. Boll rüsselkäfer Unterdrückung, Verwaltung und Beseitigung Technologie: Verfahren der Konferenz, Februar 13-15, 1974, Memphis, Tennessee. Boll Rüsselkäfer, Kontrolle, Kongresse. Abbildung 1.- Verbindungen. Ich, (+)-CI-2-Isopropenyl-l-methylcyclobutaneethanol. II, Z-3,3-dimethyl-AK | 3 - cyclohexaneethanol. Krank, Z-3,3-dimethyl-A]" - Cyclo-hexaneacetaldehyde. IV, £'-3,3-dimethyl-A1' a-Cyclo-hexaneacetaldehyde. hatte richtig gewesen, weil die spektralen Daten, die der natürlichen Komponenten und, was noch wichtiger ist, weil die synthetische Kom-ponenten erfolgreich die natürlichen im Bioassay ersetzt abgestimmt

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. Boll weevil suppression, management, and elimination technology : proceedings of a conference, February 13-15, 1974, Memphis, Tennessee. Boll weevil, Control, Congresses. Figure 1.—Compounds. I, ( + )-ci's-2-Isopropenyl-l- methylcyclobutaneethanol. II, Z-3, 3-Dimethyl-AK|3- cyclohexaneethanol. Ill, Z-3, 3-Dimethyl-A] "-cyclo- hexaneacetaldehyde. IV, £'-3, 3-Dimethyl-A1'a-cyclo- hexaneacetaldehyde. had been correct, because the spectral data matched that of the natural components and, more importantly, because the synthetic com- ponents successfully replaced the natural ones in the bioassay. The cyclobutane alcohol was a rather unusual structure because of its four- membered ring, and it was difficult to synthe- size with the appropriate substituents because four-membered rings are strained, and thus dif- ficult to close. After two unsuccessful attempts, a third was made which involved using a photochemical re- action to close the ring. This succeeded and after several more manipulations, a mixture was ob- tained which was expected to contain the desired component. The several components were sepa- rated by gas-liquid chromatography and each ex- amined until we located one which was very simi- lar in its chemical and spectral properties to what we were looking for. When we tested it with the other components, the mixture was not ac- tive. On increasing the concentration, however, activity was achieved. We went back to the mix- ture and isolated another isomer which was 200 times more active when combined with the other components. Thus, we had finally confirmed that the structures we had postulated were as active as the natural ones in the bioassay. During the next few months, R. C. Gueldner of this laboratory developed a better synthesis of grandisol which has served for the synthesis of several hundred grams of this compound by us and various vendors.- During the next year, we synthesized about 75 g of each compound for field tests. It became apparent that w

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