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Thiodicarb

Basic information Description References Safety Supplier Related

Thiodicarb Basic information

Product Name:
Thiodicarb
Synonyms:
  • CHIPCO
  • DICARBASULF
  • 3,7,9,13-TETRAMETHYL-5,11-DIOXA-2,8,14-TRITHIA-4,7,9,12-TETRAAZAPENTADECA-3,12-DIENE-6,10-DIONE
  • NIVRAL
  • SKIPPER
  • SEMEVIN(R)
  • THIODICARB
  • Bis[1-methylthioacetaldehyde-O-(N-methylcarbamoyl)oximino]sulfide
CAS:
59669-26-0
MF:
C10H18N4O4S3
MW:
354.47
EINECS:
261-848-7
Product Categories:
  • Aliphatics
  • Sulfur & Selenium Compounds
  • MolluscicidesAlphabetic
  • Alpha sort
  • MolluscicidesPesticides&Metabolites
  • Q-ZAlphabetic
  • INSECTICIDE
  • CarbamatesPesticides&Metabolites
  • Insecticides
  • Pesticides
  • TF - TO
Mol File:
59669-26-0.mol
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Thiodicarb Chemical Properties

Melting point:
168-172°C
Boiling point:
433.8±28.0 °C(Predicted)
Density 
1.4000
vapor pressure 
5.1×10-3 Pa (20 °C)
refractive index 
1.6000 (estimate)
storage temp. 
0-6°C
Water Solubility 
35 mg l-1(25 °C)
form 
neat
pka
-1.79±0.70(Predicted)
Merck 
13,9403
CAS DataBase Reference
59669-26-0(CAS DataBase Reference)
EPA Substance Registry System
Thiodicarb (59669-26-0)
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Safety Information

Hazard Codes 
T+
Risk Statements 
25-26
Safety Statements 
28-36/37-45
RIDADR 
2757
WGK Germany 
3
RTECS 
KJ4301050
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
59669-26-0(Hazardous Substances Data)
Toxicity
LD50 in rats (mg/kg): 160 orally, >1600 dermally (Sousa)
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Thiodicarb Usage And Synthesis

Description

Thiodicarb is a white crystalline powder with a slight sulphurous odour. Thiodicarb is stable in light and ambient conditions and unstable in alkaline conditions. Thiodicarb is a carbamate insecticide. Thiodicarb is commonly used to protect agricultural crops from major lepidopterous insect pests and suppresses coleopterous and some hemipterous insect pests. Thiodicarb acts as an ovicide against cotton bollworms and budworms. Thiodicarb is used primarily on cotton, sweet corn, and soybeans. Thiodicarb is formulated to include several liquid products and one powdered product that must be mixed with water before field application. Thiodicarb is reclassified as an RUP. Thiodicarb degrades rapidly to methomyl, which is already a restricted use chemical.

References

http://www.wisegeek.com/what-is-thiodicarb.htm
http://pmep.cce.cornell.edu/profiles/insect-mite/propetamphos-zetacyperm/thiodicarb/insect-prof-thiodicarb.html
http://www.inchem.org/documents/jmpr/jmpmono/v00pr09.htm#_00092120

Description

Thiodicarb, 3,7,9,13-tetramethyl-5,11- dioxa-2,8,14-trithia-4,7,9,12-tetra-azapentadeca-3,12-di ene-6,10-dione (IUPAC), consists of colorless crystals, which are sparingly soluble in water, readily soluble in dichloromethane, acetone, methanol, and xylene. Thiodicarb is produced by reaction of N,N -thiobis(methylcarbamic acid fluoride) with 2-methylthioacetaldoxim in the presence of a base.

Uses

Thiodicarb is used as an insecticide.

Uses

Insecticide.

Uses

Thiodicarb is an oxime carbamate insecticide and ovicide with both oral and contact activities against major Lepidoptera, Coleoptera, Diptera and Hemiptera pests in/on cotton, maize, fruits, soyabeans and vegetables.

General Description

Colorless to pale tan crystals. Non corrosive. Used as an insecticide.

Air & Water Reactions

Hydrolyzed by strong acid or base.

Reactivity Profile

A carbamate derivative. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Agricultural Uses

Insecticide, Molluscicide, Ovicide: Not approved for use in EU countries. Registered for use in the U.S. Thiodicarb is used primarily on cotton, sweet corn, and soybeans. The remaining usage is spread among leafy vegetables, cole crops, ornamentals, and other minor use sites. Thiodicarb acts as an ovicide against cotton bollworms and budworms.

Trade name

CGA® 45156; CHIPCO[C]; DICARBOSULF®; DICARBASULF®; LARVIN®; LEPICRON®; SEMEVIN®; NIVRAL®; UC-51762®; UC 51769®; UC 80502®

Environmental Fate

Soil. Under aerobic and anaerobic soil conditions, thiodicarb degrades to methomyl and methomyl oxime (Hartley and Kidd, 1987). The reported half-life in various soils is 3–8 days (Hartley and Kidd, 1987).

Metabolic pathway

The initial metabolic reaction of thiodicarb in soils, plants and animals is the hydrolytic or thiolytic cleavage of the N-S bond to methomyl. The subsequent metabolic pathway of methomyl involves hydrolysis / elimination reactions to yield S-methyl-N-hydroxythioacetimidate and ultimately acetonitrile and CO2 as the major terminal products. The metabolic pathways of thiodicarb are presented in Scheme l. See also the methomyl entry.

Degradation

Thiodicarb (1) is susceptible to alkaline hydrolysis (Feung and Heinzelmann, 1989). Thiodicarb was stable between pH 5 and 6, but it degraded rapidly in alkaline conditions (pH 9) with a DT50 of less than one day. The DT50 values of thiodicarb at pH 3 and 7 were 9 and 13 days, respectively. The initial degradation product of thiodicarb was methomyl (2) which was further hydrolysed to S-methyl-N-hydroxytoacetimidate (3) in alkaline solution (pH 9).
Photolysis of thiodicarb in water was not significant (Andrawes and College, 1977). The photolytic DT50 of thiodicarb was approximately 81 days. The major photolytic degradation product was methomyl(2).

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