CAS No. 1582-09-8
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ACTIVITY: Herbicide (dinitroaniline)

CAS Name: 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzenamine


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Mutat Res. 2004 Jan 10;557(1):53-62.

Evaluation of the genotoxicity of four herbicides in the wing spot test of Drosophila melanogaster using two different strains.

Kaya B, Marcos R, Yanikoglu A, Creus A.

Department of Biology, Faculty of Arts and Sciences, Akdeniz University, Antalya, Turkey.

In the present study, the herbicides bentazone, molinate, thiobencarb and trifluralin were evaluated for mutagenic and recombinagenic effects using the wing spot test of Drosophila melanogaster (somatic mutation and recombination test, SMART). Both standard (ST) and high-bioactivation (HB) fly crosses were used, the latter cross is characterised by a high sensitivity to promutagens and procarcinogens. Three-day-old larvae, transheterozygous for the multiple wing hairs (mwh, 3-0.3) and flare-3 (flr(3), 3-38.8) genes, were chronically fed with six different concentrations of each herbicide. Feeding ended with pupation of the surviving larvae and the genetic changes induced in somatic cells of the wing's imaginal discs lead to the formation of mutant clones on the wing blade. Point mutation, chromosome breakage and mitotic recombination produce single spots; while twin spots are produced only by mitotic recombination. Bentazone, usually considered as a non-mutagen, gave positive results in the wing spot test with the high-bioactivation cross. Molinate, about which information on mutagenic effects is inconclusive, gave positive responses in both the standard and the high-bioactivation crosses, while the other thiocarbamate, thiobencarb, gave positive results only in the standard cross and at the highest concentration tested (10 mM). Finally, trifluralin, one of the most widely studied herbicides for genotoxic effects, gave positive results in the wing spot test with both crosses. Apart from the interest of the results found in the genotoxic evaluation of the four selected herbicides, our results also contribute to extend the existing database on the Drosophila wing spot test, and corroborate the utility of the use of high-bioactivation strains for the genotoxic evaluation of xenobiotics.

PMID: 14706518 [PubMed - indexed for MEDLINE]

On November 24,2004, US EPA released these documents in a Proposed pesticide tolerance for residues of trifluralin in mint oil at 2.0 ppm.

August 30, 2004 - Trifluralin Risk Assessment Overview (10 pages)
May 7, 2004 - Trifluralin: Human Health Risk Assessment (55 pages)
October 2, 2003 - Toxicology Disciplinary Chapter for the Tolerance Reassessment Eligibility Decision Document Trifluralin (PC Code: 036101) (66 pages)
August 31, 2004 - Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Trifluralin  (3 pages)
Sept 21, 2004 - Clarification of the Trifluralin Drinking Water Assessment for the HED Tolerance Reassessment and Characterization on Relative Differences for USGS NAWQA Ground Water Monitoring Data and Its Comparison to SCI-GROW Model Predictions as presented in the NRDC objection (Imidacloprid FR) and the trifluralin TRED (D308490)  (2 pages)
May 12, 2004 - Review of "Dissipation of Transferable Residues of Benefin and Trifluralin on Turf Treated with a Formulation of the Pesticides"  (15 pages)
May 2, 2003 - Report of the Hazard Identification Assessment Review Committee - Trifluralin (P.C. Code 036101) - (32 pages)
May 5, 2004 - Residential Exposure Assessment and Recommendations for the Tolerance Reassessment Evaluation Decision (TRED) Document for Trifluralin (50 pages)
March 8, 2004 - Trifluralin. Anticipated Residues, Acute, Probabilistic, Chronic and Cancer Dietary Exposure Assessments for the Reregistration Eligibility Decision (68 pages)
March 9, 2004 - Trifluralin: Health Effects Division (HED) Metabolism Assessment Review Committee (MARC) Decision Document. Meeting Date: 4 February 2004. PC Code: 036101 (4 pages)
March 4, 2004 - Trifluralin: Residue Chemistry Chapter for the Tolerance Reassessment Evaluation Decision (TRED) Document (75 pages)
Dec 3, 2003 - Trifluralin - Drinking Water Assessment for Tolerance Reassessment Eligibility Decision (PC Code: 036101; DP Barcode: D296624 (109 pages)
March 9, 2004 - Review of Trifluralin Incident Reports DP Barcode D300064, Chemical# 036101 (11 pages)

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Journal of Fish Diseases 1979, 2, 35-42

Vertebral dysplasia in young fish exposed to the herbicide trifluralin


Gulf Breeze Environmental Research Laboratory, Gulf Breeze, Florida^ USA and ^Department of Biology, University of Southern Mississippi, USA

Sheepshead minnows, Cyprinodon variegatus Laeepede, exposed to 5 5 to 31 /xg/1 of the herbicide trifluralin, throughout their first 28 days of life, developed a heretofore undescribed vertebral dysplasia. This dysplasia consisted of semisymmetrical hypertrophy of vertebrae (three to 20 times normal), characterized by foci of osteoblast and fibroblasts actively laying down bone and bone precursors. Effects of the abnormal vertebral development were dorsal vertebral growth into the neural canal, ventral compression of renal ducts, and longitudinal fusion of vertebrae. Fish, exposed for 51 days to 16-6 /ng/1 trifluralin and thereafter depurated for 41 days, showed no increase in vertebral dysplasia during depuration; however, residual spinal column damage was evident. Serum calcium concentrations were elevated in adult fish exposed for 4 days to 16-6 /xg/1 trifluralin. Fluorosis or mimicry of hypervitaminosis A are considered possible mechanisms for the osseous effect, but are not considered to be the only possible causes. The highly predictable nature of this disorder in experimental exposures strengthens the probability that young flsh may serve as experimental models for determining effects of chemicals on early vertebrate ontogeny, particularly in regard to skeletal development.

Excerpts: Trifluralin (2, 6 dinitro-N, N-dipropyl-4-(trifluoromethyl) Benzamine) is a fluorine containing, pre-emergent herbicide widely used in the United States (Wiswesser 1976). Continuous laboratory exposure of early life stages of the sheepshead minnow Cyprinodon variegatus Laeepede to relatively low concentrations of trifluralin results in marked vertebral dysplasia...


Science of The Total Environment
2005 - Article in Press, Corrected Proof - Note to users This Document

Pesticide exposure of non-occupationally exposed subjects compared to some occupational exposure: A French pilot study

G. Bouvier (a, b), O. Blanchard (b), I. Momas (a) and N. Seta (a)

(a) Environment and Public Health Laboratory, Faculty of Pharmaceutical and Biological Sciences, René Descartes University- Paris 5, 4, avenue de l'Observatoire, 75270 Paris Cedex 06, France
(b) Health Risks Evaluation Unit, INERIS, Verneuil en Halatte, France

Received 7 March 2005;  revised 5 August 2005;  accepted 12 August 2005.  Available online 21 September 2005.

Data about non-dietary exposure to different chemical classes of pesticides are scarce, especially in France. Our objective was to assess residential pesticide exposure of non-occupationally exposed adults, and to compare it with occupational exposure of subjects working indoors. Twenty unexposed persons, five gardeners, seven florists and nine veterinary workers living in Paris area were recruited. Nineteen residences, two greenhouses, three florist shops and three veterinary departments were then sampled. Thirty-eight insecticides, herbicides and fungicides were measured in indoor air with an air sampler for 24 h, and on hands by wiping them with isopropanol-wetted swabs. After extraction, samples were analysed by gas and high-performance liquid chromatography. Seventeen different pesticides were detected at least once in indoor air and twenty-one on the hands. An average of 4.2 ± 1.7 different pesticides was detected per indoor air sample. The organochlorines lindane, a-endosulfan and ?-HCH were the most frequently detected compounds, in 97%, 69% and 38% of the samples, respectively. The organophosphates dichlorvos and fenthion, the carbamate propoxur and the herbicides atrazine and alachlor were detected in more than 20% of the air samples. Indoor air concentrations were often low, but could reach 200–300 ng/m3 in residences for atrazine and propoxur. Propoxur levels significantly differed between the air of veterinary places and other places (Kruskal–Wallis test, p < 0.05) and dieldrin levels between residences and workplaces (p < 0.05). There was a greater number of pesticides on hands than in air, with an average of 6.3 ± 3.3 different pesticides detected per sample, the most frequently detected being malathion, lindane and trifluralin, in more than 60% of the subjects. Maximal levels (up to 1000–3000 ng/hands) were observed either in the general population or in workers, depending on the pesticide. However, no significant difference was observed between workers and general population handwipe pesticide levels. As expected, gardeners were exposed to pesticides sprayed in greenhouses. Florists and veterinary workers, whose pesticide exposure had not been described until now, were also indirectly exposed to pesticides used for former pest control operations. Overall, general population was exposed to more various pesticides and at levels sometimes higher than in occupational places. The most frequent pesticides in residences were not the same as in US studies but levels were similar. These preliminary results need to be confirmed in a greater number of residences from different parts of the country, in order to better assess pesticide exposure of the general population and its influencing factors.


Environ Sci Technol. 2005 May 1;39(9):2952-9.

Gas-phase concentrations of current-use pesticides in Iowa.

Peck AM, Hornbuckle KC.

Department of Civil and Environmental Engineering, University of Iowa, Iowa City, Iowa 52242, USA.

Local and regional atmospheric transport of current-use pesticides is an important source of these compounds to nontarget plants and ecosystems. Current-use pesticides were measured at urban, rural, and suburban sites in eastern Iowa during 2000-2002. The most detected compounds were hexachlorobenzene and trifluralin, which were found in 89% and 78% of the samples, respectively. As expected, many pesticides showed a strong seasonal trend with the most detections and highest concentrations occurring during the spring and early summer. The average detected concentrations of five heavily used herbicides were 0.52 ng/ m3 for trifluralin, 4.6 ng/m3 for acetochlor, 2.3 ng/m3 for metolachlor, 1.1 ng/m3 for alachlor, 1.7 ng/m3 for pendimethalin, and 1.2 ng/m3 for atrazine. The most frequently detected insecticides were phorate and chlorpyrifos, which were found in 20% and 19% of the samples, respectively. The average phorate and chlorpyrifos concentrations were 25 ng/m3 and 1.0 ng/m3, respectively. The maximum phorate concentration, the highest measured for all pesticides, was 91.2 ng/m3. The most frequently detected current-use fungicides were chloroneb and etridiazole, which were found in 14% and 10% of the samples, respectively.

