N- octyl bicycloheptene dicarboximide

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Structural formula
Structural formula of N-Octyl_bicycloheptene_dicarboximide.svg
Structural formula without specifying the stereoisomerism
General
Surname N-Octyl-bicycloheptene-dicarboximide
other names
  • MGK 264
  • Sinepyrine 222
  • Pyrodons
  • N - (2-ethylhexyl) -5-norbornene-2,3-dicarboximide
  • 4- (2-Ethylhexyl) -4-aza-tricyclo [5.2.1.0 2,6 ] dec-8-ene-3,5-dione
Molecular formula C 17 H 25 NO 2
Brief description

colorless liquid

External identifiers / databases
CAS number 113-48-4
EC number 204-029-1
ECHA InfoCard 100.003.663
PubChem 8227
Wikidata Q6951386
properties
Molar mass 275.38 g mol −1
Physical state

liquid

density

1.050 g cm −3

solubility

practically insoluble in water (0.015 g l −1 at 25 ° C)

Refractive index

1.4985

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 311
P: 280-312
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N- octyl-bicyclohepten-dicarboximid or MGK 264 is a chemical compound that belongs to the group of dicarboximides and acts both as a repellent and as a synergist against insects. MGK-264 was developed by McLaughlin Gormley King as a cheap alternative to piperonyl butoxide and was first approved in the USA in the late 1940s.

Extraction and presentation

The compound can be obtained from 2-ethylhexylamine and 5-norbornene-2,3-dicarboxylic acid anhydride.

Synthesis of the insect repellent Pyrodone

Admission

N- octyl-bicyclohepten-dicarboximid is not considered a plant protection product within the meaning of Directive 91/414 / EEC or Regulation (EC) No. 1107/2009 (Plant Protection Product Regulation) . In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

  1. ↑ a b c d e Joint Meeting on Pesticide Residues (JMPR), Monograph for MGK 264, N- (2-ethylhexyl) -bicyclo- (2,2,1) hept-5-ene 2,3-dicarboximide , accessed on December 9, 2014.
  2. ↑ a b EPA: Reregistration Eligibility Decision for N-Octylbicycloheptenedicarboximide (MGK-264) p. 14
  3. ↑ a b data sheet MGK 264 analytical standard from Sigma-Aldrich , accessed on November 29, 2013 ( PDF ).
  4. ↑ Robert Krieger (Ed.): Hayes' Handbook of Pesticide Toxicology, Volume 1 . Elsevier, 1999, ISBN 978-0-12-374367-1 , pp. 295 ( limited preview in Google Book search).
  5. ^ Insect Repellents: Principles, Methods, and Use. Eds. Debboun, M., Frances, SP, Strickman, D. CRC Press, Taylor & Francis Group Boca Raton Florida. P. 362 ( limited preview in Google Book search)
  6. ↑ Patent US2476512 : N-2-ethyl hexyl-α, α'-di-keto-β, β '- (1,4-Δ 2 -cyclopentenylene) -pyrrolidines and synthesis thereof. Applied on March 8, 1947 , published July 19, 1949 , applicant: Van Dyke & Co., Inc., inventor: AA Schreiber. ‌
  7. ↑ General Directorate Health and Food Safety of the European Commission: Entry on N-octyl bicycloheptene dicarboximide in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.