376 



(1), (Z)-3,3-dimethyl-A''"-cyclohexaneacetaldehyde (2), (Z)-3, 3-dimethyl-A^ '^- 

 cyclohexaneethanol (3), and (+)- cis- 2-isopropenyl-l-methyl-cyclobutaneethanol 

 4)] that comprise the pheroraone of male boll weevil Anthonomus grandis Boheman 

 were identified and first synthesized by Tumlinson et al. These sex attractants 

 are currently of considerable interest since they may provide a generally non- 

 toxic method of surveying and controlling boll weevil population. The growing 

 concern over the environmental pollution and ecological imbalance caused by 

 insecticides has further stimulated interest in this area. The commercial 

 importance of these sex attractants prompted us to develop an efficient, high- 

 yield synthesis of these compounds. This paper describes a facile route from 

 commercially available 3-methyl-2-cyclohexenone to the E and Z aldehyde compo- 

 nents (1 and 2) in 80% overall yields. Separation of the aldehyde mixture, 



followed by reduction of aldehyde 2 with NaBH, or 9-BBN, affords a route to 



4 



the component Z alcohol (3) in an essentially quantitative yield. Scheme I 

 outlines the synthesis of sex pheromone components 1, 2, and 3. 



737. Pfrimmer, T. R. 1966. Systemic insecticides for cotton insect control 



in 1965. J. Econ. Entomol. 59; 1113-1118, 

 Systemic insecticides were evaluated for effect on insect control, plant 

 stand, and early fruiting of cotton in field tests at Stoneville, Mississippi 

 in 1965. A granular formulation of Union Carbide UC-21149 [2-methyl-2- 

 (methylthio) propionaldehyde 0-(methylcarbamoyl)oxime] applied with the seed 

 at planting gave outstanding control of tobacco thrips, Frankliniella 

 fusca (Hinds), and was effective against the tarnished plant bug, Lygus 

 lineolaris (Ptlisot de Beauvois) . Granular formulations of General Chemical 

 GC-6506 [dimethyl £-(raethylthio) phenyl phosphate] and Niagara NIA-10242 

 (2,3-dihydro-2,2-dimethylbenzofuranyl methylcarbamate) applied with the seed 

 at planting were not so effective as UC-21149. Wlien NIA-10242 and UC-21149 



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