PMID: 15926538 [PubMed - in process]


Toxicol In Vitro. 2005 Aug;19(5):595-601.
Effect of fatty acids on herbicide transport across Caco-2 cell monolayers.

Brand RM, Cetin Y, Mueller C, Cuppett SL.

Division of Emergency Medicine of Evanston, Northwestern Healthcare and Department of Medicine, Fienberg School of Medicine at Northwestern University, Evanston, IL 60201, USA; Department of Food Science and Technology, University of Nebraska, Lincoln, NE 68583-0919, USA.

Oral ingestion of pesticides can be a major exposure route. These compounds are frequently consumed in the presence of triacylglycerides, which are then hydrolyzed to free fatty acids. The purpose of this work was to examine the effect of two common fatty acids, palmitic (PA) and oleic (OA) acids, and the biological emulsifier sodium taurocholate (TC) on the absorption of three herbicides (trifluralin, alachlor and atrazine) by Caco-2 cell monolayers. Trifluralin's absorption was enhanced (p<0.05) in the presence of OA whereas the greatest absorption of atrazine and alachlor occurred with PA and the control media, respectively. Trifluralin had significantly lower absorption through the monolayer than either alachlor or atrazine (p<0.001). A mass balance study demonstrated that trifluralin accumulated within the cell monolayer (13.85% of the donor after 3h of exposure), but alachlor and atrazine (1.27% and 0.85%, respectively) did not. This response was linear with time (21.89% trifluralin after 6h of exposure), and demonstrated the potential for continued release of trifluralin after source removal. These experiments demonstrated that fatty acids and an emuslifier can influence absorption of herbicides across small intestinal epithelium.

PMID: 15896553 [PubMed - as supplied by publisher]


J Agric Food Chem. 2005 May 4;53(9):3461-7.
Transgenic rice containing human CYP2B6 detoxifies various classes of herbicides.

Hirose S, Kawahigashi H, Ozawa K, Shiota N, Inui H, Ohkawa H, Ohkawa Y.

Plant Biotechnology Department, National Institute of Agrobiological Sciences, 2-1-2, Kannondai, Tsukuba, Ibaraki 305-8602, Japan. junmai@affrc.go.jp

The human gene for CYP2B6, a cytochrome P450 monooxygenase that inactivates xenobiotic chemicals, was introduced into Oryza sativa cv. Nipponbare by Agrobacterium-mediated transformation. At germination, R(1) seeds of transgenic rice plants expressing CYP2B6 (CYP2B6 rice) showed a high tolerance to 5 microM metolachlor, a preemergence herbicide that is degraded by CYP2B6. Thin-layer chromatography after culture with (14)C-labeled metolachlor revealed that the amounts of residual metolachlor decreased in plant tissues and the medium of CYP2B6 rice faster than those of untransformed Nipponbare. CYP2B6 rice plants were able to grow in the presence of 13 out of 17 herbicides: five chloroacetamides and mefenacet, pyributicarb, amiprofos-methyl, trifluralin, pendimethalin, norflurazon, and chlorotoluron. These herbicides differ in their modes of action and chemical structures. Transgenic rice expressing a xenobiotic-degrading human CYP2B6, which has broad substrate specificity, should be good not only for developing herbicide tolerant rice but also for reducing the environmental impact of agrochemicals.

PMID: 15853388 [PubMed - in process]


Environ Toxicol Chem. 2005 Jan;24(1):31-9.

Desorption kinetics of fluoranthene and trifluralin from Lake Huron and Lake Erie, USA, sediments.

Greenberg MS, Burton GA Jr, Landrum PF, Leppanen MT, Kukkonen JV.

Institute for Environmental Quality, Wright State University, Dayton, Ohio 45435, USA. greenberg.marc@epa.gov

Desorption kinetics were determined for fluoranthene (FLU) and trifluralin (TF) spiked onto Lake Erie and Lake Huron, USA, sediments at three concentrations (10, 40, 100 mg/kg dry wt). Following four months of equilibration, desorption was measured by extraction with Tenax and the data were fit to a first-order three-compartment kinetic model. The rate constants of the rapidly (k(rap)), slowly (k(slow)), and very slowly (k(vs)) desorbing fractions were on the order of 10(-1)/h, 10(-2-3)/h, and 10(-4)/h, respectively. The t99.9 (time required for 99.9% of the FLU and TF to desorb from each pool value) for each compartment indicated that FLU and TF desorption from rapid, slow, and very slow compartments were on the order of hours, days, and years, respectively. Higher rates of desorption were observed for FLU and TF from the Lake Huron sediments and this was not apparently related to the total organic carbon (TOC), particle size distribution, or polarity (carbon-to-nitrogen ratio) of the sediments. In general, the total fraction of the initial contaminant amounts that desorbed over the time course was directly related to concentration, which we hypothesized was due to the combined effects of saturation of high-energy (slow and very slow) binding sites in the organic carbon matrix and hysteresis. In extrapolations to field conditions, FLU and TF were predicted to persist in the sediments for years due to the very slow desorption of an estimated 31 to 53% of the bulk concentrations. Based on the rapidly desorbing fractions, the bioavailable amounts of the contaminants were predicted to be between 31 to 55% of bulk sediment concentrations.

PMID: 15683165 [PubMed - indexed for MEDLINE]


Environ Pollut. 2005 Jan;133(1):25-34.
Formation of non-extractable pesticide residues: observations on compound differences, measurement and regulatory issues.

Mordaunt CJ, Gevao B, Jones KC, Semple KT.

Department of Environmental Science, Institute of Environmental and Natural Sciences, Lancaster University, Lancaster LA1 4YQ, UK.

Six major use pesticides (Atrazine, Dicamba, Isoproturon, Lindane, Paraquat and Trifluralin) with differing physico-chemical properties were evaluated for the significance of 'bound' or non extractable residue formation. Investigations were carried out in purpose-built microcosms where mineralization, volatilisation, 'soil water' extractable and organic solvent extractable residues could be quantified. Extractable residues were defined as those accessible by sequential extraction where the solvent used became increasingly non-polar. Dichloromethane was the 'harshest' solvent used at the end of the sequential extraction procedure. (14)C-labelled volatilised and (14)CO(2) fractions were trapped on exit from the microcosm. The pesticides were categorised into 3 classes based on their behaviour. (i) Type A (Atrazine, Lindane and Trifluralin) in which ring degradation was limited as was the formation of non-extractable residues; the remainder of the (14)C-activity was found in the extractable fraction. (ii) Type B (Dicamba and Isoproturon) in which approximately 25% of the (14)C-activity was mineralised and a large portion was found in the non-extractable fraction after 91 days. Finally, Type C (Paraquat) in which almost all of the (14)C-activity was quickly incorporated into the non-extractable fraction. The implications of the data are discussed, with respect to the variability and significance of regulatory aspects of non-extractable residues.

PMID: 15327853 [PubMed - in process]


Environ Sci Technol. 2004 Dec 15;38(24):6645-55.

Using 19F NMR spectroscopy to determine trifluralin binding to soil.

Strynar M, Dec J, Benesi A, Jones AD, Fry RA, Bollag JM.

National Exposure Research Laboratory, U.S. EPA, Research Triangle Park, North Carolina 27711, USA.

Trifluralin is a widely used herbicide for the control of broad leaf weeds in a variety of crops. Its binding to soil may result in significant losses in herbicidal activity and a delayed pollution problem. To investigate the nature of soil-bound trifluralin residues, 14C-labeled herbicide was incubated for 7 weeks with four soils under anoxic conditions. As determined by radiocounting, trifluralin binding ranged between 10 and 53% of the initial 14C depending on the soil tested. 19F NMR analyses of the methanol extracts and different fractions of the extracted soil suggested that bound residue formation largely involved reduced metabolites of the herbicide. A 2,6-diamino product of trifluralin reduction with zero-valent iron (Fe-TR), and the standard of a 1,2-diaminotrifluralin derivative (TR6) formed covalent bonds with fulvic acid (FA), as indicated by the 19F NMR spectra taken periodically over a 3-week contact time. At short contact times, TR6 and Fe-TR formed weak physical bonds with FA, as the respective spin-lattice relaxation times (T1) decreased from the range 1300-1831 ms for TR6 or Fe-TR analyzed in the absence of FA to the range 150-410 ms for TR6/FA or Fe-TR/FA mixtures. In general, the results indicated that trifluralin immobilization involved a variety of mechanisms (covalent binding, adsorption, sequestration), and with time it became increasingly stable.

PMID: 15669323 [PubMed - indexed for MEDLINE]


J Environ Qual. 2004 Sep-Oct;33(5):1616-28.
Environmental concentrations of agricultural herbicides in Saskatchewan, Canada: bromoxynil, dicamba, diclofop, MCPA, and trifluralin.

Waite DT, Cessna AJ, Grover R, Kerr LA, Snihura AD.

Environment Canada, 300-2365 Albert Street, Regina, SK, Canada S4P 4K1. Don.Waite@ec.gc.ca.

Herbicides are the most commonly used group of agricultural pesticides on the Canadian Prairies and, in 1990, more than 20000 Mg of herbicides were applied in the provinces of Alberta, Saskatchewan, and Manitoba. The present paper reports on environmental concentrations of five herbicides currently used in the prairie region. The herbicides bromoxynil [3,5-dibromo-4-hydroxy-benzonitrile], dicamba [3,6-dichloro-o-anisic acid], diclofop [(RS)-2-[4-(2,4-dichlorophenoxy)-phenoxy]propanoic acid], MCPA [(4-chloro-2-methylphenoxy)acetic acid], and trifluralin [alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-isopropyl-p-toluidine] were measured in the atmosphere, bulk atmospheric deposits, surface film, and dugout (pond) water at two sites near Regina, Saskatchewan, during 1989 and 1990. All five herbicides were detected in air and surface film and all but trifluralin were detected in the bulk atmospheric deposits and dugout water. Trifluralin was most frequently detected in air (79% of samples) whereas bromoxynil was present in maximum concentration (4.2 ng m(-3)). MCPA was present in maximum levels in bulk atmospheric (wet plus dry) deposits (2350 ng m(-2) d(-1)), surface film (390 ng m(-2)), and dugout water (330 ng L(-1)), whereas dicamba was most frequently detected in surface film (47%) and dugout water (97%). The highest quantities of the herbicides tended to be present during or immediately after the time of regional application.

