DDT Polymorphism and the Lethality of Crystal Forms
Jingxiang Yang
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072 P.R. China
Search for more papers by this authorDr. C. T. Hu
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
Search for more papers by this authorXiaolong Zhu
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
Search for more papers by this authorProf. Dr. Qiang Zhu
Department of Physics and Astronomy, High Pressure Science and Engineering Center, University of Nevada, Las Vegas, NV, 89154 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Michael D. Ward
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Bart Kahr
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
Department of Advanced Science and Engineering (TWins), Waseda University, 162-0056 Tokyo, Japan
Search for more papers by this authorJingxiang Yang
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072 P.R. China
Search for more papers by this authorDr. C. T. Hu
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
Search for more papers by this authorXiaolong Zhu
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
Search for more papers by this authorProf. Dr. Qiang Zhu
Department of Physics and Astronomy, High Pressure Science and Engineering Center, University of Nevada, Las Vegas, NV, 89154 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Michael D. Ward
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Bart Kahr
Department of Chemistry and Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY, 10009 USA
Department of Advanced Science and Engineering (TWins), Waseda University, 162-0056 Tokyo, Japan
Search for more papers by this authorAbstract
DDT (1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane), a contact insecticide with a rich and controversial history since its activity was discovered in 1939, has long been thought to be monomorphic. Herein we report the discovery and characterization of a second polymorph, designated Form II, which can be isolated as single crystals, but converts very slowly at room temperature to the form reported previously, now designated as Form I. Computations based on an evolutionary algorithm for crystal structure prediction revealed that Forms I and II are among the four lowest energy crystal structures of fifty calculated. A preliminary study of the contact insecticidal activity toward fruit flies (Drosophila melanogaster) indicates that Form II is more active, suggesting opportunities for more effective solid-state formulations that would allow reduced amounts of DDT, thereby minimizing environmental impact.
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References
- 1D. Kinkela, DDT and the American Century: Global Health, Environmental Politics, and the Pesticide That Changed the World, University of North Carolina Press, Chapel Hill, 2013.
- 2F. Matsumura, Toxicology of Insecticides, Plenum, New York, 1975.
10.1007/978-1-4613-4410-0 Google Scholar
- 3W. S. Gaud, Address to The Society for International Development, Washington, D. C. March 8, 1968 (http://www.agbioworld.org/biotech-info/topics/borlaug/borlaug-green.html).
- 4N. Borlaug, “Farmers Can Feed the World”, Wall Street Journal, July 31, 2009.
- 5C. Mann, Science 1997, 277, 1038–1043.
- 6J. Walsh, Science 1991, 252, 26.
- 7C. Dowswell, Science 2009, 326, 381.
- 8M. J. Large, Ecol. Law Quart. 1973, 3, 277–310.
- 9R. L. Carson, Silent Spring, Houghton Mifflin Harcourt, New York, 2002 (first publ. 1962).
- 10J. Yang, M. D. Ward, B. Kahr, Angew. Chem. Int. Ed. 2017, 56, 10026–10032; Angew. Chem. 2017, 129, 10158–10164.
- 11http://www.gettyimages.com/license/71888408.
- 12A. G. Shtukenberg, Y.-O. Punin, A. Gujral, B. Kahr, Angew. Chem. Int. Ed. 2014, 53, 672–699; Angew. Chem. 2014, 126, 686–715.
- 13A. Shtukenberg, E. Gunn, M. Gazzano, J. Freudenthal, E. Camp, R. Sours, E. Rosseeva, B. Kahr, ChemPhysChem 2011, 12, 1558–1571.
- 14X. Cui, S. M. Nichols, O. Arteaga, J. Freudenthal, F. Paula, A. G. Shtukenberg, B. Kahr, J. Am. Chem. Soc. 2016, 138, 12211–12218.
- 15A. H. McIntosh, Ann. Appl. Biol. 1947, 34, 586–610.
- 16D. K. O'Neill, Aust. J. Agric. Res. 1963, 14, 119–128.
