Synthetic approaches to the 2010-2014 new agrochemicals

Bioorganic and Medicinal Chemistry

Volumn 24, Issue 3, 2016, Pages 317-341

  Jeanmart, Stephane ^a   Edmunds, Andrew J F ^a   Lamberth, Clemens ^a   Pouliot, Martin ^a  

^a SYNGENTA CROP PROTECTION AG   (Switzerland)

Author keywords

Agrochemicals; Crop Protection; Fungicides; Herbicides; Insecticides; Nematicides; Synthesis

Indexed keywords

CROP PROTECTION; HISTORY; HUMAN; STANDARDS; SYNTHESIS;

AGRICULTURAL CHEMICAL; ANTINEMATODAL AGENT; FUNGICIDE; HERBICIDE; INSECTICIDE;

AGROCHEMICALS; ANTINEMATODAL AGENTS; FUNGICIDES, INDUSTRIAL; HERBICIDES; HISTORY, 21ST CENTURY; HUMANS; INSECTICIDES;

EID: 84955206157     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.12.014     Document Type: Article

References (172)

1. R.B. Trigg K.J. Thurlow, Chemical Nomenclature 1998 Springer The Netherlands 208 234
2. J. Li, and K.K.-C. Liu Mini-Rev. Med. Chem. 4 2004 207
3. K.K.-C. Liu, J. Li, and S. Sakya Mini-Rev. Med. Chem. 4 2004 1105
4. J. Li, K.K.-C. Liu, and S. Sakya Mini-Rev. Med. Chem. 5 2005 1133
5. S.M. Sakya, J. Li, and K.K.-C. Liu Mini-Rev. Med. Chem. 7 2007 429
6. K.K.-C. Liu, S.M. Sakya, and J. Li Mini-Rev. Med. Chem. 7 2007 1255
7. K.K.-C. Liu, S.M. Sakya, C.J. O'Donnell, and J. Li Mini-Rev. Med. Chem. 8 2008 1526
8. K.K.-C. Liu, S.M. Sakya, C.J. O'Donnell, and J. Li Mini-Rev. Med. Chem. 9 2009 1655
9. K.K.-C. Liu, S.M. Sakya, C.J. O'Donnell, A.C. Flick, and J. Li Bioorg. Med. Chem. 19 2011 1136
10. K.K.-C. Liu, S.M. Sakya, C.J. O'Donnell, A.C. Flick, and H.X. Ding Bioorg. Med. Chem. 20 2012 1155
11. H.X. Ding, K.K. Liu, S.M. Sakya, A.C. Flick, and C.J. O'Donnell Bioorg. Med. Chem. 21 2013 2795
12. H.X. Ding, C.A. Leverett, R.E. Kyne Jr., K.K. Liu, S.M. Sakya, A.C. Flick, and C.J. O'Donnell Bioorg. Med. Chem. 22 2014 2005
13. H.X. Ding, C.A. Leverett, R.E. Kyne Jr., K.K. Liu, S.J. Fink, A.C. Flick, and C.J. O'Donnell Bioorg. Med. Chem. 23 2015 1895
14. The full list of ISO common names and some details on the molecules can be found at the following website: Compendium of Pesticide Common Names; Index of new ISO common names. http://www.alanwood.net/pesticides/index-new-frame.html.
15. Dietz, J.; Grote, T.; Strathmann, S. Abstract of papers, 242nd ACS National Meeting & Exposition, Denver, USA, August 28-September 1, 2011 (2011), AGRO-81.
16. H. Walter C. Lamberth, J. Dinges, Bioactive Heterocyclic Compound Classes - Agrochemicals 2012 Wiley-VCH Weinheim 175 193
17. J. Rheinheimer W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 627 639
18. Stammler, G.; Brix, H. D.; Glaettli, A.; Semar, M.; Schoefl, U. Proc. 16th Int. Plant Prot. Congr., Glasgow, United Kingdom October 15-18, 2007 (2007) Vol. 1, pp 40-45.