PMID: 15356221 [PubMed - in process]


Pest Manag Sci. 2004 May;60(5):474-8.

Genes similar to naphthalene dioxygenase genes in trifluralin-degrading bacteria.

Bellinaso Mde L, Henriques JA, Gaylarde CC, Greer CW.

Department of Biology and Chemistry, UNIJUI, RS, Brazil.

Trifluralin (alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine) is a dinitroaniline compound which was first produced in the 1960s and has been used extensively as an agricultural herbicide. There are a few publications on the biodegradation of this xenobiotic compound, but to our knowledge nothing has been documented on the genetic aspects of its catabolism. In this article, we report the analysis of DNA isolated from bacteria previously shown to degrade trifluralin, using as probes the catabolic genes ndoB, todC, xyIX, catA and xyIE which encode the enzymes naphthalene 1,2-dioxygenase, toluene dioxygenase, toluate 1,2-dioxygenase, catechol 1,2-dioxygenase and catechol 2,3-dioxygenase respectively. Using PCR and hybridization analysis, the strong hybridization of the ndoB gene with DNA extracted from four trifluralin-degrading isolates was demonstrated, although none of them was able to degrade naphthalene, as indicated by the 'clear zone' test. The results indicated the presence in these bacteria of a dioxygenase gene, whose product could act on trifluralin as its principal substrate, or fortuitously, by cometabolism. This is the first publication on genes in trifluralin-degrading bacteria.

PMID: 15154514 [PubMed - in process]


Bull Environ Contam Toxicol. 2004 May;72(5):962-9.

Trifluralin residues in runoff and infiltration water from tomato production.

Antonious GF.

Kentucky State University, Land Grant Program, Department of Plant and Soil Science, 218 Atwood Research Facility, Frankfort, KY 40601, USA.

No Abstract Available

PMID: 15266692 [PubMed - indexed for MEDLINE]


Arch Environ Contam Toxicol. 2003 Jul;45(1):30-6.
Trace organic contaminants, including toxaphene and trifluralin, in cotton field soils from Georgia and South Carolina, USA.

Kannan K, Battula S, Loganathan BG, Hong CS, Lam WH, Villeneuve DL, Sajwan K, Giesy JP, Aldous KM.

Wadsworth Center, New York State Department of Health, Albany, New York 12201-0509, USA. kkannan@wadsworth.org

Residues of organic contaminants--including toxaphene, DDT, trifluralin, hexachlorocyclohexanes, polychlorinated biphenyls, polycyclic aromatic hydrocarbons (PAHs) and nonylphenol--were measured in 32 cotton field soils collected from South Carolina and Georgia in 1999. Toxaphene, trifluralin, DDT and PAHs were the major contaminants found in these soils. The maximum concentration of toxaphene measured was 2,500 ng/g dry weight. Trifluralin was detected in all the soils at concentrations ranging from 1 to 548 ng/g dry weight. Pesticide residues were not proportional to soil organic carbon content, indicating that their concentrations were a reflection of application history and dissipation rates rather than air-soil equilibrium. Soil extracts were also subjected to in vitro bioassays to assess dioxinlike, estrogenic, and androgenic/glucocorticoid potencies. Relatively more polar fractions of the soils elicited estrogenic and androgenic/glucocorticoid activities, but the magnitude of response was much less than those found in coastal marine sediments from industrialized locations.

PMID: 12948170 [PubMed - indexed for MEDLINE]


Chemosphere 2003 Mar;50(8):1025-34

Ozone treatment of soil contaminated with aniline and trifluralin.

Pierpoint AC, Hapeman CJ, Torrents A.

Environmental Engineering Program, Department of Civil and Environmental Engineering, University of Maryland, 1173 Glenn L. Martin Hall, 20742-3021, College Park, MD, USA

Column studies were conducted to determine the ability of ozone to degrade aniline and trifluralin in soil. Ozone rapidly degraded aniline from soil under moist soil conditions, 5% (wt). Removal of 77-98% of [UL-14C]-aniline was observed from soil columns (15 ml, i.d.=2.5 cm), exposed to 0.6% O(3) (wt) at 200 ml/min after 4 min. Initial ozonation products included nitrosobenzene and nitrobenzene, while further oxidation led to CO(2). Ring-labeled-[UL-14C]-trifluralin removal rates were slower, requiring 30 min to achieve removals of 70-97%. Oxidation and cleavage of the N-propyl groups of trifluralin was observed, affording 2,6-dinitro-4-(trifluoromethyl)-aniline, 2,6-dinitro-N-propyl-4-(trifluoromethyl)-benzamine, and 2,6-dinitro-N-propyl-N-acetonyl-4-(trifluoromethyl)-benzamine. Base solutions revealed that trifluralin was similarly oxidized to CO(2), where 72-83% of the activity recovered comprised 14CO(2). Use of ozone-rich water improved contaminant removal in trifluralin-amended soil columns, but did not improve removal in aniline, pentachloroaniline, hexachlorobenzene amended soil columns, suggesting that ozonated water may improve contaminant removal for reactive contaminants of low solubility.

PMID: 12531708 [PubMed - in process]


Water Res. 2003 Oct;37(17):4191-201.
Abiotic reduction of dinitroaniline herbicides.

Wang S, Arnold WA.

Department of Civil Engineering, University of Minnesota, 500 Pillsbury Dr. SE, Minneapolis, MN 55455, USA.

The importance of abiotic reductive transformations as a sink for four dinitroaniline herbicides (trifluralin, pendimethalin, nitralin, and isopropalin) has been evaluated. Using reductants representative of abiotic reductants found in natural systems, the results of this study indicate that nitro groups present on the dinitroaniline herbicides can be reduced by surface-bound Fe(II) species in goethite suspensions or by hydroquinone moieties such as (mercapto)juglone in a hydrogen sulfide solution. Aqueous iron species are also effective at pH values above 7.0. The reaction in aqueous Fe(II) and in Fe(II)/goethite systems is strongly pH dependent, with rates increasing with increasing pH. Montmorillonite clay, however, is not effective in mediating the reduction of dinitroaniline herbicides in the presence of Fe(II). Because the selected dinitroaniline herbicides have a mixture of electron withdrawing and electron donating groups, linear free energy relationships were developed for the H(2)S/(mercapto)juglone and Fe(II)/goethite systems. Anilines resulting from reduction of the nitro group as well as cyclization products (benzimidazoles) were observed in the degradation of trifluralin. Only one aniline product was observed for pendimethalin.

PMID: 12946901 [PubMed - indexed for MEDLINE]


J Environ Qual 2002 Sep-Oct;31(5):1636-48

Pesticides in surface water, sediment, and rainfall of the northeastern Pantanal basin, Brazil.

Laabs V, Amelung W, Pinto AA, Wantzen M, da Silva CJ, Zech W.

Institute of Soil Science and Soil Geography, University of Bayreuth, D-95440 Bayreuth, Germany. volker.laabs@covance.com

Within the last 25 years an intensive agriculture has developed in the highland regions of Mato Grosso state (Brazil), which involves frequent pesticide use in highly mechanized cash-crop cultures. To provide information on pesticide distribution and dynamics in the northeastern Pantanal basin (located in southern Mato Grosso), we monitored 29 pesticides and 3 metabolites in surface water, sediment, and rainwater of the study area during the main application season. In environmental samples, 19 pesticides and 3 metabolites were detected in measurable quantities, resulting in at least one pesticide detection in 68% of surface water samples (n = 139), 62% of sediment samples (n = 26), and 87% of rainwater samples (n = 91). Surface water samples were most frequently contaminated by endosulfan compounds (alpha-, beta-, -sulfate), ametryn, metolachlor, and metribuzin, although in low (< 0.1 microgram L-1) concentrations. Sediment samples exhibited concentrations up to 4.5 micrograms kg-1 of p,p'-DDT, p,p'-DDE, endosulfan-sulfate, beta-endosulfan, and ametryn. In contrast, rainwater was polluted with substantial amounts of endosulfan, alachlor, metolachlor, trifluralin, monocrotofos, and profenofos (maximum concentrations = 0.3 to 2.3 micrograms L-1) in the highlands. Lowland rainwater samples taken 75 km from the next application area contained 5- to 10-fold lower mean pesticide concentration than in the highlands. Cumulative deposition rates of the pesticide sum within the study period ranged from 423 micrograms m-2 in the highlands to 14 micrograms m-2 in the lowlands. The atmospheric input of pesticides to ecosystems seemed to be of higher relevance in the tropical study area than known from temperate regions.

PMID: 12371181 [PubMed - indexed for MEDLINE]


Chemosphere 2002 Jul;48(3):335-41

Uptake of trifluralin and lindane from water by ryegrass.

Li H, Sheng G, Sheng W, Xu O.


Understanding of the plant uptake of organic chemicals is essential to assessing contaminant mobility in the ecosystem, exposure to humans, and phytoremediation technologies. In this study, we measured the uptake of trifluralin and lindane from water by ryegrass as a function of uptake time for periods of 96 and 120 h, respectively. Trifluralin concentration in ryegrass increased sharply at the early stage of uptake and reached the maximum at 10 h, and then decreased with uptake time. 14C-labelled trifluralin uptake displayed a similar trend but a higher 14C-concentration than that of extracted parent compound, indicating metabolism and formation of bound residues following trifluralin uptake. Lindane concentration in ryegrass slowly increased with uptake time and approached a plateau, indicating minimal metabolism and formation of bound residues. The difference in the uptake characteristics of these two chemicals may be related to the differences in their lipophilicity, and chemical and biological reactivities. A two-compartment model accounting for the contributions of transpiration, metabolism and formation of bound residues to overall uptake was developed to assess the uptake kinetics. The model adequately described the uptake of trifluralin and lindane into ryegrass by providing the first-order rate constants of uptake, release, transpiration, and metabolism and formation of bound residues. These rate constants are used in calculating plant concentration factor (PCF). The ratios of trifluralin concentrations in ryegrass to its aqueous concentrations are between the PCF at thermodynamic equilibrium and the PCF at steady state, suggesting the utility of both PCF values.