- 17C. T. Lewis, J. Insect Physiol. 1965, 11, 683–694.
- 18W. M. Hoskins in Residue Reviews (Ed.: ), Springer, Berlin, 1962, pp. 66–91.
- 19I. Fankuchen, M. Schneider, J. Singer, Science 1946, 103, 25.
- 20E. L. Gooden, J. Am. Chem. Soc. 1945, 67, 1616–1617.
- 21T. P. DeLacy, C. H. L. Kennard, J. Chem. Soc. D 1971, 1208–1209.
- 22T. P. DeLacy, C. H. L. Kennard, J. Chem. Soc. Perkin Trans. 2 1972, 2148–2153.
- 23A. G. Shtukenberg, Yu. O. Punin, E. Gunn, B. Kahr, Chem. Rev. 2012, 112, 1805–1838.
- 24L. B. McCrone, W. C. McCrone, Microscope 2000, 48, 203–206.
- 25J. L. Kallok, U.S. Patent 2,590,544 (March 25, 1952).
- 26L. W. Hindes, H. S. Curtis, Baytown, J. R. Siemoneit, U.S. Patent 2,902,719 (September 8, 1959).
- 27P. Gerolt, J. Insect Physiol. 1969, 15, 563–578.
- 28E. C. Holst, J. Econ. Entomol. 1944, 37, 159.
- 29J. B. Buck, M. L. Keister, I. Posner, Ann. Entomol. Soc. Am. 1952, 45, 369–384.
- 30Q. Zhu, A. R. Oganov, C. W. Glass, H. T. Stokes, Acta Crystallogr. Sect. B 2012, 68, 215–226.
- 31A. O. Lyakhov, A. R. Oganov, H. T. Stokes, Q. Zhu, Comput. Phys. Commun. 2013, 184, 1172–1182.
- 32Q. Zhu, A. G. Shtukenberg, D. J. Carter, T.-Q. Yu, J. Yang, M. Chen, P. Raiteri, A. R. Oganov, B. Pokroy, I. Polishchuk, P. J. Bygrave, G. M. Day, A. L. Rohl, M. E. Tuckerman, B. Kahr, J. Am. Chem. Soc. 2016, 138, 4881–4889.
- 33W. Xu, Q. Zhu, C. Hu, Angew. Chem. Int. Ed. 2017, 56, 2030–2034; Angew. Chem. 2017, 129, 2062–2066.
- 34J. D. Gale, A. L. Rohl, Mol. Simul. 2003, 29, 291–341.
- 35B. Aradi, B. Hourahine, T. Frauenheim, J. Phys. Chem. A 2007, 111, 5678–5684.
- 36J. Klimeš, D. R. Bowler, A. Michaelides, Phys. Rev. B 2011, 83, 195131.
- 37G. Kresse, J. Furthmüller, Phys. Rev. B 1996, 54, 11169–11186.
- 38J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. Int. Ed. 1999, 38, 3440–3461;
10.1002/(SICI)1521-3773(19991203)38:23<3440::AID-ANIE3440>3.0.CO;2-# CAS PubMed Web of Science® Google ScholarAngew. Chem. 1999, 111, 3646–3669.10.1002/(SICI)1521-3757(19991203)111:23<3646::AID-ANGE3646>3.0.CO;2-H Web of Science® Google Scholar
- 39J. Gillett, V. Wigglesworth, Proc. R. Soc. London Ser. B 1932, 111, 364–376.
- 40D. Labonte, W. Federle, Soft Matter 2015, 11, 8661–8673.
- 41M. G. Langer, J. P. Ruppersberg, S. Gorb, Proc. R. Soc. London Ser. B 2004, 271, 2209.
- 42H. van den Berg, Environ. Health Perspect. 2009, 117, 1656–1663.
- 43Stockholm Convention on persistent organic pollutants. New York, NY, United Nations Environment Programme, 2001 (http://www.pops.int/documents/convtext/convtext_en.pdf).
- 44CCDC 1532664, 1532665, and 1538801 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
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