April 1947
INDUSTRIAL AND ENGINEERING CHEMISTRY
REPELLENT VALUE OF HOMOLOGS OF TABLE XI. COMPARATIVE DIMETHYL PHTHALATE (64) Av. Repellent Time, Min.
Phthalic Acid Ester Dimethyl Diethyl Di-n-propyl Diisopropyl Di-n-butyl Methyl-n-butyl Methyl ethyl
Aedes aegypti 258 118 11 3 12 11 342
Anopheles quadrimaculatus
108 21 9 3
16 7
18
administration of this compound to rabbits produced cataracts in the eyes of some of them. This compound is therefore definitely eliminated for use on the skin. iY-sec-Butylphthalimide and dimethyl carbate are also effective repellents. They are odorless and passed all pharmacological tests. A repellent does not have to be a liquid to be applied t o the skin. The extensive testing of liquids was due primarily to military preference for this type of repellent. A number of good solid repellents have also been found, but in general these are far more effective when impregnated in clothing than when applied t o the skin. Pharmacological studies of solid repellents had not been completed when the war ended. The object of testing a large number of liquids was not only to find compounds with outstanding repellent value but also t o correlate chemical constitution with repellency. If such a relation exists, it is not a simple one. Some of the difficulties that have been encountered are shown by a comparison of homologs of dimethyl phthalate in Table XI. COXCLUSION
b
Although much progress has been made in the development of new materials for combating insect pests, many problems must be solved before their utility as practical control measures is determined. It is necessary to know against what kinds of insects the product is effective, the stage a t mhich the insect is most susceptible-egg, larva, or adult-and the compatibility of the material with solvents, carriers, fungicides, or other insecticides. It must also be determined whether the material can be applied best as a dust, a spray, or an aerosol and whether it causes plant injury when applied either to the foliage or to the soil. I t s effect on beneficial insects, such as bees and various parasites and predators, and its toxicity to warm-blooded animals, especially man, must also be ascertained. These and many other factors need to be established before a new product finds full use in the field of economic entomology. LITERATURE CITED
Alsterlund, J., Pests, 14 ( 5 ) , 10 (1946). Bousquet, E. T.,U. S. Patent 2,166,120 (1939). Bruchhausen, F. v., and Gerhard, H., B e r . , 72, 830 (1939). Bushland, R. C., McAlister, L. C., Eddy, G. W., Jones, H. A., and Knipling, E. F., J . Parasitol., 30, 377 (1944). Campbell, F. L., and Sullivan, TT’. K., Soap Sanit. Chemicals, 14 (6), 119 (1938). Campbell, F. L., Sullivan, IF’.N., Smith, L. E., and Haller, H. L., J . Econ. Entomol., 27, 1176 (1934). Chandler, A . C., Calif. Mosquito Control Assoc. Proc. and Papers of lSth Annual Conf., p. 86 (1944) [Processed]. Cohen, W. D., Rsc. trav. chim., 57, 653 (1938). Cristol, S. J., and Haller, H. L., J . Am. Chem. SOC.,69,510 (1947). Cristol, S.J., Haller, H. L., and Lindquist, A . W., Science, 104, 343 (1946). Deonier, C. C., and Jones, H. A., Ibid., 103, 13 (1946). Deonier, C. C . , Jones, H. A . , Haller, H. L., Hinchey, E., and Incho, H. H., Soap Sanit. Chemicals, 22 ( l l ) , 118 (1946). Deonier, C. C., Maple, J. D., Jones, H. A., Hinchey, E., and Eide, P. AT., J . Econ. Entomol., 38, 241 (1945). Dickinson, R. G., and Bilicke, .C., J . A m . Chem. SOC.,50, 764 (1928). Eagleson, C., Soap Sanit. Chemicals, I8 (12), 125 (1942). Eddy, G. W., W a r Med., 6, 319 (1944). Ford, J. H., U. S. Patent 2,138,540 (1940). Gersdorff, W. A., Soap Sanit. ChemicaZs, 22 (3), 126 (1946)
413