PMID: 12146622 [PubMed - indexed for MEDLINE]


Toxicol Sci 2002 Jul;68(1):18-23

Transdermal penetration of atrazine, alachlor, and trifluralin: effect of formulation.

Brand RM, Mueller C.

Department of Biological Systems Engineering, 212 L.W. Chase Hall, University of Nebraska-Lincoln, 68583, USA. rbrand1@unl.edu

Commercial formulations of herbicides contain surfactants and other compounds to increase absorption by targeted plants. These chemicals, however, are also potential penetration enhancers for mammalian skin. The effect of formulation on dermal absorption of the herbicides atrazine, alachlor, and trifluralin and their commercial formulations Aatrex, Lasso, and Treflan was determined. In vitro absorption studies were performed by placing hairless mouse skin in a Bronough flow-through diffusion system. Donor solution was spiked with (14)C-labeled herbicide, and its penetration through the skin was monitored in 90-min fractions. Results demonstrate that dermal penetration of commercially formulated compound was significantly greater (p < 0.05) than that of the pure compound at the same concentration. The physical properties of a herbicide predicted penetration (r(2) = 0.97-0.99) for commercial formulations but were not as effective at predicting absorption for the pure compounds (r(2) = 0.51-0.71). The solvents associated with the hydrophobic herbicide Treflan altered dermal penetration of the more hydrophilic herbicides Lasso and Aatrex. Furthermore, although the most hydrophobic compound had the least penetration, it accumulated in the stratum corneum at the greatest rate. These studies can have important implications on future experiments performed to predict percutaneous penetration of herbicides.

PMID: 12075106 [PubMed - indexed for MEDLINE]


J Environ Qual 2002 Jan-Feb;31(1):256-68

Fate of pesticides in tropical soils of Brazil under field conditions.

Laabs V, Amelung W, Pinto A, Zech W.

Inst. of Soil Science and Soil Geography, University of Bayreuth, Germany. volker.laabs@uni-bayreuth.de

The potential of pesticides for nonpoint ground water pollution depends on their dissipation and leaching behavior in soils. We investigated the fate of 10 pesticides in two tropical soils of contrasting texture in the Brazilian Cerrado region near Cuiaba during an 80-d period, employing topsoil dissipation studies, soil core analyses, and lysimeter experiments. Dissipation of pesticides was rapid, with field half-lives ranging from 0.8 to 20 d in Ustox and 0.6 to 11.8 d in Psamments soils. Soil core analyses showed progressive leaching of polar pesticides in Psamments, whereas in Ustox pesticides were rapidly transported to 40 cm soil depth regardless of their sorption properties, suggesting that leaching was caused by preferential flow. In lysimeter experiments (35 cm soil depth), cumulative leaching was generally low, with < or = 0.02% and < or = 0.19% of the applied amounts leached in Ustox and Psamments, respectively. In both soils, all pesticides but the pyrethroids were detected in percolate at 35 cm soil depth within the first 6 d after application. Cumulative efflux and mean concentrations of pesticides in percolate were dosely correlated with their Groundwater Ubiquity Score (GUS). The presence of alachlor (2-chloro-2', 6'-diethyl-N-methoxymethylacetanilide), atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine), metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide], simazine [2-chloro-4,6-bis(ethylamino)-1,3,5-triazine], and trifluralin (2,6-dinitro-N,N-dipropyl-4-trifluoromethylaniline) throughout the soil profile and in percolate of wick lysimeters at 95 cm soil depth indicated that a nonpoint pollution of ground water resources in tropical Brazil cannot be ruled out for these substances.

PMID: 11837430 [PubMed - indexed for MEDLINE]


Pest Manag Sci 2002 Dec;58(12):1161-74

A comparison of crop and non-crop plants as sensitive indicator species for regulatory testing.

McKelvey RA, Wright JP, Honegger JL.

DuPont Haskell Laboratory for Health and Environmental Sciences, PO Box 50, 1090 Elkton Rd, Newark, DE 19714-0050, USA. robert.a.mckelvey-1@usa.dupont.com

The effectiveness of regulatory non-target plant testing using crop species to predict the phytotoxicicity of herbicides to non-crop species was evaluated for eleven herbicides. These herbicides were representative of eight chemical classes and six modes of action. Data for non-crop plants from pre-emergence and post-emergence efficacy screening studies were compared with those for the most sensitive crop species defined by regulatory tests conducted to meet US EPA requirements. Testing under pre-emergence conditions for ten compounds indicated that for five of the compounds (K-815910, trifluralin, pyridyloxy A, pyridyloxy B and cyanazine), the most sensitive crop species was more sensitive than all the non-crop species evaluated. For metsulfuron-methyl, chlorimuron-ethyl, hexazinone and bromacil, only one of the non-crop species evaluated was more sensitive than the most sensitive crop species from regulatory tests. Data for the tenth compound, chloroacetamide, showed that four of 32 non-crop species tested in efficacy screens had at least one rate at which greater visual effects were observed than were observed for the most sensitive crop response in a regulatory test. The results of post-emergence exposure comparisons for five of the compounds (pyridyloxy A, cloransulam-methyl, chlorimuron-ethyl, cyanazine and hexazinone) indicated that the most sensitive crop species were more sensitive than all the non-crop species evaluated. Data for pyridyloxy B, metsulfuron-methyl and bromacil indicated that only one of the non-crop species evaluated was more sensitive than the most sensitive crop species. For trifluralin, three of the eight non-crop species were more sensitive than the most sensitive crop species. Data for K-815910 indicated that four of the fourteen non-crop species tested were marginally more sensitive than the most sensitive crop, but were within the same range of sensitivity. These results indicate that the current regulatory test batteries and methods using crop species effectively provide suitable sensitive indicator plants for the eleven diverse herbicides evaluated. This comparison indicates that crop species sensitivity to test substances is likely to be representative of non-crop herbaceous species response, regardless of chemical class, mode of action and magnitude or route of exposure.

PMID: 12476989 [PubMed - indexed for MEDLINE]


Environ Pollut 2002;117(3):523-30

Evidence of differences in the biotransformation of organic contaminants in three species of freshwater invertebrates.

Verrengia Guerrero NR, Taylor MG, Davies NA, Lawrence MA, Edwards PA, Simkiss K, Wider EA.

Department of Biological Chemistry, Faculty of Exact and Natural Sciences, University of Buenos Aires, Argentina. noev@qb.fcen.uba.ar

Acute static bioassays were performed using three freshwater invertebrate species (the oligochaete Lumbriculus variegatus, the fingernail clam Sphaerium corneum and the larvae Chironomus riparius) exposed separately to a variety of 14C radiolabelled contaminants. The aim of this work was to investigate if the chemicals remained as parent compounds after the treatments. Chemicals used were 2,4-dichlorophenol; 2,4,5-trichlorophenol; pentachlorophenol; pyrene; Fenpropidin, and Trifluralin. Homogenates of the whole body tissue of each organism were prepared and total radioactivity was measured. Contaminants were then extracted into organic solvents and analysed by high-pressure liquid chromatography techniques. Chromatograms showed that most of the substances extracted were present as parent compounds in S. corneum and in L. variegatus. In contrast, for C. riparius a low proportion of the chemicals was recovered as parent compounds. These results suggest that different metabolic processes could take place in the different species.

PMID: 11926182 [PubMed - indexed for MEDLINE]


Genome 2001 Dec;44(6):1114-21

Heterofertilization exhibited by trifluralin-induced bicellular pollen on diploid and tetraploid maize crosses.

Kato A.

National Institute of Agrobiological Resources, Ministry of Agriculture, Forestry and Fisheries, Ibaraki, Japan. katoa@missouri.edu

The heterofertilization rates and fertility of trifluralin-induced bicellular pollen were investigated in maize (Zea mays L.). A diploid inbred line, Oh43 (r1/r1), and a tetraploid line, Q28-1 (r1/r1/r1/r1), were pollinated with a trifluralin treated diploid stock heterozygous for R1-scm2. The gene R1-scm2 conditions purple pigmentation in both the embryo and the aleurone layer. Heterofertilized kernels were detected as discordant kernels, i.e., yellow kernel with purple embryo or purple kernel with white embryo. The diploid-diploid crosses treated with 0.2-0.3% Trefanocide solution (0.09-0.13% trifluralin) resulted in incidences of discordant kernels (3.7-4.8%) that were significantly higher than the control (2.3%). Most of the seedlings (86%) of the discordant kernels in the 0.3% treatment were triploids or triploid-class aneuploids. In tetraploid-diploid crosses, trifluralin treatments increased the number of plump kernels on the tetraploid ears. In the 0.3% treatment, 5.2% of ovaries produced plump kernels on the ears and most of the seedlings (92%) were tetraploids or tetraploid-class aneuploids, whereas in the control, only 1.5% ovaries produced plump kernels and most of the seedlings (98%) were triploids or triploid-class aneuploids. A high rate of discordance was observed among the plump kernels both in the treated plots (36.1-48.0%) and in the control (33.3%). Consequently, almost all of the plump kernels from the tetraploid-diploid crosses were considered to be the results of heterofertilization.

PMID: 11768215 [PubMed - indexed for MEDLINE]


Environ Health Perspect 2001 Oct;109(10):1071-8

Agricultural pesticide use in California: pesticide prioritization, use densities, and population distributions for a childhood cancer study.

Gunier RB, Harnly ME, Reynolds P, Hertz A, Von Behren J.

