Tolylfluanid

Tolylfluanid
Names
	Preferred IUPAC name N-{[Dichloro(fluoro)methyl]sulfanyl}-N′,N′-dimethyl-N-(4-methylphenyl)sulfuric diamide
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[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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

External links[edit]

[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.

[1]

[2]