19. C.A. Berdugo, U. Steiner, H.-W. Dehne, and E.-C. Oerke Pestic. Biochem. Physiol. 104 2012 171
20. M. Semar, D. Strobel, S. Strathmann, and U. Groeger H.W. Dehne, H.B. Deising, U. Gisi, K.H. Kuck, P.E. Russell, H. Lyr, Modern Fungicides and Antifungal Compounds VI 2011 Braunschweig DPG 63 68
21. C. Torborg, and M. Beller Adv. Synth. Catal. 351 2009 3027
22. C. Lamberth, S. Jeanmart, T. Luksch, and A. Plant Science 341 2013 742
23. Zierke, T.; Maywald, V.; Smidt, S. P. WO 2010/094736, 2010 (BASF); Chem. Abstr. 2010, 153, 358710.
24. H. Jasch, J. Scheumann, and M.R. Heinrich J. Org. Chem. 77 2012 10699
25. Heinrich, M.; Jasch, H.; Höfling, S. WO 2013/132006, 2013 (BASF); Chem. Abstr. 2013, 159, 485923.
26. Walter, H.; Gribkov, D.; Tobler, H. Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014 (2014), AGRO-621.
27. H. Walter, H. Tobler, D. Gribkov, and C. Corsi Chimia 69 2015 425
28. Walter, H.; Guicherit, E.; Rambach-Jankowski, O.; Dale, S. Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014 (2014), AGRO-730.
29. Tobler, H.; Walter, H.; Ehrenfreund, J.; Corsi, C. WO 2007/048556, 2007 (Syngenta); Chem. Abstr. 2007, 146, 481833.
30. Gribkov, D.; Müller, A.; Lagger, M.; Giordano, F. WO 2011/015416, 2011 (Syngenta); Chem. Abstr. 2011, 154, 207606.
31. S. Tsukuda Jpn. J. Pestic. Sci. 39 2014 89
32. T. Veloukas, and G.S. Karaoglanidis Pest Manag. Sci. 68 2012 858
33. H. Rieck, and P.-Y. Coqueron W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 639 645
34. C.M. Piqueras, B.A. Latorre, and R. Torres Cien. Inv. Agr. 41 2014 365
35. AgroNews, September 5, 2014; http://news.agropages.com/News/NewsDetail - -13086.htm.
36. Nakamura, Y.; Mitani, S.; Yoneda, T. WO 2006/016708, 2006 (Ishihara Sangyo Kaisha); Chem. Abstr. 2006, 144, 207362.
37. Oda, M.; Morishita, Y. WO 2010/122794, 2010 (Nihon Nohyaku); Chem. Abstr. 2010, 153, 555210.
38. H.-G. Hahn Agric. Chem. Biotechnol. 45 2002 37
39. C.-L. Liu, Z.-M. Li, and B. Zhong J. Fluorine Chem. 125 2004 1287
40. Pasteris, R. J.; Hanagan, M. A. Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014 (2014), AGRO-622.
41. R.J. Pasteris, M.A. Hanagan, J.J. Bisaha, B.L. Finkelstein, L.E. Hoffman, V. Gregory, J.L. Andreassi, J.A. Sweigard, B.A. Klyashchitsky, Y.T. Henry, and R.A. Berger Bioorg. Med. Chem. 24 2016 354 10.1016/j.bmc.2015.07.064
42. Hanagan, M. A.; Pasteris, R. J. Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014 (2014), AGRO-740.
43. Sweigard, J.; Andreassi, J.; Pember, S.; Gutteridge, S.; Pasteris, R.; Hanagan, M. A.; Carrol, A.; Sopa, J.; Nesnow, D. Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, USA, August 10-14, 2014 (2014), AGRO-911.
44. P. Ji, and A.S. Csinos Ann. Appl. Biol. 166 2015 229
45. P. Ji, A.S. Csinos, L.L. Hickman, and U. Hargett Plant Dis. 98 2014 1551
46. Hanagan, M. A.; Oberholzer, M. R.; Pasteris, R. J.; Shapiro, R. WO 2010/123791, 2010 (E. I. Du Pont De Nemours and Company); Chem. Abstr. 2010, 153, 573289.
47. Hanagan, M. A.; Pasteris, R. WO 2009/094407, 2009 (E. I. Du Pont De Nemours and Company); Chem. Abstr. 2009, 151, 234956.
48. H. Sauter W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 584 627
49. Hirato M.; Takimoto, M.; Yamaoka, T.; Onogawa, Y. WO 2013/002266, 2013 (Sumitomo Chemical Company); Chem. Abstr. 2013, 158, 131474.
50. Ishida, H.; Hirota, M. WO2009/157589, 2009 (Sumitomo Chemical Company); Chem. Abstr. 2009, 152, 74736.
51. Toriumi, T. WO 2012/141015, 2012 (Sumitomo Chemical Company); Chem. Abstr. 2012, 157, 708273.
52. Ishida, H.; Hirota, M.; Tagami, Y.; Mizushima, Y. WO 2010/093059, 2010 (Sumitomo Chemical Company); Chem. Abstr. 2010, 153, 286715.