Environmental Health Investigations Branch, California Department of Health Services, 1515 Clay St., Oakland, CA 94612, USA. bgunier@dhs.ca.gov

Several studies have suggested an association between childhood cancer and pesticide exposure. California leads the nation in agricultural pesticide use. A mandatory reporting system for all agricultural pesticide use in the state provides information on the active ingredient, amount used, and location. We calculated pesticide use density to quantify agricultural pesticide use in California block groups for a childhood cancer study. Pesticides with similar toxicologic properties (probable carcinogens, possible carcinogens, genotoxic compounds, and developmental or reproductive toxicants) were grouped together for this analysis. To prioritize pesticides, we weighted pesticide use by the carcinogenic and exposure potential of each compound. The top-ranking individual pesticides were propargite, methyl bromide, and trifluralin. We used a geographic information system to calculate pesticide use density in pounds per square mile of total land area for all United States census-block groups in the state. Most block groups (77%) averaged less than 1 pound per square mile of use for 1991-1994 for pesticides classified as probable human carcinogens. However, at the high end of use density (> 90th percentile), there were 493 block groups with more than 569 pounds per square mile. Approximately 170,000 children under 15 years of age were living in these block groups in 1990. The distribution of agricultural pesticide use and number of potentially exposed children suggests that pesticide use density would be of value for a study of childhood cancer.

PMID: 11689348 [PubMed - indexed for MEDLINE]


Bull Environ Contam Toxicol 2001 Apr;66(4):514-21

No Abstract available

Influence of soil aggregate size on atrazine and trifluralin leaching.

Novak SM, Portal JM, Schiavon M.

Centre de Pedologie Biologique, CNRS FRE 2111, H. Poincare University, B.P. 5, 54501 Vandoeuvre-les-Nancy Cedex, France..

PMID: 11443316 [PubMed - indexed for MEDLINE]


Environ Toxicol 2001;16(1):9-19

Fluorescent Pseudomonas isolates from Mississippi Delta oxbow lakes: in vitro herbicide biotransformations.

Zablotowicz RM, Locke MA, Hoagland RE, Knight SS, Cash B.

U.S. Department of Agriculture-ARS, Southern Weed Science Research Unit, Stoneville, Mississippi 38776, USA. rzablotowicz@ars.usda.gov

Fluorescent pseudomonads were a major component [log (10) 4.2-6.1 colony-forming units mL-1] of the culturable heterotrophic gram-negative bacterioplankton observed in three Mississippi Delta oxbow lakes in this study. Pure cultures of fluorescent pseudomonads were isolated from three Mississippi Delta oxbow lakes (18 per lake), using selective media S-1. Classical physiological tests and Biolog GN plates were used in criteria for taxonomic identification. Most isolates were identified as biotypes of Pseudomonas fluorescens 55% (II), 7% (III), and 25% (V). About 7% of the isolates were identified as P. putida and 7% as non-fluorescent Pseudomonas-like. Cell suspensions of these isolates were tested for their ability to metabolize/co-metabolize six 14C-radiolabeled herbicides (2,4-dichlorophenoxyacetic acid (2,4-D), cyanazine, fluometuron, metolachlor, propanil, and trifluralin) that are commonly used for crop production in this geographical area. Almost all (53 of 54) isolates transformed trifluralin via aromatic nitroreduction. Most isolates (70%) dechlorinated metolachlor to polar metabolites via glutathione conjugation. About 60% of the isolates hydrolyzed the amide bond of propanil (a rice herbicide) to dichloroaniline, with the highest frequency of propanil-hydrolyzing isolates observed in the lake from the watershed with rice cultivation. All propanil-hydrolyzing isolates were identified as P. fluorescens biotype II. No metabolism of cyanazine or fluometuron was observed by any isolates tested, indicating little or no potential for N-dealkylation among this group of bacterioplankton. No mineralization of 2,4-D labeled in either the carboxyl or ring position was observed. These results indicate that reductive and hydrolytic pathways for herbicide co-metabolism (aromatic nitroreduction, aryl acylamidase, and glutathione conjugation) are common in Mississippi Delta aquatic fluorescent pseudomonads; however, the potential for certain oxidative transformations (N-dealkylation, cyano group oxidation) may be rare in this group of bacterioplankton.

PMID: 11345550 [PubMed - indexed for MEDLINE]


Environ Pollut. 2000 Mar;107(3):399-405.
Laboratory study on the interaction between herbicides and sediments in water systems.

Ying GG, Williams B.

Department of Environmental Science and Management, The University of Adelaide, Roseworthy Campus, Roseworthy, SA 5371, Australia.

Interaction between herbicides and sediments in water systems is an important process occurring in water, which influences the behaviour of the herbicides in water. This paper reports on the sorption of herbicides norflurazon, oxadiazon and trifluralin on soil and the interaction between the herbicides and sediments under stirred and non-stirred conditions. The sorption coefficients of the herbicides on soils are 3.58 and 5.41 for norflurazon, 23.43 and 28.07 for oxadiazon and 890.73 and 1217.20 for trifluralin. The sorption of the herbicides is related to the organic carbon content in the soils. This study shows a greater sorption of the herbicides on stirred sediments than on non-stirred sediments due to more significant contact under stirred conditions. The relative concentrations of the herbicides in water systems containing sediments were higher than those in pure water 6 and 13 days after treatment. When these herbicides were sorbed on sediments, their persistence in water increased. Sorption of herbicides on sediments in aquatic systems could protect them from degradation in water.

PMID: 15092986 [PubMed]


Sci Total Environ 2000 Apr 5;248(2-3):169-79

Detection of persistent organic pollutants in the Mississippi Delta using semipermeable membrane devices.

Zimmerman LR, Thurman EM, Bastian KC.

University of Kansas Center for Research, Lawrence 66045, USA. izimmer@usgs.gov

From semipermeable membrane devices (SPMDs) placed in five Mississippi Delta streams in 1996 and 1997, the persistent organic pollutants (POPs) aldrin, chlordane, DCPA, DDT, dieldrin, endrin, heptachlor, mirex, nonachlor, and toxaphene were detected. In addition, the insecticides chlorpyriphos, endosulfan, and hexachlorocyclohexanes were detected. Two low-solubility herbicides not detected commonly in surface water, pendimethalin and trifluralin, were also detected.

PMID: 10805237 [PubMed - indexed for MEDLINE]

J Environ Sci Health B 2000 Mar;35(2):121-41
Laboratory study on leachability of five herbicides in South Australian soils.

Ying GG, Williams B.

Department of Environmental Science & Management, University of Adelaide, Roseworthy, Australia.

Norflurazon, oxadiazon, oxyfluorfen, trifluralin and simazine are herbicides widely used in the vineyards of the Barossa Valley, South Australia. The leaching behaviour of norflurazon, oxadiazon, oxyfluorfen and trifluralin was investigated on four key soils in the Barossa Valley. Leaching potential on packed soil columns and actual mobility using intact soil columns were investigated. On the packed soil columns, norflurazon was the most leachable herbicide. More of the herbicides were detected in the leachates from the sandy soils (Mountadam and Nuriootpa) than from the clayey soils (Lyndoch and Tanunda). Organic matter is generally low in soils in the Barossa region. Porosity and saturated conductivity significantly affect herbicide movement and in the sandy Mountadam and Nuriootpa soils, the water flux is greater than for the higher clay content Lyndoch and Tanunda soils. Increasing the time interval between herbicide application and the incidence of "rainfall" reduced the amounts of herbicides found in the leachates. The use of intact soil columns and including simazine for comparison showed that both norflurazon and simazine were present in the leachates. Simazine was the first herbicide to appear in leachates. Sectioning of the intact soil columns after leaching clearly demonstrated that norflurazon and simazine reached the bottom of the soil columns for all soils studied. Greater amounts of norflurazon were retained in the soil columns compared with simazine. The other herbicides were mostly retained in the initial sections of the soil columns.

PMID: 10736764 [PubMed - indexed for MEDLINE]


J Environ Sci Health B 2000 Jan;35(1):51-9

Monitoring of pesticide residues in a cotton crop soil.

Luchini LC, Peres TB, de Andrea MM.

Instituto Biologico, Centro de Protecao Ambiental, Sao Paulo, Brazil.

This paper reports on the residues of methyl parathion (O,O-dimethyl O-4-nitrophenyl phosphorothioate), trifluralin (alpha, alpha, alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine), endosulfan [(1, 4, 5, 6, 7, 7-hexachloro-8, 9, 10-trinorborn-5-en-2, 3-ylenebismethylene) sulfite] and dimethoate (O, O-dimethyl S-methylcarbamoylmethyl phosphorodithioate) in a cotton crop soil. Soil samples (0-15 cm) were collected at different periods from the cotton crop farm and subjected to Soxhlet extraction. The extracted material was analysed after clean-up by a HP5890 II gas chromatograph equipped with a 63Ni electron-capture detector (ECD-63Ni) and fitted with a 25 m x 0.2 mm i.d. fused silica capillary column [Ultra-2 (5% phenylmethyl polysiloxane)]. The recoveries of the pesticide residues from the spiked control soil were determined after Soxhlet extraction and C18 cartridges clean-up by using radiotracer techniques with the corresponding 14C-pesticides. The results show that in the cotton crop soil the pesticide residues under study were present in the range of 0.1 to 0.4 mg.kg-1. Endosulfan was found to be rapidly degraded in the soil and formed a sulfate metabolite.

PMID: 10693054 [PubMed - indexed for MEDLINE]


Ecotoxicol Environ Saf 1999 Jun;43(2):213-21

Effects of trifluralin on carp: biochemical and histological evaluation.

Poleksic V, Karan V.

Faculty of Agriculture, University of Belgrade, Nemanjina 6, Beograd, YU-11080, Yugoslavia. poleksic@EUnet.yu

Acute and subacute toxicity of the herbicide trifluralin on fish was investigated in laboratory toxicity tests with carp. Median lethal concentrations were determined in acute tests. The 96-h LC50 value was 0.045 (0.036-0.051)mg/L. Fish were exposed to subacute concentrations of the herbicide (0.005, 0.01, and 0.02 mg/L trifluralin) in the 14-day toxicity tests and the effects on the relative growth rate, some biochemical parameters [alkaline phosphatase (ALP), aspartate aminotransferase (AST), alanin aminotransferase (ALT) activities in serum, gills, liver, and kidney], gills, liver, and kidney structure were studied. A decrease in relative growth rate was found. An increase of functional enzyme activities in blood serum and the organs examined, particularly in the highest concentration of trifluralin indicated changes in the vital organs, was confirmed by histological analysis. The most severe changes (although mostly reversible) were found in the gills and kidney of the fish examined. Copyright 1999 Academic Press.

