Cartap hydrochloride CAS 15263-52-2

Introduction：Basic information about Cartap hydrochloride CAS 15263-52-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Cartap hydrochloride Basic information

• Product Name: Cartap hydrochloride
• Synonyms: CADAN(R) HYDROCHLORIDE;CARTAP HYDROCHLORIDE;S,S'-[2-(dimethylamino)-1,3-propanediyl] dicarbamothioate hydrochloride;PADAN(R);S,S'2-DIMETHYLAMINOTRIMETHYLENE BIS-(THIOCARBAMATE) HYDROCHLORIDE;SUNTAP(R);SUNVEX(R);VEGETOX(R) HYDROCHLORIDE
• CAS: 15263-52-2
• MF: C7H16ClN3O2S2
• MW: 273.79
• EINECS: 239-309-2
• Product Categories: Nereistoxin analogue;Alpha sort;C;CA - CGPesticides;CAlphabetic;Insecticides;Pesticides&Metabolites;INSECTICIDE;OLED
• Mol File: 15263-52-2.mol

Cartap hydrochloride Chemical Properties

• density: 1.4008 (rough estimate)
• vapor pressure: Negligible
• refractive index: 1.6100 (estimate)
• storage temp.: 2-8°C
• solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• pka: 7.61 (base)
• Water Solubility: ca. 200 g l^-1 (20 °C, pH 5)
• BRN: 5157539
• Major Application: agriculture environmental
• InChI: 1S/C7H15N3O2S2.ClH/c1-10(2)5(3-13-6(8)11)4-14-7(9)12;/h5H,3-4H2,1-2H3,(H2,8,11)(H2,9,12);1H
• InChIKey: MSHXTAQSSIEBQS-UHFFFAOYSA-N
• SMILES: Cl[H].CN(C)C(CSC(N)=O)CSC(N)=O
• EPA Substance Registry System: Carbamothioic acid, S,S'-(2-(dimethylamino)-1,3-propanediyl) ester, monohydrochloride (15263-52-2)

Safety Information

• Hazard Codes: Xn;N,N,Xn
• Risk Statements: 21/22-50/53
• Safety Statements: 2-36/37-60-61
• RIDADR: 2771
• WGK Germany: 3
• RTECS: FD1225000
• HazardClass: 6.1(b)
• PackingGroup: III
• Storage Class: 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
• Hazard Classifications: Acute Tox. 3 Oral Acute Tox. 4 Dermal Aquatic Acute 1 Aquatic Chronic 1
• Toxicity: LD50 oral in rat: 250mg/kg

Cartap hydrochloride Usage And Synthesis

Chemical Properties

Fenitrothion is usually made into hydrochloride, the appearance of white crystals, with a slight strange odor. m.p. 183 ~ 183.5 ° C (decomposition) (melting point of the original drug is 179 ~ 181 ° C). Slightly soluble in methanol, insoluble in ethanol, insoluble in organic solvents such as acetone, ether, chloroform, hexane, benzene, etc.; solubility in water is 200g/L at 25°C. It is stable in acidic medium, unstable in alkaline medium. It is stable in acidic medium, unstable in alkaline medium, no change when stored at 40℃ and 60℃ for 3 months, no change when stored in airtight at room temperature, slightly hygroscopic, corrosive to iron and other metals. Its free alkali melting point is 130.5～131℃.

Uses

Cartap hydrochloride is used to control sucking and chewinginsects (particularly Lepidoptera and Coleoptera), at almost all stages ofdevelopment, on many crops including rice, potatoes, cabbage and othervegetables. It is also used on soya, peanuts, sunflower, maize, sugar beet,wheat, pearl barley, pome, stone and citrus fruit, vines, tea, chestnuts,ginger, cotton and sugar cane.

Agricultural Uses

Insecticide: Cartap hydrochloride is used to control chewing and sucking insects on many crops, including rice, potatoes, cabbage and other vegetables, soy beans, peanuts, sunflowers, maize, sugar beet, wheat, pearl barley, pome fruit, stone fruit, citrus fruit, vines, chestnuts, ginger, tea, cotton, and sugar cane. Not currently registered in the U.S. or registered for use in EU countries. There are approximately 15 global suppliers.

Trade name

CADAN®; CALDAN®; KRITAP®; NTD 2®; PADAN®; PATAP®; SANVEX®; THIOBEL®; TI1258®; VEGETOX®

Safety Profile

Poison by ingestion andintravenous routes. An experimental teratogen. Aninsecticide. When heated to decomposition it emits verytoxic fumes of NOx, SOx, and HCl.

Metabolic pathway

Nereistoxin, 4-N,N-dimethylamino-1,2-dithiolane, isproduced from cartap hydrochloride as a main productthrough photoreaction under UV irradiation in aqueousand methanolic solutions, and on glass and silica gelsurfaces. Cartap hydrochloride is also oxidized withN-bromosuccinimide (NBS) to give nereistoxin.

Degradation

Cartap hydrochloride was hydrolysed to dihydronereistoxin (2) whenautomatically titrated with sodium hydroxide solution and subsequentlyoxidised to nereistoxin (3) (see Scheme 1). The hydrolysis was a basecatalysed pseudo-first-order reaction with a half-life of 10 minutes at pH 7and 25 °C. Nereistoxin was so stable that no degradation was observedafter 24 hours at 100 °C and with pH in the range 1-4. The DT₅₀ s of nereistoxin at 100 °C and at the higher pH values of 7/10 and 12.3 were 26,20and 7.9 hours, respectively. It was predicted that nereistoxin (3) wouldbe hydrolysed by alkali to the 3-mercaptopropanesulfenic acid (4) whichwould be oxidised to the sulfinic acid (5) and thence to the sulfonic acid(6) (Asahi and Yoshida, 1977).
An aqueous solution of unlabelled cartap hydrochloride was exposedto sunlight for a period of 5 days. Analysis was by IR, UV and MSmethods. Three products were isolated after irradiation and the majorof these was identified as a polymer of nereistoxin (7) and represented 80% of applied dose. The polymer (7) was not toxic to fish (Oryzias latips).
Cartap was hydrolysed to nereistoxin (3) via dihydronereistoxin (2).Nereistoxin (3) was converted into the polymer (7) probably after photolyticformation of a nereistoxin diradical as shown in Scheme 1 (Obayashiand Asaka, 1983).