Abstracts
Sulfentrazone
CAS No. 122836-35-5
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ACTIVITY: Herbicide (triazolone)

CAS Name: N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]methanesulfonamide

Structure:




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

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 - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10432190&dopt=Abstract

Cell Mol Biol (Noisy-le-grand) 1999 Jun;45(4):433-44

Protoporphyrin IX fluorescence kinetics in C6 glioblastoma cells after delta-aminolevulinic acid incubation: effect of a protoporphyrinogen oxidase inhibitor.

Carre J, Eleouet S, Rousset N, Vonarx V, Heyman D, Lajat Y, Patrice T

Departement Laser, Hopital Laennec, Nantes, France.

PpIX synthesis after incubation with delta-aminolevulinic acid (ALA) is highly variable from one cell to another within a single cell population and in human glioblastomas in vivo. To improve PpIX synthesis, we attempted to modify the PpIX synthesis pathway in a C6 glioma cell model. To perform this experiment we used confocal microspectrofluorometry to analyse the effects of a highly purified form of sulfentrazone (FP846) on the kinetics of PpIX synthesis after ALA administration to living C6 cells. Our results show that PpIX fluorescence was maximal (seven-fold higher than basal values) 3 to 4 hrs. after the beginning of incubation with ALA. FP846 depressed this increase in fluorescence nearly to basal levels not only in C6 cells but also in HT29 and HepG2 cells. Fluorescence spectra shape were not affected by FP846, except for intensity. ALA/PpIX-induced photocytoxicity was perfectly correlated with fluorescence intensity recorded in cell cytoplasm. ALA alone (100 microg/ml) did not induce a significant decrease in cell survival, but irradiation of 25 J/cm2 leading to an overall cell death of 60%. FP846 added together with ALA suppressed ALA/PpIX-induced phototoxicity. The fact that the FP846-induced decrease in PpIX synthesis was not the same in animal and plant cells suggests that the porphyrin metabolic pathway differs due to the relative amounts of substrate or the effect of inhibitor and that another chemical would be needed alone or in combination with FP846 to improve PpIX synthesis.

PMID: 10432190, UI: 99359137


From Toxline at Toxnet

WEED SCIENCE; 46 (2). 1998. 271-277.

Evaluation of soybean injury from sulfentrazone and inheritance of tolerance.

SWANTEK JM, SNELLER CH, OLIVER LR

Dep. Agron., Univ. Arkansas, Fayetteville, AR 72704, USA.

BIOSIS COPYRIGHT: BIOL ABS. Experiments were conducted in the field and greenhouse to evaluate the effects of cultivar and sulfentrazone rate on soybean injury and yield from soil-applied sulfentrazone and to determine soybean inheritance of sulfentrazone tolerance. Excessive rainfall and cool growing conditions in 1996 enhanced sulfentrazone injury and caused yield reduction in the susceptible cultivars 'KS4895' and 'Hutcheson at 0.56 kg ai ha-1 and KS4895 at 0.42 kg ha-1. Yields of tolerant cultivars 'Deltapine 3478' and 'Manokin' were not reduced. Sulfentrazone at 0.42 kg ha-1 reduced soybean stand 17 and 35% for tolerant and susceptible cultivars, respectively. Field and greenhouse inheritance studies were conducted on plant families developed from two crosses: Manokin (tolerant) by 'Asgrow A4715' (susceptible) and 'Northrup King S59-60' (tolerant) by KS4895 (susceptible). The sulfentrazone tolerance of Manokin and Northrup King S59-60 appeared to be controlled by a single gene, with tolerance


From Toxline at Toxnet

Source: 214TH AMERICAN CHEMICAL SOCIETY NATIONAL MEETING, LAS VEGAS, NEVADA, USA, SEPTEMBER 7-11, 1997. ABSTRACTS OF PAPERS AMERICAN CHEMICAL SOCIETY; 214 (1-2). 1997. AGRO 114.

THE TRUE STORY SULFENTRAZONE METABOLITES IN VARIOUS CROPS

CHEN AW

BIOSIS COPYRIGHT: BIOL ABS. RRM MEETING ABSTRACT PLANT SULFENTRAZONE HERBICIDE METABOLISM UPTAKE 3-HYDROXYMETHYL SULFENTRAZONE METABOLITE SULFENTRAZONE-3-CARBOXYLIC ACID DECARBOXYLATION 3-DESMETHYL SULFENTRAZONE PESTICIDES BIOCHEMISTRY AND BIOPHYSICS AGRONOMY


From Toxline at Toxnet

Source: 213TH NATIONAL MEETING OF THE AMERICAN CHEMICAL SOCIETY, SAN FRANCISCO, CALIFORNIA, USA, APRIL 13-17, 1997. ABSTRACTS OF PAPERS AMERICAN CHEMICAL SOCIETY; 213 (1-3). 1997. AGRO 96.

