Chlorophenylsilatrane

Last updated
1-(4-Chlorophenyl)silatrane
Chlorophenylsilatrane dativebond.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
Appearanceodorless, white powder [1]
Melting point 230-235 °C [1]
<0.2 g/L [1]
Solubility in Chloroform, Benzenesoluble [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]

Contents

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

Related Research Articles

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<span class="mw-page-title-main">Rotenone</span> Chemical compound

Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids. Rotenone was used in the past as a broad-spectrum insecticide, and is still used as a piscicide to remove alien fish species,

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<span class="mw-page-title-main">Rodenticide</span> Chemical used to kill rodents

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<span class="mw-page-title-main">Aldrin</span> Chemical compound

Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.

<span class="mw-page-title-main">Theobromine poisoning</span> Overdose reaction to the xanthine alkaloid theobromine

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<span class="mw-page-title-main">Tetramethylenedisulfotetramine</span> Chemical compound

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<span class="mw-page-title-main">Azinphos-methyl</span> Chemical compound

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<span class="mw-page-title-main">Methiocarb</span> Chemical compound

Methiocarb is a carbamate pesticide which is used as an insecticide, bird repellent, acaricide and molluscicide since the 1960s. Methiocarb has contact and stomach action on mites and neurotoxic effects on molluscs. Seeds treated with methiocarb also affect birds. Other names for methiocarb are mesurol and mercaptodimethur.

<span class="mw-page-title-main">Tutin (toxin)</span> Chemical compound

Tutin is a poisonous plant derivative found in New Zealand tutu plants. It acts as a potent antagonist of the glycine receptor, and has powerful convulsant effects. It is used in scientific research into the glycine receptor. It is sometimes associated with outbreaks of toxic honey poisoning when bees feed on honeydew exudate from the sap-sucking passion vine hopper insect, when the vine hoppers have been feeding on the sap of tutu bushes. Toxic honey is a rare event and is more likely to occur when comb honey is eaten directly from a hive that has been harvesting honeydew from passionvine hoppers feeding on tutu plants.

<span class="mw-page-title-main">Phenylsilatrane</span> Chemical compound

Phenylsilatrane is a convulsant chemical which has been used as a rodenticide. Phenylsilatrane and some of its analogs with 4-substituents of H, CH3, Cl, Br, and CSi(CH3)3 are highly toxic to mice. They have been observed in the laboratory to inhibit the 35S-tert-butylbicyclophosphorothionate (TBPS) binding site (GABA-gated chloride channel) of mouse brain membranes.

<span class="mw-page-title-main">2,3,7,8-Tetrachlorodibenzodioxin</span> Polychlorinated dibenzo-p-dioxin, chemical compound

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<span class="mw-page-title-main">Tetramethylammonium</span> Polyatomic ion (N(CH₃)₄, charge +1)

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<span class="mw-page-title-main">Monocrotaline</span> Chemical compound

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References

  1. 1 2 3 4 5 6 7 8 9 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. 1 2 3 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.