Chemistry and fate of triazolopyrimidine sulfonamide herbicides

Reviews of Environmental Contamination and Toxicology

Volumn 193, Issue , 2008, Pages 31-52

  Jabusch, Thomas W ^a   Tjeerdema, Ronald S ^b  

^a SAN FRANCISCO ESTUARY INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOLACTATE SYNTHASE; HERBICIDE; SULFONAMIDE;

ANIMAL; CHEMISTRY; DRUG RESISTANCE;

ACETOLACTATE SYNTHASE; ANIMALS; DRUG RESISTANCE; HERBICIDES; SULFONAMIDES;

EID: 77956015389     PISSN: 01795953     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-0-387-73163-6_2     Document Type: Article

References (76)

1. Barnes JW, Oliver LR (2004) Cloransulam absorption, translocation, and effificacy on common broadleaf weed species. Weed Sci 52:634-641.
2. Barnwell P, Cobb AH (1994) Graminicide antagonisms by broadleaf weed herbicides. Weed Technol 18:763-772.
3. Baron J (2001) IR-4 New Products/Transitional Solution List-March, 2001. Rutgers, The State University of New Jersey, North Brunswick, NJ.
4. Baskaran S, Lauren DR, Holland, PT (1996) High-performance liquid chromatographic determination of flfl umetsulam, a newly developed sulfonamide in soil. J Chromatogr A 746:25-30.
5. Battaglin WA, Furlong ET, Burkhardt MR, Peter, CJ (2000) Occurrence of sulfonylurea, sulfonamide, imidazolinone, and other herbicides in rivers, reservoirs and ground water in the Midwestern United States, 1998. Sci Total Environ 248: 123-133.
6. Bernasconi P, Woodworth AR, Rosen BA, Subramanian MV, Siehl DL (1995) A naturally occurring point mutation confers broad range tolerance to herbicides that target acetolactate synthase. J Biol Chem 270(29):17381-117285
7. Borges JH, García-Montelongo FJ, Cifuentes A, Rodríguez- Delgado MÁ (2005a) Analysis of triazolopyrimidine herbicides in soils using fifi eld-enhanced sample injection-coelectroosmotic capillary electrophoresis combined with soli-phase extraction. J Chromatogr A 1100:236-242.
8. Borges JH, García-Montelongo FJ, Cifuentes A, Rodríguez- Delgado MÁ (2005b) Determination of herbicides in mineral and stagnant waters at ng/L levels using capillary electrophoresis and UV detection combined with solid-phase extraction and sample stacking. J Chromatogr A 1070:171-177.
9. Borges JH, Rodríguez-Delgado MÁ, García-Montelongo FJ, Cifuentes A (2005c) Analysis of pesticides in soy milk combining solid-phase extraction and capillary electrophoresis-mass spectrometry. J Sep Sci 28:948-956.
10. Boutsalis P, Powles SB (1995) Inheritance and mechanism of resistance to herbicides inhibiting acetolactate synthase in Sonchus oleraceus L. Theor Appl Genet 91:242-247.
11. Concha M, Shepler K, Merritt D (1994) Photodegradation of (14C)-XDE-564 in aqueous buffered solution at pH 5 by natural sunlight. Dow Agro Sciences, Indianapolis, IN.
12. CambridgeSoft Corporation (2006) ChemFinder.com. http://chemfifinder. cambridgesoft.com/.
13. Cupples AM, Sims GK, Hultgren RP, Hart SE (2000) Effect of soil conditions on the degradation of cloransulam-methyl. J Environ Qual 29(3):786-794.
14. deBoer GJ, Thornburgh S, Ehr RJ (2006) Uptake, translocation and metabolism of the herbicide flflorasulam in wheat and broadleaf weeds. Pestic Manag Sci 62:316-324.
15. Devine M, Eberlein CV (1997) Physiological, biochemical and molecular aspects of herbicide resistance based on altered target sites. In Roe RM, Burton JD, Kuhr RJ (eds) Herbicide Activity: Toxicology, Biochemistry and Molecular Biology. IOS Press, Amsterdam, pp 159-186.
