RESUMO
The rice stalk stink bug, Tibraca limbativentris Stål, is an important rice pest in Brazil, causing significant damage to rice plants and consequently yield losses, with a high invasive potential in Mexico and USA. The male-produced sex pheromone of this species was recently identified as a 7:3 mixture of (3S,6S,7R)-1,10-bisaboladien-3-ol (1) and (3R,6S,7R)-1,10-bisaboladien-3-ol (5) (a.k.a. zingiberenols). The aim of this study was to evaluate field responses of T. limbativentris females to the racemic mixture and stereoisomers of 1,10-bisaboladien-3-ol, including the male-produced sex pheromone. The results obtained in two rice-producing areas of Brazil (Rio Grande do Sul and Santa Catarina) showed that traps baited with the main component 1 alone, the racemic mixture, and a mixture of 1 and 5 were attractive to females of T. limbativentris. The minor component 5 was unable to attract females when used alone. The results indicate that the sex pheromone of T. limbativentris and racemic mixture of 1,10-bisaboladien-3-ol were equally attractive to co-specific females in rice fields, and they could be a tool to incorporate in rice stalk stink bug management programs.
Assuntos
Heterópteros , Oryza , Feromônios/química , Sesquiterpenos , Atrativos Sexuais , Animais , Feminino , Sesquiterpenos/química , Atrativos Sexuais/químicaRESUMO
7-epi-sesquithujene (1) is a bicyclic sesquiterpene isolated from phoebe oil, an essential oil of the Brazilian walnut tree, Phoebe porosa. It is also produced by stressed ash trees and has been shown to elicit strong electrophysiological responses on emerald ash borer, Agrilus planipennis, antennae. In the course of the development of a synthetic 7-epi-sesquithujene lure for field testing against the emerald ash borer, we found that the absolute configuration of this compound had not been determined. We isolated >95% pure 7-epi-sesquithujene from phoebe oil via successive fractionation and conventional and argentation (HPLC) chromatographies. The specific optical rotation of this compound matched that of a synthetic product of known configuration. We also synthesized two other stereoisomers of sesquithujene and developed a chiral GC method to separate all four. Based on the specific rotation, stereoselective syntheses, and chiral GC analyses, 7-epi-sesquithujene present in phoebe oil and white ash was found to have the 2S,6S,7R absolute configuration.