Alkyl aryl methanone oxime ethers

Chemistry. The majority of the alkyl aryl methanone oxime ethers were synthesized as shown in Figure 1. The alkyl aryl methanones were prepared by either of two methods. In the first method, the appropriately-substituted benzonitrile was treated with the desired alkylmagnesium halide to give the desired ketone(8). 

Figure 1. Synthesis of Alkyl Aryl Methanone Oxime Ethers.

Alkyl aryl methanone oxime ethers QSAR analysis, 183 insecticidal activity, 175-176 structure-activity relationships, 183-185 synthesis, 174-178... 

The alkyl aryl methanone oximes can be converted to oxime ethers by several methods. The usual alkylation procedure utilized was a phase transfer catalyzed alkylation wherein the E-alkyl aryl... 

The replacement of the ester linkage of pyrethroids by alternatives was known to lead to compounds of diminished biological activity. Thiol esters and amides are two such isosteric replacements that lead to a loss in biological activitv(13.14). The exception to this trend was the replacement by the oxime function-alitv(2.3). The alkyl aryl oxime ethers are not susceptible to alkaline hydrolysis and esteric attack as are the pyrethroid esters(15). The present study details our investigation of the biological activity of [1,1 -biphenyl]-3-methanols when combined with alkyl aryl methanone oximes. 

E,Z-Alkyl aryl methanone oximes, 176 Alkyl aryl methanones, 176 Alkyl aryl oxime ethers combined with alcohols, 182... 

Next, the effect on activity with respect to the size of the alkyl group in our series compared to that disclosed in the literature (2,4) was of interest. The effectiveness of alkyl groups is reported to be cyclopropyl > isopropyl > ethyl > methyl. In fact, this trend was followed in the [1,1 -biphenyl]-2-methyl-3-methanol derived alkyl aryl oxime ethers. This is illustrated with the (E,Z)-4-trifluoromethoxyphenyl(alkyl)methanone oxime ethers, Compounds 14, 16, 19 (Table V). The activity of this series increases with increasing size of the alkyl group. However, when cyclobutyl was incorporated, activity was lost. The cyclopropyl was the most effective while the isopropyl group was somewhat less effective. Other alkyl changes resulted in a rapid loss of activity. 

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