16. Ferguson GM, Hamill AS, Tardif FJ (2001) ALS inhibitor resistance in populations of Powell amaranth and redroot pigweed. Weed Sci 49:448-453.
17. Foes MJ, Liu L, Tranel PJ, Wax LM, Stoller EW (1998) A biotype of common waterhemp (Amaranthus rudis) resistant to triazine and ALS herbicides. Weed Sci 46(5):514-520.
18. Frear DS, Swanson HR, Tanaka FS (1993) Metabolism of flfl umetsulam (DE-498) in wheat, corn, and barley. Pestic Biochem Physiol 45:178-192.
19. Gerwick BC, Kleschick WA (1991) DE-498: a new broad spectrum herbicide for soybeans and other crops. Weed Sci Abstr 31:28.
20. Hashem A, Bowran D, Piper T, Dhammu H (2001) Resistance of wild radish (Raphanus raphanistrum) to acetolactase synthase-inhibiting herbicides in the Western Australian wheat belt. Weed Technol 15:68-74.
21. Jabusch TW, Tjeerdema RS (2005) Partitioning of penoxsulam, a new sulfonamide herbicide. J Agric Food Chem 53(18):7179-7183.
22. Jabusch TW, Tjeerdema RS (2006a) Microbial degradation of penoxsulam in flfl ooded rice soils. J Agric Food Chem 54:5962-5967.
23. Jabusch TW, Tjeerdema RS (2006b) Photodegradation of penoxsulam. J Agric Food Chem 54:5958-5961.
24. Jackson R, Ghosh D, Paterson G (2000) The soil degradation of the herbicide flflorasulam. J Agric Food Chem 56:1065-1072.
25. Kemp MS, Moss SR, Thomas TH (1990) Herbicide resistance in Alopecurus myosuroides. In: Green MR, LeBaron HM, Moberg WM (eds) Managing Resistance to Agrochemicals: From Fundamental Research to Practical Strategies. American Chemical Society, Washington, DC.
26. Kleschick WA, Gerwick BC (1989) The chemistry and biochemistry of triazolopyrimidinesulfonanilide herbicides, a new class of acetolactate synthase inhibitors. In: Copping L, Dodge AD, Dlaziel J (eds) Prospects for Amino Acid Biosynthesis Inhibitors in Crop Protection and Pharmaceutical Chemistry. Lavenham Press, Lavenham, UK, pp 133-145.
27. Kleschick WA, Gerwick BC, Carson CM, Monte WT, Snider SW (1992) DE-498, a new acetolactate synthase inhibiting herbicide with multicrop selectivity. J Agric Food Chem 40:1083-1085.
28. Krieger MS, Pillar F, Ostrander JA (2000a) Effect of temperature and moisture on the degradation and sorption of flfl orasulam and 5-hydroxyflflorasulam in soil. J Agric Food Chem 48:4757-4766.
29. 2. J Chromatogr A 897:405-413.
30. Krieger MS, Yoder RN, Gibson R (2000c) Photolytic degradation of flflorasulam on soil and in water. J Agric Food Chem 48:3710-3717.
31. Krynitsky AJ (1997) Determination of sulfonylurea herbicides in water by capillary electrophoresis and by liquid chromatography/mass spectrometry. J AOAC Int 80(2):392-400.
32. Laganà A, Fago G, Marino A, Penazzi VM (2000) Liquid chromatography mass spectrometry tandem for multiresidue determination of selected post-emergence herbicides after soil column extraction. Anal Chim Acta 415:41-56.
33. Landstein D, Arad S, Barak Z, Chipman DM (1993) relationships among the herbicide and functional sites of acetohydroxy acid synthase from Chlorella emersonii. Planta (Berl) 191:1-6.
34. Lehmann RG, Miller JR, Fontaine DD, Laskowski DA, Hunter JH, Cordes RC (1992) Degradation of a sulfonamide herbicide as a function of soil sorption. Weed Res 32:197-205.
35. Lewer P, Finney-Brink KL, Duebelbeis DO (2000) Nature of the residue of [14C]cloransulam-methyl in lactating goats. J Agric Food Chem 48:2532-2546.
36. Madafifi glio GP, Medd RW, Cornisch PS, Van de Ven R (2000) Temperaturemediated responses of flflumetsulam and metosulam on Raphanum raphanistrum. Weed Res 40:387-395.
