Spinosyn insecticides
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Spinosyn insecticides Raghavendra Ramachanderan1 · Bernd Schaefer2 Received: 26 February 2020 / Accepted: 26 April 2020 © Springer Nature Switzerland AG 2020
Abstract The spinosyns found in the bacterial species Saccharopolyspora spinosa were first isolated from a soil sample from an abandoned rum distillery on the British Virgin Islands. Their anti-insecticidal activity against several commercially relevant pests is based on the allosteric, agonistic binding at the nicotinic acetylcholine receptor and an antagonistic effect on the γ-aminobutyric acid receptor. Spinosyns result from the polyketide pathway. The biosynthesis of the tetracyclic lactone comprises an enzymatic Diels–Alder and a Rauhut–Currier-like reaction followed by glycosylation with rhamnose and forosamine. The spinosyns, constituting the insecticidal active ingredients in Spinosad® and Spinetoram® from Dow AgroSciences, are manufactured by fermentation. However, in recent years, facilitated by computer-aided molecular modeling and bioactivity directed synthesis, novel highly potent, structurally simplified spinosyn analogs were discovered, which might be accessible in the future by total synthesis on an industrial scale. Graphic abstract
Spinosyn A
Keywords Spinosyn® · Spinetoram® · Macrolide · Insecticide · Diels–Alder reaction · Rauhut–Currier reaction · Cu(OAc)2 ·Cu3(As3O6)2
Introduction Since ancient times people have tried to protect themselves, their crops, and their food stocks against insects. For instance, Pliny the Elder (23/24–79 AD) describes the use * Bernd Schaefer [email protected] 1
Department of Biosystems Science and Engineering, ETH Zurich, Basel, Switzerland
Ruprecht-Karls-Universität Heidelberg, BASF SE, RCS/ON, B009, 67056 Ludwigshafen am Rhein, Germany
2
of salts of arsenic to fight insects [1]. In the Middle Ages, as we know from Marco Polo (1254–1324), similar methods were applied in China. In most cases, however, their efforts failed, such as the fight against locust swarms. Paris green [Cu(OAc)2·Cu3(As3O6)2, copper(II) acetoarsenite], a bright green pigment originally used in paints, constituted the first synthetic insecticide [2] to combat the Colorado potato beetle (Leptinotarsa decemlineata) and the tobacco budworm (Heliothis virescens) as early as in the 1880s, and after World War I also the malaria-spreading anopheline mosquitos in Italy, Sardinia, and Corsica [3, 4]. Antinonnin (3,5-dinitro-o-cresol), brought to the market by
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ChemTexts
Bayer in 1892, is considered to be the first synthetic organic compound used as an insecticide. With the blossoming of preparative organic chemistry in the twentieth century, numerous classes of organic insecticides appeared on the fast-growing crop protection market [5, 6]. Most of those suffered from numerous adverse effects, not only to humans, such as the bioaccumulating organochlorines or the highly poisonous organophosphates, but also to non-target organisms, jeopardizing bird populations, aqua
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