Structure-Activity Relationships of Phenylpropanoids as Antifeedants for the Pine Weevil Hylobius abietis was written by Bohman, B.;Nordlander, G.;Nordenhem, H.;Sunnerheim, K.;Borg-Karlson, A.-K.;Unelius, C. R.. And the article was included in Journal of Chemical Ecology in 2008.Electric Literature of C11H12O4 This article mentions the following:
Et cinnamate has been isolated from the bark of Pinus contorta in the search for antifeedants for the pine weevil, Hylobius abietis. Based on this lead compound, a number of structurally related compounds were synthesized and tested. The usability of the Topliss scheme, a flow diagram previously used in numerous structure-activity relationship (SAR) studies, was evaluated in an attempt to find the most potent antifeedants. The scheme was initially followed stepwise; subsequently, all compounds found in the scheme were compared. In total, 51 phenylpropanoids were tested and analyzed for SARs by using arguments from the field of medicinal chem. (rational drug design). Individual Hansch parameters based on hydrophobicity, steric, and electronic properties were examined The effects of position and numbers of substituents on the aromatic ring, the effects of conjugation in the mols., and the effects of the properties of the parent alc. part of the esters were also evaluated. It proved difficult to find strong SARs derived from single physicochem. descriptors, but our study led to numerous new, potent, phenylpropanoid antifeedants for the pine weevil. Among the most potent were Me 3-phenylpropanoates monosubstituted with chloro, fluoro, or Me groups and the 3,4-dichlorinated Me 3-phenylpropanoate. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Electric Literature of C11H12O4).
3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Electric Literature of C11H12O4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem