The discovery of isocycloseram: A novel isoxazoline insecticide

Author:

Cassayre Jérôme,Smejkal Tomas,Blythe Judith,Hoegger Patrik,Renold Peter,Pitterna Thomas,Prasanna C.S.,Smits Helmars,Godineau Edouard,Luksch Torsten,Berthon Guillaume,Rawal Girish,Patre Rupesh,Lal Mukul,Boussemghoune Mohamed,Masala Simonetta,Barreteau Fabien,Flaeschel Michael,Vogt Juliane,El Qacemi Myriem

Publisher

Elsevier

Reference97 articles.

1. Inspired from: Sparks, T. C. Insecticide Discovery: An Evaluation and Analysis. Pest. Biochem. Physiol. 2013, 107, 8–17. The use of nicotine as insecticide was described in a patent application: Wilson, J. GB 7805090, 1878. The use of some arsenic oxides such as cuprous acetoarsenite (Paris Green) for the control of Colorado potato beetle was reported in 1871, see Kuhar, T. P.; Kamminga, K.; Philips, C.; Wallingford, A.; Wimer, A. Chemical Control of Potato Pests. In Insect Pests of Potato: Global Perspectives on Biology and Management; Giordanengo, P., Vincent, C., Alyokhin, A. Eds.; Elsevier: Waltham, MA, 2013; pp 375–397. The history of the use of pyrethrins as insecticides is described in Ujváry, I. Pest Control Agents From Natural Products. In Hayes’ Handbook of Pesticide Toxicology, 3rd ed.; Krieger, R., Ed.; Academic Press, 2010; Vol. 1, pp 119–230. Dimetan, a commercialized carbamate pesticide, was described for the first time in a patent application: Gysin, H. US 2592890, 1952. The use of DDT (a commercialized organochlorine pesticide) as a pesticide was described in patent applications: Muller, P. US 2329074 and CH 226180, 1943. The use of Parathion, a commercialized organophosphate pesticide, was described: Engels, O. Use and Handling of the Most Important Preparations for the Control of Pests. Seifensieder-Zeitung 1946, 72, 108–110. The use of Bioallethrin (a commercialized pyrethroid pesticide) as an insecticide was described: Schechter, M. S.; Green, N.; LaForge, F. B. Constituents of Pyrethrum Flowers. XXIII. Cinerolone and the Synthesis of related Cyclopentenolones. J. Am. Chem. Soc. 1949, 71, 3165–3173. The anthelmintic activities of some mectins were described in the late 1970s: Burg, R. W.; Miller, B. M.; Baker, E. E.; Birnbaum, J.; Currie, S. A.; Hartman, R.; Kong, Y. L.; Monaghan, R. L.; Olson, G.; Putter, I.; Tunac, J. B.; Wallick, H.; Stapley, E. O.; Oiwa, R.; Ōmura, S. Avermectins, New Family of Potent Anthelmintic Agents: Producing Organism and Fermentation. Antimicrob. Agents Chemother. 1979, 15 (3), 361–367. The use of Nithiazine (a commercialized neonicotinoid pesticide) as an insecticide was first described in a patent application: Powell, J. E.; Roman, S. A. US 3907790, 1975. The use of diflubenzuron (a commercialized benzoylphenyl urea pesticide) as an insecticide was first described in a patent application: Wellinga, K.; Mulder, R. BE 767161, 1971. The use of fipronil (a commercialized fiprole pesticide) as an insecticide was first described in a patent application: Buntain, I. G.; Hatton, L. R.; Hawkins, D. W.; Pearson, C. J.; Roberts, D. A. EP 295117, 1988. The use of Tebufenozide (a commercialized diacylhydrazine pesticide) as an insecticide was first described in a patent application: Hsu, A. C.-T.; Aller, H. E. EP236618, 1987. The discovery of spinosins as insecticides is described: Thompson, G. D.; Dutton, R.; Sparks, T. C. Spinosad – A Case Study: An Example From a Natural Products Discovery Programme. Pest. Manage. Sci. 2000, 56, 696–702. The discovery of the 1,2-diamides as insecticides is described in: Selby, T. P.; Lahm, G. P.; Stevenson, T. M. A retrospective Look at Anthranilic Diamide Insecticides: Discovery and Lead Optimization to Chlorantraniliprole and Cyantraniliprole. Pest. Manage. Sci. 2017, 73, 658–665. The discovery of tetronic acids as insecticides is described in: Bretschneider, T.; Benet-Buchholz, J.; Fischer, R.; Nauen, R. Spirodiclofen and Spiromesifen – Novel Acaricidal and Insecticidal Tetronic Acid Derivatives with a New Mode of Action. Chimia 2003, 57, 697–701. The discovery of isoxazolines and 1,3-metadiamides is described in: El Qacemi, M; Rendine, S.; Maienfisch, P. Recent Applications of Fluorine in Crop Protection – New Discoveries Originating From the Unique Heptafluoroisopropyl Group. In Fluorine in Life Sciences: Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals. Haufe, G.; Leroux, F.; 1st ed.; Academic Press, 2018; pp 607–629.

2. See report, “The Evolution of the crop protection industry since 1960”, written by market analysts Phillips McDougall in April 2019.

3. Fernandez-Cornejo, J.; Nehring, R.; Osteen, C.; Wechsler, S.; Martin, A.; Vialou, A. Pesticide Use in U.S. Agriculture: 21 Selected Crops, 1960–2008, EIB-124. U.S. Department of Agriculture, Economic Research Service, May 2014.

4. Mita, T.; Kikuchi, T.; Mizukoshi, T.; Yaosaka, M.; Komoda, M. First Patent Application Disclosing the Isoxazoline Class of Insecticides. WO 2005/085216, 2005.

5. First Patent Application Disclosing the Isoxazoline Class of Insecticides;Nakao;Insect Biochem. Mol. Biol.,2013

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