Insect juvenile hormone analogues

Edwards, J.P., Short, J.E. and Abraham, L. (1991) Large-scale evaluation of the insect juvenile hormone analogue fenoxycarb as a long-term protectant of stored wheat. Journal of Stored Products Research 27, 31-39. 

Recent studies have shown that the insect juvenile hormone analogues juvabione (87) and derivatives (88)—(90), produced by Abies alba, occur in 4R,VR and 4R,1 S diastereomeric forms. It has been suggested that these sesquiterpenoids (c/. Vol. 8, p. 67) may be of value in chemosystematic studies of... 

Pheromones.—Further use has been made of Bestmann s unitized construction principle to synthesize a variety of 1,5- and 1,6-alkadiene pheromones. Standard Wittig methods have been used to synthesize (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene (142) (Scheme 19) (now identified as a sex pheromone of the winter moth O. brumata), sex attractants (143) of Lasiocampidae species, and the trail pheromone (144) of Pharaoh s ant. A variety of 2,4-dienoic ester insect juvenile hormone analogues (145) with terminal cyclohexene, cyclohexane, or pinene rings have been prepared by phosphonate olefination. The queen... 

Both enantiomers of the biologically active Bower s compound, a potent analogue of an insect juvenile hormone [103] (Scheme 18) were prepared using Aspergillus sp. cells in 96% ee. Interestingly, biological tests showed that the (6i )-antipode was about ten times more active than the (6S)-counterpart against the yellow meal worm Tenebrio molitor. 

Mundall E. C., Szibbo C. M. and Tobe S. S. (1983) Vitellogenin induced in adult male Diploptera punctata by juvenile hormone and juvenile hormone analogue identification and quantitative aspects. J. Insect Physiol. 29, 201-207. 

Fluoroketone analogues are also inhibitors of esterases. For example, the difluoro-ketone analogue 36 of sn-glycerol phospholipids is a potent competitive inhibitor of phospholipase A27 while the trifluoromethyl ketone 37 analogue of an insect juvenile hormone 38 is a potent and selective inhibitor of juvenile hormone esterase78. 

With a number of juvenile hormone analogues it could be shown that the concept of insect control by interaction with their hormone system is valid (28, 29). In view of the slow progress with compounds affecting the hormone system of ecdysteroids (30) the introduction of brassinosteroids may give some new impetus to the search for ecdysteroid-based insect growth regulators. 

Effective doses of these derivatives against Pyrrhocoris apterus and Dysdercus cingulatus are 51 0.5,52 0.01,53 0.000 04,54 0.000 01 and 55 0,000 002 pg/insect. The latter derivative is the most potent juvenile hormone analogue known so far. Only the isomers of S-configuration of this type are active, while those containing... 

Many secondary metabolites found in plants deter phytophagous invertebrates, sometimes even modifying insect growth and development if included in the diet [8]. Natural products can often act as insecticides via different pathways, as is the case with the analogues of insect juvenile hormones produced by plants. Thus, some derivatives of these analogues are used as commercial insecticides while others act as ecdysteroid antagonists [8]. 

Webster, R.P., and R.T. Carde The Effects of Mating, Exogenous Juvenile Hormone and a Juvenile Hormone Analogue on Pheromone Titre, Calling and Oviposi-tion in the Omnivorous Leafroller Moth. Platynota stultana). J. Insect Physiol. 30, 113-118(1984). 

Robinson, G.E. Effects of a Juvenile Hormone Analogue on Honey Bee Foraging Behaviour and Alarm Pheromone Production. J. Insect Physiol. 31, 277-282 (1985). 

Retinoic Acid Receptor. Most of the biological effects of retinoids are mediated through the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). Both all-/ran.s-retinoic acid and 9-d.v-rctinoic acid serve as agonists of RAR, while only 9-d.v-rctinoic acid functions as an agonist of RXR. The functional RAR exists as a heterodimer with RXR, while functional RXR exists as a homodimer. Methoprene is a juvenile hormone III analogue that mimics the activity of this insect hormone. 

B. Synthesis of Tritium-labelled Analogues of Juvenile Insect Hormones... 

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