PMID: 10375424 [PubMed - indexed for MEDLINE]


J Environ Sci Health B 1999 May;34(3):397-411

Herbicide residues in grapes and wine.

Ying GG, Williams B.

Department of Environmental Science and Management, University of Adelaide, Australia.

The persistence of several common herbicides from grapes to wine has been studied. Shiraz, Tarrango and Doradillo grapes were separately sprayed with either norflurazon, oxyfluorfen, oxadiazon or trifluralin-persistent herbicides commonly used for weed control in vineyards. The dissipation of the herbicides from the grapes was followed for 28 days following treatment. Results showed that norflurazon was the most persist herbicide although there were detectable residues of all the herbicides on both red and white grapes at the end of the study period. The penetration of herbicides into the flesh of the grapes was found to be significantly greater for white grapes than for red grapes. Small-lot winemaking experiments showed that norflurazon persisted at levels close to the initial concentration through vinification and into the finished wine. The other herbicides degraded, essentially via first-order kinetics, within the period of "first fermentation" and had largely disappeared after 28 days. The use of charcoal together with filter pads, or with diatomaceous earth was shown to be very effective in removing herbicide residues from the wine. A 5% charcoal filter removed more than 96% of the norflurazon persisting in the treated wine.

PMID: 10227191 [PubMed - indexed for MEDLINE]


Environ Health Perspect 1998 Aug;106(8):437-45

Mode of carcinogenic action of pesticides inducing thyroid follicular cell tumors in rodents.

Hurley PM.

Office of Prevention, Pesticides and Toxic Substances, U.S. Environmental Protection Agency, Washington, DC 20460 USA.

Of 240 pesticides screened for carcinogenicity by the U.S. Environmental Protection Agency Office of Pesticide Programs, at least 24 (10%) produce thyroid follicular cell tumors in rodents. Thirteen of the thyroid carcinogens also induce liver tumors, mainly in mice, and 9 chemicals produce tumors at other sites. Some mutagenic data are available on all 24 pesticides producing thyroid tumors. Mutagenicity does not seem to be a major determinant in thyroid carcinogenicity, except for possibly acetochlor; evidence is less convincing for ethylene thiourea and etridiazole. Studies on thyroid-pituitary functioning, including indications of thyroid cell growth and/or changes in thyroxine, triiodothyronine, or thyroid-stimulating hormone levels, are available on 19 pesticides. No such antithyroid information is available for etridiazole, N-octyl bicycloheptene dicarboximide, terbutryn, triadimefon, and trifluralin. Of the studied chemicals, only bromacil lacks antithyroid activity under study conditions. Intrathyroidal and extrathyroidal sites of action are found: amitrole, ethylene thiourea, and mancozeb are thyroid peroxidase inhibitors; and acetochlor, clofentezine, fenbuconazole, fipronil, pendimethalin, pentachloronitrobenzene, prodiamine, pyrimethanil, and thiazopyr seem to enhance the hepatic metabolism and excretion of thyroid hormone. Thus, with 12 pesticides that mode of action judgments can be made, 11 disrupt thyroid-pituitary homeostasis only; no chemical is mutagenic only; and acetochlor may have both antithyroid and some mutagenic activity. More information is needed to identify other potential antithyroid modes of thyroid carcinogenic action.

PMID: 9681970 [PubMed - indexed for MEDLINE]


Vet Hum Toxicol 1998 Feb;40(1):5-10

Effect of 2,4-dicholorophenoxyacetic acid, trifluralin and triallate herbicides on immune function.

Blakley BR, Yole MJ, Brousseau P, Boermans H, Fournier M.

Department of Veterinary Physiological Sciences, Western College of Veterinary Medicine, University of Saskatchewan, Saskatoon, Canada.

The commercial formulations of 3 commonly used herbicides (the amine salt of 2,4-dichlorophenoxyacetic acid, trifluralin and triallate) were evaluated for effects on immune function in male Fisher 344 rats. The herbicides were prepared in an olive oil vehicle and administered by oral gavage twice weekly for 28 d at the following doses: 10.0 mg 2,4-D/kg; 17.5 mg trifluralin/kg; 5.0 mg triallate/kg/treatment. Normal body weight and organ/body weight ratios indicated the rats tolerated the herbicide treatments without difficulty. Exposure to 2,4-D did not alter lymphocyte blastogenesis, 1 gm antibody production (anti-sheep red blood cell), lymphocyte cell surface marker expression or phagocytic function of peritoneal macrophages. Trifluralin acted as a weak mitogen, but impaired T-lymphocyte blastogenesis induced by phytohemagglutinin and concanavalin A. Other immunological measurements were unaffected by trifluralin exposure. Triallate exposure reduced peritoneal macrophage phagocytosis by 33%, showed weak mitogenic properties and impaired T-lymphocyte blastogenesis in the presence of phytohemagglutin. Triallate also increased the anti-sheep red blood cell response expressed/spleen by 43%, a phenomenon suggestive of a compensatory response to minimize the impact on overall immune function. The changes in lymphocyte or macrophage function due to the herbicide treatments were not associated with changes in lymphocyte cell surface antigen expression.

PMID: 9467199 [PubMed - indexed for MEDLINE]


Chemosphere 1998 Dec;37(14-15):2935-47

Comparative sensitivity of 20 bioassays for soil quality.

Bierkens J, Klein G, Corbisier P, Van Den Heuvel R, Verschaeve L, Weltens R, Schoeters G.

Flemish Institute for Technological Research-VITO, Mol, Belgium.

Increasing evidence suggests that the use of a single bioassay will never provide a full picture of the quality of the environment. Only a test battery, composed of bioassays of different animal and plant species from different trophic levels will reduce uncertainty, allowing an accurate assessment of the quality of the environment. In the present study, a test battery composed of 20 bioassays of varying biological endpoints has been compared. Apart from lethality and reproductive failure in earthworms, springtails, nematoda, algae and vascular plants, these endpoints also included bioavailibility of metals (bacteria), heat-shock induction (nematodes, algae), DNA damage (bacteria, earthworm, vascular plants), beta-galactosidase (Daphnia) and esterase activity (algae) and a range of immunological parameters (earthworm). Four chemicals (cadmium, phenol, pentachlorophenol and trifluralin)--each representing a different toxic mode of action--were applied in a dilution series (from 1 mg/kg up to 1000 mg/kg) onto OECD standard soil. The tests have been performed both on these artificially contaminated soil samples and on aqueous extracts subsequently obtained from these soils. The results show that the immunological parameters and the loss of weight in the earthworms were among the most sensitive solid-phase assays. Esterase inhibition and heat-shock induction in algae were shown to be extremely sensitive when applied to soil extracts. As previously shown at the species level, no single biological endpoint was shown to be the most sensitive for all four modes of toxic action.

PMID: 9839407 [PubMed - indexed for MEDLINE]


Nature 1998 May 21;393(6682):260-3

Herbicide resistance caused by spontaneous mutation of the cytoskeletal protein tubulin.

Anthony RG, Waldin TR, Ray JA, Bright SW, Hussey PJ.

School of Biological Sciences, Royal Holloway University of London, Surrey, UK.

The dinitroaniline herbicides (such as trifluralin and oryzalin) have been developed for the selective control of weeds in arable crops. However, prolonged use of these chemicals has resulted in the selection of resistant biotypes of goosegrass, a major weed. These herbicides bind to the plant tubulin protein but not to mammalian tubulin. Here we show that the major alpha-tubulin gene of the resistant biotype has three base changes within the coding sequence. These base changes swap cytosine and thymine, most likely as the result of the spontaneous deamination of methylated cytosine. One of these base changes causes an amino-acid change in the protein: normal threonine at position 239 is changed to isoleucine. This position is close to the site of interaction between tubulin dimers in the microtubule protofilament. We show that the mutated gene is the cause of the herbicide resistance by using it to transform maize and confer resistance to dinitroaniline herbicides. Our results provide a molecular explanation for the resistance of goosegrass to dinitroanaline herbicides, a phenomenon that has arisen, and been selected for, as a result of repeated exposure to this class of herbicide.

PMID: 9607761 [PubMed - indexed for MEDLINE]


J Toxicol Environ Health A 1998 May 8;54(1):21-36

Effects of the pesticides carbofuran, chlorpyrifos, dimethoate, lindane, triallate, trifluralin, 2,4-D, and pentachlorophenol on the metabolic endocrine and reproductive endocrine system in ewes.

Rawlings NC, Cook SJ, Waldbillig D.

Department of Veterinary Physiological Sciences, Western College of Veterinary Medicine, University of Saskatchewan, Saskatoon, Canada. rawlings@sask.usask.ca

Many pesticides are used in the agricultural environment, and some may have the potential to disrupt reproductive or endocrine function. Ewes, in separate groups of 6, received orally into their rumen either empty gelatin capsules or capsules containing chlorpyrifos (12.5 mg/kg), trifluralin (17.5 mg/kg), lindane (2.5 mg/kg), or pentachlorophenol (2 mg/kg) 2 times per week for 43 d. Dimethoate (0.2 mg/kg), carbofuran (0.30 mg/kg), 2,4-dichlorophenoxyacetic acid (10 mg/kg), or triallate (5 mg/kg) was given 3 times per week. After 36 d of treatment, blood samples were taken every 12 min for 6 h for hormone analysis. Ewes were euthanized at the end of the study for necropsy and histopathology. No overt signs of toxicity were seen, and body weight was not affected by treatment. Carbofuran caused a significant increase in serum concentrations of thyroxine compared to control ewes, but all other pesticides, except trifluralin, resulted in a marked decrease in thyroxine concentrations. Serum concentrations of cortisol were significantly increased by trifluralin and chlorpyrifos. Concentrations of insulin in serum were markedly increased in ewes given dimethoate, lindane, trifluralin, triallate, and pentachlorophenol, and concentrations of estradiol were also significantly increased in ewes given lindane and trifluralin. Mean serum concentrations of LH were markedly decreased by trifluralin, and basal LH concentrations were significantly decreased by lindane, dimethoate, and trifluralin but increased by triallate. Both pentachlorophenol and triallate caused a significant increase in severity of oviductal intraepithelial cysts in ewes. Data suggest that several currently used pesticides could influence serum concentrations of reproductive and metabolic hormones, particularly thyroxine, the major secretory product of the thyroid and a principal regulator of metabolism.

