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Review
. 2019;95(7):378-400.
doi: 10.2183/pjab.95.027.

Discovery and development of pyrethroid insecticides

Noritada Matsuo  1   2
Affiliations
Review

Discovery and development of pyrethroid insecticides

Noritada Matsuo. Proc Jpn Acad Ser B Phys Biol Sci. 2019.

Abstract

Pyrethroid insecticides contain natural pyrethrins extracted from pyrethrum flowers, and their synthetic derivatives, pyrethroids. The present article provides an overview of the structure of natural pyrethrins, and the discovery and development of pyrethroids with an emphasis on the background of selected compounds. The stereochemical relationships among pyrethroid secondary alcohols, and toxicologic and environmental effects of pyrethroids are also discussed. Finally, the pyrethroid resistance of mosquitoes and future aspects of pyrethroids are addressed.

Keywords: insecticide; pyrethrins; pyrethroid resistance; pyrethroids; stereochemistry.

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Figures

Figure 1.
Figure 1.
(a) Pyrethrum flowers; (b) Mosquito coil.
Figure 2.
Figure 2.
Structures of natural pyrethrins.
Figure 3.
Figure 3.
Structure of allethrin.
Figure 4.
Figure 4.
Comparison of commercial processes of DDT and allethrin.
Figure 5.
Figure 5.
Development of pyrethroids shown in the tree.
Figure 6.
Figure 6.
Background story of the invention of tetramethrin (Ueda and Kato 1964).
Figure 7.
Figure 7.
Background of imiprothrin (Itaya 1979).
Figure 8.
Figure 8.
Moving distance of German cockroaches after treatment with 1.0% oil-based aerosol formulation.
Figure 9.
Figure 9.
“Darts” test for knockdown activity against cockroaches.
Figure 10.
Figure 10.
Invention of phenothrin (Itaya and Kamoshita 1968).
Figure 11.
Figure 11.
Background of cyphenothrin (Matsuo 1971).
Figure 12.
Figure 12.
Commercial pyrethroids containing α-cyano-3-phenoxybenzyl alcohol.
Figure 13.
Figure 13.
Pyrethroid leading products, total $2,852M (2015) (Philips McDougall Product Section).
Figure 14.
Figure 14.
Background of deltamethrin (Elliott 1974).
Figure 15.
Figure 15.
“Olyset Net” (Photograph ©M. Hallahan/Sumitomo Chemical).
Figure 16.
Figure 16.
Background of fenvalerate (Ohno and Hirano 1973).
Figure 17.
Figure 17.
Background of silafluofen (Katsuda 1984).
Figure 18.
Figure 18.
Invention of terallethrin (Matsui and Kitahara 1967).
Figure 19.
Figure 19.
“Vinylogous relationship” of momfluorothrin (Matsuo 2010).
Figure 20.
Figure 20.
Background of empenthrin-1.
Figure 21.
Figure 21.
Background of empenthrin-2 (Kitamura 1973).
Figure 22.
Figure 22.
Background of prallethrin (Matsuo 1978).
Figure 23.
Figure 23.
Biochemical hydrolysis of allethrolone acetate (Oritani 1975), and PG-lon acetate (Matsuo 1977).
Figure 24.
Figure 24.
Optical resolution of PG-lon phthalate (Tsushima and Matsuo 1981).
Figure 25.
Figure 25.
Practical synthesis of (S)-PG-lon using asymmetric lipase hydrolysis (Umemura and Mitsuda 1988).
Figure 26.
Figure 26.
Structure of prallethrin.
Figure 27.
Figure 27.
Norchrysanthemic acid and its esters.
Figure 28.
Figure 28.
Structure-activity relationships of insecticidally more important stereoisomers (1).
Figure 29.
Figure 29.
Structure-activity relationships of insecticidally more important isomers (2).
Figure 30.
Figure 30.
Structure activity relationships of insecticidally more important isomers (3).
Figure 31.
Figure 31.
Detoxification by cytochrome P450 enzymes on the phenoxybenzyl ring and block against detoxification by P450 enzymes on the polyfluorobenzyl ring.
Figure 32.
Figure 32.
A new 2-bromo derivative against pyrethroid-resistant mosquitoes (Matsuo 2017).
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