Insecticide
2-dimethylaminopropane-1,3-dithiol



NOMENCLATURE
cartap
Common name cartap (BSI, E-ISO, (m) F-ISO, JMAF)
IUPAC name S,S'-(2-dimethylaminotrimethylene) bis(thiocarbamate) 
Chemical Abstracts name S,S'-[2-(dimethylamino)-1,3-propanediyl] dicarbamothioate 
CAS RN [15263-53-3]  Development codes TI-1258 (Takeda) 

cartap hydrochloride
Common name cartap hydrochloride
CAS RN [15263-52-2] cartap monohydrochloride; [22042-59-7] cartap, unspecified hydrochloride  EEC no. 239-309-2 

PHYSICAL CHEMISTRY
cartap
Mol. wt. 237.3  M.f. C₇H₁₅N₃O₂S₂ 

cartap hydrochloride
Mol. wt. 273.8  M.f. C₇H₁₆ClN₃O₂S₂  Form Colourless crystalline, slightly hygroscopic solid with slight odour.  M.p. 179-181 ºC (decomp.)  V.p. Negligible  Solubility In water c. 200 g/l (25 ºC). Very slightly soluble in methanol and ethanol. Insoluble in acetone, diethyl ether, ethyl acetate, chloroform, benzene, and hexane.  Stability Stable in acidic conditions, but hydrolysed in neutral or alkaline media.

APPLICATIONS
Biochemistry Analogue or propesticide of the natural toxin nereistoxin. Nicotinergic acetylcholine blocker, causing paralysis by blocking cholinergic transmissions in the central nervous systems of insects.  Mode of action Systemic insecticide with stomach and contact action. Insects discontinue feeding, and die of starvation.

cartap hydrochloride
Uses Cartap hydrochloride is used, at c. 0.4-1.0 kg/ha, for control of chewing and sucking insects (particularly Lepidoptera and Coleoptera), at almost all stages of development, on many crops, including rice (Chilo suppressalis, Cnaphalocrocis medinalis, Lissorhoptrus oryzophilus and rice-leaf beetle), potatoes, cabbage and other vegetables (Agromyzidae, Leptinotarsa decemlineata and Plutella xylostella); also on soya beans, peanuts, sunflowers, maize, sugar beet, wheat, pearl barley, pome fruit, stone fruit, citrus fruit, vines, chestnuts, ginger, tea, cotton, and sugar cane.  Phytotoxicity May be phytotoxic to cotton, tobacco, and apples, under certain soil and climatic conditions.  Formulation types DP; GR; SP.  Compatibility Not compatible with pesticides which are alkaline.

ANALYSIS
Product analysis by colorimetry (CIPAC Handbook, 1988, D, 24). Residue analysis by glc or by polarography (K. Nishi et al., Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 371).

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 74 (see part 2 of the Bibliography).

cartap
ADI (JMPR) ADI withdrawn [1995]. 

cartap hydrochloride
Oral Acute oral LD₅₀ for male rats 345, female rats 325, male mice 150, female mice 154 mg/kg.  Skin and eye Acute percutaneous LD₅₀ for mice >1000 mg/kg; no irritation to skin or eyes in rabbits.  Inhalation LC₅₀ (6 h) for rats >0.54 mg/l.  NOEL (2 y) for rats 10 mg/kg b.w. daily; (1.5 y) for mice 20 mg/kg b.w. daily.  Toxicity class WHO (a.i.) II; EPA (formulation) II  EC hazard Xn; R21/22

ECOTOXICOLOGY
cartap hydrochloride
Fish LC₅₀ for carp 1.6 mg/l (24 h) and 1.0 mg/l (48 h).  Other aquatic spp. LC₅₀ (24 h) for Moina macrocopa 12.5-25 mg/l.  Bees Moderately toxic to honeybees. 

ENVIRONMENTAL FATE
EHC 76 (WHO, 1988).  Animals In rats, the carbonyl carbon is hydrolysed, and the sulfur oxidised, with N-demethylation of thiomethyl derivatives. No accumulation occurs in tissues. Rapidly excreted in the urine.  Soil/Environment DT₅₀ in soil c. 3 d.