ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synergists of pyrethrum. XI. Addition of O,O-dialkyldithiophosphoric acids to double bonds of diene adducts of N-substituted maleic imides with fulvenes

V. Sutoris

Faculty of Natural Sciences, Komenský University, Bratislava

Abstract: cf. CA 60, 7929h. Addn. products of O,O-dialkyldithiophosphoric acids (I) with N-substituted endo,cis- 7-isopropylidene (-diphenylmethylene, -methylphenylmethylene, -furfurylmethylene)bicyclo[1.2.2]hept-5-ene-2,3-dicarboximides (II) and I with monoallylamide of endo,cis-7-isopropylidenebicyclo-[1.2.2]hept-5-ene-2,3-dicarboxylic acid (III) were prepd. The synergetic action of these products was tested biol. on Musca domestica; addn. of O,O-diethyl(IV) or O,O-diisopropyldithiophosphoric acid (V) to III increased the activity of pyrethum 50-100%. Addn. of IV or V to II decreased the activity an av. of 7%. Addn. of pure I to the olefins gave abnormal addn. products. Com. I probably contained a specific catalyst which could eliminate the peroxides present in the olefins, which were the cause of the abnormal reaction. To prep. the addn. product of IV or V with N-substituted endo,cis-7-isopropylidene(methylphenylmethylene)bicyclo [1.2.2] hept-5-ene-2,3-dicarboximide (VI), 0.022 mole I and 0.02 mole VI was heated at 60-70° on a water bath 4-6 hrs., cooled, dissolved in C₆H₆, and the soln. washed twice with 30 cc. 10% Na₂CO₃ and evapd. The reaction was quant. and the products pure. To prepare other endo-cis and exo-cis products the same procedure was used except that the proportion of I was higher (0.1 mole).

Full paper in Portable Document Format: 175a307.pdf (in Slovak)

Chemical Papers 17 (5) 307–317 (1963)