Abstracts
Flumetsulam
CAS No. 98967-40-9
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Adverse Effects

ACTIVITY: Herbicide (triazolopyrimidine)

CAS NAME: N-(2,6-difluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide

Structure:

 

From Science Direct

The Science of The Total Environment; Volume 248, Issues 2-3 , 5 April 2000, Pages 123-133

Occurrence of sulfonylurea, sulfonamide, imidazolinone, and other herbicides in rivers, reservoirs and ground water in the Midwestern United States, 1998

W. A. Battaglin (a), E. T. Furlong (b), M. R. Burkhardt (b) and C. J. Peter (c)

a U.S. Geological Survey, Office of the Regional Hydrologist, Box 25046 MS 406, D.F.C., Denver, CO 80225, USA
b U.S. Geological Survey, Methods Research and Development, Box 25046 MS 407, D.F.C., Denver, CO 80225, USA
c DuPont Agricultural Products, Barley Mill Plaza, P.O. Box 80015, Wilmington, DE 19880-0015, USA

Sulfonylurea (SU), sulfonamide (SA), and imidazolinone (IMI) herbicides are relatively new classes of chemical compounds that function by inhibiting the action of a plant enzyme, stopping plant growth, and eventually killing the plant. These compounds generally have low mammalian toxicity, but plants demonstrate a wide range in sensitivity to SUs, SAs, and IMIs with over a 10 000-fold difference in observed toxicity levels for some compounds. SUs, SAs, and IMIs are applied either pre- or post-emergence to crops commonly at 1/50th or less of the rate of other herbicides. Little is known about their occurrence, fate, or transport in surface water or ground water in the USA. To obtain information on the occurrence of SU, SA, and IMI herbicides in the Midwestern United States, 212 water samples were collected from 75 surface-water and 25 ground-water sites in 1998. These samples were analyzed for 16 SU, SA and IMI herbicides by USGS Methods Research and Development Program staff using high-performance liquid chromatography/mass spectrometry. Samples were also analyzed for 47 pesticides or pesticide degradation products. At least one of the 16 SUs, SAs or IMIs was detected above the method reporting limit (MRL) of 0.01 g/l in 83% of 130 stream samples. Imazethapyr was detected most frequently (71% of samples) followed by flumetsulam (63% of samples) and nicosulfuron (52% of samples). The sum of SU, SA and IMI concentrations exceeded 0.5 g/l in less than 10% of stream samples. Acetochlor, alachlor, atrazine, cyanazine and metolachlor were all detected in 90% or more of 129 stream samples. The sum of the concentration of these five herbicides exceeded 50 g/l in approximately 10% of stream samples. At least one SU, SA, or IMI herbicide was detected above the MRL in 24% of 25 ground-water samples and 86% of seven reservoir samples.


September 24, 2004, Federal Register: Tolerance Reassessment Decision (TRED) for Low Risk Pesticide; Notice of Availability.
The following is from the HED Risk Assessment for the Tolerance Reassessment Eligibility Document (TRED).
-- Flumetsulam is in the triazolopyrimidine chemical class and has a mode of action similar to the sulfonylurea herbicides that are acetolactate synthase inhibitors (regulate plant growth).
-- The kidney appears to be the primary target organ of rats and dogs following subchronic to chronic exposures.
-- A neurotoxicity study was not conducted, however, flumetsulam showed no indication of being a neurotoxicant in the reviewed studies.
-- A 90-day inhalation study and a subchronic dog study were not conducted, but it is doubtful these would provide any additional useful information.
-- A developmental neurotoxicity study is not required since there was no evidence of neurotoxicity or neuropathy from the available studies.
-- Due to the lack of repeated dose inhalation toxicity study, oral studies were selected for the appropriate duration of exposure. Absorption via inhalation is assumed to be equivalent to oral absorption.

Date Title Some details Federal Register Docket Identification Number
Sept 9, 2004

Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Flumetsulam

5 pages

Signed by:
Debra Edwards,
Director, Special Review and Reregistration Div.

Mika J. Hunter - contact for questions regarding this decision.

EPA OPPT (7508C)
Aug 31, 2004

Flumetsulam: HED Risk Assessment for the Tolerance Reassessment Eligibility Document (TRED).

23 pages

Memorandum From:

Elissa Reaves, Toxicologist Reregistration Branch II, Health Effects Div. (7509C)

EPA OPPT (7509C)
Aug 30, 2004

Flumetsulam. Chronic Dietary Exposure Assessment for the TRED document.

8 pages

Memorandum From:

Samuel Ary, Chemist, Reregistration Branch II, Health Effects Div. (7509C)

EPA OPPT (7509C)

DP Barcode: D306279

PC Code: 129016

Aug 31, 2004

Flumetsulam. Summary of Analytical Chemistry and Residue Data for the Tolerance Reassessment Eligibility Decision (TRED) Document.

