanid Alters Adipocyte Metabolism via Glucocorticoid Receptor Activation. Mol Endocrinol 27(3):394-406. DOI: 10.1210/me.2012-1270. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3589671/.
Regnier SM, Kirkley AG, Ye H, El-Hashani E, Zhang X, Neel BA, Kamau W, Thomas CC, Williams AK, Hayes ET, Massad NL, Johnson DN, Huang L, Zhang C, Sargis RM. 2015. Dietary exposure to the endocrine disruptor tolylfluanid promotes global metabolic dysfunction in male mice. Endocrinology 156(3):896-910. DOI: 10.1210/en.2014-1668. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4330315/.
Sargis RM, Johnson DN, Choudhury RA, Brady MJ. 2010. Environmental endocrine disruptors promote adipogenesis in the 3T3-L1 cell line through glucocorticoid receptor activation. Obesity (Silver Spring) 18(7):1283-1288. DOI: 10.1038/oby.2009.419. URL: http://onlinelibrary.wiley.com/doi/10.1038/oby.2009.419/full.
Sargis RM, Neel BA, Brock CO, Lin Y, Hickey AT, Carlton DA, Brady MJ. 2012. The novel endocrine disruptor tolylfluanid impairs insulin signaling in primary rodent and human adipocytes through a reduction in insulin receptor substrate-1 levels. Biochim Biophys Acta 1822(6):952-960. DOI: 10.1016/j.bbadis.2012.02.015. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3338892/.