Cyclohexane-1,3-dione Oxime Ether Grass-Specific Herbicides and the Discovery of Butroxydim1
Keith G. Watson A BA ICI Australia Central Research Laboratories, Newsom Street, Ascot Vale, Vic. 3032, Australia.
B Present address: Walter and Eliza Hall Institute of Medical Research, 1G Royal Parade, Parkville, Vic. 3050, Australia. Email: kwatson@wehi.edu.au
Australian Journal of Chemistry 64(4) 367-372 https://doi.org/10.1071/CH10366
Submitted: 6 October 2010 Accepted: 29 November 2010 Published: 18 April 2011
Abstract
The cyclohexanedione oxime ether herbicides are an important and widely used class of weed-control agents that selectively kill grass species. Since 1975, eight cyclohexanedione herbicides have been commercialized, including six compounds for grass weed control in broad-leaf crops such as cotton, soybeans and vegetables. One cyclohexanedione has been developed for wild oat control in wheat and also one compound for selective removal of barnyard grass in rice. A brief overview of the cyclohexanedione herbicide field is given, together with a more detailed account of the discovery and development of the herbicide butroxydim.
References
[1] R. B. Warner, K. G. Watson, G. Bird, G. M. Farrell, C. A. Spinks, W. D. McClellan, B. Kowalczyk, British Crop Protection Conference Proceedings – Weeds 1987, 1, 19 (British Crop Protection Council, CODEN: BCWEFI).[2] K. G. Watson, Chemistry in Australia 1988, 55, 193.
| 1:CAS:528:DyaL1cXkvVyjurk%3D&md5=6cb01fdf062aeb49eb931e17ac641275CAS |
[3] J. T. O’Donovan, K. N. Harker, R. E. Blackshaw, R. N. Stougaard, Weed Technol. 2003, 17, 149.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXntVSmurk%3D&md5=7a370b18860ea25eeb624867ae17e558CAS |
[4] H. Ishikawa, I. Iwataki, M. Sawaki, J. Pestic. Sci. 1985, 10, 301.
| 1:CAS:528:DyaL28XmsVSguw%3D%3D&md5=148c8db067ba2ce82940798414dd015fCAS |
[5] I. Iwataki, Y. Hirono, Advances in Pesticide Science 1979, Part 2, p. 235 (Ed. H. Geissbuhler) (Pergamon: Oxford).
[6] R. B. Warner, A. Serban, K. G. Watson, G. J. Bird, L. E. Cross, see for example US Patent 4,717,418 1988 (derived from Australian Patent Application No. 90,459 1982).
[7] The Merck Index, 14th edn 2006, 1644 pp. (Ed. M. J. O’Neil) (Merck & Co: Whitehouse Station, NJ, USA).
[8] S. T. Hadfield, A. Wilson, S. F. Kuet, R. Mason, Pestic. Sci. 1994, 40, 193.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXjtFOks7o%3D&md5=5f9eee599a9d2569134d8a6ab1033a76CAS |
[9] Y. Frater, A. Brady, E. A. Lock, F. De Matteis, Arch. Toxicol. 1993, 67, 179.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXks1Git7Y%3D&md5=d9318988259a43a3db292e189b1f03f3CAS | 8494497PubMed |
[10] S. M. Kobus, S. G. W. Wong, G. S. Marks, Can. J. Physiol. Pharmacol. 2001, 79, 814.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXnsVChs70%3D&md5=be23354e0b010ae82eb2bcbcd4c81035CAS | 11599783PubMed |
[11] J. W. Gronwald, Biochem. Soc. Trans. 1994, 22, 616.
| 1:CAS:528:DyaK2cXlslaqs7Y%3D&md5=fc2946c2fc3c02024b7d01e20b6d6ce7CAS | 7821649PubMed |
[12] K. G. Watson, L. A. Garson, G. J. Bird, L. E. Cross, G. J. Farquharson, see for example US Patent 4,666,510 1987 (derived from Australian Patent Application No. 11,116 1983).
[13] G. J. Bird, K. G. Watson, PCT Patent Application WO 98/04510 1998 (US equivalent 6,147,260).
[14] P. Chalmers, A. F. Kirby, R. Heath, US Patent 5,354,889 1994 (derived from Australian Patent Application No. 88249 1991).
[15] J. M. Lloyd, US Patent 5,846,903 1998 (derived from New Zealand Patent Application No. 241388 1992).
[16] AGROW, 1995, 224, 17.
[17] Australian Pesticide & Veterinary Medicines Authority (APVMA) Gazette, 2008, 4, 1 April, p. 3, Approval No: 61984/1207.
[18] A. Takahashi, S. Yamada, K. Tanaka, Weed Biol. Manage. 2002, 2, 84.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XntVyis7k%3D&md5=59f4e59a90e17f481ee7425d6fac22c4CAS |
[19] Queensland Department of Primary Industry, Chickpea weed management. Available at: www.dpi.qld.gov.au/26_4503.htm (verified 17 December 2010).
[20] A. J. Liepa, A. Hoffman, R. H. Nearn, C. T. Bui, PCT Patent Application WO 94/26696 1994.
[21] C. Finley, M. Landes, B. Sievernich, U. Misslitz, U. Schofl, British Crop Protection Conference Proceedings – Weeds 1999, 1, 65 (British Crop Protection Council, CODEN: BCWEFI).
[22] A. Serban, K. G. Watson, G. J. Bird, G. J. Farquharson, US Patent 4,511,391 1985 (derived from Australian Patent Application No. PF4118 1983).
[23] T.-J. Kim, J.-S. Kim, K. S. Hong, I.-T. Hwang, K. M. Kim, H.-R. Kim, K. Y. Cho, Pest Manag. Sci. 2004, 60, 909.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXntlCltrc%3D&md5=0d01526c4ef1424436039040615cfa2bCAS | 15382506PubMed |
[24] S. Xiang, M. M. Callaghan, K. G. Watson, L. Tong, Proc. Natl. Acad. Sci. USA 2009, 106, 20723.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXksFOmtA%3D%3D&md5=2501f7b577c437ec76c62a514aa19b3fCAS |