59669-26-0 Usage
Description
Thiodicarb, also known as 3,7,9,13-tetramethyl-5,11-dioxa-2,8,14-trithia-4,7,9,12-tetra-azapentadeca-3,12-diene-6,10-dione (IUPAC), is a white crystalline powder with a slight sulphurous odour. It is a carbamate insecticide and ovicide, stable in light and ambient conditions but unstable in alkaline conditions. Thiodicarb is used as an insecticide and is primarily used to protect agricultural crops from major lepidopterous insect pests and suppresses coleopterous and some hemipterous insect pests. It is also used as an ovicide against cotton bollworms and budworms.
Uses
Used in Agricultural Industry:
Thiodicarb is used as an insecticide and ovicide for protecting agricultural crops from major Lepidoptera, Coleoptera, Diptera, and Hemiptera pests. It is primarily used on cotton, sweet corn, and soybeans, with the remaining usage spread among leafy vegetables, cole crops, ornamentals, and other minor use sites.
Thiodicarb is used as an insecticide for controlling pests in/on cotton, maize, fruits, soyabeans, and vegetables due to its oral and contact activities against these pests.
Thiodicarb is also used as a molluscicide and ovicide, although it is not approved for use in EU countries. It is registered for use in the U.S. and acts as an ovicide against cotton bollworms and budworms.
Thiodicarb is formulated to include several liquid products and one powdered product that must be mixed with water before field application. It is reclassified as a Restricted Use Pesticide (RUP) and 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
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.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 59669-26-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,6,6 and 9 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 59669-26:
(7*5)+(6*9)+(5*6)+(4*6)+(3*9)+(2*2)+(1*6)=180
180 % 10 = 0
So 59669-26-0 is a valid CAS Registry Number.
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+
59669-26-0Relevant articles and documents
Synthesis method of thiodicarb
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Paragraph 0020-0062, (2021/03/13)
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
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Paragraph 0004; 0025; 0026, (2018/06/28)
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.