Indium-promoted Conversion of Allylic Bromide to Alcohol Moiety and Synthesis of Pipermethystine Skeletons

2016 ◽  
Vol 63 (9) ◽  
pp. 818-824 ◽  
Author(s):  
Bo-Sian Liou ◽  
Shang-Shing Peter Chou
Keyword(s):  
Allylic Bromide ◽  
Alcohol Moiety

ChemInform Abstract: TEAF Mediated Hydroxylation of Allylic Bromide: A Facile Synthesis of 4-Methoxycarbonyl-2(5H)-furanone.

ChemInform ◽  
2010 ◽  
Vol 28 (22) ◽  
pp. no-no
Author(s):  
I. BELTAIEF ◽  
R. BESBES ◽  
H. AMRI ◽  
J. VILLIERAS
Keyword(s):  
Facile Synthesis ◽  
Allylic Bromide

scholarly journals Insecticidal and Nerve Effects of Photoreactive Pyrethroid Containing a Diazirine Group in the Alcohol Moiety

1996 ◽  
Vol 21 (2) ◽  
pp. 179-185
Author(s):  
Kazuhiko MATSUDA ◽  
Koji IHARADA ◽  
Koichiro KOMAI ◽  
Hiroshi OKIMOTO ◽  
Tamio UENO ◽  
...  
Keyword(s):  
Alcohol Moiety

Synthesis of alkynes and alkynyl iodides bearing a protected amino alcohol moiety as functionalized amino acids precursors

2010 ◽  
Vol 53 (9) ◽  
pp. 1921-1926 ◽  
Author(s):  
Charfedinne Ayed ◽  
Julien Picard ◽  
Nadège Lubin-Germain ◽  
Jacques Uziel ◽  
Jacques Auge
Keyword(s):  
Amino Acids ◽  
Amino Alcohol ◽  
Functionalized Amino Acids ◽  
Alcohol Moiety

Section 10. Pyrethroid resistance: resistance breaking pyrethroids

1993 ◽  
Vol 1 ◽  
pp. 83-96 ◽  
Author(s):  
Neil W. Forrester ◽  
Matthew Cahill ◽  
Lisa J. Bird ◽  
Jacquelyn K. Layland
Keyword(s):  
Resistant Strain ◽  
Pyrethroid Resistance ◽  
Residual Activity ◽  
Susceptible Strain ◽  
Piperonyl Butoxide ◽  
Monooxygenase System ◽  
Acid Moiety ◽  
Resistance Factors ◽  
Resistance Breaking ◽  
Alcohol Moiety

SummaryThe structural requirements for designing a resistance breaking pyrethroid to overcome oxidative metabolic pyrethroid resistance in Helicoverpa armigera were studied. A range of pyrethroid structures were tested on a well defined pure breeding pyrethroid resistant strain of H. armigera (homozygous for a metabolic detoxification mechanism fully suppressible by piperonyl butoxide, presumably via a microsomal monooxygenase system). Highest resistance factors were to the ester bonded phenoxybenzyl alcohol pyrethroids, particularly to those with an aromatic acid moiety. Changes to the alcohol moiety alone could overcome most, if not all, resistance. Simple benzyl alcohols were the most effective followed by cyclopentenolones and a methylated biphenyl alcohol. However, the benzylfurylmethyl alcohol (bioresmethrin) was not effective. The incorporation of a synergophore grouping into the alcohol moiety was fully effective for Scott's Py III (methylenedioxyphenyl) and prallethrin (propynyl) but only partially effective for tetramethrin (N-alkyl). Changes to the acid moiety had little effect except for the incorporation of a synergophore methylenedioxyphenyl grouping (Cheminova I) which was just as effective as for the same insertion in the alcohol moiety. The change to a central ether bond from the conventional ester bond lowered resistance. Reversion to an unsubstituted alpha carbon analogue from the conventional alpha cyano group also lowered resistance.Piperonyl butoxide (Pbo) had little effect on pyrethroid toxicity in the susceptible strain except for the single isomers deltamethrin and esfenvalerate. However, it was more than fully effective in overcoming resistance and actually reduced resistance factors to significantly below one in the resistant strain. This indicated the possibility that Pbo could be acting both as a classical monooxygenase inhibitor and a preferential penetration synergist in resistant larvae.Partial or full resolution of racemic mixtures had minimal impact on increasing toxicity in the susceptible strain. However, partially or fully resolved isomers were clearly much more toxic on resistant strains, indicating a possible blocking effect of the inactive isomers during the toxication process with the higher pyrethroid doses applied to resistant larvae. Cis isomers had only slightly higher resistance factors than trans isomers.Seven fully effective resistance breaking pyrethroids were identified in this study and one of these (the simple benzyl alcohol, Series Two) was shown to be equally effective on both adults and larvae of H. armigera. It was also shown to work equally well on laboratory or field material and gave results similar to a pyrethroid/Pbo combination. However, none of the resistance breakers identified so far are able to satisfy all of the requirements necessary for an ideal resistance breaking pyrethroid (i.e. good resistance breaking activity at low rates, photostability, residual activity similar to current pyrethroids and safety to mammals). Factors acting against the possible commercialization of successful resistance breaking compounds are discussed.

YTTERBIUM METAL/TMSCL PROMOTED REACTION OF IMINES WITH ALLYLIC BROMIDE

2001 ◽  
Vol 31 (2) ◽  
pp. 273-277 ◽  
Author(s):  
Weike Su ◽  
Jinghua Li ◽  
Yongmin Zhang
Keyword(s):  
Allylic Bromide
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