EVIDENCE FOR CIS-11-HEXADECEN-1-OL ACETATE AS A MAJOR COMPONENT OF THE SEX PHEROMONE OF THE BERTHA ARMYWORM, MAMESTRA CONFIGURATA (LEPIDOPTERA: NOCTUIDAE)

1975 ◽  
Vol 107 (4) ◽  
pp. 361-366 ◽  
Author(s):  
M. D. Chisholm ◽  
W. F. Steck ◽  
A. P. Arthur ◽  
E. W. Underhill
Keyword(s):  
Sex Pheromone ◽  
Biological Response ◽  
Retention Data ◽  
Synthetic Materials ◽  
Lepidoptera Noctuidae ◽  
Army Worm ◽  
Antennal Responses ◽  
Laboratory Bioassays ◽  
Bertha Armyworm ◽  
Insect Sex

AbstractA potent sex pheromone produced by female bertha army worm moths was isolated. A 16 carbon, unsaturated, alkenol acetate was indicated from chemical degradative and GLC retention data. The location and configuration of the double bond was determined from the antennal responses (EAG) of male moths to a series of cis and trans mono-unsaturated alken-1-ol acetates; cis-11-hexadecen-1-ol acetate elicited the greatest EAG response. GLC retention times of the purified insect sex pheromone corresponded exactly with those of authentic cis-11-hexadecen-1-ol acetate on several analytical columns. Maximum biological response in laboratory bioassays of synthetic materials was obtained from a mixture of approximately 85% cis- and 15% trans-11-hexadecen-1-ol acetates.

SEX PHEROMONE TRAPS IN POPULATION MONITORING OF ADULTS OF THE BERTHA ARMYWORM, MAMESTRA CONFIGURATA (LEPIDOPTERA: NOCTUIDAE)

1979 ◽  
Vol 111 (1) ◽  
pp. 91-95 ◽  
Author(s):  
Warren Steck ◽  
E. W. Underhill ◽  
M. D. Chisholm ◽  
C. C. Peters ◽  
H. G. Philip ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Population Monitoring ◽  
Pheromone Traps ◽  
Light Traps ◽  
Mamestra Configurata ◽  
Sex Pheromone Traps ◽  
Lepidoptera Noctuidae ◽  
Army Worm ◽  
Bertha Armyworm ◽  
Prairie Provinces

AbstractTraps baited with the sex pheromone of the bertha army worm moth, Mamestra configurata (Walker), were operated at 36 sites across the prairie provinces in 1976 and 1977. They captured ca. 15 times as many bertha moths as did light traps and were considered to constitute a useful method for detection of adults of this species.

RELATION BETWEEN POD DAMAGE CAUSED BY LARVAE OF BERTHA ARMYWORM, MAMESTRA CONFIGURATA WALKER (LEPIDOPTERA: NOCTUIDAE), AND YIELD LOSS, SHELLING, AND SEED QUALITY IN CANOLA

1987 ◽  
Vol 119 (4) ◽  
pp. 365-369 ◽  
Author(s):  
G.K. Bracken
Keyword(s):  
Yield Loss ◽  
Seed Quality ◽  
Control Measures ◽  
Feeding Duration ◽  
Plot Yield ◽  
Control Decision ◽  
Field Plots ◽  
Lepidoptera Noctuidae ◽  
Army Worm ◽  
Bertha Armyworm

AbstractCanola plants in 0.84-m2 field plots were exposed to 120 bertha army worm larvae per square metre, beginning at mid 5th instar, for increasing durations. Yield loss increased with feeding duration throughout the feeding period whereas the proportion of pods damaged increased rapidly at first then leveled at 45%. Pod damage was negatively correlated with plot yield but the regression was not statistically significant. More seed shelled from plants with damaged pods than from plants with no pod damage under field conditions simulating drying in the swath. Seed from damaged pods had greater proportions of green and broken seeds causing lower seed grade and these defects were evident in seed from plots with 21% or more damaged pods. Although control measures for bertha armyworm should not be undertaken before pod damage is observed, a control decision should be made before 20% of the pods are damaged.

EFFECTS OF SOME SEMIOCHEMICALS ON THE SEX PHEROMONE OF THE BERTHA ARMYWORM, MAMESTRA CONFIGURATA (LEPIDOPTERA: NOCTUIDAE)

1984 ◽  
Vol 116 (4) ◽  
pp. 619-623 ◽  
Author(s):  
W. F. Steck ◽  
B. K. Bailey ◽  
E. W. Underhill
Keyword(s):  
Sex Pheromone ◽  
Mamestra Configurata ◽  
Tetradecenyl Acetate ◽  
Lepidoptera Noctuidae ◽  
Bertha Armyworm

AbstractInclusion of traces of (Z)-11-hexadecenol in synthetic sex lure traps for bertha armyworm moths resulted in diminished trapping; substantial amounts of (Z)-9-hexadecenol or (Z)-11-hexadecenal were also suppressant. Of 22 other oxyolefins tested, (Z)-7-dodecenyl acetate acted in conjunction with the bertha lure components to attract Euagrotis tepperi (Walker) to traps, and (Z)-7-tetradecenyl acetate similarly to attract Lacinipolia vicina (Grote). No tested additive improved either the potency or the specificity of the original bertha blend.

