Uses
The pheromone is used for trapping and control of the European
grapevine moth (Lubesia butrana).
Application
(7Z,9E)-dodecadienyl acetate is a polyunsaturated fatty acid ester compound that can be used in the following areas:
(1) Pest management: By placing a small amount of this product in a lure, male moths are captured in traps, thereby disrupting mating; this is suitable for pest prevention and control in vineyards.
(2) Experimental research: Elucidating the metabolic pathways involved in the synthesis of this substance within pests through in vivo labelling; identifying key genes associated with the synthesis of this product via transcriptomic sequencing, facilitating its production in microorganisms or plants using genetic engineering techniques.
Metabolic pathway
Facile hydrolysis to the alcohol (2) would be expected in alkaline solution.
No published information is available but generally compounds of this
class are rapidly degraded biologically and their behaviour is similar to
that of typical long chain alkenoic acids.
Degradation
The effect of heat, sunlight, radicals and oxidants on isomerisation of the
double bonds has been investigated. The compound is degraded by
heating at 50 °C (6 mg remained of 100 mg after 6 days) but the process
may be slowed by the addition of antioxidants. Isomerisation occurs readily
in sunlight in the presence of a photosensitiser. Within 100 minutes an
equilibrium mixture containing 76% E,E and 12-14% of each of the
E,Z- and Z,E-isomers was formed. In the absence of photosensitiser,
degradation was faster than photoequilibration. Photo-oxidation in the
presence of Rose Bengal as a singlet oxygen generator gave a furan
derivative (4) (see Scheme 1). This takes place after isomerisation of 1 to
the E,E-isomer (3) (Shani et al., 1981).
