PMID- 10552436
OWN - NLM
STAT- MEDLINE
DCOM- 20000821
LR  - 20190723
IS  - 0021-8561 (Print)
IS  - 0021-8561 (Linking)
VI  - 47
IP  - 3
DP  - 1999 Mar
TI  - Reduction of Carpophilus freemani dobson (Coleoptera: nitidulidae) aggregation 
      pheromone response by synthetic analogues.
PG  - 1189-95
AB  - Analogues of (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene, the major component of 
      the aggregation pheromone of Carpophilus freemani Dobson (Coleoptera: 
      Nitidulidae), were synthesized and the potency of these compounds in suppressing 
      the response of C. freemani to its pheromone in a wind tunnel bioassay was 
      determined. The most potent compounds reduced behavioral response to pheromone 
      83-96% when the inhibitors were present in 10-fold excess. These compounds are 
      (1Z, 3E,5E)-1-methoxy-3-ethyl-5-methyl-1,3,5-heptatriene, (1E,3E, 
      5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene, and (1Z,3E, 
      5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene. In the presence of 
      fermenting bread dough (a pheromone synergist), the most potent inhibitory 
      compound, (1Z,3E, 5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene, was less 
      effective in reducing mean landings (69% vs 99%) than when dough was absent. This 
      inhibitory compound causes a reduction of response to pheromone but does not 
      cause a reduction of response to fermenting food-type volatiles such as 
      fermenting bread dough. Analogues of pheromones that strongly reduce response to 
      pheromones by insects might be useful as biochemical probes to study the 
      pharmacophoric (three-dimensional structure) requirements for pheromone 
      perception.
FAU - Petroski, R J
AU  - Petroski RJ
AD  - USDA, REE, Agricultural Research Service, National Center for Agricultural 
      Utilization Research, Bioactive Agents Research and Analytical Support Units, 
      1815 North University Street, Peoria, Illinois 61604, USA. 
      petrosrj@mail.ncaur.usda.gov
FAU - Weisleder, D
AU  - Weisleder D
LA  - eng
PT  - Journal Article
PL  - United States
TA  - J Agric Food Chem
JT  - Journal of agricultural and food chemistry
JID - 0374755
RN  - 0 (4,8-dimethyl-1,3,7-nonatriene)
RN  - 0 (Pheromones)
RN  - 0 (Terpenes)
SB  - IM
MH  - Animals
MH  - Biological Assay
MH  - Bread
MH  - *Coleoptera
MH  - Fermentation
MH  - Models, Molecular
MH  - Molecular Conformation
MH  - Pheromones/chemical synthesis/*chemistry/*pharmacology
MH  - Structure-Activity Relationship
MH  - Terpenes/chemical synthesis/*chemistry/pharmacology
EDAT- 1999/12/20 09:00
MHDA- 2000/08/29 11:01
CRDT- 1999/12/20 09:00
PHST- 1999/12/20 09:00 [pubmed]
PHST- 2000/08/29 11:01 [medline]
PHST- 1999/12/20 09:00 [entrez]
AID - jf9809378 [pii]
AID - 10.1021/jf9809378 [doi]
PST - ppublish
SO  - J Agric Food Chem. 1999 Mar;47(3):1189-95. doi: 10.1021/jf9809378.