37. Maycock R, Hastings M, Portwood D (1995) Ultra-trace analysis of metosulam, a new triazolopyrimidine herbicide. Int J Environ Anal Chem 58:1-4.
38. Mourad G, King J (1992) Effect of four classes of herbicides on growth and acetolactase-synthase activity in several variants of Arabidopsis thaliana. Planta (Berl) 188:491-497.
39. Murphy GP, Shaw DR (1997) Field mobility of flflumetsulam in three Mississippi soils. Weed Sci 45(4):564-567.
40. O' Sullivan J, Thomas RJ, Bouw WJ (1999) Effect of flflumetsulam and clopyralid soil residues on several vegetable crops and on sweet corn cultivars grown in rotation. Weed Technol 13:303-307.
41. PAN (2006) PesticideInfo Version 7.1. http://www.pesticideinfo.org/Index. html.
42. Parnell JS, Hall JC (1998) Development of an enzyme-linked immunosorbent assay for the detection of metosulam. J Agric Food Chem 46:152-156.
43. Patzoldt WL, Tranel PJ (2002) Molecular analysis of cloransulam resistance in a population of giant ragweed. Weed Sci 50:299-305.
44. Patzoldt WL, Tranel PJ, Alexander AL, Schmitzer PR (2001) A common ragweed population resistant to cloransulam-methyl. Weed Sci 49:485-490.
45. Peterson HG, Boutin C, Martin PA, Freemark KE, Ruecker NJ, Moody MJ (1994) Aquatic phyto-toxicity of 23 pesticides applied at expected environmental concentrations. Aquat Toxicol 28:275-292.
46. Renew JE, Huang C-H (2004) Simultaneous determination of flfluoroquinolone, sulfonamide, and trimethoprim antibiotics in wastewater using tandem solid phase extraction and liquid chromatography-electrospray mass spectrometry. J Chromatogr A 1042:113-121.
47. Roberts DW, Knuteson JA, Jackson R (2003) The dissipation of penoxsulam in flfl ooded rice fifi elds. In: Pesticides in Air, Plant, Soil & Water Systems: XII Symposium Pesticide Chemistry, Piacenza, Italy, pp 349-357.
48. Rouchaud J, Neus O, Eelen H, Bulcke R (2002a) Dissipation and mobility of flflumetsulam in the soil of corn crops. Meded Fac Landbouwwet Rijksuniv Gent 67(3):401-407.
49. Rouchaud J, Neus O, Eelen H, Bulcke R (2002b) Soil persistence and mobility in corn fifi elds of flflumetsulam applied at low doses. Bull Environ Contam Toxicol 69:785-791.
50. Rubin B (1996) Herbicide-resistant weeds-the inevitable phenomenon: mechanisms, distribution and signifificance. Z Pflfl anzenkr Pflfl anzenschutz XV:17-32.
51. Saari LL, Cotterman JC, Thill DC (1994) Resistance to acetolactase-inhibiting herbicides. In: Powles SB, Holtum JAM (eds) Plants: Biology and Biochemistry. Lewis, Boca Raton, FL, pp 88-139.
52. Schmitzer PR, Eilers RJ, Cséke C (1993) Lack of cross-resistance of imazaquinresistant Xanthium strumarium acetolactase synthase to flflumetsulam and chlorimuron. Plant Physiol 103:281-283.
53. Shackelford DD, Duebelbeis DO, Snell BE (1996) Determination of residues of cloransulam-methyl in soybeans and soybean forage, hay, and processed commodities by capillary gas chromatography with mass spectrometric detection. J Agric Food Chem 44:3570-3575.
54. Shaner DL, Singh BK (1997) Acetohydroxyacid synthase inhibitors. In: Roe RM, Burton JD, Kuhr RJ (eds) Herbicide Activity: Toxicology, Biochemistry and Molecular Biology. IOS Press, Amsterdam, pp 69-110.
55. Shaw DR, Murphy GP (1997) Field persistence of bioavailable flflumetsulam. Weed Sci 45(4):568-572.
56. Sibony M, Rubin B (2003) Molecular basis for multiple resistance to acetolactate synthase-inhibiting herbicides and atrazine in Amaranthus blithoides (prostrate pigweed). Planta (Berl) 216:1022-1027.