(19) Gersdorff. IT’, 4..and McGovran, E. R., Ibid., 21 ( l l ) , 117 (1945). Gertler, S.I., U. S. Patent 2,389,427 (1946). Gertler, S. I., Fales, J. H., and Haller, H. L., Soap Sanit. Chemicals, 19 (4), 105 (1943). Goodhue, L. D., ISD. ESG.CHEM.,34, 1466 (1942). Goodhue, L. D., Sci. Monthly, 61, 413 (1945). Granett, P., and Haynes, H. L., J . Econ. Entomol., 38, 671 (1945). Hall, S. A , , Travis, B. V., and Jones, 13. A , , U. S. Patent 2,390,249 (1945). Haller, H. L., Bartlett, P. D., Drake, N. L., Newman, M. S., Cristol, S. J., et al., J . A m . Chem. SOC.,67, 1591 (1945). Haller, H. L., hlcGovran, E. R., Goodhue. L. D., and Sullivan, TT’. N., J . Ow. Chem., 7, 183 (1942). Hyslop, J . A , , U. S. Bur. Entomol. and Plant Quarantine, E 4 4 4
IProcessedl. Jones, H. A.,’Incho, H. H., and Deonier, C. C., J . Econ. Entomol., 39 A72 - - flR4AI. I
\ - - - - ,
Kilgore. L. B., U. S. Patent 2,070,603 (1937). Kirkwood, S.,and Phillips, P. H., J . Biol. Chem., 163, 251 (1946). KnirJlina. E. F., and Dove, W.E., J . Econ. Entomol., 37, 477 (i944J. Liuger, P., Helv. Chim. Acta, 27, 71 (1944). Lauger, P., Martin, H., and Muller, P., Ibid., 27, 892 (1944). LaForge, F. B., and Barthel, W. F., J . Org. Chem., 12, 199 (1947). LaForge, F. B., and Haller, H. L., J . A m . Chem. SOC.,54, 810 (1932). Ibid., 58, 1777 (1936). LaForge, F. B., Haller, H. L., and Smith, L. E., Chem. Revs., 12, 181 (1933). Latta, R., and Yeomans, A. H., J . E c ( J ~Entomol., . 36, 402 (1943). Mail, G. A , , Ibid., 29, 1144 (1936). Martin, H., and Wain, R. L., Nature, 154, 512 (1944). Moore, W., and Buc, H . E., U. S. Patent 1,727,305 (1929). Muller, P., Swiss Patent 226,180 (1940); U.5 . Patent 2,329,074 (Sept. 7, 1943); Reissue 22,700 (Dec. 4, 1945). Pictet, ii., and Rotschy, A., Ber., 37, 1225 (1904). Prill, E. A., Hartaell, A,, and Arthur, J. M., Contrib. Boycs Thompson Inst., 14 (31, 127 (1946). Prill, E. A., Hartaell, -4., and Arthur, J. &I., Science, 101, 464 (1945).
Questel, D. D., and Gertler, S.I., U. S. Bur. Entomol. and Plant Quarantine, E-612 [Processed]. Siegler, E. H., and Gertler, S. I., J . Econ. Enfomol., 37, 845 (1944).
Simmons, J. S.,Kentucky Med. Jour. (1945). Slade, R. E., Chem. Trade J., 116 (3017), 279 (1945); Chemiat r y & Industry, 64, 314 (1945). Staudinger, H., and Ruzicka, L.. Helv. Chim. Acta, 7, 177 (1924).
Sulliran, TT’. N., Goodhue, L. D., and Fales, J. H., J . Econ. Entomol., 35, 48 (1942). Travis, B. V., and Jones, H. A., U. S.Patent 2,356,801 (1944). U. S. Bur. of Entomol. and Plant Quarantine, Rept. 158 to Com. on bled. Research of O.S.R.D., Natl. Research Council Insect Control Corn. (A4pril1942 to Oct,. 1946). Vance, A. M., U. S. Bur. Entomol. and Plant Quarantine, Insect Pest Survey, Special S u p p l . No. 4 (May 1, 1946) [Processed]. Whitlaw-Gray. R., Speakman, J. B., and Campbell, J. H. P., PTOC.R o y . SOC.(London), A102, 600 (1922). Zuckel, J. TV,, J . Econ. Entmol., 37, 796 (1944). PRESENTED before the Division of Organic Chemistry at the 110th Meeting Of the AMERICAN CHEMICAL S O C I E T Y , Chicago, 111
Acetic Acid-Ethyl Ether-Water S y s t e m (Correction) Attention has been called to the following errors in our article ASD which appeared in the August 1946, issue of INDUSTRIAL ENGISEERIXG CHEMISTRY. Page 836, Figure 6: The ordinate and abscissa should be -cl),’cl” labeled “cl/(l -cl)” and “cz ’(1 -e*)’’ instead of ‘,(l and “(1-cz)/cl”, respectively. Page 836, column 2, line 6 should read “c~,’(l-el) against log ct/(l -cz)” instead of “(1 -c,)/c1 against log (1-cz)/cz)’. It m-ill be noted that a logarithmic plot of (l-cl)/c, against (1 - c2)/c2 will also yield a straight line for each of the three sets of C. J. MAJORASD 0. J. SWENSON tie line data for this system.
