F T

R = H, permethrin R = CN, cypermethrin

jasmolone

bioresmethrin

bioresmethrin

Figure 5.18

electrophilic addition giving tertiary cation

loss of proton via cyclopropyl ring formation

Figure 5.19

hydrolysis of phosphate ester; oxidation of alcohol to acid

,OPP

xco2H

chrysanthemic acid

CO2H

linolenic acid

CO2H

CO2H

jasmonic acid

Figure 5.19

CO2H

P-oxidation etc fl

jasmolone

P-oxidation etc fl jasmonic acid

12-oxophytodienoic acid

Figure 5.20

jasmolone pathway operates in the formation of jasmonic acid (Figure 5.20), which forms part of a general signalling system in plants, particularly the synthesis of secondary metabolites in response to wounding or microbial infection.

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