BERTHA ARMYWORM (LEPIDOPTERA: NOCTUIDAE): DETECTION OF A SEX PHEROMONE AND THE STIMULATORY EFFECT OF SOME SYNTHETIC CHEMICALS

1975 ◽  
Vol 107 (4) ◽  
pp. 355-359 ◽  
Author(s):  
D. L. Struble ◽  
M. Jacobson ◽  
N. Green ◽  
J. D. Warthen
Keyword(s):  
Sex Pheromone ◽  
Maximum Response ◽  
Laboratory Bioassay ◽  
Mamestra Configurata ◽  
Synthetic Chemicals ◽  
Sexual Responses ◽  
Lepidoptera Noctuidae ◽  
Bertha Armyworm

AbstractA sex pheromone, detected in female moths of the bertha armyworm, Mamestra configurata Wlk., was extracted from females that were more than 3 days old. Males responded to the pheromone from 2 days of age until they died; younger males were not tested. Chemical and bioassay analyses indicated that the pheromone was an acetate.The stimulatory effect of several chemicals was determined with males in a laboratory bioassay. Sexual responses were induced by Z7-, Z9-, Z10-, Z11-, and Z13-hexadecen-1-ol acetates. The maximum response in the laboratory was from the Z10-isomer, but this compound was only weakly attractive to males in the field.

MINOR SEX-PHEROMONE COMPONENTS OF MAMESTRA CONFIGURATA (LEPIDOPTERA: NOCTUIDAE) AND IMPROVED BLENDS FOR ATTRACTION OF MALE MOTHS

1984 ◽  
Vol 116 (1) ◽  
pp. 103-105 ◽  
Author(s):  
D. L. Struble ◽  
G. L. Ayre ◽  
J. R. Byers
Keyword(s):  
Sex Pheromone ◽  
Field Conditions ◽  
Mamestra Configurata ◽  
Sex Pheromone Components ◽  
Southern Alberta ◽  
Pheromone Components ◽  
Tetradecenyl Acetate ◽  
Lepidoptera Noctuidae ◽  
Number Of Males ◽  
Bertha Armyworm

The sex pheromone of bertha armyworm, Mamestra configurata (Walker), was reported to be (Z)-11-hexadecenyl acetate (Z11-16:Ac) and an unidentified tetradecenyl acetate. Electroantennogram responses of male antennae to synthetic isomeric tetradecenyl acetates and attractancy tests under field conditions showed that the highest number of males were captured with a blend of Z9-14:Ac: Z11-16:Ac in a ratio of 1:19 (Underhill et al. 1977). This blend has been useful for monitoring the relative abundances of bertha armyworm; however, in 162 monitor traps in southern Alberta from 1979 to 1982, the catches consisted of 18.4% Agroperina cogitata (Sm)

HOSTS OF BANCHUS FLAVESCENS (HYMENOPTERA: ICHNEUMONIDAE) AND ATHRYCIA CINEREA (DIPTERA: TACHINIDAE) IN MANITOBA

1979 ◽  
Vol 111 (6) ◽  
pp. 747-748 ◽  
Author(s):  
H.G. Wylie ◽  
G.L. Ayre
Keyword(s):  
Mamestra Configurata ◽  
Lepidoptera Noctuidae ◽  
Athrycia Cinerea ◽  
Army Worm ◽  
Bertha Armyworm

Banchus flavescens Cress. and Athrycia cinerea (Coq.) were reared each year (1972–1975) from larvae of bertha army worm, Mamestra configurata Walk. (Lepidoptera: Noctuidae), collected during an outbreak of this species on rapeseed in Manitoba. Neither parasite was reared from other Lepidoptera collected at that time from rapeseed; two separate attempts to propagate the parasites on native Lepidoptera other than M. configurata were unsuccessful (Wylie and Bucher 1977; Ewen and Arthur 1976). Since 1975 M. configurata has been rare in Manitoba. In 1976 both B. flavescens and A. cinerea were reared from bertha armyworm larvae from temporary artificial populations on rapeseed at Glenlea, south of Winnipeg. The presence of the two parasites in this locality, where M. configurata was not found during the outbreak, suggested that both B. flavescens and A. cinerea parasitize other lepidopterous species in Manitoba, especially when bertha armyworms are not present.

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

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