Abstract
Synthetic sex pheromones could provide valuable alternative
means of pest control in Integrated Pest Management (IPM)
strategies. Their uses could include population monitoring with
pheromone traps to guide other control methods, by mass trapping
and mating disruption.
(Z)-ll-Hexadecenal (Z-11-C4Hg CH=CH (CHZ) 9 CHO) and (Z)-llhexadecen-
l-ol (Z-ll-C/H",CH=CH(CH1 )oCH10H), the major components of '1 £ J £.
spotted stalk borer, Chilo pert el Lue (swinhoe) fernale sex
pheromone, were prepared in good yields from readily available
l,10-decanediol by an acetylenic route, and (Z) -9-tetradecenyl
fonnate (Z-9-C"HnCH=CH(CH1),CH10-CHO), an analogous structure -was 't j £ J l.
prepared from l,S-octanediol by the analogous acetylenic route.
Simple distillation of the 1-bromo-l0-(2-tetrahydropyranyloxy)
decane, coupling with 1-hexyne in liquid ammonia and litharnide
followed by deprotection gave ll-hexadecyn-l-01 (CIHoC=C(CH1)OCH10H) 1 J £.1"
(b.p 96-9S0 C/0.04 mmHg; 75% yield). Partial hydrogenation of 11-
hexadecyn-l-ol on a Lindlar catalyst gave (Z)-ll-hexadecen-l-ol
(b.p 75° C/O.Ol mmHg, 95% yield) which on oxidation gave (Z)-llhexadecenal
(Z-11-C!HaCH=CH(CH1)nCHO) (b.p 71° C/O.Ol mmHgi SO% ': ) I. '}
yield) containing 1.3% of the (E) isomer by GC analysis on a methyl
silicone column. (E)-11-Hexadecenal and (E)-11-hexadecen-l-ol were
prepared via sodium/liquid ammonia reduction of the intermediate
- "T"T !-"-I"(="1J"g*' _.T...TI1' 1 j 1 nom1Hn.l:-,
, £ .LV giving the final product containing 1% of. the
(Z)-isomer. Pyridinium chlorochromate in dichloromethane was used
for the oxidation of the olefinic alcohols to the corresponding
xiv
aldehydes (yield, 76-79%). The other analogues were obtained by
derivatizing the aldehydes or alcohols of the intermediates or the
final products in the synthesis.
The Electroantennographic (EAG) tests showed that the
compounds differed in their ability to evoke EAG responses and they
were lower than (Z)-ll-hexadecenal. The EAG responses conf inned
that (Z)-ll-hexadecenal was a better stirnulant
corresponding alcohol (Z)-ll-hexadecen-l-ol.
than the
'"
w, W (2021). Synthesis And Bioassaye Of Chilo Partellus Female Sex Pheromones And Their Analogues. Afribary. Retrieved from https://afribary.com/works/synthesis-and-bioassaye-of-chilo-partellus-female-sex-pheromones-and-their-analogues
W, Wanjala "Synthesis And Bioassaye Of Chilo Partellus Female Sex Pheromones And Their Analogues" Afribary. Afribary, 07 May. 2021, https://afribary.com/works/synthesis-and-bioassaye-of-chilo-partellus-female-sex-pheromones-and-their-analogues. Accessed 23 Dec. 2024.
W, Wanjala . "Synthesis And Bioassaye Of Chilo Partellus Female Sex Pheromones And Their Analogues". Afribary, Afribary, 07 May. 2021. Web. 23 Dec. 2024. < https://afribary.com/works/synthesis-and-bioassaye-of-chilo-partellus-female-sex-pheromones-and-their-analogues >.
W, Wanjala . "Synthesis And Bioassaye Of Chilo Partellus Female Sex Pheromones And Their Analogues" Afribary (2021). Accessed December 23, 2024. https://afribary.com/works/synthesis-and-bioassaye-of-chilo-partellus-female-sex-pheromones-and-their-analogues