53. The Fungicide Resistance Action Committee (FRAC) created in February 2015 a new group within melanin biosynthesis for tolprocarb (I3: polyketide synthase in melanin biosynthesis; FRAC Code number 16.3).
54. T. Hamada, M. Asanagi, T. Satozawa, N. Araki, S. Banba, N. Higashimura, T. Akase, and K. Hirase J. Pestic. Sci. 39 2014 152
55. Umetani, H.; Kohno, T.; Kamekawa, H. WO 2012/039132, 2012 (Mitsui Chemicals Agro); Chem. Abstr. 2012, 156, 449967.
56. The synthesis of trifluoroethyl chloroformate from trifluoroethanol and phosgene is described in the following patent: Kamekawa, N.; Morizane, K. JP 2012/067030, 2012 (Mitsui Chemicals Agro). Chem. Abstr. 2012, 156, 449966.
57. N. Kimura, M. Hashizume, K. Yanagisawa, H. Ishida, M. Miura, T. Morimoto, and K. Ose Sumitomo Kagaku 2014 4
58. K.-H. Kuck, K. Stenzel, and J.-P. Vors W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 761 805
59. For example see S. Han Kim, W. Jang, M. Kim, J.G. Verkade, and Y. Kim Eur. J. Org. Chem. 27 2014 6025
60. J. You, and J.G. Verkade J. Org. Chem. 68 2003 8003
61. Hatano, R.; Miyaoka, S.; Abe, S. WO 2010/143598, 2010 (Sumitomo Chemical Company), 2010; Chem. Abstr. 2010, 154, 30329.
62. Miura, M.; Kojio, M. WO 2012/063791, 2012 (Sumitomo Chemical Company); Chem. Abstr. 2012, 156, 638061.
63. The FRAC created in February 2015 a new unknown group for picarbutrazox (FRAC Code number U17).
64. Inoue, H.; Noda, K. WO 2011/111705, 2011 (Nippon Soda Company); Chem. Abstr. 2011, 155, 407344.
65. Kutose, K.; Inoue, H.; Tsubokura, S. WO 2011/125568, 2011 (Nippon Soda Company); Chem. Abstr. 2011, 155, 535996.
66. The synthesis of the tetrazoyloxime is described in the following two patents: (a) Suzuki, T.; Sugiura, T.; Ito, Y. WO 2010/103783, 2010 (Nippon Soda Company); Chem. Abstr. 2010, 153, 382965. (b) Noda, K.; Matsumoto, T. JP 2014/024811, 2014 (Nippon Soda Company); Chem. Abstr. 2014, 160, 278930.
67. The yield and reaction condition for this transformation have only been explicitly reported in Nippon Soda Company patents using the 6-(bromomethyl)pyridine derivative instead of the chloro-analog depicted here. See: Miyazaki, H.; Yanaka, S.; Tsubokura, S.; Sugiura, T.; Noda, K.; Suzuki, K. WO 2011/111831, 2011 (Nippon Soda Company); Chem. Abstr. 2011, 155, 431686.
68. W. Draber Chem. Ber. 100 1967 1559
69. Seitz, T.; Wachendorff-Neumann, U.; Benting, J.; Dahmen, P.; Voerste, A.; Dunkel, R.; Hillebrand, S.; Tietjen, Klaus-Guenther; Brunet, S. WO 2010/043319, 2010 (Bayer CropScience). Chem. Abstr. 2010, 152, 471787.
70. Himmler, T.;Volz, F.; Geller, T. WO 2012/028588, 2012 (Bayer CropScience); Chem. Abstr. 2012, 156, 337322.
71. A. Valla, D. Cartier, F. Zentz, and R. Labia Synth. Commun. 36 2006 3591
72. A. Kunova, C. Pizzatti, M. Bonaldi, and P. Cortesi Pest Manag. Sci. 2015 10.1002/ps.4060
73. Nishide, H.; Ogawa, M.; Tanimura, T.; Higuchi, K.; Kominami, H.; Okamoto, T.; Nishimura, A. WO 2004/039155, 2004 (Ishihara Sangyo Kaisha); Chem. Abstr. 2004, 140, 391204.
74. Nishimura, S.; Kanamori, F.; Hisamoto, M. WO 2006/115171, 2006 (Ishihara Sangyo Kaisha); Chem. Abstr. 2006, 145, 471402.
