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Synthesis and X‐ray study of hexahydro‐ and tetrahydrophospholo‐[2,3‐ d ]isoxazoles, a new class of heterocycles of potential fungicidal activity
Author(s) -
Machetti Fabrizio,
Anichini Beatrice,
Cicchi Stefano,
Brandi Alberto,
Wieczorek Wanda,
Pietrusiewicz K. Michal,
Gehret JeanClaude
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330416
Subject(s) - chemistry , benzonitrile , botrytis cinerea , phosphole , cycloaddition , oxide , medicinal chemistry , stereochemistry , organic chemistry , botany , catalysis , biology
Hexahydro‐, 5b‐1 and 6a,f,1 and tetrahydrophospholo[2,3‐ d ]isoxazoles 8, 9 and 10 were synthesized by 1,3‐dipolar cycloaddition of nitrones 3b‐1 and benzonitrile oxide ( 4 ) to 2,3‐dihydro‐1‐phenyl‐1 H ‐phosphole 1‐oxide ( 1 ) and 2,3‐dihydro‐1‐ethoxy‐1 H ‐phosphole 1‐oxide ( 2 ). The structural assignment to the compounds was confirmed by an X‐ray study of two compounds of the series 5a and 5m . The compounds show a good activity as fungicides against Plasmopara viticola on vines and against Botrytis cinerea on apples. Compounds 5a‐d showed weak to moderate activity as herbicides.