Synthetic pyrethroids containing a C-C triple bond

Abstract

:The three commercial synthetic pyrethroids containing a carbonÈ carbon triple bond, a-ethynyl-2-methylpent-2-enyl (1R)-trans-chrysanthemate, (S)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1R)-trans,cis-chrysanthemate and [2,5-dioxo-3-(2-propynyl)-1-imidazolidinyl]methyl (1R)-trans-chrysanthemate are reviewed with emphasis on their inventive histories. Their chemistry and efficacy are described brieÑy. The relationship between stereochemistry and the biological activity is also discussed.

New trends in pest control: the search for greener insecticides

“…The activity of these compounds is due to their high affinity to insect Na + -channels, causing neuronal hyperexcitability. 15,26 Subsequent research 24,27,28 meant the replacement of some of the structural elements of pyrethrins. For example, the pentadienyl side chain of pyrethrins I and II was replaced by more accessible moieties with similar steric and electronic behaviour.…”

Identification of Metabolites of [1,2,3-13C]Propargyl Alcohol in Rat Urine by 13C NMR and Mass Spectrometry

“…The metabolism of PA and other acetylenic compounds has not been investigated extensively. Although a number of commercial pyrethroid insecticides containing a carbon-carbon triple bond (Matsuo, 1998) have been synthesized, the only literature cited has been a report by Tomigahara et al (1994) who presented evidence for the addition of one molecule of acetylcysteine to the internal carbon of the triple bond of the pyrethroid insecticide, Etoc. However, attempts at preparing the metabolite by chemical synthesis resulted in addition to the external carbon of the triple bond.…”

A Simple Structure-Based Calculator for Estimating Vapor Pressure

“…Predicting the vapor pressure of various agrochemicals, not used in the development of the calculator, offers an example of the utility of this simple vapor pressure calculator. These predictions are summarized in Table 4 for the compounds listed in Figure 3 (Ammermann et al, 1992;Deege et al, 1995;Hanai et al, 1993;Hartwig et al, 1992;Longhurst et al, 1992;Luscombe et al, 1995;Matsuo, 1998;Meister, 1995;Miura et al, 1993;Neumann et al, 1992;Prosch et al, 1997;Russell et al, 1992;Snel et al, 1995;Suntio et al, 1988;Tomlin, 1997). A plot of the predicted versus measured vapor pressure values is presented in Figure 4.…”