Tolylfluanid

Tolylfluanid
Names
	IUPAC name N-[dichloro(fluoro)methyl]sulfanyl-N-(dimethylsulfamoyl)-4-methylaniline
Identifiers
CAS Number	731-27-1 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.010.898
PubChem CID	12898;
UNII	382277YXSG ;
CompTox Dashboard (EPA)	DTXSID8042478 ;
	InChI InChI=1S/C10H13Cl2FN2O2S2/c1-8-4-6-9(7-5-8)15(18-10(11,12)13)19(16,17)14(2)3/h4-7H,1-3H3 Key: HYVWIQDYBVKITD-UHFFFAOYSA-N;
	SMILES CC1=CC=C(C=C1)N(SC(F)(Cl)Cl)S(=O)(=O)N(C)C;
Properties
Chemical formula	C10H13Cl2FN2O2S2
Molar mass	347.244 g/mol
Appearance	colourless, odourless crystals
Density	1.52 g/cm3
Melting point	93°C
Boiling point	Decomposes on distillation
Solubility in water	water, 0.9 mg/L at 20°C. Miscible in all proportions with acetone, ethanol, ethyl acetate, methylene chloride
Vapor pressure	<1.3 mPa (20°C)
Related compounds
Related compounds	Dichlofluanid
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1000 mg/kg (oral); 5000 mg/kg (skin absorption);
LC50 (median concentration)	0.02-0.3 mg/L
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Tolylfluanid is an organic chemical compound that is used as an active ingredient in fungicides and wood preservatives.

Synthesis

The synthesis of tolylfluanid begins with the reaction of dimethylamine and sulfuryl chloride. The product further reacts with p-toluidine and dichlorofluoromethanesulfenyl chloride to yield the final product.[1]

Use

Tolylfluanid is used on fruit and ornamental plants against gray mold (Botrytis), against late blight on tomatoes and against powdery mildew on cucumbers.

Environmental behavior

Tolylfluanid hydrolyzes slowly in acidic conditions. The half-life is shorter when the pH is high; at pH = 7, it is at least 2 days. In aerobic media (pH = 7.7-8.0), tolylfluanid hydrolytically and microbially decomposes to N,N-dimethyl-N-(4-methylphenyl) sulfamide (DMST) and dimethylsulfamide. After 14 days, tolylfluanid is generally considered to have degraded. The half-life of DMST is 50-70 days. [2]

Absorption, metabolism and excretion

Tolylfluanid is rapidly and almost completely absorbed in the gastrointestinal tract. The highest concentrations are found in the blood, lungs, liver, kidneys, spleen and thyroid gland. 99% is excreted in the urine within two days, although there is some accumulation in the thyroid gland. [2]

References

Thomas A. Unger (1996). Pesticide Synthesis Handbook. William Andrew. p. 985. ISBN 0-8155-1853-6.
Svensk Chemicals Inspection : Tolylfluanid (PDF). Archived from the original (PDF) on 2007-09-27.

External links

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[synthesis-1] Thomas A. Unger (1996). Pesticide Synthesis Handbook. William Andrew. p. 985. ISBN 0-8155-1853-6.

[kemi-2] Svensk Chemicals Inspection : Tolylfluanid (PDF). Archived from the original (PDF) on 2007-09-27.