75. (a) Boehm, J.; Davis, R. S.; Kerns, J.; Lin, G.; Murdoch, R.; Nie, H. WO 2013/006596, 2013 (Glaxo Group); Chem. Abstr. 2013, 158, 158657. (b) Gibson, C.; Tradler, T.; Schnatbaum, K.; Pfeifer, J.; Locardi, E.; Scharn, D.; Paschke, M.; Reimer, U.; Richter, U.; Hummel, G.; Reineke, U. WO 2008/116620, 2008 (Jerini); Chem. Abstr. 2008, 149, 425812.
76. Maywald, V.; Hoffmann, N.; Keil, M.; Vogelbacher, U. J.; Wevers, J. H. WO 2004/054953, 2004 (BASF); Chem. Abstr. 2004, 141, 71349.
77. Kikugawa, H.; Satake, Y.; Tonks, D. J.; Grove M.; Nagayama S.; Tsukamoto, M. 55th Annual Meeting of the Weed Science Society of America, Lexington, KY, United States, 9-12 February 2015 (2015), Abstract 275.
78. Shimoharada, H.; Tsukamoto, M.; Ikeguchi, M.; Kikugawa, H.; Sano, M.; Kitahara, Y.; Kominami, H.; Okita, T. WO 2007/069771, 2007 (Ishihara Sangyo Kaisha); Chem. Abstr. 2007, 147, 72752.
79. (a) Siddall, T. L.; Edmonds, M. V. M.; Krumel, K. L.; Schomaker, J. M.; Zettler, M. W.; Shinkle, S. L.; Webster, J. D. WO 98/42677, 1998 (Dow AgroSciences); Chem. Abstr. 1998, 129, 290132. (b) Oya, E.; Watanabe, J.; Kondo, Y.; Kakuta, T.; Suzuki, K.; Nawamaki, T.; Watanabe, S. EP 352543, 1990 (Nissan Chemical Industries); Chem. Abstr. 1990, 113, 40672.
80. Several industrial like synthesis of the ethyl pyrazoline are known. See for example Baba, M.; Tanaka, N.; Suzuki, H., EP 240001, 1987 (Nissan Chemical Industries); Chem. Abstr. 1987, 108, 94546.
81. Tsukamoto, M.; Kikugawa, H.; Nagayama, S.; Okita, T.; Hata, H. WO 2009/142318, 2009 (Ishihara Sangyo Kaisha); Chem. Abstr. 2009, 152, 12342.
82. One referee pointed out that 82 may be formed in an intermolecular reaction. Other examples for the preparation of 82 have used O-acylation of the pyrazole 81, and then cyanohydrin catalyzed rearrangement (via the acyl cyanide) to the C-acylated product 82. See; Shimoharada, H.; Tsukamoto, M.; Ikeguchi, M.; Kikugawa, H.; Nagayama, S.; Sano, M.; Kitahara, Y.; Kominami, H.; Okita, T. WO 2008/093840, 2008 (Nissan Chemical Industries); Chem. Abstr. 2008, 149, 240681.
83. Amano, Y.; Kobayashi, M.; Nagamatsu, A.; Nakano, Y.; Tamai, R.; Ito, M.; Murakami, S. from Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014 (2014), AGRO-870.
84. Ito, M.; Ikumi, A. WO 2013/089002, 2013 (Ihara Chemical Industry Company and Kumiai Chemical Industry Company); Chem. Abstr. 2013, 159, 118412.
85. A.J.F. Edmunds, and J.A. Morris W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 235 262
86. Tsukamoto, Y.; Komai, H.; Kadotani, J.; Koi, K.; Mio, S.; Takeshiba, H. WO 2003/016286, 2003, (Sankyo Agro); Chem. Abstr. 2003, 138, 187781.
87. Kadotani, J.; Isarai, K.; Sakamoto, T.; Tamaru, H.; Ohara, S.; Nakashima, A.; Tsukamoto, Y. JP 2004/262935, 2004 (Sankyo Agro); Chem. Abstr. 2011, 141, 273012.
88. Ikishima, H.; Kondo, N.; Takada, T.; Tsukamoto, Y.; Yoshitomi, H.; Mita, H. WO 2011/040445, 2011 (Mitsui Chemicals Agro); Chem. Abstr. 2011, 154, 434928.