PMID: 9588346 [PubMed - indexed for MEDLINE]


Bull Environ Contam Toxicol 1998 Apr;60(4):569-76

No Abstract available

Influence of spray adjuvants on the behavior of trifluralin in the soil.

Swarcewicz MK, Mulinski Z, Zbiec I.

Department of General Chemistry, Agricultural University, Szczecin, Poland.

PMID: 9557194 [PubMed - indexed for MEDLINE]


Rev Environ Contam Toxicol 1997;153:1-64

Environmental fate of trifluralin.

Grover R, Wolt JD, Cessna AJ, Schiefer HB.

Research Station, Agriculture Canada, Regina, Saskatchewan.

Trifluralin, a preemergence, soil-applied and soil-incorporated herbicide, has been in agricultural use since 1963. The environmental chemistry and fate of dinitroaniline herbicides, including trifluralin, has been studied extensively in agricultural soils. Probst et al. (1975) and Helling (1976) have summarized pre-1975 data on the mobility, persistence, and degradation or metabolism of dinitroaniline herbicides as a group. Since then, numerous studies have been carried out on the fate of dinitroanilines, especially trifluralin, in the environment to understand further their degradation in soil, potential for mobility and persistence, and environmental concentration in water and air. The present review, while summarizing briefly earlier data, concentrates primarily on the post-1975 data on degradation, mobility, and persistence of trifluralin in soils and its potential concentrations in water and air. Trifluralin is readily degraded under sunlight in all media, with half-lives (t1/2) of minutes to several months, depending on the substrate. In addition, other dissipation processes, such as microbial and chemical, are also operative in soils, water, and sediments. Several degradation products of trifluralin have been identified and characterized, both under photolysis and following aerobic and anaerobic metabolism in soils and water-sediment systems. The differences between various degradative pathways of trifluralin appear to be more quantitative than qualitative in nature, leading eventually to the same end products that are subject to binding or mineralization with time. The general lack of accumulation of the breakdown products of trifluralin suggests that these are also subject to the same degradative mechanisms as the parent compound. Trifluralin has low water solubility and is strongly bound to soil components; mean Koc values range from 4,000 to 13,000. Once applied and incorporated into the soil, trifluralin remains relatively immobile with minimal or no potential for contamination of groundwaters under or near the treated zones. Trifluralin residues in soil surface layers are subject to loss via transport in runoff water or volatilization into the air. Seasonal losses in surface runoff are consistently less than 0.5% of the amounts applied, with concentrations in edge-of-the-field run-off water typically < 1.0 microgram L-1. Consequently, trifluralin is infrequently detected in surface waters and, if present, usually occurs below levels of quantification. Seasonal trifluralin losses into the atmosphere can be as high as 25% of that applied. Maximum trifluralin residues in the air above treated fields are in the 2-3 micrograms m-3 range following application, decreasing to < 100 ng m-3 in ambient air of intensive use areas, indicating its rapid dissipation in air. Trifluralin residues at < 100 pg m-3 in the atmosphere of remote nonuse regions have been reported, suggesting its potential for long-range transport. However, there is a general lack of understanding of the mechanisms controlling its potential for long-distance transport, especially considering its rapid photodegradation in vapor and solution states. The persistence of trifluralin in agricultural soils following incorporation is highly variable, depending on several factors such as depth of incorporation, soil moisture, soil temperature, soil air, and soil organic matter content. Estimated half-lives under a variety of agronomic conditions range from 25 to > 201 d, thus categorizing its persistence from 'moderate' to 'persistent'. The estimated half-life data for trifluralin under agronomic conditions, however, cannot be extrapolated to other potential scenarios, such as its dissipation in nontarget areas where trifluralin residues, if any, are essentially deposited on surfaces. Surface deposits on nontarget areas, unlike soil-incorporated residues, would be subject to volatilization and photolysis and thus more short lived. (ABSTRACT TRUNCATED)

Publication Types:

  • Review
  • Review, Tutorial

PMID: 9380893 [PubMed - indexed for MEDLINE]


No Abstract available

Bull Environ Contam Toxicol 1997 Nov;59(5):750-6

14C-Residues of trifluralin in soil and melon.

Tiryaki O, Maden S, Tuncbilek AS.

Ankara Nuclear Research and Training Center, Turkish Atomic Energy Authority, Saray, 06105 Ankara, Turkey.

PMID: 9323224 [PubMed - indexed for MEDLINE]


Bull Environ Contam Toxicol 1997 Jul;59(1):58-64

No Abstract available

14C-Residues of trifluralin in a soil and their uptake by carrots.

Tiryaki O, Gozek K, Khan SU.

Ankara Nuclear Research and Training Center, Turkish Atomic Energy Authority, Saray, Ankara, 06105, Turkey.

PMID: 9184041 [PubMed - indexed for MEDLINE]


Arch Toxicol 1997;71(3):193-7

In vivo genotoxicity of selected herbicides in the mouse bone-marrow micronucleus test.

Gebel T, Kevekordes S, Pav K, Edenharder R, Dunkelberg H.

Medical Institute for General Hygiene and Environmental Health, Georg-August-Universitat, Gottingen, Germany.

The herbicides alachlor, atrazine, terbuthylazine, gluphosinate-ammonium, isoproturon, pendimethaline and trifluralin were tested for genotoxicity in the mouse bone-marrow micronucleus test (MNT). Both atrazine and trifluraline caused a significant increase in the number of micronuclei at doses of 1,400 mg/kg body weight in female mice only. Alachlor, terbuthylazine, gluphosinate-ammonium, isoproturon and pendimethaline did not have any genotoxic effect in the mouse bone-marrow micronucleus test in either female or male animals.

From Toxline at Toxnet

Mutation Research, Vol. 371, Nos. 1/2, pages 15-21, 30 references, 1996

Genotoxic Evaluation of the Herbicide Trifluralin on Human Lymphocytes Exposed In Vitro

Ribas G, Surralles J, Carbonell E, Xamena N, Creus A, Marcos R

The genotoxicity of trifluralin (1582-09-8) was examined in human lymphocytes. Lymphocyte cultures were established from blood samples drawn from two healthy young male donors. These were treated with 0 to 200 micrograms per milliliter (microg/ml) trifluralin with or without metabolic activation from S9 mix for up to 72 hours (hr). Induction of sister chromatid exchanges (SCEs) was assessed after 2 or 48hr of incubation with trifluralin. Micronuclei induction was evaluated after 72hr of trifluralin treatment. Induction of chromosome aberrations was assessed after 30hr of incubation with trifluralin. Cytotoxicity was assessed by measuring changes in the proliferative rate index (PRI), determined by examination of the first three metaphases, and the cytokinesis block proliferative index (CBPI). Trifluralin treatment for 48hr in the absence of S9 mix caused a slight, but statistically significant increase in SCE frequency in lymphocytes from both donors at 50microg/ml, the highest concentration tested. Treatment with 25microg/ml trifluralin in the absence of S9 mix also caused a significant increase in SCE frequency in lymphocytes from one donor. Treatment with 200microg/ml trifluralin for 2hr in the presence of S9 mix caused a significant increase in SCE frequency in lymphocytes from both donors. These effects were accompanied by slight decreases in the PRI and CBPI. Trifluralin did not increase the frequency of chromosome aberrations or micronuclei above the background level. The authors conclude that trifluralin is able to exert weak cytotoxic and genotoxic effects in cultured human lymphocytes. The SCE assay seems to be more sensitive for detecting these types of effects than the chromosome aberration or micronucleus assays.


Bull Environ Contam Toxicol 1996 Apr;56(4):655-62

No Abstract available

Vertebral deformity susceptibilities of marine fishes exposed to herbicide.

Koyama J.

Environmental Conservation Division, National Research Institute of Fisheries Science, Yokosuka, Japan.

PMID: 8645926 [PubMed - indexed for MEDLINE]


Mutat Res 1995 Aug;344(1-2):41-54

Herbicide-induced DNA damage in human lymphocytes evaluated by the single-cell gel electrophoresis (SCGE) assay.

Ribas G, Frenzilli G, Barale R, Marcos R.

Departament de Genetica i de Microbiologia, Universitat Autonoma de Barcelona, Bellaterra, Spain.

The genotoxicity of the herbicides, alachlor, atrazine, maleic hydrazide, paraquat and trifluralin has been evaluated in the single-cell gel electrophoresis (SCGE) assay by using human peripheral blood lymphocytes. All treatments were conducted with and without the presence of an external bioactivation source (S9 mix). The results indicate that all the herbicides tested are able to give positive results by increasing the comet tail length, which would confirm both the genotoxicity of the herbicides and the sensitivity of the assay in front of these chemicals. Alachlor and atrazine give similar results in treatments with and without S9, while when the S9 mix was not used paraquat and trifluralin genotoxicity was higher. On the other hand, although maleic hydrazide genotoxicity was higher when S9 mix was used at normal pH (7.4), our data show that its genotoxicity depends largely on the pH solution, increasing as the pH decreased.

PMID: 7565891 [PubMed - indexed for MEDLINE]


Environ Mol Mutagen 1995;25(2):148-53

Mutagenicity testing of nine herbicides and pesticides currently used in agriculture.

Kale PG, Petty BT Jr, Walker S, Ford JB, Dehkordi N, Tarasia S, Tasie BO, Kale R, Sohni YR.

Department of Biology, Alabama A. & M. University, Normal 35762, USA.

Nine herbicides and pesticides were tested for their mutagenicity using the Drosophila sex-linked recessive lethal mutation assay. These are Ambush, Treflan, Blazer, Roundup, 2,4-D Amine, Crossbow, Galecron, Pramitol, and Pondmaster. All of these are in wide use at present. Unlike adult feeding and injection assays, the larvae were allowed to grow in medium with the test chemical, thereby providing long and chronic exposure to the sensitive and dividing diploid cells, i.e., mitotically active spermatogonia and sensitive spermatocytes. All chemicals induced significant numbers of mutations in at least one of the cell types tested. Some of these compounds were found to be negative in earlier studies. An explanation for the difference in results is provided. It is probable that different germ cell stages and treatment regimens are suitable for different types of chemicals. larval treatment may still be valuable and can complement adult treatment in environmental mutagen testing.

