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Substance Name: Thiophanate-methyl [ANSI:BSI:ISO]
RN: 23564-05-8
UNII: K4N81R84L8
InChIKey: QGHREAKMXXNCOA-UHFFFAOYSA-N

Note

  • Nematocide used in livestock; also has fungicidal properties.

Molecular Formula

  • C12-H14-N4-O4-S2

Molecular Weight

  • 342.399
 

Classification Codes

  • Agricultural Chemical
  • Anthelmintics
  • Anti-Infective Agents
  • Antinematodal Agents
  • Antiparasitic Agents
  • Fungicide
  • Fungicide, Bactericide, Wood Preservative
  • Fungicides, Industrial
  • Mutation Data
  • Pesticides
  • Reproductive Effect

Names and Synonyms

Results Name

  • Thiophanate-methyl [ANSI:BSI:ISO]

Name of Substance

  • Thiophanate
  • Thiophanate methyl
  • Thiophanate-methyl [ANSI:BSI:ISO]

MeSH Heading

  • Thiophanate

Synonyms

  • 1,2-Bis(3-(methoxycarbonyl)-2-thioureido)benzene
  • 1,2-Bis(methoxycarbonylthioureido)benzene
  • 1,2-Di-(3-methoxycarbonyl-2-thioureido)benzene
  • AI3-27905
  • BAS 32500F
  • BRN 0937942
  • Caligran
  • Caswell No. 375A
  • CCRIS 6101
  • Cercobin M
  • Cercobin methyl
  • Cycosin
  • Dimethyl ((1,2-phenylene)bis-(iminocarbonothioyl))bis(carbamate)
  • Dimethyl 4,4'-o-phenylenebis(3-thioallophanate)
  • Ditek
  • Easout
  • EINECS 245-740-7
  • Enovit M
  • Enovit methyl
  • Enovit Super
  • EPA Pesticide Chemical Code 102001
  • F 6385
  • Fungo
  • Fungo 50
  • HSDB 6937
  • Methyl thiophanate
  • Methyl topsin
  • Methylthiofanate
  • Methylthiophanate
  • Metoben
  • Mildothane
  • Neotopsin
  • NF 44
  • NSC 170811
  • o-Bis(3-methoxycarbonyl-2-thioureido)benzene
  • PEI 190
  • PELT 14
  • PELT-44
  • Rilon
  • Sipcaplant
  • Sipcasan
  • Sipcavit
  • TD 1771
  • Thiopan
  • Thiophanate M
  • Thiophanate methyl
  • Thiophanate-methyl
  • Tiofanate metile
  • Tiofanate metile [Italian]
  • Topsin M
  • Topsin Methyl
  • Topsin NF 44
  • Topsin NF-44
  • Topsin turf and ornamentals
  • Topsin WP methyl
  • Topsin-M
  • Trevin
  • UNII-K4N81R84L8

Systematic Names

  • Allophanic acid, 4,4'-o-phenylenebis(3-thio-, dimethyl ester
  • Carbamic acid, (1,2-phenylenebis(iminocarbonothioyl))bis-, dimethyl ester
  • Thiophanate
  • Thiophanate-methyl

Superlist Names

  • Carbamic acid, (1,2-phenylenebis(iminocarbonothioyl)bis-, dimethyl ester
  • Dimethyl ((1,2-phenylene)bis(iminocarbonothioyl))bis(carbamate)
  • RCRA waste no. U409
  • Thiophanate-methyl

Registry Numbers

CAS Registry Number

  • 23564-05-8

FDA UNII

  • K4N81R84L8

Other Registry Number

  • 50814-12-5

System Generated Number

  • 0023564058

Structure Descriptors

InChI

1S/C12H14N4O4S2/c1-19-11(17)15-9(21)13-7-5-3-4-6-8(7)14-10(22)16-12(18)20-2/h3-6H,1-2H3,(H2,13,15,17,21)(H2,14,16,18,22)

InChIKey

QGHREAKMXXNCOA-UHFFFAOYSA-N

Smiles

c1(c(NC(NC(OC)=O)=S)cccc1)NC(NC(OC)=O)=S

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 4gm/kg (4000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Toxicology and Applied Pharmacology. Vol. 23, Pg. 606, 1972.
guinea pig LD50 oral 3640mg/kg (3640mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Toxicology and Applied Pharmacology. Vol. 23, Pg. 606, 1972.
guinea pig LD50 skin > 10gm/kg (10000mg/kg)   Japan Pesticide Information. Vol. (5), Pg. 38, 1970.
mouse LD50 intraperitoneal 790mg/kg (790mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN OLFACTORY NERVE: OLFACTION
Toxicology and Applied Pharmacology. Vol. 23, Pg. 606, 1972.
mouse LD50 oral 3400mg/kg (3400mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN OLFACTORY NERVE: OLFACTION

BEHAVIORAL: TREMOR
Toxicology and Applied Pharmacology. Vol. 23, Pg. 606, 1972.
mouse LD50 skin > 10gm/kg (10000mg/kg)   Japan Pesticide Information. Vol. (5), Pg. 38, 1970.
quail LD50 skin > 5gm/kg (5000mg/kg)   Pesticide Manual. Vol. 9, Pg. 820, 1991.
rabbit LD50 oral 2270mg/kg (2270mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Toxicology and Applied Pharmacology. Vol. 23, Pg. 606, 1972.
rabbit LD50 skin > 10gm/kg (10000mg/kg)   Japan Pesticide Information. Vol. (5), Pg. 38, 1970.
rat LC50 inhalation 1700mg/m3/4H (1700mg/m3)   Farm Chemicals Handbook. Vol. -, Pg. C302, 1991.
rat LD50 intraperitoneal 1140mg/kg (1140mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN OLFACTORY NERVE: OLFACTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 23, Pg. 606, 1972.
rat LD50 oral 6640mg/kg (6640mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN OLFACTORY NERVE: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 23, Pg. 606, 1972.
rat LD50 skin > 10gm/kg (10000mg/kg)   Japan Pesticide Information. Vol. (5), Pg. 38, 1970.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 172 dec deg C   EXP
pKa Dissociation Constant 7.28 (none)   EXP
log P (octanol-water) 1.4 (none)   EXP
Water Solubility 26.6 mg/L 20 EXP
Vapor Pressure 7.13E-08 mm Hg 25 EXP
Henry's Law Constant 1.21E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.66E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.