- Environmental degradation of the insect growth regulator methoprene (isopropyl (2E,4E) 11 methoxy 3,7,11 trimethyl 2,4 dodecadienoate). I. Metabolism by alfalfa and rice
-
The metabolic fate of isopropyl (2E, 4E) 11 methoxy 3,7,11 trimethyl 2,4 dodecadienoate, a new insect growth regulator (common name, methoprene; trademark Altosid), was studied in alfalfa and rice as a function of time. The major metabolic pathways involved ester hydrolysis, O demethylation, and oxidative scission of the 4 ene double bond. The principal nonpolar metabolite was 7 methoxycitronellal which was isolated from vapors evolved from the plants. Chromatographic evidence strongly suggests the incorporation of radiolabel from the extensively degraded (2E) [5 14C]methoprene molecule into carotenoids, chlorophylls, and other higher molecular weight plant constituents. Yields of primary metabolites were grossly inflated (10x too high) unless thin layer chromatography was accompanied by prior purification by gel permeation chromatography, because much radioactivity was attributed to coeluting natural products. Rapid metabolism of methoprene to biologically inocuous derivatives was characteristic of both rice and alfalfa.
- Quistad,Staiger,Schooley
-
-
Read Online
- Universal approach to the synthesis of juvenoid hydroprene and methoprene from 4-methyltetrahydropyran
-
A universal approach to the synthesis of juvenoid hydroprene and methoprene was developed on the basis of monoalkylation of acetoacetate by 1-acetoxy-5-bromo-3-methylpentane, the product of acidic decyclization of 4-methyltetrahydropyran.
- Ishmuratov,Yakovleva,Galyautdinova,Faifer,Kharisov,Zorin,Tolstikov
-
p. 486 - 489
(2007/10/03)
-
- Synthesis and spectroscopy of chemically modified spheroidenes
-
The syntheses and spectroscopic properties of the all-E isomers of 11',12'-dihydrospheroidene (2), 3,4,11',12'-tetrahydrospheroidene (3), 3,4-dihydrospheroidene (4), 3,4,5,6-tetrahydrospheroidene (5), 3,4,7,8-tetrahydrospheroidene (6) and 15,15'-didehydrospheroidene (7) are described.Spheroidenes 2-6 have the same overall shape as native spheroidene (1), which is the carotenoid bound in the photosynthetic reaction centre of Rhodobacter sphaeroides 2.4.1, but they have instead polyene chromophores of nine (4), eight (2, 5) or seven (3, 6) conjugated double bonds.In 7, the central double bond is substituted by a triple bond.The observed λmax values of 2-6 are generally in good agreement with those calculated via the Fieser-Kuhn rules.In the mass spectra of 2-6, fragments due to bis-allylic fragmentation occur, whereas 1 and 7 do not show this type of fragmentation.A detailed analysis od the 1H- and 13C-NMR spectra of 1-7 has been achieved by mutual cmparison.
- Gebhard, R.,Dijk, J. T. M. van,Ouwerkerk, E. van,Boza, M. V. T. J.,Lugtenburg, J.
-
p. 459 - 469
(2007/10/02)
-
- PREPARATION OF DERIVATIVES OF CITRONELLAL
-
The hydrogenation of citronellal and citral, if not separated from ethereal oils, leads regioselectively to dihydrocitronellal and citronellal, respectively.The reaction of citral with (+)-ephedrin or L-aspartic acid, followed by hydrogenation and deblocking the aldehyde function, yields optically active citronellal.Reacting the aldehyde function of citronellal with diethanolamine, piperidine or morpholine, the alcohol addition to the 6,7-double bond results in 7-alkoxy substituted citronellals with acceptable yield.The formation of 7-hydroxy-6,7-dihydrocitronellal during this reaction has been proved and the effect of reaction parameters on the yield have been discussed.
- Koertvelyessy, Gyula
-
p. 347 - 354
(2007/10/02)
-
- Studies on Potential Juvenile Hormone Analogs: Part II - Synthesis of Some New Ethers, Schiff Bases, Hydrazides and Hydrazones Derived from 7-Hydroxycitronellal
-
A number of ethers, schiff bases, hydrazides and hydrazones derived from 7-hydroxycitronellal hyve been synthesized and tested on common Indian red cotton bug (Dysdercus koenigii) for JH activity.Only compounds 2 and 9 show marginal activity.
- Gupta, Anurag Ateet,Rastogi, Anita,Gupta, M. M.,Srivastava, Neera,Sengupta, A. K.,Athar, Mohd
-
p. 948 - 951
(2007/10/02)
-