32 pages

Memorandum From:

Samuel Ary, Chemist
Reregistration Branch II, Health Effects Div. (7509C)

This summary of analytical chemistry and residue data document was originally prepared under contract by Versar, Inc. (Springfield, VA 22151; submitted June 11, 2004).

EPA OPPT (7509C)

DP Barcode: D306242

PC Code: 129016

May 19, 2004

Drinking Water Assessment for Flumetsulam for Uses on Field Corn and Soybeans

15 pages

Memorandum From:

James Lin, Environmental Engineer,
Stephanie Syslo, RAPL
Environmental Risk Branch III Environmental Fate and Effects Div. (7507C)

EPA OPP (7507C)

PC Code: 129016

DPBarcode: 301361

 

http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12428154&dopt=Abstract

Bull Environ Contam Toxicol. 2002 Dec;69(6):785-92.

No Abstract available

Soil persistence and mobility in corn fields of flumetsulam applied at low doses.

Rouchaud J, Neus O, Eelen H, Bulcke R.

Phytopharmacy Laboratory, Catholic University of Louvain, 3, Place Croix du Sud, SCI. 15D, 1348 Louvain-la-Neuve, Belgium.

PMID: 12428154 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10805233&dopt=Abstract

Sci Total Environ. 2000 Apr 5;248(2-3):123-33.

Occurrence of sulfonylurea, sulfonamide, imidazolinone, and other herbicides in rivers, reservoirs and ground water in the Midwestern United States, 1998.

Battaglin WA, Furlong ET, Burkhardt MR, Peter CJ.

U.S. Geological Survey, Office of the Regional Hydrologist, Denver, CO 80225, USA. wbattagl@usgs.gov

Sulfonylurea (SU), sulfonamide (SA), and imidazolinone (IMI) herbicides are relatively new classes of chemical compounds that function by inhibiting the action of a plant enzyme, stopping plant growth, and eventually killing the plant. These compounds generally have low mammalian toxicity, but plants demonstrate a wide range in sensitivity to SUs, SAs, and IMIs with over a 10,000-fold difference in observed toxicity levels for some compounds. SUs, SAs, and IMIs are applied either pre- or post-emergence to crops commonly at 1/50th or less of the rate of other herbicides. Little is known about their occurrence, fate, or transport in surface water or ground water in the USA. To obtain information on the occurrence of SU, SA, and IMI herbicides in the Midwestern United States, 212 water samples were collected from 75 surface-water and 25 ground-water sites in 1998. These samples were analyzed for 16 SU, SA and IMI herbicides by USGS Methods Research and Development Program staff using high-performance liquid chromatography/mass spectrometry. Samples were also analyzed for 47 pesticides or pesticide degradation products. At least one of the 16 SUs, SAs or IMIs was detected above the method reporting limit (MRL) of 0.01 microg/l in 83% of 130 stream samples. Imazethapyr was detected most frequently (71% of samples) followed by flumetsulam (63% of samples) and nicosulfuron (52% of samples). The sum of SU, SA and IMI concentrations exceeded 0.5 microg/l in less than 10% of stream samples. Acetochlor, alachlor, atrazine, cyanazine and metolachlor were all detected in 90% or more of 129 stream samples. The sum of the concentration of these five herbicides exceeded 50 microg/l in approximately 10% of stream samples. At least one SU, SA, or IMI herbicide was detected above the MRL in 24% of 25 ground-water samples and 86% of seven reservoir samples.

PMID: 10805233 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12809295&dopt=Abstract

J Environ Qual. 2003 May-Jun;32(3):949-56.

Soil sorption of acidic pesticides: modeling pH effects.

Spadotto CA, Hornsby AG.

Embrapa Environment. C.P. 69, 13820-000 Jaguariuna, SP, Brazil. spadotto@cnpma.embrapa.br

A model of acidic pesticide sorption in soils was developed from theoretical modeling and experimental data, which initially considered a combination of a strongly acidic pesticide and a variable-charge soil with high clay content. Contribution of 2,4-D [(2,4-dichlorophenoxy) acetic acid] anionic-form sorption was small when compared with molecular sorption. Dissociation of 2,4-D was not sufficient to explain the variation in Kd as a function of pH. Accessibility of soil organic functional groups able to interact with the pesticide (conformational changes) as a function of organic matter dissociation was proposed to explain the observed differences in sorption. Experimental 2,4-D sorption data and K(oc) values from literature for flumetsulam [N-(2,6-difluorophenyl)-5-methyl [1,2,4] triazolo [1,5-a] pyrimidine-2-sulfonamide] and sulfentrazone [N-[2,4-dichloro-5-[4-(difluromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl] phenyl] methanesulfonamide] in several soils fit the model.

PMID: 12809295 [PubMed - in process]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12696407&dopt=Abstract

Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet. 2002;67(3):401-7.

Dissipation and mobility of flumetsulam in the soil of corn crops.

Rouchaud J, Neus O, Eelen H, Bulcke R.

Phytopharmacy Laboratory, Catholic University of Louvain, 3 Place Croix du Sud, SCI. 15D, 1348 Louvain-la-Neuve, Belgium.

