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

Phosphorylated isothioureas. V. Preparation and properties of 3-phosphorylated and 3-thiophosphorylated 1,1,2-trisubstituted isothioureas

Ľ. Kuruc, V. Konečný, Š. Kováč, and Š. Truchlík

Research Institute of Agrochemical Technology, 810 04 Bratislava

Abstract: The synthesis and properties of 3-[(R¹,R²)-phosphoryl- and -thiophosphoryl]-1,1-(R³, R⁴)-2-(R⁵)isothioureas are described. They were prepared by alkylation of 3-(0,0-dialkylthiophosphoryl)-1,1-dialkyl- and -1,1-(3'-oxapentamethylene)thioureas with alkyl halides, aralkyl halides, and dimethyl sulfate in organic solvent in the presence of agents binding hydrogen halide or with diazomethane in ether, further by the reaction of dialkyl amidothiophosphates with mercaptoformamide chlorides in benzene in the presence of triethylamine, or by the reaction of 3-(0,0-dialkylthiophosphoryl)-1,1-dialkyl-2-alkylisothioureas with alkyl halides in the presence or absence of a solvent, by the reaction of 3-(0,0-dialkylthiophosphoryl)-1,1-dialkylthioureas with alkyl halides, by the reaction of О, О-dialkyl chlorothiophos- phate with the appropriate thiouronium salts, and by the reaction of N¹,N¹diethyl-N²-dichlorophosphoryOchloroformamidine with butane thiol and methanol in acetonitrile in the presence of triethylamine. The i.r., u.V., and ¹H-n.m.r. spectra of the synthesized compounds are interpreted and the results of tests for pesticidal activity are discussed.

Full paper in Portable Document Format: 353a373.pdf

Chemical Papers 35 (3) 373–387 (1981)