Synthesis, insecticidal activity, and phytotoxicity of novel chiral amides

BACKGROUND The lesser grain borer, Rhyzopertha dominica (F.) (Coleoptera: Bostrychidae), is an important pest of stored grains worldwide. Chemical control is the main method used to manage this pest, but the continuous use of insecticides can lead to the selection of resistant R. dominica strains. T...

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Bibliographic Details
Published in:	Pest management science Vol. 75; no. 6; pp. 1689 - 1696
Main Authors:	Aguiar, Alex R, Alvarenga, Elson S, Silva, Eliete MP, Farias, Elizeu S, Picanço, Marcelo C
Format:	Journal Article
Language:	English
Published:	Chichester, UK John Wiley & Sons, Ltd 01-06-2019 Wiley Subscription Services, Inc
Subjects:	Amides Amides - chemical synthesis Amides - chemistry Amides - toxicity Animals Biological Assay Borers Chemical control Chemical synthesis Chemistry Techniques, Synthetic Coleoptera d‐mannitol Grain storage insecticide Insecticide resistance Insecticides Insecticides - chemical synthesis Insecticides - chemistry Insecticides - toxicity Mortality Organic chemistry Pests Phytotoxicity Rhyzopertha dominica Seeds Stereoisomerism Toxicity Triticum - drug effects Triticum sativum Wheat Triticum sativum insecticide Rhyzopertha dominica d-mannitol
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Summary:	BACKGROUND The lesser grain borer, Rhyzopertha dominica (F.) (Coleoptera: Bostrychidae), is an important pest of stored grains worldwide. Chemical control is the main method used to manage this pest, but the continuous use of insecticides can lead to the selection of resistant R. dominica strains. Thus, there is a constant demand for the development of new insecticide molecules. This study describes the synthesis of 14 chiral amides and evaluation of their insecticidal activity against R. dominica. Their phytotoxicity to wheat (Triticum sativum) seeds is also evaluated. RESULTS In the screening assay, compounds 8i and 8j caused 100% and 87% mortality of R. dominica. These values did not differ from the mortality caused by Bifenthrin® (75%). Amide 8i presented similar toxicity (LD50 = 27.98 µmol g−1, CI95 = 25.14–30.71) and speed of action (LT50 = 22 h, CI95 = 19.34–24.66) to amide 8j (LD50 = 29.37 µmol g−1, CI95 = 27.43–31.09, and LT50 = 19 h, CI95 = 17.05–20.95) against the pest. Both amides inhibited less than 44% of wheat growth. CONCLUSION Among the tested amides, only 8i and 8j were effective in R. dominica control and presented no considerable phytotoxicity towards wheat seeds. Therefore, these amides are promising as insecticides for the management of R. dominica. © 2018 Society of Chemical Industry The enantioselective route from the natural d‐mannitol provided 14 chiral amides which were evaluated against the lesser grain borer, Rhyzopertha dominica. Two amides were as active as the pyrethroid Bifenthrin®.
ISSN:	1526-498X 1526-4998
DOI:	10.1002/ps.5289