Basic information
- Standard SMILES
CN(C)C(CSC(N)=O)CSC(N)=O.Cl- InChIKey
MSHXTAQSSIEBQS-UHFFFAOYSA-N- Molecular formula
- C7H16ClN3O2S2
- Average molar mass
- 273.8 g/mol
- Monoisotopic mass
- 273.03724643
Names & identifiers
- Preferred name
- Cartap hydrochloride
- IUPAC
- S-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydrochloride
- English name
- Cartap
- Molecular formula
- C7H16ClN3O2S2
- Molecular weight
- 273.8
Names & synonyms
Show more names
Database identifiers
- CAS
15263-52-2、22042-59-7- PubChem CID
- 30913
- DTXSID
DTXSID9058315- ChEMBL
CHEMBL2270409- UNII
- IWO0R06728
- EC Number
- 239-309-2、803-058-2
Properties
Computed structural properties
- Topological polar surface area
- 140 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 193
Experimental & physicochemical properties
Physicochemical properties
- storage temp.
- 0 · 0-6°C
- EPA Substance Registry System
- Carbamothioic acid, S,S'-(2-(dimethylamino)- 1,3-propanediyl) ester, monohydrochloride(22042-59-7)
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 410 · H410-H302+H312
- Precautionary statements
- 273 · P273-P391-P501
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- RTECS
- 1225000 · FD1225000
- Hazardous Substances Data
- 22042 · 22042-59-7(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)
Warning
H302+H312 (41.8%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)
Hazard information
Hazards Summary
In animal studies, doses up to 100 mg/kg during pregnancy caused minor skeletal changes attributed to maternal toxicity; In 2 year feeding study, no effects at 10 mg/kg/day and reduced body weight in 20 and 40 mg/kg/day diets with no significant changes in urine, blood, or tissues; Not irritating to skin and eyes; In insects, causes paralysis by ganglionic blocking of CNS; [HSDB] May cause irritation; Effects in high-dose animal studies include convulsions or effect on seizure threshold; [MSDSonline]
DOT Hazard Classification
Cartap hydrochloride
Marine pollutant
Hazard Classes and Categories
Acute Tox. 4 (98.5%)
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 4
Acute Tox. 4 *
Shipment Methods and Regulations
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Safety & protection
Toxicology
Ecotoxicity Values
LC50 Pomacea canaliculata (snail) (young) 2.0 ppm/48 hr /Conditions of bioassay not specified/
LC50 Pomacea canaliculata (snail) (adult) 1.9 ppm/48 hr /Conditions of bioassay not specified/
Environmental Fate
In aqueous medium, cartap hydrochloride hydrolyzed with loss of two -H2N-C=O to yield 1,3-dimercapto-2-(N,N-dimethylamino)propane. The latter oxidizes readily to the cyclic disulfide, 4-(N,N-dimethylamino)-1,2-dithiolane. At pH 7 and 25 °C, the half-life of cartap hydrochloride was 10 minutes. The half-life for compound III (nereistoxin) was calculated to be 2.4 years at pH 7. At pH 1.1 and 100 °C, the half-life was 2.2 hr and the hydrolysis product was 2-(N,N-dimethylamino)-3-mercaptopropanesulfenic acid.
Non-Human Toxicity Excerpts
... This insecticide /was studied/ in pregnant mice, rats, and hamsters. Doses up to 100 mg/kg given during organogenesis caused only minor skeletal changes which were ascribed to the maternal toxicity which occurred.
Safety of cartap soluble powder (Padan) to fish was evaluated when it was applied to the root zone of rice plants in a paddy field. Water samples in the rice paddy field were collected with water pump on 0 (3 hr after application), 1, 3, 6, 10 and 14 days after the application. Fish toxicity of each water sample was tested for 3 kinds of fish, goldfish (Carassius auratus), medaka (Oryzias latipes) and Asian pond loach (Cobitis angullicaudatus), in a room, temperature of which was 24.3-25.5 °C. None of the water samples showed toxicity to the three kinds of fish. For comparison, LC50 values of cartap hydrochloride to the fish were obtained through another study. LC50 values to goldfish, medaka and Asian pond loach were 0.58, 0.36 and 0.095 ppm, respectively. At the same time, residue of the active ingredient of cartap soluble powder, cartap hydrochloride, in each of the water samples was detected by gas chromatography. Residue of cartap hydrochloride was 0.006 ppm on 0 day after application and not detected, less than 0.001 ppm, 3 days after. It was concluded that root zone application of cartap soluble powder mixed with paste-fertilizer was very safe to the fish.
The feeding inhibitory efficiency of cartap was very high. In the submerged application of cartap granules (4 kg/10 a), feeding by the young snails was completely inhibited during 15 days after treatment. In the case of nursery box-treatment with cartap and granules (60 g or 100 g/box), feeding by the adult snails was almost completely inhibited during 21 day after transplanting. These results suggest that cartap is able to protect the rice plant from feeding by the snails for about 3 weeks in paddy field.
Non-irritating to skin and eyes (rabbits).
In 3 month feeding trials, rats receiving 25, 50, or 100 mg/kg/day showed no significant changes in urine, blood, and tissues in the 25 and 50 mg/kg groups. In the 2 year feeding trials on rats, no pathological alterations were caused by 10 mg/kg/day diet, and only a reduction in body weight with 20 and 40 mg/kg/day diets.
Non-Human Toxicity Values
LD50 Rat oral 340 mg/kg /Cartap/
LD50 Rat female acute oral 325 mg/kg
LD50 Rat male acute oral 345 mg/kg
LD50 Mouse acute percutaneous > 1000 mg/kg
Safety data
- rtecs
- FD1225000
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xn
- Hazard statements
- H410-H302+H312
- Precautionary statements
- P273-P391-P501
- Hazardous Substances Data
- 22042-59-7(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used as insecticide for control of chewing and sucking insects on rice, potatoes, cabbage, other vegetables, soya beans, groundnuts, maize, sugar beet, wheat, pome fruit, stone fruit, citrus fruit, tea, cotton, and sugar cane; [HSDB]
Farming (Pesticides) [Category: Industry]
Control of chewing and sucking insects, at almost all stages of development, on many crops, including rice, potatoes, cabbage and other vegetables, soya beans, groundnuts, maize, sugar beet, wheat, pome fruit, stone fruit, citrus fruit, tea, cotton, and sugar cane. Particularly effective against chewing insects belonging to the orders of Lepidoptera and Coleoptera, such as rice borers, diamond back moths, Colorado beetles.
Applications
DescriptionCartap is a largely obsolete insecticide. It is highly soluble in water, has a low volatility and tends not to persist in soil systems. There are data gaps regarding its human health effects but is known to be moderately toxic. There are also data gaps regarding its ecotoxicity but is highly toxic to aquatic vertebrates and moderately toxic to fish.
Suppliers38 total
Related reactions
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