Nicosulfuron Degradation Path
J. Agric. Food Chem., Vol. 50, No. 3, 2002 531
(13) Berger, B. M.; Wolfe, N. Lee. Hydrolysis and biodegradation
of sulfonylurea herbicides in aqueous buffers and anaerobic
water-sediment systems: assessing fate pathways using molecular
descriptors. EnViron. Toxicol. Chem. 1996, 15, 1500-1507.
(14) Ukrainczyk, L.; Rashid, N. Irreversible sorption of nicosulfuron
on clay minerals. J. Agric. Food Chem. 1995, 43, 855-857.
(15) Gonzalez, J. M.; Ukrainczyk, L. Adsorption and desorption of
nicosulfuron in soils. J. EnViron. Qual. 1996, 25, 101-107.
(16) Gonzalez, J. M.; Ukrainczyk, L. Transport of nicosulfuron in
soil columns. J. EnViron. Qual. 1999, 28, 1186-1192.
(17) Sabadie, J. Behavior of four sulfonylurea herbicides in the
presence of hydroxy compounds. J. Agric. Food Chem. 2000,
48, 4752-4756.
(18) Beyer, E. M.; Duffy, M. J.; Hay, J. V.; Schlueter, D. D.
Sulfonylureas. In Herbicides Chemistry, Degradation and Mode
of Action; Kearney, P. C., Kaufman, D. D., Eds.; Marcel
Dekker: New York, 1988; Vol. 3, pp 117-189.
(19) Brown, H. M. Mode of action, crop selectivity, and soil rela-
tions of the sulfonylurea herbicides. Pestic. Sci. 1990, 29, 263-
281.
(20) Sabadie, J. Alcoholysis and chemical hydrolysis of bensulfuron-
methyl. Weed Res. 1996, 36, 441-448.
(21) Shalaby, L. M.; Bramble, F. Q., Jr.; Lee, P. W. Application of
thermospray LC/MS for residue analysis of sulfonylurea herbi-
cides and their degradation products. J. Agric. Food Chem. 1992,
40, 513-517.
(22) Scrano, L.; Bufo, S. A.; Perucci, P.; Meallier, P.; Mansour, M.
Photolysis and hydrolysis of rimsulfuron. Pestic. Sci. 1999, 55,
955-961.
(23) Teaney, S. R.; Armstrong, L.; Bentley, K.; Cotterman, D.; Leep,
D.; Liang, P. H.; Powley, C.; Summers, J. DPX-KE459 - A
new sulfonylurea for postemergence grass and broadleaf weed
control in cereals. Brighton Crop Prot. Conf.- Weeds 1995, 49-
56.
Nicosulfuron appears quite distinguishable from rimsulfuron
or flupyrsulfuron-methyl by its hydrolysis path and by its
metabolism in maize previously described by Koeppe and
Brown (4). These results encourage us to envisage studying the
behavior of flazasulfuron, another pyridylsulfonylurea herbicide.
LITERATURE CITED
(1) Brown, H. M.; Cotterman, J. C. Recent advances in sulfonylurea
herbicides. Chem. Plant Prot. 1994, 10, 47-81.
(2) Murai, S.; Nakamura, Y.; Akagi, T.; Sakashita, N.; Haga, T.
Synthesis and quantitative structure-activity relationships of
pyridylsulfonylurea herbicides. In Synthesis and Chemistry of
Agrochimicals III; ACS Symposium Series No. 504; Baker, D.
R., Fenyes, J. G., Steffens, J. J., Eds.; American Chemical
Society: Washington, DC, 1992; Chapter 6, pp 43-55.
(3) Andrea, T. A.; Artz, S. P.; Ray, T. B.; Pasteris, R. J. Structure-
activity relationships of sulfonylurea herbicides. In Rational
Approaches to Structure, ActiVity, and Ecotoxicology of Agro-
chemicals; Draber, W., Fujita, T., Eds.; CRC Press: Boca Raton,
FL, 1992; Chapter 15, pp 373-395.
(4) Koeppe, M. K.; Brown, H. M. Sulfonylurea herbicide plant
metabolism and crop selectivity. Agro-Food-Ind. Hi-Tech 1995,
6 (nov-dec), 9-14.
(5) Schneiders, G. E.; Koeppe, M. K.; Naidu, M. V.; Horne, P.;
Brown, A. M.; Mucha, C. F. Fate of rimsulfuron in the
environment. J. Agric. Food Chem. 1993, 41, 2404-2410.
(6) Vicari, A.; Zimdahl, R. L.; Cranmer, B. K.; Dinelli, G.
Primisulfuron and rimsulfuron degradation in aqueous solution
and adsorption in six Colorado soils. Weed Sci. 1996, 44, 672-
677.
(7) Galeazzi, R.; Marucchini, C.; Orena, M.; Porzi, G. The cleavage
of sulfonylurea herbicide rimsulfuron under basic conditions: a
computational investigation. Heterocycles 2000, 53, 2517-2526.
(8) Pantani, O.; Pusino, A.; Calamai, L.; Gessa, C.; Fusi, P.
Adsorption and degradation of rimsulfuron on Al hectorite. J.
Agric. Food Chem. 1996, 44, 617-621.
(9) Rouchaud, J.; Neus, O.; Callens, D.; Bulcke, R. Soil metabolism
of the herbicide rimsulfuron under laboratory and field condi-
tions. J. Agric. Food Chem. 1997, 45, 3283-3291.
(10) Martins, J. M. F.; Mermoud, A. Transport of rimsulfuron and
its metabolites in soil columns. Chemosphere 1999, 38, 601-
616.
(11) Koch Singles, S.; Dean, G. M.; Kirkpatrick, D. M.; Mayo, B.
C.; Langford-Pollard, A. D.; Barefoot, A. C.; Bramble, F. Q.
Fate and behaviour of flupyrsulfuron-methyl in soil and aquatic
systems. Pestic. Sci. 1999, 55, 288-300.
(24) Shea, P. J. Chlorsulfuron dissociation and adsorption on selected
adsorbents and soils. Weed Sci. 1986, 34, 474-478.
(25) Ukrainczyk, L.; Ajwa, H. A. Primisulfuron sorption on minerals
and soils. Soil Sci. Soc. Am. J. 1996, 60, 460-467.
(26) Sabadie, J. De´gradation du chlorimuron-e´thyle de´pose´ sur divers
mine´raux et sur acides humiques. Weed Res. 1995, 35, 295-
302.
(27) Sabadie, J. Degradation of bensulfuron-methyl on various
minerals and humic acids. Weed Res. 1997, 37, 411-418.
Received for review July 9, 2001. Revised manuscript received
November 6, 2001. Accepted November 7, 2001.
(12) Rouchaud, J.; Neus, O.; Cools, K.; Bulcke, R. Flupyrsulfuron
soil dissipation and mobility in winter wheat crops. J. Agric.
Food Chem. 1999, 47, 3872-3878.
JF010873S