59669-26-0

Basic information

• Product Name: Thiodicarb
• Synonyms: LARVIN;LARVIN(R);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)
• CAS NO: 59669-26-0
• Molecular Formula: C₁₀H₁₈N₄O₄S₃
• Molecular Weight: 354.47
• EINECS: 261-848-7
• Product Categories: INSECTICIDE;Alpha sort;MolluscicidesPesticides&Metabolites;Q-ZAlphabetic;MolluscicidesAlphabetic;CarbamatesPesticides&Metabolites;Insecticides;Pesticides;TF - TO;Aliphatics;Sulfur & Selenium Compounds
• Mol File: 59669-26-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 168-172°C
• Boiling Point: 433.8 °C at 760 mmHg
• Flash Point: 216.2 °C
• Appearance: Colorless to pale tan crystals
• Density: 1.4000
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 0-6°C
• PKA: -1.79±0.70(Predicted)
• Water Solubility: 35 mg l-1(25 °C)
• Merck: 13,9403
• CAS DataBase Reference: Thiodicarb(CAS DataBase Reference)
• NIST Chemistry Reference: Thiodicarb(59669-26-0)
• EPA Substance Registry System: Thiodicarb(59669-26-0)

Safety Data

• Hazard Codes: T+
• 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)

Usage

Description

Different sources of media describe the Description of 59669-26-0 differently. You can refer to the following data:
1. 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.
2. 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.

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

Uses

Different sources of media describe the Uses of 59669-26-0 differently. You can refer to the following data:
1. Thiodicarb is used as an insecticide.
2. Insecticide.
3. 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.

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).

InChI:InChI=1/C10H18N4O4S3/c1-7(19-5)11-17-9(15)13(3)21-14(4)10(16)18-12-8(2)20-6/h1-6H3/b11-7+,12-8+

Upstream product

• 16752-77-5 Methomyl 

Relevant articles and documents

Synthesis method of thiodicarb

The invention provides a synthesis method of thiodicarb, and the method comprises the following steps: synthesizing a ligand, and synthesizing thiodicarb. According to the invention, trialkyl tertiaryamine is used as a catalyst for synthesis of thiodicarb, and during synthesis of thiodicarb, the reaction pressure is increased, and the industrial synthesis reaction time is shortened to 5 hours; inthe thiodicarb synthesis process, the temperature is controlled in three stages, the reaction temperature is controlled at 10-15 DEG C for 1-1.5 hours, the reaction temperature is controlled at 20-25DEG C for 1-1.5 hours, the reaction temperature is controlled at 30-35 DEG C for 1-2 hours, and gradient heating is adopted, so the defect of multiple side reactions caused by always reacting at a relatively high temperature is avoided.

Preparation method of thiodicarb

The invention discloses a preparation method of thiodicarb. The preparation method comprises the following steps: (1) dividing a solvent into two portions, dissolving methomyl in one of the two portions to obtain a methomyl solution, and dissolving 4-dimethylaminopyridine in the other portion to obtain a solvent which contains a catalyst; and (2) dividing sulfur dichloride into two portions, dropwise adding one portion of the sulfur dichloride in the solvent which contains the catalyst under a closed condition, meanwhile, dropwise adding the other portion of sulfur dichloride and carrying outdropwise adding reaction on the other portion of sulfur dichloride and the methomyl solution obtained in step (1), and carrying out insulating reaction after dropwise adding is finished to obtain thethiodicarb. The preparation method of the thiodicarb has the advantages that the reaction selectivity is high, the purity of the obtained product is high, the content of thiodicarb isomer is smaller than 0.4%, the yield is high and the like.