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Synergists of pyrethrum. X. The study of the reaction of bicyclo[1.2.2]hept-5-ene-2,3-dicarboximide and its N-methylol derivative with aliphatic halogen compounds

M. Furdík and V. Sutoris

Komensky University, Bratislava

Abstract:   The following I were prepd. from bicyclo[1.2.2]hept-5-ene-2,3-dicarboximide or its N-methylol deriv. by refluxing with the corresponding halogen compds. (X, m.p., and % yield given): CO₂Et, 53°,84.2; CO₂Pr, 54°, 85.6; CO₂Pr-iso, 49°, 80.7; Ac, 153°, 95.8; Bz, 148-9°, 97; CH2OH, 89°, 61.8; OAc, 64°, 97.3; O₂CEt, 95°, 97.9; O₂CCH₂CH₂Cl, 94°, 98.7; O₂CPr, 42°, 96.8; O₂CPr-iso, 122°, 98.7; Cl, 125-6°, 95.8; bicyclo[1.2.2]hept-5-ene-2,3-dicarboximido, 229-30°, 89; 3-(bicyclo[1.2.2]hept-5-ene-2,3-dicarboximido)propyl, 213-14°, 94. Tests of synergoinsecticide effect of these compds. in combination with pyrethrum showed increased toxicity index of the Cl-substituted compd. comparable to Me substitution. Other non-hydrocarbon substituents caused lowering of the toxicity index.

Full paper in Portable Document Format: 171a31.pdf (in Slovak)

Chemical Papers 17 (1) 31–40 (1963)