89. (a) Holenz, J.; Karlstroem, S.; Kihlstroem, J.; Kolmodin, K.; Lindstroem, J.; Rakos, L.; Rotticci, D.; Swahn, B.-M.; Von Berg, S. WO 2011/002409, 2011 (AstraZeneca). Chem. Abstr. 2011, 154, 109655. (b) A radical approach to this intermediate has been reported by Mitsui chemists, see Mita, H.; Kawaguchi, A.; Mitamura, T.; Takada, T. JP 2013/194011, 2013 (Mitsui Chemicals Agro). Chem. Abstr. 2013, 159, 516262.
90. 3, see Pouzet, P.; Anderskewitz, R.; Dollinger, H.; Fiegen, D.; Fox, T.; Goeggel, R.; Hoenke, C.; Martyres, D.; Nickolaus, P.; Klinder, K. WO 2009/050242, 2009 (Boehringer Ingelheim International); Chem. Abstr. 2009, 150, 447982.
91. O. Ort W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 50 88
92. R. Anana, P.N.P. Rao, Q.-H. Chen, and E.E. Knaus Bioorg. Med. Chem. 14 2006 5259
93. Sandmeyer idodination of 2-aminobenzenesulfonic amide has also been reported. Bhatnagar, N.; Buendia, J.; Griffoul, C. US 5391732, 1995 (Roussel-UCLAF); Chem. Abstr. 1995, 122, 265376.
94. Waldraff, C.; Mueller, K.-H.; Gesing, R. F. E.; Dittgen, J.; Feucht, D.; Kraehmer, H.; Hills, M.; Bonfig-Picard, G.; Hess, M.; Schreiber, D.; Rosinger, C. WO 2009/053058, 2009 (Bayer CropScience); Chem. Abstr. 2009, 150, 465775.
95. Ford, M. J.; Karig, G. WO 2012/028162, 2012 (Bayer CropScience); Chem. Abstr. 2012, 156, 337157.
96. Siegel, K.; Karig, G. US 2011/0275832, 2011 (Bayer CropScience); Chem. Abstr. 2011, 155, 615104.
97. Karig, G.; Ford, M. J.; Siegel, K. WO 2012/084855, 2012 (Bayer CropScience); Chem. Abstr. 2012, 157,165627.
98. Karig, G.; Ford, M. J.; Siegel, K.; Schnatterer, S. WO 2012/084854, 2012 (Bayer CropScience); Chem. Abstr. 2012, 157,165628.
99. Karig, G.; Ford, M. J.; Siegel, K. WO 2012/084857, 2012 (Bayer CropScience); Chem. Abstr. 2012, 157,165626.
100. The methylation step of the synthesis of triafamone has only been reported in the first patent disclosing its synthesis and is certainly not optimized: Araki, K.; Sato, Y.; Gomibichi, T.; Endo, K.; Shirakura, S.; Nakamura, S.; Rosinger, C.; Feucht, D. WO 2007/031208, 2007 (Bayer CropScience); Chem. Abstr. 2007, 146, 332488.
101. E. Nagano, R. Sato, M. Yamada, Y. Funaki, R. Furuta, T. Fujisawa, and S. Kawamura Sumitomo Kagaku 2001 14
102. R. Weiler, G. Johann, M. Ganzer, and M. Mach Proceed. Brighton Crop Prot. Conf. - Weeds 1 1993 29
103. Dochnahl, M.; Götz, R.; Gebhardt, J.; Gelbacher, U. J.; Frasetto, T.; Rack, M.; Maywald, V.; Wolf, B. WO 2014/026893 (BASF); Chem. Abstr. 2014, 160, 370186.
104. J.B. Epp, A.L. Alexander, T.W. Balko, A.M. Buysse, W.K. Brewster, K. Bryan, J.F. Daeuble, S.C. Fields, R.E. Gast, R.A. Green, N.M. Irvine, W.C. Lo, C.T. Lowe, J.M. Renga, J.S. Richburg, J.M. Ruiz, N.M. Satchivi, P.R. Schmitzer, T.L. Siddall, J.D. Webster, M.R. Weimer, G.T. Whiteker, and C.N. Yerkes Bioorg. Med. Chem. 24 2016 362 10.1016/j.bmc.2015.08.011
105. Renga, J. M.; Whiteker, G. T.; Arndt, K. E.; Lowe, C. T. US 2010/0311981, 2010 (Dow AgroSciences); Chem. Abstr. 2010, 154, 30191.
106. Oppenheimer, J.; Emonds, M.; Derstine, C. W.; Clouse, R. C. WO 2013/102078, 2013 (Dow AgroSciences); Chem. Abstr. 2013, 159, 196874.
