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Facile syntheses and antimicrobial studies of 6‐(aryloxy/arylthio/chloroethoxy)‐2,10‐dichloro‐4,8‐dinitro‐12‐trichloromemyl‐12 H ‐dibenzo[ d,g ][13,2]dioxaphosphocin 6‐oxides
Author(s) -
Kumar K. Ananda,
Kasthuraiah M.,
Reddy C. Suresh,
Berlin K. D.
Publication year - 2003
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.5570400224
Subject(s) - chemistry , triethylamine , aspergillus flavus , fusarium solani , alternaria alternata , aryl , antimicrobial , rhizoctonia solani , alternaria solani , fusarium oxysporum , medicinal chemistry , pyricularia , antibacterial activity , stereochemistry , organic chemistry , microbiology and biotechnology , fungicide , bacteria , alkyl , botany , food science , genetics , biology
Synthesis of several novel 6‐aryloxy/arylmio/chloroethoxy‐2,10‐dichloro‐4,8‐dinitro‐12‐trichloro‐memyl‐12 H ‐dibenzo[ d,g ][1,3,2]dioxaphosphocin 6‐oxides ( 4a‐k ) was accomplished by reacting 2,2‐bis (2‐hydroxy‐5‐chloro‐3‐nitrophenyl)‐1,1,1‐trichloroethane 2 with different aryl phosphorodichloridates ( 3a‐g ) and O ‐2‐chloroethyl phosphoryldichloride ( 3h ) in the presence of triethylamine in dry toluene at 60–65 °C. Actually some of these compounds were prepared by reacting monochloride 5 resulting from the condensation of phosphorus oxychloride with 2 in situ , with different phenols and thiophenols. The chemical structures were confirmed by elemental, ir and 1 H, 13 C, 31 P nmr and mass spectral data analyses. These compounds were screened for antifungal activity against Aspergillus flavus, Alternaria alternata, Fusarium solani, Curvularia lunata and Pyricularia oryzae and antibacterial activity on Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas syringae and Klebsiella pneumoniae . Some of them possessed significant activity.