Substance trehalostatin and process for the preparation thereof

Details Substance trehalostatin and process for the preparation thereof Substance trehalostatin and process for the preparation thereof

C - Chemistry, Metallurgy

12

P

195/122.5, 260/2

C12P 19/18 (2006.01) A01N 63/00 (2006.01) C07H 17/08 (2006.01) C07H 19/02 (2006.01) C07H 19/24 (2006.01) C12N 1/20 (2006.01) C12P 19/26 (2006.01) C12P 19/28 (2006.01)

Patent

CA 2028117

This invention relates to a novel substance Trehalostatin which is a white powder soluble in water but hardly or only slightly soluble in hexane, benzene, ethers and petroleum ether, shows no absorption maxima at 220 nm or above in its ultraviolet visible light absorption spectrum, is positive in Rydon-Smith reaction and negative in ninhydrin reaction, 3,6-dinitrophthalic acid reaction and Elson-Morgan reaction, has an Rf value of 0.37 in Merk Kieselgal 60 G254 thin layer chromatography using a 3:1:2 mixture of n-butanol, acetic acid and water as a developing solvent, and Rt of 11.0 minutes in YMC PA03 (0.7 x 27cm) high performance liquid chromatography using 65% v/v acetonitrile (in H2O) as a solvent at a flow rate of 1.0 ml/min, has a molecular weight of 366 and a specific rotatory power [.alpha.]D of +115°, and presents an NMR spectrum described below: H-NMR/D2O: 3.3 (ppm), dd, 1H 3.5 (ppm), m, 1H 3.5 (ppm), t, 1H 3.6 (ppm), d, 1H 3.6 (ppm), d, 1H 3.7 (ppm), d, 1H 3.7 (ppm), d, 1H 3.8 (ppm), ddd, 1H -29- 4.1 (ppm), dd, 1H 4.2 (ppm), d, 1H 4.8 (ppm), ddd, 1H 5.2 (ppm), d, 1H 13c-NMR/D2o: 63.5 (ppm) 64.8 (ppm) 72.4 (ppm) 72.8 (ppm) 74.8 (ppm) 75.8 (ppm) 76,2 (ppm) 83.0 (ppm) 83.2 (ppm) 83.4 (ppm) 85.6 (ppm) 89.9 (ppm) 163.8 (ppm) to a process for preparing said substance, and to actinomycetes capable of producing said substance. Trehalostatin of the present invention shows an inhibitory effect against trehalase in insects, especially Aldrichina grahami, even at a very low concentration and is therefore useful as an insecticide.

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