Abstract
The larvicidal activity against Culex pipiens of all stereoisomers of dihydroguaiaretic acid (DGA) and secoisolariciresinol was measured, and these DGAs were found to be potent. Sixteen (-)-DGA derivatives were then newly synthesized to analyze their structure-activity relationship. Two derivatives monohydroxylated at the 3- or 4-position of the 7-phenyl group of DGA induced acute paralytic activity in the mosquitoes. Derivatives with several hydroxyl groups had lower activity than the natural compound, suggesting that hydrophobicity was probably an important factor for their insecticidal activity.
MeSH terms
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Animals
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Butylene Glycols* / chemical synthesis
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Butylene Glycols* / pharmacology
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Culex / drug effects*
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Culex / growth & development
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Disease Vectors
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Guaiacol / analogs & derivatives*
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Guaiacol / chemical synthesis
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Guaiacol / pharmacology
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Hydrophobic and Hydrophilic Interactions
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Hydroxylation
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Insect Control / methods*
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Insecticides* / chemical synthesis
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Insecticides* / pharmacology
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Larva / drug effects*
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Larva / growth & development
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Lethal Dose 50
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Lignans* / chemical synthesis
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Lignans* / pharmacology
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Butylene Glycols
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Insecticides
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Lignans
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dihydroguaiaretic acid
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Guaiacol
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secoisolariciresinol