Pheromone Study on Acarid Mites VIII. Primary (Z)-2-Alkenyl Formate Responsible for the Alarm Pheromone Activity against the Mold Mite, Tyrophagus putrescentiae (Schrank) (Acarina : Acaridae)

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Abstract
Using (Z)-3,7-dimethyl-2-octenyl formate(II) as a lead compound and preserving its (Z)-allylic primary formate moiety, a total of 15 aliphatic nonterpenoids were prepared by modification of the main chain and the substitution at C3 position from alcoholic function, and their alarm pheromone activities were determined against the mold mite T. putrescentiae (Schrank). Twelve compounds were active. The basic requisite for developing the alarm pheromone activity was elucidated as the presence of (Z)-allylic primary alcohol formate moiety with a suitable chain length in a molecule. Substitution of methyl residue at C3 enhanced the activity 100 times from nonsubstituted (Z)-2-alkenyl formate. Substitution of methyl residue at C7 of each (Z)-octenyl formate also improved the activity 10 times, when the comparison was done between those of (Z)-2-octenyl formate and (Z)-2-nonenyl formate with or without 3-methyl or 3-ethyl substitution.

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