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Cartap hydrochloride

Basic information Safety Supplier Related

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
  • INSECTICIDE
  • Pesticides&Metabolites
Mol File:
15263-52-2.mol
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Cartap hydrochloride Chemical Properties

Density 
1.4008 (rough estimate)
vapor pressure 
Negligible
refractive index 
1.6100 (estimate)
solubility 
DMSO (Slightly), Methanol (Slightly), Water (Slightly)
pka
7.61 (base)
Water Solubility 
ca. 200 g l-1 (20 °C, pH 5)
BRN 
5157539
EPA Substance Registry System
Carbamothioic acid, S,S'-(2-(dimethylamino)-1,3-propanediyl) ester, monohydrochloride (15263-52-2)
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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
Toxicity
LD50 oral in rat: 250mg/kg

MSDS

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Cartap hydrochloride Usage And Synthesis

Uses

Cartap hydrochloride is used to control sucking and chewing insects (particularly Lepidoptera and Coleoptera), at almost all stages of development, on many crops including rice, potatoes, cabbage and other vegetables. 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, is produced from cartap hydrochloride as a main product through photoreaction under UV irradiation in aqueous and methanolic solutions, and on glass and silica gel surfaces. Cartap hydrochloride is also oxidized with N-bromosuccinimide (NBS) to give nereistoxin.

Degradation

Cartap hydrochloride was hydrolysed to dihydronereistoxin (2) when automatically titrated with sodium hydroxide solution and subsequently oxidised to nereistoxin (3) (see Scheme 1). The hydrolysis was a base catalysed pseudo-first-order reaction with a half-life of 10 minutes at pH 7 and 25 °C. Nereistoxin was so stable that no degradation was observed after 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 26,20 and 7.9 hours, respectively. It was predicted that nereistoxin (3) would be hydrolysed by alkali to the 3-mercaptopropanesulfenic acid (4) which would 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 exposed to sunlight for a period of 5 days. Analysis was by IR, UV and MS methods. Three products were isolated after irradiation and the major of 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 photolytic formation of a nereistoxin diradical as shown in Scheme 1 (Obayashi and Asaka, 1983).

Cartap hydrochloride Supplier

Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810
Email
sales@sunlidabio.com
TargetMol Chemicals Inc.
Tel
021-33632979 15002134094
Email
marketing@targetmol.com
TianJin Alta Scientific Co., Ltd.
Tel
022-65378550-8551
Email
contact@altascientific.com
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com