Synthesis and fungicidal activity of some sulphide derivatives of O-phenyl-N-substituted phenylcarbamates (original) (raw)
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New sulfone and sulfanyl derivatives with antifungal activity
Medycyna Doświadczalna i Mikrobiologia, 2018
Introduction: Increasing occurrence of fungal infections raises the need to develop novel antifungal agents. In this context, an inhibition of morphological switch may provide an alternative approach to find compounds with a potential to control the Candida albicans infections. Methods: A series of 17 sulfone and sulfanyl derivatives was synthesized and evaluated for activity against the C. albicans wild type (SC5314, ATCC) and SAP-deficient mutant strains using the broth microdilution method M27-A3. Afterwards, phase-contrast microscopy was applied to evaluate the inhibition of fungal morphogenesis under the influence of randomly selected active compounds: 1, 5 and 6. Results: By in vitro susceptibility testing of C. albicans, we identified the effective antifungal agents displaying moderate-to-good activity. Newly synthesized sulfanyl and sulfone derivatives strongly inhibited the C. albicans morphogenetic transition under the hyphae inducing conditions. Conclusions: The leading c...
Design, Synthesis and Bioactivity of Benzimidazole–2–Carbamates as Soil–Borne Anti–Fungal Agents †,‡
Chemistry Proceedings
The design and synthesis of new, safe and potent molecules to apply against soil-borne pathogens is a critical goal for organic and bio-medicinal chemists. Herein, we designed and synthesized a series of benzimidazole-based carbamate derivatives (7a–f), as soil-borne anti-fungals. The derivatives 7a–f were all synthesized in multi-step reactions with acceptable yields. The structures of 7a–f were all identified and characterized using 1H-NMR, IR, HRMS, and melting point calculations. The final compounds were tested on five soil-borne pathogens. The results of various bio-assays showed that compounds 7a-3, 7a-2, 7b-2, 7a-1 and 7b-1 significantly affected the growth of Pythium aphanidermatum, a serious pathogen affecting vegetable crops worldwide. Compounds 7a-1 and 7b-1 were the most efficacious, which resulted in a 96% growth inhibition in Pythium at 100 mg L−1. In conclusion, we reported the potent carbamate derivatives as soil-borne anti-fungals, and believe that the synthesis of ...
In the present study, a series of O-substituted carbamates have been synthesized. The reaction of 4-(aminomethyl) phenol (1) with phenylchloroformate (2) yielded N-(4-hydroxyphenyl)-N- methyl-O-phenyl carbamate (3). This product 3 on treatment with alkyl/aryl halides in the presence of lithium hydride yielded ten different O-substituted carbamates. All newly synthesized compounds were characterized by IR, EI-MS and H-NMR spectra and then screened against a-chymotrypsin, acetylcholinesterase, and butyrylcholinesterase enzymes. The results revealed that N-(4-benzoxyphenyl)-N-methyl-O-phenyl carbamate (8b), N-[4-(2-chlorobenzoxy)phenyl]-N-methyl-O-phenyl carbamate (8c), and N-[4-(4-chlorobenzoxy)phenyl]-N-methyl-O-phenyl carbamate (8e) exhibited good inhibitory potential against acetylcholinesterase and butyrylcholinesterase and are possible target molecule for the treatment of Alzheimer's disease.
Novel fungicidal benzylsulfanyl-phenylguanidines
Bioorganic & Medicinal Chemistry Letters, 2011
A series of substituted benzylsulfanyl-phenylamines was synthesized, of which four substituted benzylsulfanyl-phenylguanidines (665, 666, 667 and 684) showed potent fungicidal activity (minimal fungicidal concentration, MFC 6 10 lM for Candida albicans and Candida glabrata). A benzylsulfanyl-phenyl scaffold with an unsubstituted guanidine resulted in less active compounds (MFC = 50-100 lM), whereas ⇑ Corresponding author. Tel.: +32 16329688; fax: +32 16321966.
Sugar, glyceryl, and (pyridylalkoxy)sulfinyl derivatives of methylcarbamate insecticides
Journal of Agricultural and Food Chemistry, 1983
A series of sugar, glyceryl, and (pyridinea1koxy)sulfinyl derivatives of methylcarbamate esters were prepared and examined for insecticidal and anticholinesterase activity and for mouse toxicity. Several of the derivatives showed good insecticidal activity, and on a mole basis some showed higher activity than the parent methylcarbamate. Overall, the derivatives exhibited poorer anticholinesterase activity and were less toxic to mice than the methylcarbamate. The sulfinylated derivatives were readily hydrolyzed or solvolyzed to the methylcarbamate, indicating that the parent methylcarbamate is released in biological systems and is responsible for intoxication.
Liebigs Annalen der Chemie, 1987
Chlorosdfonyl isocyanate reacts with hydroxynitrostyrenes 1 to give the corresponding Nunsubstituted aubamates 3. The latter undergo traosesterilication with ptoluenesulfonyl chloride to give the corresponding sulfonates 4. The analogous phosphates 5 are obtained by treating diethyl chlorophosphate with 1. Compounds 3.4, and 5 present a novel series of aryl-@nitroalkenes of pesticidal importance. Compounds 3 react with o-phenylenediamine to afford benzimidazolone along with the corresponding 2-arylbenzimidazoles 7. The molluscicidal and antimicrobial activities of the products am discussod.
Synthesis of F-alkyl N-sulfonyl carbamates and thiocarbamates
Journal of Fluorine Chemistry, 1999
The syntheses of F-alkyl (alkoxy) and aroxysulfonyl carbamates and thiocarbamates result by addition of F-alkyl alcohols and thiols to alkoxy and aroxysulfonyl isocyanates. At room temperature the reaction occurs rapidly with very good yields.
Journal of Inorganic Biochemistry, 2009
a b s t r a c t and (5), respectively, were obtained by the reaction of the appropriate potassium N-R-sulfonyldithiocarbimate (RSO 2 N@CS 2 K 2 ) with nickel(II) chloride hexahydrate or zinc(II) acetate dihydrate in metanol:water 1:1. The elemental analyses and the IR data are consistent with the formation of the expected bis(dithiocarbimato)metal(II) complexes. The 1 H and 13 C NMR spectra showed the signals for the tetrabutylammonium cation and the dithiocarbimate moieties. The compounds 1, 2 and 5 were also characterized by X-ray diffraction techniques. The nickel(II) is coordinated by two N-4-fluorophenylsulphonyldithiocarbimato(2-) ligands forming a planar coordination. The zinc(II) exhibits distorted tetrahedral configuration in compounds 2 and 5 due to the chelation effect of two sulfur atoms of the N-R-sulfonyldithiocarbimate ligands. The antifungal activities of the compounds were tested in vitro against Colletotrichum gloeosporioides, an important fungus that causes the plant disease known as anthracnose in fruit trees. All the complexes were active.