Abstract

New fluorine substituted 6-(5’-fluoro-2’-triphenylphosphiniminophenyl) 3-thioxo-1,2,4-triazin-5 (2H, 4H) one (2) was obtained via Wittig’s reaction of the corresponding 6-(5’-fluoro-2’-amino-phenyl)-3-thioxo-1,2,4-triazinone (1). Behavior of compound 2 towards alkylating agents and/or oxidizing agents was studied were, N-hydroxyl (3), Mannich base (4,5), S-alkyl (6,7,8) and thiazolo [3,2-b][1,2,4] triazinones (10-14) and or 3-disulfide (18), 3-sulfonic acid 19 and 1,2,4-triazin-3,5-Dionne (20) derivatives obtained. Structures of the new products are established by elemental and spectral data. The new targets obtained screened as Molluscicidalagents against Biomophlaria Alexandrina snails responsible for Bilharziasis diseases, in compare with Baylucide as standard drug.

Highlights

  • The incorporation of fluorine atoms into a heterocyclic nitrogen molecule frequently provides properties of pharmacological interest as compared to their non-fluorinated analogs [1]-[5]

  • Bonded phosphorus atoms with S, O, N and C-atoms of heterocyclic systems enhance their important properties as herbicides, pesticides and insecticides [6]-[11]

  • The present work aims to synthesis and chemical reactivity of 1,2,4-triazinone bearing, fluorine, phosphorus and sulfur atoms through alkylation reactions and the new systems as Molluscicidal agents against Biomophalaria Alexandrina snails by removal from the wastewater (Clean water)

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Summary

Experimental

Melting points were determined with an electro-thermal Bibbly Stuart Scientific Melting point SMPI (UK). [6-(5’-Fluoro-2’-triphenylphosphiniminophenyl)-5-oxo-1,2,4-triazine-3-yl]thioacetic acid (6) Equimolar mixture of 2 and monochloroacetic acid in DMF (20 ml) warm for 30/min, poured onto ice. The solid yielded filtered off and crystallized form EtOH to give 6 as faint yellow crystals. 1,1-Di[6-(5’-Fluoro-2’-triphenylphosphiniminophenyl)-5-oxo-1,2,-4-triazine-3'yl]dimercaptoacetic acid (7) A mixture of 2 (0.02 mol) and 1,1-dicholoracetic acid (0.01 mol) in DMF (20 ml) reflux for 30 min, cold poured into ice. The resulted solid filtered off and crystallized from dioxin to give 7 as faint yellow crystals, yield (60%) m.p. 238 ̊C - 240 ̊C. 6(5’-Fluoro-2’-triphenylphosphiniminophenyl)-5-oxo-3-(cyanomethylthia)-2H-1,2,4-triazine (10) A mixture of 2 (0.01 mol) and chloroacetinitrile (0.01 mol) in DMF (20 ml) warm (10 min) cold and poured onto ice. The result solid filtered off and crystallized from dioxan to give 10 as faint Yellow crystals.

Chemistry
Elucidation the Former Structures
Molluscicidal Activity
Conclusion
Full Text
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