Thirty known dialkanoates of ethylene, propylene and diethylene glycols were synthesized by reacting the glycols with acyl chlorides and their structures confirmed by IR, NMR and mass spectral analyses. They exhibited significant antifungal activity against two phytopathogenic fungi Rhizoctonia solani Kuehn and Sclerotium rolfsii Sacc in a dose dependent manner. Propylene glycol dipentanoate was the most active against R. solani. followed by diethylene glycol dibutanoate and ethylene glycol dibutanoate. Against S. rolfsii ethylene glycol diheptanoate was found to be most active followed by diethylene glycol diisobutanoate As compared to the standard reference benomyl (EC50 5.16 μg/mL), the potential alkanediol dialkanoates showed EC50 in the range of 33 – 60 μg/mL.
SeversonRF, ArrendaleRF, ChortykOT, JohnsonAW, JacksonDM, GwynnGR, ChaplinJF, StephensonMG. (1984) Quantitation of the major cuticular components from green leaf of different tobacco types. Journal of Agriculture and Food Chemistry, 32, 566–570.
2.
SeversonRF, ArrendaleRF, ChortykOT, GreenCR, ThomeFA, StewartJL, JohnsonAW. (1985) Isolation and characterization of the sucrose esters of the cuticular waxes of green tobacco leaf. Journal of Agriculture and Food Chemistry, 33, 870–875.
3.
GoffredaJC, MutschlerMA, AveDA, TingeyWM, SteffensJ C. (1989) Aphid deterrence by glucose esters in glandular trichome exudates of the wild tomato, Lycopersicon pennellii. Journal of Chemical Ecology, 15, 2135–2147.
4.
LapointeSL, TingeyWM. (1984) Feeding response of the green peach aphid (Homoptera:Aphididae) to potato glandular trichomes. Journal of Economic Entomology, 77, 386–389.
5.
KatoA, ArimaK. (1971) Inhibitory effect of sucrose ester of lauric acid on the growth of Escherichia coli. Biochemical and Biophysical Research Communication, 42, 596–601.
6.
KatoN, ShibasakiI. (1975) Comparison of antimicrobial activities of fatty acids and their esters. Journal of Fermentation Technology, 53, 793–801.
7.
MarshallDL, BullermanLB. (1986) Antimicrobial activity of sucrose fatty acid emulsifiers. Journal of Food Science, 51, 468–470.
8.
NealJWJr, ButaJG, PittarelliGW, LusbyWR, BentzJA. (1994) Novel sucrose esters from Nicotiana gossei: Effective biorationals against selected horticultural insect pests. Journal of Economic Entomology, 87, 1600–1607.
9.
WaliaS, KumarJ, ParmarBS. (2001) Ecologically sound botanical pesticides: Development and use. (Eds. KoulO.; DhaliwalG. S.; MarwahaS. S.; AroraJ. K.). Proceedings Biopesticides: Emerging Trends, Society of Biopesticides Science, Chandigarh. 56–63.
10.
WaliaS, KoulO. (2008) Exploring plant biodiversity for botanical insecticides. In Sustainable crop protection: Biopesticide strategies (Eds. KoulO.; DhaliwalG. S.; KoulV. K.), Kalyani Publishers, New Delhi.
11.
ArimotoY, ItakuraJ, YamaguchiI. (1998) Control of Spider Mite by using propylene glycol ester of fatty acid. 9thInternational Congress, Pesticide Chemistry, The Food-Environment Challenge, Westminster, London, UK, Book of Abstracts: I, 3A – 050.
12.
PruskyD, KeenNT, SimsJJ, MidlandSL. (1982) Possible involvement of an antifungal diene in the latency of Colletotrichum gloeosporioides. Phytopathology, 72, 1578–1582.
13.
DomergueF, HelmsGL, PruskyD, BrowseJ. (2000) Antifungal compounds from idioblast cells isolated from avocado fruits. Phytochemistry, 54, 183–189.
14.
WaliaS, ShuklaP, ParmarBS. (2007) Preparation of alkane polyol alkanoate fungicides and nematicides. Indian Patent IN A 20070928.
15.
DonghyunK, ParkKH, LeeSG, MoonJ, EomS, RewDS. (2008) Synthetic method of glycol diesters from reaction of glycol monoesters and linear aliphatic carboxylic acids. US Patents 7453008 B2.
16.
de LimaC, HectorR. (1959) Synthesis method for glycol diesters by catalytic action of metal halides of groups VIII, II, and V (iron, zinc, and antimony). Revista de la Sociedad Venezolana Química, 30, 44–51.
17.
BaileyAV, BoudreauxGJ, SumrellG. (1976) Antimicrobial properties of some mixed diesters of aliphatic diols. Journal of the American Oil Chemists Society, 53, 632–633.
18.
FrankenfeldJW, KarelM, LabuzaTP, SinskeyAJ. (1974) Aliphatic diols and their esters as antimicrobial additives for cheese and meat. US Patent 3806615.
19.
NeneYL, ThapliyalPN. (1979) Fungicides in plant disease control. Oxford and IBH Publishing Co.; New Delhi, India, 314–413.
20.
TrevorsJT. (1986) A basic programme for estimating LD50 values using the IBM-PC. Bulletin of Environmental Contamination and Toxicology, 37, 18–26.
