Tolylfluanid

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

Tolylfluanid
Names
Preferred IUPAC name
N-{[Dichloro(fluoro)methyl]sulfanyl}-N′,N′-dimethyl-N-(4-methylphenyl)sulfuric diamide
Identifiers
3D model (JSmol)
ECHA InfoCard 100.010.898
UNII
  • 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
  • CC1=CC=C(C=C1)N(SC(F)(Cl)Cl)S(=O)(=O)N(C)C
Properties
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
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):
  • 1000 mg/kg (oral)
  • 5000 mg/kg (skin absorption)
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

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