Even with the use of integrated pest management (IPM), control of insects in agriculture relies heavily on pesticides, a practice that is increasingly limited by evolution of pesticide-resistant insects and increased health and environmental concerns. Several pests including, whiteflies (Bemisia tabaci (Gennadius) or Bemisia argentifolii Bellows & Perring; sweetpotato whitefly B biotype or silverleaf whitefly) are difficult to eliminate with chemical or biological methods. However, acylsugars exuded from type IV glandular trichomes of S. pennellii mediate the resistance of S. pennellii to several pest species. The non-toxicity and broad spectrum of the resistance are major advantages for use in production. Field tomatoes with acyl-sugar mediated insect resistance are being developed at Cornell University. However, one major consideration in using this resistance in protected culture (greenhouse and high tunnel) is the effect of acylsugars on beneficial insects used in greenhouse production. Thus, access to chemically produced compounds to do trials on the effects of acylsugar on beneficial insects is vital.     The synthesis of these potential insecticides begins with a hexose in particular glucose. Protection of the anomeric position using N,O-dimethylhydroxylamine provided the stabilized sugar. Kinetic protection of the primary alcohol revealed the triol that are esterified using the acid chloride in pyridine to provide the fully protected sugar. This fully protected sugar was then be treated with t-butyl ammonium fluoride to remove the silyl ether and finally oxidative deprotection of the anomeric position revealed the desired glucose derivative in five steps from the starting sugar. The acid chlorides can be propionyl chloride, octanoyl chloride, decanoyl chloride, or dodecanoyl chloride to provide all of the desired monosaccaride triesters needed for agricultural studies.

Synthesis of acyl sugars for agricultural pest control

247th National Meeting (2014)

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