Tolylfluanid

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Tolylfluanid
Tolyfluanid.svg
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 Edit this at Wikidata
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).

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]

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

External links[edit]