Synthesis, antifungal activity and structure-activity relationships of vanillin oxime-N-O-alkanoates

Natural Product Communications

Volumn 7, Issue 12, 2012, Pages 1635-1638

  Ahluwalia, Vivek ^a,b   Garg, Nandini ^a,c   Kumar, Birendra ^a   Walia, Suresh ^a   Sati, Om P ^b  

^a INDIAN AGRICULTURAL RESEARCH INSTITUTE   (India)

^b H N B GARHWAL UNIVERSITY   (India)

^c STONY BROOK UNIVERSITY   (United States)

Author keywords

Antifungal activity; Macrophomina phaseolina; Oxime esters; Rhizoctonia solani; Sclerotium rolfsii; Structure activity relationships; Vanillin

Indexed keywords

ANTIFUNGAL AGENT; UNCLASSIFIED DRUG; VANILLIN OXIME N O ALKANOATE DERIVATIVE; ALKANE; BENZALDEHYDE DERIVATIVE; OXIME; VANILLIN;

ANTIFUNGAL ACTIVITY; ARTICLE; ATHELIA ROLFSII; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS; IN VITRO STUDY; INFRARED SPECTROSCOPY; MACROPHOMINA PHASEOLINA; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; THANATEPHORUS CUCUMERIS; CHEMISTRY; DRUG EFFECT; ELECTROSPRAY MASS SPECTROMETRY; MICROBIAL SENSITIVITY TEST; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ALKANES; ANTIFUNGAL AGENTS; BENZALDEHYDES; CHROMATOGRAPHY, THIN LAYER; FUNGI; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; OXIMES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

MLCS; MLOWN;

EID: 84875029236     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1200701224     Document Type: Article

References (18)

1. Walton NJ, Mayer MJ, Narbad A. (2003) Molecules of interest vanillin. Phytochemistry, 63, 505-515.
2. Sun R, Sacalis JN, Chin CK, Still CC. (2001) Bioactive aromatic compounds from leaves and stem of Vanilla fragrance. Journal of Agricultural and Food Chemistry, 49, 5161-5164.
3. Cerrutti P, Alzamora SM. (1996) Inhibitory effect of vanillin in some food spoilage yeasts in laboratory media and fruit purees. International Journal of Food Microbiology, 29, 379-386.
4. Fitzgerald DJ, Stratford M, Gasson MJ, Narbad A. (2004) The potential application of vanillin in preventing yeast spoilage of ready-to-drink beverages. Journal of Food Protection, 67, 391-395.
5. Burri J, Graf M, Lambelet P, Loliger J. (1989) Vanillin: more than a flavouring agent-a potential antioxidant. Journal of the Science of Food and Agriculture, 48, 49-56.
6. Boonchird C, Flegel TW. (1982) In vitro antifungal activity of eugenol and vanillin against Candida albicans and Cryptococcus neoformans. Canadian Journal of Microbiology, 28, 1235-1241.
7. Fitzgerald DJ, Stratford M, Gasson MJ, Narbad A. (2005) Structure-function analysis of the vanillin molecules and its antifungal properties. Journal of Agricultural and Food Chemistry, 53, 1769-1775.
8. Bull MJ, Davies HJ, Robert JG, Henry AC. (1980) Alkyl aryl ketone oxime-O-ethers, a novel group of pyrethroids. Pesticide Science, 44, 249-256.
9. Walia S, Saxena VS, Mukerjee SK. (1985) Synthesis and synergistic activity of oxime ethers containing a benzo-1, 3-dioxole group. Journal of Agricultural and Food Chemistry, 33, 308-310.
10. Walia S, Gujar GT. (1993) Bioactivity of some substituted benzo-1-3-dioxole oxime ethers against Dysdercus koenigii. Pesticide Research Journal, 5, 205-208.
11. Chowdhury H, Saxena VS, Walia S. (1998) Synthesis and insect growth regulatory activity of alkoxy-substituted benzaldoxime ethers. Journal of Agricultural and Food Chemistry, 46, 731-736.
12. Sun R, Li Y, Lu M, Xiong L, Wang Q. (2010) Synthesis, larvicidal activity, and SAR studies of new benzoylphenylureas containing oxime ether and oxime ester group. Bioorganic & Medicinal Chemistry Letters, 20, 4693-4699.
13. Paul R, Walia S, Mondal A, Kumar J, Pankaj. (2009) Synthesis and nematicidal activity of 2-tridecanone and its oxime esters against Meloidogyne incognita. Annals of Plant Protection Sciences, 17, 453-455.
14. Choudhary G, Walia S, Kumar J. (2007) Synthesis and antifungal activity of citral oxime esters against two phytopathogenic fungi Rhizoctonia solani and Sclerotium rolfsii. Pesticide Research Journal, 19, 15-19.
15. Abeysinghe A. (2009) Efficacy of combined use of biocontrol agents on control of Sclerotium rolfsii and Rhizoctonia solani of Capsicum annuum. Archieves of Phytopathology and Plant Protection, 42, 221-227.
16. Dikusar EA, Kozlov NG, Zhukovskaya NA, Moiseichuk KL. (2004) Esters of vanillin and vanilla oximes. Chemistry of Natural Compounds, 40, 180-183.
17. Shukla P, Walia S, Ahluwalia V, Parmar BS, Nair MG. (2012). Activity of alkanediol alkanoates against pathogenic plant fungi Rhizoctonia solani and Sclerotium rolfsii. Natural Product Communications, 7, 1219-1222
18. 50 values using the IBM-PC. Bulletin of Environmental Contamination and Toxicology, 37, 18-26.