Thiodicarb

Bezeichnung:Thiodicarb

CAS-Nr59669-26-0

Englisch Name:Thiodicarb

CBNumberCB9185450

SummenformelC10H18N4O4S3

Molgewicht354.47

MOL-Datei59669-26-0.mol

Synonyma

Dimethyl-N,N'-[thiobis[(methylimino)carbonyloxy]]bis(thioimidoacetat)

Thiodicarb

Thiodicarb physikalisch-chemischer Eigenschaften

Schmelzpunkt	168-172°C
Siedepunkt	433.8±28.0 °C(Predicted)
Dichte	1.4000
Dampfdruck	5.1×10^-3 Pa (20 °C)
Brechungsindex	1.6000 (estimate)
storage temp.	0-6°C
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Wasserlöslichkeit	35 mg l^-1(25 °C)
pka	-1.79±0.70(Predicted)
Merck	13,9403
CAS Datenbank	59669-26-0(CAS DataBase Reference)
EPA chemische Informationen	Thiodicarb (59669-26-0)

Sicherheit

Kennzeichnung gefährlicher	T+
R-Sätze:	25-26
S-Sätze:	28-36/37-45
RIDADR	2757
WGK Germany	3
RTECS-Nr.	KJ4301050
HazardClass	6.1(b)
PackingGroup	III
Giftige Stoffe Daten	59669-26-0(Hazardous Substances Data)
Toxizität	LD50 in rats (mg/kg): 160 orally, >1600 dermally (Sousa)

Gefahreninformationscode (GHS)

Thiodicarb Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R26:Sehr giftig beim Einatmen.
S-Sätze Betriebsanweisung:
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
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.
Verwenden
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.
Verwenden
Thiodicarb is used as an insecticide.
Allgemeine Beschreibung
Colorless to pale tan crystals. Non corrosive. Used as an insecticide.
Air & Water Reaktionen
Hydrolyzed by strong acid or base.
Reaktivität anzeigen
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.
Landwirtschaftliche Anwendung
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.
Handelsname
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).
Stoffwechselwegen
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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