The synthesis of a series of mono‐ and disubstituted biphenyl‐3‐ylmethyl esters of 3‐(2,2‐dichlorovinyl)‐2,2‐dimethylcyclopropanecarboxylic acid is described. The bioactivity of these compounds against Spodoptera eridania, Epilachna varivestis, Oncopeltus fasciatus, Acrythosiphon pisum and Tetranychus urticae is presented and discussed. Substitution of fluorine, chlorine and methyl groups in the 2‐position of the biphenyl ring generally led to an increase in activity over the unsubstituted parent biphenyl ester. In addition, pyrethroid esters derived from these 2‐substituted biphenyl‐3‐ylmethanols appeared to have a broader spectrum of activity than ‘classical’ pyrethroids. For example, the (1RS)‐cis‐3‐(2,2‐dichlorovinyl)‐2, 2‐dimethylcyclopro‐panecarboxylic acid ester of 2‐methylbiphenyl‐3‐ylmethanol was acaricidal, while maintaining a level of activity against other insects that was equal to or greater than cis‐permethiin. Biological data on other esters of this novel alcohol are also presented.

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Following the above procedure identically, 1.0 g of 17 was oxidized and the crude reaction product, was recrystallized from ethvl acetate to yield 480 mg of 16b: mp 144-150°; nmr, 68 (17ÍCH3), 72 (19-CH3), 225 (multiplet, 21-CH2), 344 (4-H) cps.Anal. Caled for C21H30O2: C, 80.21; H, 9.62. Found: C, 80.21; H, 9.37. 17af-(3-Hydroxypropyl)-3-methoxy-17/3-methylgona-l,3,5(10),-13-tetraene (9b) and 13,173-Epoxy-3-methoxy-17/3-methyl-17apropyl-13a-gona-l,3,5(10)-triene (13b).-A reaction mixture of 25 g of 17«-(3-hydroxypropy 1 )-3-methoxy-1,3,5( 10 )-est ratri en-17#3-ol (6d),n 100 ml of ethanol, and 25 ml of concentrated HC1 was stirred and refluxed for 45 min with solution being complete after 10 min. It was cooled and stirred, and 350 ml of cold HaO was added producing an oil which congealed when cooled to 5°. The oil was collected, washed with H20, dried, and recrvstallized from ethyl acetate to give 8.0 g of 9b. A sample was recrystallized from acetone for analysis: mp 85-90°; X™xcl3 2.76 µ; nmr, 61 (17-CH3), 216 (triplet, 22-CH2), 226 (OCH3) cps.