The triazolopyrimidine sulfonanilide herbicide flumetsulam has been applied pre- or post-emergence at the rate of 20 g a.i. ha-1 on corn crops grown on sandy-loam or loamy-sand soils. A procedure has been developed for the analysis of flumetsulam in soil using gas-chromatography and gas-chromatography combined with mass spectrometry, after methylation of flumetsulam and purification of the soil extracts by repeated thin-layer chromatographies. The dissipation of flumetsulam in the 0-8 cm surface soil layer followed a first order kinetics. The flumetsulam soil half-life was about 41 days for the crops grown on sandy-loam soil, and 30 days for the crop grown on loamy-sand soil. At the corn harvest in September, only 9 to 13% of the applied dose of flumetsulam remained in soil, what is a common value for the herbicides at the crop harvest. The heavy rains and the soft temperatures of the autumn should dissipate these low residues within the one or two months period after the harvest. When applied at the rate of 20 g a.i. ha-1, the persistence of flumetsulam in field soil thus was moderate. During the crops and until the harvest, in the 8-15 cm surface soil layer, low concentrations of flumetsulam at the limit of the analytical sensitivity (0.3 microgram flumetsulam kg-1 dry soil) were observed temporarily; in the 15-20 cm surface soil layer, flumetsulam was never detected, showing that flumetsulam was strongly adsorbed onto the soil and its organic matter.

PMID: 12696407 [PubMed - indexed for MEDLINE]


From Toxline at Toxnet

WEED RES; 33 (2). 1993. 187-195.

Soil degradation of flumetsulam at different temperatures in the laboratory and field.

LEHMANN RG, FONTAINE DD, OLBERDING EL

Health and Environmental Sci., Dow Corning Corporation, Midland, MI 48686-0994, USA.

BIOSIS COPYRIGHT: BIOL ABS. The degradation rate of the herbicide flumetsulam was examined in Hoytville clay soil at five temperatures and optimal moisture. Half-lives were 246 days at 7.5ê C, 115 days at 15.0ê C, 49 days at 26.1ê C, 34 days at 35.9ê C, and 27 days at 44.0ê C. Construction of an Arrhenius diagram (ln k = -Ea + ln A) allowed the rate constant k to be calculated for any temperature T. When k was inserted into the first order rate equation (c = c0e-kr), the concentration of flumetsulam could be calculated on a monthly basis for any soil. Predictions from this theoretical model were compared with data from three US field locations and found to accurately predict soil residues of flumetsulam under favorable moisture conditions, but not during periods of drought.


From Toxline at Toxnet

Source: DUKE, S. O., J. J. MENN AND J. R. PLIMMER (ED.). ACS SYMPOSIUM SERIES, 524. PEST CONTROL WITH ENHANCED ENVIRONMENTAL SAFETY; 203RD NATIONAL MEETING OF THE AMERICAN CHEMICAL SOCIETY, SAN FRANCISCO, CALIFORNIA, USA, APRIL 5-10, 1992. X+357P. AMERICAN CHEMICAL SOCIETY: WASHINGTON, DC, USA. ISBN 0-8412-2638-5.; 0 (0). 1993. 48-61.

SYNERGIZING PESTICIDES TO REDUCE USE RATES

GRESSEL J

BIOSIS COPYRIGHT: BIOL ABS. RRM HERBICIDE WEED CONTROL METABOLIC SYNERGIST ENZYME INHIBITION

CAS Registry Numbers:
113036-87-6
98967-40-9
82097-50-5
51338-27-3
51218-45-2
49866-87-7
40843-25-2
34123-59-6
25057-89-0
15545-48-9


From Toxline at Toxnet

Source: SSSA SPECIAL PUBLICATION; 0 (32). 1993. 1-26.

COUPLING BIODEGRADATION OF ORGANIC CHEMICALS TO SORPTION AND TRANSPORT IN SOILS AND AQUIFERS PARADIGMS AND PARADOXES

RAO P SC, BELLIN CA, BRUSSEAU ML

BIOSIS COPYRIGHT: BIOL ABS. RRM LITERATURE REVIEW SOIL CONTAMINATION AGRICHEMICAL

CAS Registry Numbers:
98967-40-9
98967-40-9

2764-72-9
1646-88-4
1646-87-3
116-06-3
108-88-3
101-21-3
100-46-9
94-75-7
92-87-5
91-22-5
91-20-3
84-74-2
71-43-2


From Toxline at Toxnet

Source: 203RD ACS (AMERICAN CHEMICAL SOCIETY) NATIONAL MEETING, SAN FRANCISCO, CALIFORNIA, USA, APRIL 5-10, 1992. ABSTR PAP AM CHEM SOC; 203 (1-3). 1992. ENVR243.

ANAEROBIC AQUATIC DEGRADATION OF FLUMETSULAM

WOLT JD, SCHWAKE JD, BATZER FR, BROWN SM, MCKENDRY LH, MILLER JR, ROTH GA, STANGA MA, PORTWOOD D


 

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