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Synthesis and biological properties of some organophosphorus compounds

I. Pastorek, J. Drábek, and Š. Truchlík

Forschungsinstitut für agrochemische Technologie, Bratislava

 

Abstract: Structural analogs of-O,O-dimethyl O-(3-methyl-4-nitrophenyl) thiophosphate, MeX-(R1O)P(Y)OR2 (I) were prepd. as potential insecticides. Thus, into a suspension of a phenol, R2OH, anhyd. K2CO3, and Cu powder in a suitable solvent, MeX(R1O)P(Y)Cl or MeXP(Y)Cl2 was added dropwise at a fixed temp. with stirring; heating with stirring was then continued to complete the reaction. X, Y, R1, R2, b.p. or m.p., d20, nD20, % yield; O, S, Me, 3-MeC6H4, 115-20° (0.1-0.15 mm.), 1.1907, 1.5262, 95.3; O, S, Me, 4,2-Me(O2N)C6H3, 140-4° (0.01 mm.), 1.3118, 1.5420 (25°), 81.4; O, S, Me, 3,4-Me(O2N)C6H3, 159.5 (0.15 mm.), 1.3404, 1.5205, 90.5; O, S, Me, 2-MeC6H4, 87.5-9.0° (0.07 mm.), 1.1941, 1.5269, 66.6; O, S, Me, 4-MeC6H4, 97-100° (0.07-0.08 mm.), 1.1903, 1.5255, 71.8; O, S, Me, 2,6-Me(O2N)C6H3, 47-8°, --, --, 83.0; O, S, Et, 3,4-Me(O2N)C6H3, --, 1.2824, 1.5425, 85.9; S, S, Me, 3,4-Me(O2N)C6H3, --, --, --, 53.2; O, S, Me, 2,4-(O2N)2C6H3, 94-5°, --, --, 71.6; O, S, Me, 3,2,4-Me(O2N)2C6H2, --, 1.4189, 1.5530, 93.0; O, S, Me, 3,4,6-Me(O2N)2C6H2, --, --, 1.5642, 53.5; O, S, 3,4-Me(O2N)C6H3, 3,4-Me(O2N)C6H3, 92.5-3.5°, --, --, 80.4; S, S, 3,4-Me(O2N)C6H3, 3,4-Me(O2N)C6H3, 84-5°, --, --, 60.3; O, O, 3,4-Me(O2N)C6H3, 3,4-Me(O2N)C6H3, 84-4.5°, --, --, 94.7 A mixt. of NaOR2 and solvent was treated with MeX(R1O)P(Y)Cl or MeXP(Y)Cl2 analogously. In these ways were prepd. the tabulated I.

Full paper in Portable Document Format: 195a413.pdf (in Slovak)

 

Chemical Papers 19 (5) 413–419 (1965)

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