commercialized under the brand DuPont™ Salibro™ nematode control, and the active ingredient (fluazaindolizine)
will be branded as Vellozine™ nematode control. Use of the formulated product in the field, under the proposed
directions for use, has demonstrated consistent root protection and the potential for increased yields in the crops
tested.
Intrinsic sensitivities differ to fluazaindolizine, with plant parasitic nematodes being of higher sensitivity than other
groups of the soil nematode community. Fluazaindolizine works by contact with nematodes in the soil pore water,
and is not considered systemic in plants by soil application. It has a highly favourable profile for operators and also
for non-target organisms making it an ideal product for use in integrated pest management (IPM) systems. In
particular, fluazaindolizine has been shown to be highly compatible with a broad range of naturally occurring or
introduced biological control agents, such as beneficial fungi and nematodes, bacteria and other important non target
organisms that inhabit the soil rhizosphere and help sustain crop and soil health.
In summary fluazaindolizine has demonstrated excellent control of plant parasitic nematodes and the damage they
cause to plant roots, resulting in higher quality crops and increased potential in crop yields. Specificity for
nematodes, coupled with the absence of activity against target sites of commercial nematicides, suggests that it has a
novel mode of action. Fluazaindolizine promises to offer farmers around the world a valuable new tool for crop
protection and plant parasitic nematode management.
References and notes
1) Lahm, G.P., Lett, R.M., Smith, B.T., Smith, B.K., Tyler, A.C. World Patent 10/129500, 2010. Chem. Abstr.
2010, 153, 609287.
2) Sasser, J.N., Freckman, D.W. A World Prospective in Nematology. The Role of Society. In: Veech, J.A.,
Dickson, D.W., eds., Vista on Nematology, Society of Nematologists, Hyattsville, MD, 1987: 7-14.
3) Decraemer W., Hunt D.J. Structure and classification. In: Perry R.N., Moens M., eds. Plant nematology. CAB
14.11.16.
4) Haydock, P.J., Woods, S.R., Grove, G., Hare, M.C. Chemical control of nematodes. In: Perry R.N., Moens M.,
eds.
Plant
nematology.
CAB
International,
Wallingford,
Cambridge
2006:
392-408.
5) Crop Protection Manufacturers Report 2010: A Strategic Market Analysis of the U.S. Crop Protection Industry.
Report #P0110 | © 2011 Kline & Company, Inc./Prochaska & Company
6) Greul, J.N., Mansfield, D., Fuesslein, M., Rieck, H., Riedrich, M., Rodefeld, L., Kather, K., Malsam, O.,
Loesel, P., Voerste, A., Schwarz, H.G., Ilg, K., Goergens, U., Carles, L., Coqueron, P.Y., Desbordes, P.,
Meresse, P., World Patent 13/064460, 2013. Chem. Abstr. 2013, 158, 633200.
7) Watanabe, Y., Ishikawa, K., Otsu, Y., Shibuya, K., Abe, T., World Patent 01/002378, 2001. Chem. Abstr. 2001,
134, 100860.
8) Oka, Y.; Shuker, S.; Tkachi, N. Pest Manag Sci. 2012; 68(2): 268-275.
9) Synthesis and characterization of compound D25: To 8-chloro-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-
carboxylic acid (243 mg, 0.92 mmol) was added a solution of 4-(dimethylamino)pyridine (340 mg, 2.76 mmol)
and 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (232 mg, 2.3 mmol) in t-butanol (5 mL)
and dichloromethane (5 mL). The reaction mixture was stirred for 15 min and then 2-chloro-5-
methoxybenzenesulfonamide (190 mg, 0.86 mmol) was added, and the mixture was left to stir at room
temperature overnight. Dichloromethane (200 mL) was then added and the mixture was extracted with 1 N
hydrochloric acid (3 x 100 mL). The organic phase was dried over magnesium sulfate and concentrated under
reduced pressure to afford a solid. The solid was rinsed with diethyl ether to afford 240 mg of D25 as a white
1
solid, m.p. 211-212 °C. HNMR (CDCl3) δ10.10 (br s, 1H), 8.46 (s, 1H), 8.27 (s, 1H), 7.86 (d, 1H), 7.54 (s,
1H), 7.38 (d, 1H), 7.09 (dd, 1H), 3.91 (s, 3H); 13C NMR (100 MHz, DMSO) δ56.57, 116.45 (q, JC-F 34.5 Hz),