107. Krumel, K. L.; Bott, C. J.; Gullo, M. F.; Hull, J. W., Jr.; Scortichini, C. L. WO 2001/051684, 2001 (Dow AgroSciences); Chem. Abstr. 2001, 135, 98860.
108. Holyoke, C. W. Jr; Zhang, W.; Pahutski, T. F. Jr.; Lahm, G. P.; Tong, M.-H.T.; Cordova, D.; Schroeder, M. E.; Benner, E. A.; Rauh, J.J.; Dietrich, R. F.; Leighty, R. M.; Daly, R. F.; Smith, R. M.; Vincent. D. R. Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014 (2014), AGRO-446.
109. Cordova, D.; Benner, E. A.; Schroeder, M. E.; Holyoke, C. W. Jr; Zhang, W.; Lahm, G. P.; Tong, M.-H.T.; Pahutski, T. F. Jr.; Vincent, D. R.; Leight Y. R. M. Abstracts of Papers, 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014 (2014), AGRO-836.
110. Pahutski, T. F. Jr. WO 2012/092115, 2012 (E. I. du Pont de Nemours and Company); Chem. Abstr. 2012, 157, 165599.
111. Similar reactions have been reported using a di-acid chloride: Hoffmann, C.; Zhang, W.; Chen, Y. WO 2013/192035, 2013 (E. I. du Pont de Nemours and Company); Chem. Abstr. 2013, 160, 126945.
112. Zhang, W.; Holyoke, Caleb W., Jr.; Hughes, K. A.; Lahm, G. P.; Pahutski, T. F., Jr.; Tong, M.-H. T.; Xu, M. WO 2011/017342, 2011 (E. I. du Pont de Nemours and Company); Chem. Abstr. 2011, 154, 250059.
113. Hoffmann, C.; Zhang, W.; Chen, Y. WO 2013/192035, 2013 (E. I. du Pont de Nemours and Company); Chem. Abstr. 2013, 160, 126945.
114. R. Nauen, P. Jeschke, R. Velten, M.E. Beck, U. Ebbinghaus-Kintscher, W. Thielert, K. Woelfel, M. Haas, K. Kunz, and G. Raupach Pest Manag. Sci. 71 2015 850
115. P. Jeschke, R. Nauen, O. Gutbrod, M.E. Beck, S. Matthiesen, M. Haas, and R. Velten Pest. Biochem. Physiol. 121 2015 31
116. P. Jeschke, and R. Nauen W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 1127 1165
117. Methods for the synthesis of CCMP have been reviewed in Ref. 115, page 1192.
118. Lui, N.; Heinrich, J.-D. WO 2009/036898, 2009 (Bayer CropScience); Chem. Abstr. 2009, 150, 374015.
119. Jeschke, P.; Velten, R.; Schenke, T.; Schallner, O.; Beck, M.; Pontzen, R.; Malsam, O.; Reckmann, U.; Nauen, R.; Goergens, U.; Pitta, L.; Mueller, T.; Arnold, C.; Sanwald, E. DE 102006015467, 2007 (Bayer CropScience); Chem. Abstr. 2007, 147, 427231.
120. Lui, N.; Heinrich, J.-D.; Funke, C. WO 2011/018180, 2011(Bayer CropScience); Chem. Abstr. 2011, 154, 234478.
121. Lui, N.; Heinrich, J.-D. WO 2010/105779, 2010 (Bayer CropScience); Chem. Abstr. 2010.
122. Lui, N; Warsitz, R.; Funke, C.; Severins, C. WO 2012/095403, 2012 (Bayer CropScience); Chem. Abstr. 2012, 157, 201451.
123. Lui, N.; Funke, C.; Heinrich, J.-D.; Mueller, T. N. WO 2012/062703, 2012 (Bayer CropScience); Chem. Abstr. 2012, 156, 637592.
124. Lui, N.; Heinrich, J.-D.; Funke, C.; Schlegel, G.; Mueller, T. N. WO 2012/062702, 2012 (Bayer CropScience); Chem. Abstr. 2012, 156, 637593.
125. A. Jeanguenat Pest Manag. Sci. 69 2013 7
126. (a) Freudenberger, J. H.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2003/016283, 2003 (E. I. du Pont de Nemours and Company). Chem. Abstr. 2003, 138, 205053; (b) Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2003/015519, 2003 (E. I. du Pont de Nemours and Company). Chem. Abstr. 2003, 138, 200332.
