Juvenile hormone analogs

The use of polylactides for delivery of insect hormone analogs and other veterinary compounds (115,116) has been studied. Microspheres, pellets, and reservoir devices based on polyglycolide, poly-(DL-Iactide), poly(L-lactide), and various copolymers have been used to deliver methoprene and a number of juvenile hormone analogs. ... 

Analogs of juvenile hormones found in plants include the juvoclmenes in Ocimum basillcum, juvablone in Abies balsamea, and farnesol in many plant oils (lA). These natural plant products have never been used commercially as a source of insecticides, but they have served as model compounds for the development of synthetic juvenile hormone analogs such as kinoprene and methoprene (Figure 5). 

Chen N. M., Borden J. H. and Pierce H. D., Jr (1988) Effect of juvenile hormone analog, fenoxycarb, on pheromone production by Ips paraconfusus (Coleoptera Scolytidae). J. Chem. Ecol. 14, 1087-1098. 

Dickens J. C., McGovern W. L. and Wiygul G. (1988) Effects of antennectomy and a juvenile hormone analog on pheromone production in the boll weevil (Coleoptera Curculionidae). J. Entomol. Sci. 23, 52-58. 

First Juvenile Hormone Analog (United States)... 

Rogers, I. H., Manville, J. F., and Sahota, T. (1974). Juvenile hormone analogs in conifers. II. Isolation, identification, and biological activity of c/s-4-[r(R)-5 -dimethyl-3 -oxohexyl]-cyclohexane-1-carboxylicacidand(+)-4(R)-[l (R)-5 -dimethyl-3 -oxohexyl]-1-cyclohex-ene-1-carboxylic acid from Douglas-fir wood. Can. ). Chem. 52, 1192-1199. 

The two naturally occurring drug and insecticide adjuvants, sesamin and sesamolin from sesame oil, were found to posses modest juvenile hormone activity and served as models for the design of the first aromatic juvenile hormone analogs (12. 13.). 

Methoprene, a juvenile hormone analog, is structurally similar to insect juvenile hormones (Figure 4.11) such as juvenile hormone III. It is used for control of mosquitoes (floodwater mosquitoes, 2-4 instars), cigarette beetles, horn flies, fungus gnats (on mushroom), fleas, etc. The oral LD50 for methoprene in rats is >34,600 mg/kg. 

Hydroprene, a juvenile hormone analog, is registered for use against cockroaches. It has an oral LD50 in rats of >34,000 mg/kg. 

Slade, M. and Wilkinson, C.F., Juvenile hormone analogs A possible case of mistaken identity, Science, 1811, 672,1973... 

Figure 9.10 Structures of juvenile hormone analogs. ZR-512, hydroprene ZR-515, methoprene.

Induction of carboxylesterases and epoxide hydroloases would also affect the toxicity of insecticides. For example, host plant induction of 1-naphthyl acetate esterase would decrease the toxicity of certain insecticides containing an ester linkage such as organo-phosphates, pyrethroids, and some juvenile hormone analogs and, possibly, carbamates. 

Terriere, L.C. and Yu, S.J., Juvenile hormone analogs in vitro metabolism in relation to biological activity in blow flies and flesh flies, Pestic. Biochem. Physiol., 7,161,1977. 

Knowledge and understanding of how hormones regulate cellular processes in mosquitoes may be of great importance for controlling their reproduction. Conceivably, new types of insecticides may be developed that interfere with hormonal regulation, as for example, does the juvenile hormone analog (methoprene). 

Rearrangements of cyclopropanes. Cyclopropanes are interesting not only by themselves, but also because they are easily converted into important synthons in organic chemistry. Recently, rearrangements of cyclopropanes have appeared in the synthesis of, namely, steroids (pregn-4-en-one) [58], 19-norsteroids (estrone, 19-norandrost-4-en-3-17-dione, estradiol-17,8)and 19-nortestosterone [59], insect juvenile hormone analogs [60]. 

The codling moth sex pheromone (CCLV) has been synthesized by applying this cuprate addition procedure (Bowlus and Katzenellenbogen, 1973a,b Cooke, 1973). The stereoselective conjugate addition has been utilized for the synthesis of juvenile hormone analogs as well (Anderson et al., 1975). 

Juvenile Hormone Analogs and Anti-JuvenUe Hormone Agents for Insect Control... 

Despite the low titers of JHE detected in vivo, some feeding inhibition was noted on infection of first instar larvae of the cabbage looper T. ni, with the recombinant baculovirus. This inhibition, and subsequent decline in growth, was partially reversed by dorsal application of the juvenile hormone analog, epofenonane, to larvae previously infected with the recombinant virus 47). 

REAL LIFE MEDICINE 12-1 Juvenile Hormone Analogs in the Battle Against... 

Archelas, A., Delbecque, J.R and Furstoss, R. (1993) Microbiological transformations. 30. Enantioselective hydrolysis of racemic epoxides the synthesis of enantiopure insect juvenile hormone analogs (Bower s compound). Tetrahedron Asymmetry, 4,2445-2446. 

Freeman, P. K., Siggel, L., Chamberlain, P. H., and Clapp, G. E., The photochemistry of methyl geranate, a model chromophore for insect juvenile hormone analogs. Tetrahedron, 44, 5051,1988. 

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