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Natural products as insecticides: the biology, biochemistry and quantitative structure–activity relationships of spinosyns and spinosoids
Author(s) -
Sparks Thomas C,
Crouse Gary D,
Durst Gregory
Publication year - 2001
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.358
Subject(s) - heliothis virescens , spinosad , pyrethroid , quantitative structure–activity relationship , biology , toxicology , pesticide , chemistry , stereochemistry , pest analysis , botany , ecology , noctuidae
Abstract The spinosyns, a novel family of insecticidal macrocyclic lactones, are active on a wide variety of insect pests, especially lepidopterans and dipterans. The biological activity of a mixture (spinosad; Tracer®, Spin‐Tor®, Success®) of the two most abundant spinosyns (spinosyns A and D) against pest insects is on a par with that of many pyrethroid insecticides. The spinosyns also exhibit a very favorable environmental and toxicological profile, and possess a mode of action that appears unique, with studies to date suggesting that both nicotinic and gamma ‐aminobutryic acid receptor functions are altered in a novel manner. Compared to pyrethroids such as cypermethrin, spinosyn A is slow to penetrate into insect larvae such as tobacco budworm larvae ( Heliothis virescens ); however, once inside the insect, spinosyn A is not readily metabolized. To date, more than 20 spinosyns and more than 800 spinosoids (semi‐synthetic analogs) have been isolated or synthesized, respectively. Artificial neural network‐based quantitative structure activity relationship (QSAR) studies for the spinosyns suggested that modification of the 2′,3′,4′‐tri‐ O ‐methylrhamnosyl moiety could improve activity and several spinosoids incorporating these modifications exhibited markedly improved lepidopteran activity compared to spinosad. Multiple linear regression‐based QSAR studies also suggest that whole molecule properties such as CLogP and MOPAC dipole moment can explain much of the biological activity observed for the spinosyns and closely related spinosoids. © 2001 Society of Chemical Industry