127. Koyanagi, T.; Nakamoto, K. WO 2008/155990, 2008 (Ishihara Sangyo Kaisha); Chem. Abstr. 2008, 150, 77672.
128. M. Poirier, F. Chen, C. Bernard, Y.-S. Wong, and G.G. Wu Org. Lett. 3 2001 3795
129. 3-Methyl-5-nitro-1H-pyrazole is commercially available and can be synthesized by nitration of 3-methyl-1H-pyrazole.
130. Synthesis of 1-cyclopropylethanamine was reported by ISK. In: Koyanagi, T.; Yamamoto, K.; Yoneda, T.; Kanbayashi, S.; Tanimura, T.; Taguchi, Y.; Yoshida, T. WO 2008/072745, 2008 (Ishihara Sangyo Kaisha); Chem. Abstr. 2008, 149, 79593.
131. Volz, F.; Himmler, T.; Mueller, T. N.; Lehmann, S.; Von Morgenstern, S.; Moradi, W. A.; Pazenok, S.; Lui, N. WO 2013/007603, 2013 (Bayer Intellectual Property); Chem. Abstr. 2013, 158, 187179.
132. F. Effenberger, R. Maier, K.-H. Schönwälder, and T. Ziegler Chem. Ber. 115 1982 2766
133. M.A.P. Martins, A.P. Sinhorin, A. Da Rosa, A.F.C. Flores, A.D. Wastowski, C.M.P. Pereira, D.C. Flores, P. Beck, R.A. Freitag, S. Brondani, W. Cunico, H.G. Bonacorso, and N. Zanatta Synthesis 2002 2353
134. The process for the synthesis of aryl-substituted pyrazoles has been patented by Bayer CropScience: Pazenok, S.; Lui, N. WO 2011/009551, 2011 (Bayer CropScience); Chem. Abstr. 2011, 154, 158455.
135. Pazenok, S.; Lui, N.; Volz, F.; Olenik, B.; Funke, C.; Fischer, R.; Gaertzen, O.; Hinz, M.-H.; Neeff, A. WO 2011/157664, 2011 (Bayer CropScience); Chem. Abstr. 2011, 156, 74453.
136. T. Nakao, and S. Banba Bioorg. Med. Chem. 24 2016 372 10.1016/j.bmc.2015.08.008
137. T. Nakao, S. Banba, M. Nomura, and K. Hirase Insect Biochem. Mol. Biol. 43 2013 366
138. Y. Ozoe, T. Kita, F. Ozoe, T. Nakao, and K. Sato Pestic. Biochem. Physiol. 107 2013 285
139. Aoki, Y.; Kobayashi, Y.; Daido, H.; Katsuka, H., Tsukada, H.; Hirabayashi, A.; Takahashi, Y., Nomura, M.; Kawahara, A. WO 2010/018857, 2010 (Mitsui Chemicals Agro); Chem. Abstr. 2010, 152, 262375.
140. Kobayashi, Y.; Katsuta, H.; Nomura, M.; Tsukada, H.; Hirabayashi, A.; Daido, H.; Takahashi, Y.; Banba, S. WO 2010/013567, 2010 (Mitsui Chemicals Agro); Chem. Abstr. 2010, 152, 238610.
141. Okura, H. WO 2013/150988, 2013 (Mitsui Chemicals Agro); Chem. Abstr. 2013, 159, 577001.
142. Mitsudera, H. WO 2009/005110, 2009 (Sumitomo Chemical Company); Chem. Abstr. 2009, 150, 121221.
143. Nishiguchi, N.; Terada, T.; Ikari, K. JP 2015/151363, 2015 (Sumitomo Chemical Company); Chem. Abstr. 2015, 163, 346444.
144. Nishiguchi, N.; Terada, T.; Ikari, K. JP 2015/131776, 2015 (Sumitomo Chemical Company); Chem. Abstr. 2015, 163, 226554.
145. Okamoto, H. JP 2011/231040, 2011 (Sumitomo Chemical Company); Chem. Abstr. 2011, 155, 657024.
146. T.C. Sparks, and R. Nauen Pestic. Biol. Phys. 121 2015 122
147. Hirota, M.; Miyazaki, H.; Itoh, T. WO 2011/019076, 2011 (Sumitomo Chemical Company); Chem. Abstr. 2011, 154, 234218.
