/ 



/ 



461 



Z-3,3-dimethyl-Al»a-cyclohexaneethanol (2), Z-3, 3-dimethyl-Al '<^-cyclohexane- 

 acetaldehyde (3), and E-3,3-diraethyl-A^ '"-cyclohexaneacetaldehyde (4), were 

 identified as the coiaponents of the male sex pheromone of the boll weevil. 

 The synthesis and structural assignments of the four compounds are also re- 

 ported. 



905. ; Hardee, D. D.; Gueldncr, R. C; Thompson, A. C; and Minyard, J. P. 

 1969. Sex pheromones produced by male boll weevil: isolation, identifi- 

 cation, and synthesis. Science 166: 1010-1012. 



The response of female boll weevils to males, Anthonomus grandis Boheman, in 

 laboratory bioassays can be reproduced by exposure to a mixture of compounds 

 I, II, and either III or IV, all isolated from male weevils and their fecal 

 material. The same response was elicited by mixtures of the synthesized com- 

 pounds. Compound I is (+)-cis-2-isopropenyl-l-methylcyclcbutaneethanol; II, 

 cis-3,3-dimethyl-A^ »^-cyclohexaneethanol; III, cis-3,3-dimethyl-A^ »"- 



cyclohexaneacetaldehyde; and IV, trans-3,3-dimethyl-A^ '"-cyclohexaneacetaldehyde. 



I 



906. ; Hardee, D. D.; Minyard, J. P.; Thompson, A. C; Cast, R. T. ; and 



Hedin, P. A. 1968. Boll weevil sex attractant: isolation studies. J. -^ 



Econ. Entomol. 61: 470-474. 



Techniques for isolating the sex attractant of the boll weevil Anthonomus 



grandis Boheman, were studied. Aeration of live insects, extraction procedures, "j 



/ 

 column chromatography on Florisii® and Carbowax 20M® coated silica gel, and /' 



steam distillation of male and mixed weevils and of fecal material are des- 

 cribed. Bioassays of the fractions obtained indicated that steam distillation 

 of male or mixed insects or fecal material is the preferred method of isolating 

 the attractant. 



