TY - JOUR
T1 - Polyenylcyclopropane carboxylic esters with high insecticidal activity
AU - Ferroni, Claudia
AU - Bassetti, Lucio
AU - Borzatta, Valerio
AU - Capparella, Elisa
AU - Gobbi, Carlotta
AU - Guerrini, Alberto
AU - Varchi, Greta
N1 - Publisher Copyright:
© 2014 Society of Chemical Industry.
Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.
PY - 2015/5/1
Y1 - 2015/5/1
N2 - Pyrethroids are synthetic derivatives of naturally occurring pyrethrum. These molecules are widely used in agriculture for ant, fly and mosquito control and for lawn and garden care. Pyrethroids are the optically active esters of 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropane carboxylic acid, also known as chrysanthemic acid. However, their intense use has resulted in the development of resistance in many insect species. Herein, specific structural modifications of the pyrethroid scaffold and their effect on insecticidal activity, especially on resistant pests strains, are reported. RESULTS: The exposure to (1R)-trans-(E/Z)-2,3,5,6-tetrafluorobenzyl-3-(buta-1,3-dienyl)-2,2-dimethyl cyclopropanecarboxylate and its diastereomers produced 100% mortality in yellow fever mosquitoes (Aedes aegypti), house mosquitoes (Culex quinquefasciatus) and houseflies (Musca domestica). Moreover, this compound provided complete knockdown within 15min of exposure against cockroaches (Blattella germanica) and maintained an excellent knockdown activity at 10 days after treatment. CONCLUSION: Novel pyrethroid derivatives obtained from 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylic acid are described. These derivatives display high insecticidal activity, a wide spectrum of action and no toxicity towards mammalians. The proposed synthetic procedures are highly efficient and inexpensive, and therefore suitable for industrial scale-up.
AB - Pyrethroids are synthetic derivatives of naturally occurring pyrethrum. These molecules are widely used in agriculture for ant, fly and mosquito control and for lawn and garden care. Pyrethroids are the optically active esters of 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropane carboxylic acid, also known as chrysanthemic acid. However, their intense use has resulted in the development of resistance in many insect species. Herein, specific structural modifications of the pyrethroid scaffold and their effect on insecticidal activity, especially on resistant pests strains, are reported. RESULTS: The exposure to (1R)-trans-(E/Z)-2,3,5,6-tetrafluorobenzyl-3-(buta-1,3-dienyl)-2,2-dimethyl cyclopropanecarboxylate and its diastereomers produced 100% mortality in yellow fever mosquitoes (Aedes aegypti), house mosquitoes (Culex quinquefasciatus) and houseflies (Musca domestica). Moreover, this compound provided complete knockdown within 15min of exposure against cockroaches (Blattella germanica) and maintained an excellent knockdown activity at 10 days after treatment. CONCLUSION: Novel pyrethroid derivatives obtained from 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylic acid are described. These derivatives display high insecticidal activity, a wide spectrum of action and no toxicity towards mammalians. The proposed synthetic procedures are highly efficient and inexpensive, and therefore suitable for industrial scale-up.
KW - Blattella germanica
KW - Ethyl chrysanthemate
KW - Insecticidal activity
KW - Pyrethroids
KW - Resistance
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U2 - 10.1002/ps.3842
DO - 10.1002/ps.3842
M3 - Article
C2 - 24899413
AN - SCOPUS:84940296391
VL - 71
SP - 728
EP - 736
JO - Pest Management Science
JF - Pest Management Science
SN - 1526-498X
IS - 5
ER -