148. Kawamura, M. DE 102014004684, 2014 (Sumitomo Chemical Company); Chem. Abstr. 2014, 161, 566369.
149. B. Zeynizadeh, and E. Amjadi Asian J. Chem. 21 2009 3611
150. M. Nakano, N. Yasokawa, A. Suwa, S. Fujioka, T. Furuya, and K. Sakata J. Pestic. Sci. 40 2015 19
151. T. Van Leeuwen, L. Tirry, A. Yamamoto, R. Nauen, and W. Dermauw Pestic. Biochem. Phys. 121 2015 12
152. Furuya, T.; Kanno, H.; Machiya, K.; Suwa, A.; Yasokawa, N.; Fujioka. S. WO 2007/020986, 2007 (Nihon Nohyaku Company); Chem. Abstr. 2007, 146, 274360.
153. Furuya, T.; Yamaguchi, M.; Tohnishi, M.; Seo, A.; Morimoto, M.; Takemoto, T.; Fujioka, S. WO 2002/096882, 2002 (Nihon Nohyaku Company); Chem. Abstr. 2002, 138, 14057.
154. Q. Li, S. Jiao, B. Chai, J. Yang, Y. Song, and G. Yang Nongyao 53 2014 15
155. Kato, T.; Kai, R.; Kobayashi, Y. WO 2013/015203, 2013 (Nippon Light Metal Company); Chem. Abstr. 2013, 158, 215677.
156. Kato, Y.; Shimano, S.; Morikawa, A.; Hotta, H.; Yamamoto, K.; Nakanishi, N.; Minowa, N.; Kurihara, H. WO 2010/007964, 2010 (Nippon Kayaku); Chem. Abstr. 2010, 152, 168815.
157. C.A. Leichter, N. Thompson, B.R. Johnson, and J.G. Scott Pestic. Biochem. Phys. 107 2013 169
158. S. Omura, H. Tomoda, Y.K. Kim, and H. Nishida J. Antibiot. 46 1993 1168
159. H. Tomoda, Y.K. Kim, R. Nishida, R. Masuma, and S. Omura J. Antibiot. 47 1994 148
160. Y.K. Kim, H. Tomoda, H. Nishida, T. Sunazuka, R. Obata, and S. Omura J. Antibiot. 47 1994 154
161. H. Tomoda, H. Nishida, Y.K. Kim, R. Obata, T. Sunazuka, S. Omura, J. Bordner, M. Guadliana, P.G. Dormer, and A.B. Smith J. Am. Chem. Soc. 116 1994 12097
162. H.-J. Wang, J.B. Gloer, D.T. Wicklow, and P.F. Dowd Appl. Environ. Microbiol. 61 1995 4429
163. http://www.agro.basf.com/agr/AP-Internet/en/content/news-room/news/meiji-seika-kaisha-ltd-and-BASF-exclusive-insecticide-co-development-agreement.
164. Bonnekessel, M.; Reichert, W.; Hoock, R.; Kaeding, T.; Koradin, C.; Pletsch, A.; Ehresmann, M.; Schröder, H. WO 2014/111398, 2014 (BASF); Chem. Abstr. 2014, 161, 246540.
165. O. Loiseleur, B. Slaats, and P. Maeinfish W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 1367 1387
166. J. Kearn, E. Ludlow, J. Dillon, V. O'Connor, and L. Holden-Dye Pestic. Biochem. Phys. 109 2014 44
167. T. Pitterna, M. Böger, and P. Maienfisch Chimia 58 2004 108
168. Watanabe, Y.; Ishikawa, K.; Otsu, Y.; Shibuya, K. WO 2001/02378, 2001 (Nihon Bayer Agrochem); Chem. Abstr. 2001, 134, 100860.
169. Straub, A. US 2006/0004196, 2006 (Bayer CropScience); Chem. Abstr. 2006, 140, 94093.
170. Slomczynska, U.; South, M. S.; Bunkers, G.; Edgecomb, D.; Wyse-Pester, D.; Selness, S.; Ding, Y.; Christiansen, J.; Ediger, K.; Miller, W.; Charumilind, P.; Hartmann, G.; Williams, J.; Dimmic, M.; Shortt, B.; Haakenson, W.; Wideman, A:; Crawford, M.; Hresko, M.; McCarter, J. 248th ACS National Meeting & Exposition, San Francisco, CA, United States, August 10-14, 2014 (2014), AGRO-39.
171. Miller, W. H.; Graham, C. R.; Brown, D. L. WO 2014/008257, 2014 (Monsanto Technology); Chem. Abstr. 2014, 160, 175239.
172. F.W. Goldberg, J.G. Kettle, T. Kogej, M.W.D. Perry, and N.P. Tomkinson Drug Discov. Today 20 2015 11