FORMATION AND DECLINE OF MAJOR SULFENTRAZONE PHOTOPRODUCTS IN BUFFERED AQUEOUS SOLUTION BY SIMULATED SUNLIGHT

WILLUT JM, MCLAUGHLIN TM, SHOMO RE, FANG XP, GRAVELLE WD, VARANYAK LA

BIOSIS COPYRIGHT: BIOL ABS. RRM MEETING ABSTRACT PESTICIDES SULFENTRAZONE FILTERED XENON LAMP BUFFERED AQUEOUS SOLUTION PHOTOLYSIS SIMULATED SUNLIGHT EQUIPMENT


 

From Toxline at Toxnet

WEED SCIENCE; 45 (5). 1997. 733-738.

Sulfentrazone adsorption and mobility as affected by soil and pH.

GREY TL, WALKER RH, WEHTJE GR, HANCOCK HG

1733 N. Longgrove Rd., Cecilia, KY 42724, USA.

BIOSIS COPYRIGHT: BIOL ABS. Laboratory experiments were conducted to evaluate soil adsorption and mobility of sulfentrazone. Sulfentrazone is a new phenyl triazolinone herbicide intended for use in soybean. Adsorption was evaluated through a soil solution technique, and mobility was evaluated with soil thin-layer chromatography. Experimental variables included soil, sulfentrazone concentration (adsorption study only), and pH. Adsorption was influenced by all experimental variables; however, pH had the greatest effect. Adsorption generally decreased in response co increasing pH. However, the greatest decrease occurred above the pKa of sulfentrazone (i.e., 6.56). Mobility generally reflected adsorption.


Pesticide Biochemistry and Physiology; Volume 53, Issue 3 , November 1995, Pages 172-179

Microbioassays to Determine the Activity of Membrane Disrupter Herbicides

Molin W. T. and Khan R. A.

Univ Arizona, Dept Plant Sci, Tucson, AZ 85721, USA

Two methods to determine the activity of membrane disrupter herbicides on leakage from cucumber (Cucumis sativa L., "Medalist") cotyledon discs are described. In these bioassays, leakage could be measured from a single disc (4 mm diameter) in 300 l of incubation solution. The 96-well microtiter plates were convenient assay containers because a large number of replications and herbicide concentrations could be rested side-by-side without an excessive space requirement. In the first assay, nitrite leakage was measured from discs incubated in nitrate solution. Nitrite was sequestered in cells as long as the membranes remained intact. A loss in membrane integrity, caused by membrane disrupter herbicides (acifluorfen, oxyfluorfen, paraquat, oxadiazon, sulfentrazone), resulted in the leakage of nitrite into the incubation solutions. Membrane disruption was also measured directly with N-methyl benzothionoline hydrazone hydrochloride which forms a stable chromatophore with saturated and unsaturated aldehydes, ketones, keto acids, and many other related compounds. Leakage of ammonia and malonyl dialdehyde were also measured. These assays may have advantages in industrial or academic laboratories where comparison of the activities of herbicides under several experimental conditions is necessary.


From Toxline at Toxnet

Journal of Agricultural and Food Chemistry, Vol. 39, No. 8, pages 1509-1514, 6 references, 1991

Metabolism and Distribution of the Experimental Triazolone Herbicide F6285 (1-(2,4-dichloro-5-(N-(methylsulfonyl)amino)phenyl)-1, 4-dihydro-3-methyl-4-(difluoromethyl)-5H-triazol-5-one) in the Rat, Goat, and Hen

Leung LY, Lyga JW, Robinson RA

A series of investigations was conducted in Sprague-Dawley-rats, lactating dairy goats, and white-leghorn-laying-hens to gain an understanding of the comparative metabolism of F6285 (122836355) in animals. Oral doses of carbon-14 radiolabeled F6285 were administered to rats at 10mg/kg; to lactating dairy goats at 2mg/kg, 300 parts per million (ppm) in feed daily for 5 days; and to hens at 3mg/kg, 45ppm in diet daily for 7 days. These doses were quantitatively excreted in the urine, feces or hen excreta. In all the species examined, unchanged F6285 and two nonconjugated metabolites were noted. These metabolites were isolated and characterized by mass spectrophotometry or nuclear magnetic resonance as the 3-hydroxymethyl derivative of F6285 and the corresponding 3-carboxylic acid. The latter decomposed at high temperatures or acid pH to give the corresponding 3-demethyl compound. In the rat, a minor metabolite, tentatively characterized as the 2,3-dihydro-3-hydroxymethyl derivative of F6285 was also detected. A minimal residence was observed in edible animal tissue, milk and eggs.


 

 

 
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