57. Sprague CL, Stoller EW, Wax LM (1997) Response of an acetolactase synthase (ALS)-resistant biotype of Amaranthus rudis to selected ALS inhibiting and alternative herbicides. Weed Res 37:93-101.
58. Subramanian MV, Loney V, Pao L (1989) Mechanism of action of 1,2,4-triazolo[1,5-a]pyrimidine sulfonamide herbicides. In: Copping LG, Dalziel J, Dodge AD (eds) Prospects for Amino Acid Biosynthesis Inhibitors in Crop Protection and Pharmaceutical Chemistry. Society of Chemical Industry, Farnham, UK, pp 97-100.
59. Tjeerdema RS, Hill J, Fisher A, TenBrook P, Gunasekara A, Jabusch TW (2005) Project No. RP-5: The Environmental Fate of Pesticides Important to Rice Culture. Report to the California Rice Research Board. Department of Environmental Toxicology, College of Agricultural and Environmental Sciences, University of California, Davis, CA.
60. USEPA (1997) Pesticide Fact Sheet: Cloransulam. USEPA Offifice of Prevention, Pesticides and Toxic Substances, Washington, DC.
61. USEPA (2004a) Penoxsulam, 2-(2,2-diflfl uoroethoxy)-N-(5,8-dimethoxy[1,2, 4] triazolo[1,5-c]pyrimidin-2-yl)-6-(triflfl uoromethyl)benzenesulfonamide; pesticide tolerance. Fed Reg 69(185):57188-57197.
62. USEPA (2004b) Pesticide Fact Sheet: Penoxsulam. USEPA Offifice of Prevention, Pesticides and Toxic Substances, Washington, DC.
63. USEPA (2006) Pesticide products; registration applicants. Fed Reg 71(192): 58603-58604.
64. van Weesenbeeck IJ, Havens PL (1999) A groundwater exposure assessment of cloransulam-methyl in the U.S. soybean market. J Environ Qual 28(2): 513-522.
65. van Weesenbeeck IJ, Zabik JM, Wolt JD, Bormett GA, Roberts DW (1997) Field dissipation of cloransulam-methyl at four sites in the U.S. soybean market. J Agric Food Chem 45:3299-3307.
66. van Weesenbeeck IJ, Peacock AL, Havens PL (2001) Measurement and modeling of diclosulam runoff under the inflfluence of simulated severe rainfall. J Environ Qual 30:553-560.
67. Ware GW, Whitacre DM (2004) The Pesticide Book. Meister Pro Information Resources, Willoughby, OH.
68. Wauchope RD, Yeh SJ, Linders BHJ, Kloskowski R, Tanaka K, Rubin B, Katayama A, Kördel W, Gerstl Z, Lane M, Unsworth JB (2002) Pesticide soil sorption parameters: theory, measurement, uses, limitations and reliability. Pestic Manag Sci 58:419-445.
69. Whaley CM, Wilson HP, Westwood JH (2006) ALS resistance in several smooth pigweed (Amaranthus hybridus) biotypes. Weed Sci 54:828-832.
70. Whitcomb CE (1999) An introduction to ALS-inhibiting herbicides. Toxicol Ind Health 15:232-240.
71. Wolt JD, Schwake JD, Batzer FR, Brown SM, McKendry LH, Miller JR, Roth GA, Stanga MA, Portwood D, Holbrook DL (1992) Anaerobic aquatic degradation of flflumetsulam [N-2,6-diflfl uorophenyl)-5-methyl[1,2,4]triazolo[1,5-a] pyrimidine-2-sulfonamide. J Agric Food Chem 40:2302-2308.
72. Wolt JD, Smith JK, Sims GK, Duebelbeis DO (1996) Products and kinetics of cloransulam-methyl aerobic soil metabolism. J Agric Food Chem 44:324-332.
73. Wood A (2006) Compendium of common pesticide names. http://www.alanwood. net/pesticides/index.html.
74. Yoder RN, Huskin MA, Kennard LM, Zabik JM (2000) Aerobic metabolism of diclosulam on U.S. and South American Soils. J Agric Food Chem 48:4335-4340.
75. Zabik JM, van Weesenbeeck IJ, Peacock AL, Kennard LM, Roberts DW (2001) Terrestrial fifield dissipation of diclosulam at four sites in the United States. J Agric Food Chem 49:3284-3290.
76. Zheng D, Patzoldt WL, Tranel PJ (2005) Association of the W574L ALS substitution with resistance to cloransulam and imazamox in common ragweed (Ambrosia artemisiifolia). Weed Sci 53:424-430.