| Title: | "Determination of chirality in 5-hydroxy-4-methyl-3-heptanone, the aggregation pheromone ofSitophilus oryzae (L.) andS. zeamais Motschulsky" |
| Author(s): | Walgenbach CA; Phillips JK; Burkholder WE; King GG; Slessor KN; Mori K; |
| Address: | "Stored Products and Household Insects Laboratory Agricultural Research Service, U.S. Department of Agriculture, USA" |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| 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" |
| Notes: | "PubMed-not-MEDLINEWalgenbach, C A Phillips, J K Burkholder, W E King, G G Slessor, K N Mori, K eng 1987/12/01 J Chem Ecol. 1987 Dec; 13(12):2159-69. doi: 10.1007/BF01012564" |
