Chlorophenylsilatrane

1-(4-Chlorophenyl)silatrane
Names
IUPAC name
1-(4-Chlorophenyl)-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecane
Other names
RS-150
Caswell No. 213B
1-(p-Chlorophenyl)silatrane
5-(p-Chlorophenyl)silatrane
5-(4-Chlorophenyl)silatrane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.252.129 Edit this at Wikidata
UNII
  • InChI=1S/C12H16ClNO3Si/c13-11-1-3-12(4-2-11)18-15-8-5-14(6-9-16-18)7-10-17-18/h1-4H,5-10H2
    Key: IKFVTMCLFHXPQF-UHFFFAOYSA-N
  • c1cc(ccc1[Si]23OCCN(CCO2)CCO3)Cl
Properties
C12H16ClNO3Si
Molar mass 285.8 g/mol
Appearance odorless, white powder[1]
Melting point 230-235 °C[1]
<0.2 g/L[1]
Solubility in Chloroform, Benzene soluble[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Extremely toxic
Lethal dose or concentration (LD, LC):
1-4 mg/kg (rats, oral)[1]
3000 mg/kg (rats, dermal)[1]
0.9-2.0 mg/kg (mice, oral)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-(4-Chlorophenyl)silatrane is an extremely toxic[2] organosilicon compound which was developed by M&T Chemicals as a single-dose rodenticide.[1] It was never registered as rodenticide,[2] except for experimental use.[1] 1-(4-Chlorophenyl)silatrane was one of the chemicals studied in the Project Coast.[3][4]

Toxicity

1-(4-Chlorophenyl)silatrane is a GABA receptor antagonist[5] and it destroys nervous functions in the central nervous system of vertebrates, primarily in the brain and possibly in the brain stem.[6][7][8] It's a rapid acting convulsant, causing convulsions within 1 minute in mice and rats. Death occurred within 5 minutes.[9] It is therefore likely to induce poison shyness.[2] In field trials, it was less effective than zinc phosphide against wild rats.[10]

See also

References

  1. ^ a b c d e f g h i Crabtree, D. Glen; Beiter, Charles B.; Schwarcz, Morton (1970). "5-p-Chlorophenyl silatrane, a new single-dose rodenticide". Chemical Report by M&T Chemicals Inc.
  2. ^ a b c Lund, M. (1977). "New Rodenticides Against Anticoagulant-resistant Rats and Mice". EPPO Bulletin. 7 (2). Wiley: 503–508. doi:10.1111/j.1365-2338.1977.tb02750.x. ISSN 0250-8052.
  3. ^ "South Africa Chemical Chronology" (PDF). NTI.org. Nuclear Threat Initiative. 2005-04-23. Retrieved 2020-07-31.
  4. ^ Bale, Jeffrey M. (2006). "South Africa's Project Coast: "Death Squads," Covert State-Sponsored Poisonings, and the Dangers of CBW Proliferation". Democracy and Security. 2 (1). Informa UK Limited: 27–59. doi:10.1080/17419160600623434. ISSN 1741-9166. S2CID 143175071.
  5. ^ Casida, JE; Lawrence, LJ (September 1985). "Structure-activity correlations for interactions of bicyclophosphorus esters and some polychlorocycloalkane and pyrethroid insecticides with the brain-specific t-butylbicyclophosphorothionate receptor". Environmental Health Perspectives. 61: 123–32. doi:10.2307/3430066. JSTOR 3430066. PMC 1568750. PMID 2415350.
  6. ^ Casida, John E.; Eto, Morifusa; Moscioni, A.David; Engel, Judith L.; Milbrath, Dean S.; Verkade, John G. (1976). "Structure-toxicity relationships of 2,6,7-trioxabicyclo[2.2.2]-octanes and related compounds". Toxicology and Applied Pharmacology. 36 (2). Elsevier BV: 261–279. Bibcode:1976ToxAP..36..261C. doi:10.1016/0041-008x(76)90006-5. ISSN 0041-008X. PMID 1084063.
  7. ^ Mattson, H.; Brandt, K.; Heilbronn, E. (21–26 August 1977). Proceedings of the International Society of Neurochemistry. Sixth International Meeting of the International Society for Neurochemistry. Copenhagen, Denmark. p. 56.
  8. ^ Voronkov, Michail G. (1979). "Biological activity of silatranes". Topics in Current Chemistry. Vol. 84. Berlin/Heidelberg: Springer-Verlag. pp. 77–135. doi:10.1007/bfb0048523. ISBN 3-540-09347-8. PMID 388722.
  9. ^ Greaves, JH; Redfern, R; Tinworth, H (August 1974). "Laboratory tests of 5-p-chlorophenyl silatrane as a rodenticide". The Journal of Hygiene. 73 (1): 39–43. doi:10.1017/s0022172400023810. PMC 2130561. PMID 4529452.
  10. ^ Rennison, B. D. (1974). "Field trials of the rodenticide 5-p-chlorophenyl silatrane against wild rats (Rattus norvegicus Berk.)". Journal of Hygiene. 73 (1). Cambridge University Press: 45–48. doi:10.1017/s0022172400023822. ISSN 0022-1724. PMC 2130558. PMID 4529041.