| abstract |
1474937 Insecticidal substituted alkenes ELI LILLY & CO 23 April 1974 [27 April 1973] 17778/74 Headings C2C and C2P The invention relates to compounds of formula wherein each of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> is independently methyl or ethyl; Z<SP>1</SP> and Z<SP>2</SP> taken together represent a carbon to carbon bond; and Y is 3,4- methylenedioxyphenyl, 3,4 - ethylenedioxyphenyl, p - chlorophenyl or p - bromophenyl. These compounds may be prepared by reacting an alcohol of formula wherein R<SP>1</SP>, R<SP>2</SP>, and R<SP>3</SP> are as defined above, with a halogenating agent, reacting the resulting aliphatic halide with magnesium metal and an aldehyde of formula Y-CHO wherein Y is as defined above, and dehydrating the resulting substituted secondary alcohol. Alternatively, these compounds may be prepared by reacting a substituted halide of formula wherein X is a halide and Q is as defined above, with an alkyl phosphite to form a phosphonate and reacting the resulting phosphate with an alkali metal hydride or amide and an aldehyde of formula wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are as defined above. The following intermediates are prepared in the examples: Citronellyl Bromide, by the reaction of citronellol with PBr 3 at -5 to 0 C. in the presence of petroleum ether. 4,8 - Dimethyl - 1 - (3,4 - methylenedioxyphenyl) - 7 - nonenyl - 1 - ol, by treating citronellyl magnesium bromide (prepared by the reaction of citronellyl bromide with elemental magnesium) with piperonal. Diethyl - 3,4 - methylenedioxybenzyl phosphonate by treating 3,4-methylenedioxybenzyl chloride with P(OC 2 H 5 ) 3 . The invention also comprises an insecticidal formulation which contains as an active ingredient a compound of Formula I in association with an inert carrier therefor. |