Studies on pesticidal oxadiazole derivatives. Part II. Synthesis and biological activity of O,O-dialkyl S-(5-aryl-1,3,4-oxadiazol-2(3H)-on-3-yl)methyl phosphorothioates and phosphorodithioates.

A novel thermally stable and semiconducting polyheterocycle, poly(l,3,4-thiadiazole amine), was synthesized from 2-(p-aminophenyl)-l,3,4-oxadiazoline-5-thione via ring-opening. The polymer is a new class of ordered alternating copoly(ani1ine) containing 1,3,4-thiadiazole heterocyclic units. An investigation of the reaction of 2-phenyl-l,3,4-oxadiazoline-5-thione with aniline was conducted as a model reaction for the polymerization, and poly(phosphoric acid) (PPA) and phosphorus pentoxide/methanesulfonic acid (PPMA) were found to be favorable both as condensing agent and solvent for the formation of 2-anilino-5-phenyl-l,3,4-thiadiazole as a model compound. The polymerization was carried out both by two-step procedure that included ring-opening self-polyaddition giving poly(1-benzoylthiosemicarbazide), followed by cyclodehydration to poly(l,3,4-thiadiazole amine), and by a one-step procedure including cyclodehydration in situ. The poly(1 -benzoylthiosemicarbazide) which was formed in the first step in m-cresol had reduced viscosities up to 0,42 dL . g-', and it was converted to poly(l,3,4-thiadiazole amine) by treating in PPA or PPMA. Poly(l,3,4-thiadiazole amine) having reduced viscosities up to 0,25 dL . g was also synthesized by the direct one-step polymerization in PPA or PPMA.The polymer is highly thermally stable and exhibited no weight loss up to 350 "C under nitrogen.Its electric conductivity was less than lo-'' S * cm-' at ambient temperature, but markedly increased to 2,9. lo-' S . cm-' upon doping with iodine.

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Studies on pesticidal oxadiazole derivatives. Part II. Synthesis and biological activity of O,O-dialkyl S-(5-aryl-1,3,4-oxadiazol-2(3H)-on-3-yl)methyl phosphorothioates and phosphorodithioates.

Abstract: Some phosphorus derivatives of oxadiazoles were synthesized to seek insecticidal lead compounds. The l,3,4-oxadiazol-2-ones were converted via the 7V-methylol derivatives to the corresponding JV-chloromethyl derivatives. From these derivatives a variety of 0,0-dimethyl

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Reaction of 1,3,4‐oxadiazolones with free L‐α‐amino acids: A facile synthesis of novel 3,5‐disubstituted hydantoins

Reaction of 1,3,4‐oxadiazolones with free L‐α‐amino acids: A facile synthesis of novel 3,5‐disubstituted hydantoins

Synthesis and characterization of poly(1‐benzoylthiosemicarbazide) and poly(1,3,4‐thiadiazole amine) from 2‐(p‐aminophenyl)‐1,3,4‐oxadiazoline‐5‐thione via ring‐opening process

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