Insecticidal isomers of 4-tert-butyl-1-(4-ethynylcyclohexyl)-2,6,7-trioxabicyclo [2.2.2]octane and 5-tert-butyl-2-(4-ethynylcyclohexyl)-1,3- dithiane
1995
Weston, J.B. | Larkin, J.P. | Pulman, D.A. | Holden, I. | Casida, J.E.
4-tert-Butyl-2,6,7-trioxabicyclo[2.2.2]octanes and 5-tert-butyl-1,3-dithianes with the 4-ethynylcyclohexyl substituent in the 1- and 2-positions, respectively, are potent insecticides modeled on their 4-ethynylphenyl and hex-5-ynyl analogs. The compounds were prepared from dimethyl 1,4-cyclohexane-dicarboxylate, 4-(2,2-dibromovinyl)cyclohexanecarboxylic acid, methyl 4-(1-chlorovinyl)cyclohexanecarboxylate, and 4-ethynylcyclohexylmethanol by well-established chemistry. The cis and trans isomers of the 1-cyclohexyl-trioxabicyclooctane and all four geometric isomers of the 2-cyclohexyl-1,3-dithiane were separated by chromatography of the final products or suitable intermediates. High levels of insecticidal activity were found against houseflies, German cockroaches and aphids for trioxabicyclooctanes and dithianes with the trans ethynylcyclohexyl configuration.
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