Zur Chemie von GS 13005, einem neuen insektiziden Phosphorsäureester

Rüfenacht, K.

doi:10.1002/hlca.19680510314

Cited by 30 publications

(3 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Rüfenacht [30] used potassium methyl xanthate and hydrazine hydrate to form O -methylester. Phosgene was introduced to O- methyl ester to produce 5-amino-2-methoxy-1,3,4-thiadiazole by a cyclization reaction.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and In Vitro Evaluation of Novel Acyclic and Cyclic Nucleoside Analogs with a Thiadiazole Ring

Zhao

McCarthy

Párkányi

2013

ISRN Organic Chemistry

View full text Add to dashboard Cite

The synthesis of six thiadiazole nucleoside analogs is reported: 5-diacetylamino-1,2,4-thiadiazol-3-one (1), 5-amino-2- (tetrahydrofuran-2-yl)-1,2,4-thiadiazol-3-one (2), 5-amino-3-[(2′-hydroxyethoxy)methyl]-1,3,4-thiadiazol-2-one (3), 5-amino-3-(4′-hydroxy-2′-hydroxymethyl-butyl)-1,3,4-thiadiazole-2-thione (4), (R)-5-amino-3-(2′,3′-dihydroxypropyl)-1,3,4-thiadiazole-2-thione (5), and (S)-5-amino-3-(2′,3′-dihydroxypropyl)-1,3,4-thiadiazole-2-thione (6). The synthesis, characterization, and properties of these new synthesized thiadiazole derivatives are discussed. A dimerization of 5-amino-3H-1,3,4-thiadiazole-2-thione (14) by sodium nitrite resulting in di-(5-amino-1,3,4-thiadiazol-2-yl) disulfide (19) is also reported. The preliminary in vitro evaluation of these newly synthesized compounds is discussed.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and In Vitro Evaluation of Novel Acyclic and Cyclic Nucleoside Analogs with a Thiadiazole Ring

Zhao

McCarthy

Párkányi

2013

ISRN Organic Chemistry

View full text Add to dashboard Cite

show abstract

“…-Unter den Herstellungsmethoden fur a Methidathion )) 4a2) ist bereits in der 1.Mitt. dieser Reihe [2] …”

unclassified

Arbeiten über Phosphorsäure‐ und Thiophosphorsäureester mit einem heterocyclischen Substituenten. 8. Mitteilung. Das Stäubli‐Verfahren, eine Eintopf‐Kondensation von Thiophosphorverbindungen (, XO,S), Aldehyden und Heterocyclen (mit saurer NH‐Gruppe)

Rüfenacht¹

1974

Helvetica Chimica Acta

View full text Add to dashboard Cite

The condensation reaction of thiophosphoric compounds 1, aldehydes and heterocycles 3 with an acidic NH‐group in strong mineral acid of specific concentration to asymmetrical compounds 4, called Stäubli procedure, differs from the Mannich‐type reaction catalyzed by weak or dilute acid (aminoalkylation of Hellmann & Opitz) and from the Tscherniac‐Einhorn‐type condensation in concentrated sulfuric acid (amidomethylation of Hellmann). Its main feature is the acidity of the two condensation participants 1 and 3; therefore an attuned concentration of mineral acid is required to activate them each to its individual optimum extent. Their pK difference, however, is sufficient to differentiate their nucleophility and reactivity and to prevent a simultaneous reaction of both of them with the aldehyde provocating side reactions to symmetrical by‐products such as 13, 14 and 15.

show abstract

“…Bande bei 1040 cm-l und das des Metaboliten I1 mit Randen bei 1310 und 1130 cm-1 fur die SO,-Gruppe.Diese Strukturen wurden durch Vergleich mit den entsprechenden synthetischen Referenzsubstanzen[5] bestatigt.Damit kann folgender Abbauweg formuliert werden: Bei der Spaltung des Dithiophosphorsaureesters verbleibt der Schwefel auf der Seite des Heterozyklus (analog der chemischen Hydrolyse in alkalischem Milieu). Die entstandene Thiol-Verbindung wird anschliessend methyliert und zum polaren Sulfoxid oxydiert.…”

unclassified

Der Abbau des Insektizides GS 13005 in der Ratte. Strukturaufklärung der wichtigsten Metabolite [1]

Esser¹,

Mücke²,

Alt³

1968

Helvetica Chimica Acta

View full text Add to dashboard Cite

Suvnvnary. The structures of the essential metabolites which are excreted by the rat after oral application of GS 13005 (O,O-dimethyl-S-[(Z-methoxy-1, 3,4-thiadiazole-5(4Hj-one-4-y1)methyl] dithiophosphate) have been elucidated. The product of final oxidation, CO,, was found to be the main metabolite (up to 36% of the dose applied). Among the degradation products excreted in the urine (up to 45% of the dose applied) the two most important were isolated. They are 4-methylsulfinylmethyl and 4-methylsulfonylmethyl derivatives respectively of the intact Z-methoxy-l,3,4-thiadiazole-5-one heterocycle (metabolites 111 and 11, in amounts of 20-25y0 and 557% of the dose applied, respectively). These metabolites originate by methylation and subsequent oxidation from the mercaptotnethyl derivative liberated after hydrolysis of the P-S bond of the dithiophosphoric acid ester.

show abstract

Zur Chemie von GS 13005, einem neuen insektiziden Phosphorsäureester

Cited by 30 publications

References 2 publications

Synthesis and In Vitro Evaluation of Novel Acyclic and Cyclic Nucleoside Analogs with a Thiadiazole Ring

Synthesis and In Vitro Evaluation of Novel Acyclic and Cyclic Nucleoside Analogs with a Thiadiazole Ring

Arbeiten über Phosphorsäure‐ und Thiophosphorsäureester mit einem heterocyclischen Substituenten. 8. Mitteilung. Das Stäubli‐Verfahren, eine Eintopf‐Kondensation von Thiophosphorverbindungen (, XO,S), Aldehyden und Heterocyclen (mit saurer NH‐Gruppe)

Der Abbau des Insektizides GS 13005 in der Ratte. Strukturaufklärung der wichtigsten Metabolite [1]

Contact Info

Product

Resources

About