ISSN:
1573-1561
Keywords:
Chirality
;
enantiomers
;
5-hyroxy-4-methyl-3-heptanone, stereoisomer
;
Sitophilus oryzae
;
Sitophilus zeamais
;
rice weevil
;
maize weevil
;
aggregation pheromone
;
Coleoptera
;
Curculionidae
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
Abstract The chirality of the pheromone of the rice weevil,Sitophilus oryzae (L.), and the maize weevil,S. zeamais (Motschulsky), 5-hydroxy-4-methyl-3-heptanone, was determined using an acetyl lactate derivatization procedure. Maize weevils were shown to produce 〉98% 4S,5R. Determination was more difficult with rice weevils due to a smaller quantity of insect extract, but they were shown to produce at least 92% 4S, 5R. The attractancy of the four synthetic stereoisomers of 5-hydroxy-4-methyl-3-heptanone was tested using rice and maize weevils. As expected, both species were most strongly attracted to the 4S, 5R enantiomer. Maize weevils also showed low but significant responses (P 〈 0.05) to both 4R, 5R and 4S,5S. Rice weevils showed a highly significant (P 〈 0.01) response to 4R, 5S, although it was only about one third the response to 4S, 5R. Thus, (4S,5R)-5-hydroxy-4-methyl-3-heptanone is clearly the major component of the pheromone of bothS. zeamais andS. oryzae.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01012564