PMID: 7698107 [PubMed - indexed for MEDLINE]


Toxicol Appl Pharmacol 1994 Nov;129(1):138-45

Body size and the toxicokinetics of trifluralin in rainbow trout.

Schultz IR, Hayton WL.

Division of Pharmaceutics and Pharmaceutical Chemistry, College of Pharmacy, Ohio State University, Columbus 43210-1291.

Rainbow trout (Oncorhynchus mykiss) ranging from 0.2 to 3395 g were exposed to trifluralin (TF) in water at concentrations of 0.6-2.0 micrograms/liter. Trout of all body sizes rapidly accumulated TF from the water. The uptake clearance (P, ml hr-1g-1) of TF from the water decreased as body weight (BW, g) increased. This decrease followed the allometric equation P (ml/hr) = 182.BW0.66. Other kinetic parameters affected by body size were the steady-state volume of distribution which had a BW exponent value of 1.07 and the biological half-life which increased in larger fish. The relatively larger volume of distribution in larger fish reflected an increased capacity for TF in peripheral compartment-associated tissues. Metabolic elimination and the bioconcentration factor of TF did not change systematically with changes in body size. Variation in total body lipid content could not adequately explain the increase in peripheral storage capacity for TF; the decreased plasma protein binding that was observed in larger trout may also have been involved.

PMID: 7974487 [PubMed - indexed for MEDLINE]


J Am Acad Dermatol 1994 Dec;31(6):1057-8

No Abstract available

Allergic contact dermatitis from the herbicides trifluralin and benefin.

Pentel MT, Andreozzi RJ, Marks JG Jr.

Department of Medicine, Pennsylvania State University College of Medicine, Hershey.

PMID: 7962759 [PubMed - indexed for MEDLINE]


Teratology 1993 Feb;47(2):147-57

Additional endpoints and overview of a mouse skeletal variant assay for detecting exposure to teratogens.

Beck SL.

Department of Biological Sciences, DePaul University, Chicago, Illinois 60614.

CD-1 mice were exposed in utero to one of 14 treatment regimes, several of them being replicated, with close agreement between series. Prenatal exposure to a teratogenic dose at a sensitive time enabled detection of 10 of 14 teratogen regimes by alterations in frequency or severity of a substantial number of the 88 variants in the Skeletal Variant Assay System (SVAS) screen when examined at 60-65 days post natal (DPN). These included 2,4,5-T (245T), Trifluralin (TFL), Maneb (MNB), Decamethrin (DMT), Acetazolamide (ACZM) either at 8 days post-coitus (DPC) or days 9-11 PC, trypan blue (TB), or 5' Bromodeoxyuridine (BUDR) on either 7 DPC, 8 DPC, or 9 DPC. Most of these observations have been reported elsewhere. All of the treatment regimes mentioned above, and another group of treatments, could be detected in the exposed CD-1 cohorts when additional endpoints were employed. One such endpoint was "frequently responding variants." These were: Interfrontals (IF), Parted Frontals (PF), Preoptic Sutures (PS), Foramina Transversaria Imperfecta of the first cervical (C) vertebra (FTI C1), FTI of the axis (C2), Accessory (Acc) Transverse Foramina (TF) of C3-C6, malformations of C3-C7, Fourteen (14) Ribs, Carpal Fusions (Fus), Lumbar Fus, 27-Presacral Vertebrae (PSV), and Sacral Fus. This endpoint revealed significant differences in the initial group of 10, plus Captan (CAPT) and Phenytoin (DPH). Yet another useful endpoint reported here was the existence of high magnitude effects (i.e., dramatic alterations in frequency of occurrence of a variant). These included IF in TB and ACZM; PF in ACZM; PS in BUDR; FTI-C1 in TB and 245T; FTI-C2 in 245T; 14 Ribs in ACZM, BUDR, and TFL; Carpal Fus in TB; 27-PSV in ACZM; Fewer than (<) 30 Caudal Vertebrae (Vert) in 245T, TFL; Caudal Fus in TB, ACZM-D9. Eight treatment regimes in all could be detected by the existence of 3 or more high magnitude effects (245T, MNB, TB, ACZM8, ACZM9-11, phenytoin, and possibly BUDR on days 7 or 8, each seen in one of two series only). Clusters of related variants were affected in 9 of the 14 groups: Frontal (F) bones and C Vert in 245T; F bones in ACZM-D8; Fus in Posterior Vert Column in ACZM-D9-11; C Vert and Fus in Vert and articular skeleton in TB; Thoracic (Th) Vert and rib-cage effects in BUDR.(ABSTRACT TRUNCATED AT 400 WORDS)

PMID: 8446928 [PubMed - indexed for MEDLINE]


Environ Pollut. 1993;80(1):31-9.
Pesticides in rainfall and air in Italy.

Trevisan M, Montepiani C, Ragozza L, Bartoletti C, Ioannilli E, Del Re AA.

Istituto di Chimica Agraria ed Ambientale, Facolta di Agraria, Universita Cattolica del Sacro Cuore, Via Emilia Parmense 84, 29100 Piacenza, Italy.

The presence of pesticide residues in rain, throughfall, stemflow and in ambient air in two Italian forests affected by the forest damage phenomenon were investigated. Pesticides measured were: alachlor, atrazine, carbaryl, 2,4-d, diazinon, dichlobenil, fluazifop-butyl, MCPA, parathion, phorate and trifluralin. Rainwater samples were collected from May to October 1988 at Vallombrosa and Renon, air and atmospheric particulates were sampled during April-June 1989, only at Vallombrosa. A total of 146 samples of rainfall and 20 samples of ambient air were analysed and 49 out of 166 samples contained at least one active ingredient. Herbicides were more frequent than insecticides, and their concentrations were also higher (max 3.44 microg litre(-1)).

PMID: 15091869 [PubMed - in process]

From Dart Special at Toxnet

Chemically Induced Birth Defects 1993;2:675-721


Schardein JL

International Research and Development Corporation, Mattawan, MI.

Medical Subject Headings (MeSH):
*Abnormalities, Drug-Induced
2,4,5-Trichlorophenoxyacetic Acid/TOXICITY

Substance (CAS Registry Number): [Too many to list]

Sodium fluoroacetate (62-74-8)

[Note: the following organofluorines were included]
Diflubenzuron (35367-38-5)
Ethalfluralin (55283-68-6)
Flusilazole (85509-19-9)
Gliftor (8065-71-2) - [Synonym: 1-Chloro-3-fluoro-2-propanol mixt. with 1,3-difluoro-2-propanol]
N-Methyl-N- 1-naphthyl fluoroacetamide [Nissol] (5903-13-9)
Sarin [Synonym: (+-)-Isopropyl methylphosphonofluoridate] (107-44-8)
Sodium fluoroacetate (62-74-8)
Sodium hexafluorosilicate [also known as Sodium fluorosilicate] (16893-85-9)
Soman [Synonym: 1,2,2-Trimethylpropyl methylphosphonofluoridate] (96-64-0)
Sulfuryl fluoride (2699-79-8)
Trifluralin (1582-09-8)


Food Chem Toxicol 1992 Dec;30(12):1031-44

Toxicology and hazard potential of trifluralin.

Ebert E, Leist KH, Hack R, Ehling G.

Hoechst Aktiengesellschaft, Frankfurt am Main, Germany.

This paper reviews the results of toxicity studies conducted in laboratory animals to evaluate the safety of the herbicide trifluralin (TFL). The data show that TFL is slightly toxic following single oral exposure. Testing for embryotoxicity in rats and rabbits indicated no teratogenic potential, and many different mutagenicity tests showed that TFL was non-genotoxic. Subchronic and chronic toxicity testing in rats, mice and dogs indicated that TFL was haematotoxic (anaemia and methaemoglobinaemia), particularly in the dog, and slightly hepatotoxic. No-observed-effect levels of 4.8 and 41 mg/kg body weight/day, respectively, were determined in dogs and rats exposed chronically to TFL. Oncogenicity studies in rats and mice revealed no carcinogenic potential. Since the data for TFL indicated no mutagenic or other special toxicological risks, it is suggested that a safety factor of 100 could be used for the determination of the acceptable daily intake of TFL, which would be 0.05 mg/kg body weight/day.

Publication Types:

  • Review
  • Review, Academic

PMID: 1473797 [PubMed - indexed for MEDLINE]

From Toxline at Toxnet

Canadian water quality guidelines Vol:Appendix XI (1992) pp 24-29



Raw Water for Drinking Water Supply: Existing Canadian Drinking Water Guideline: An interim maximum acceptable concentration for trifluralin in drinking water of 45 ug.L-1 has been proposed by the Federal-Provincial Advisory Committee on Environmental and Occupational Health (Health and Welfare Canada 1989) as this herbicide is under review by this agency.
Recreational Water Quality and Aesthetics: Guideline: At present, there is no evidence to indicate that recreational water quality and aesthetics would be adversely affected by trifluralin residues when this herbicide is used according to label instructions. Therefore, a water quality guideline is not recommended at this time.
Freshwater Aquatic Life: Guideline: A guideline of 0.1 ug.L-1 trifluralin for the protection of freshwater aquatic life is recommended.
Irrigation: Guideline: There are insufficient data to propose a specific guideline or interim guideline for trifluralin in irrigation water.
Livestock Watering: Guideline: An interim water quality guideline for livestock watering is 45 ug.L-1 trifluralin.
Industrial Water Supplies: Guideline: To date, there is no indication that trifluralin poses or has the potential to pose a threat to the quality of water used for industry when used according to registered use patterns. Although of potential concern if found in water supplies, a water quality guideline for trifluralin in industrial water supplies has not been determined.


Toxicol Lett 1991 Dec;59(1-3):175-85

The effect of structurally divergent herbicides on mouse liver xenobiotic-metabolizing enzymes (P-450-dependent mono-oxygenases, epoxide hydrolases and glutathione S-transferases) and carnitine acetyltransferase.

Moody DE, Narloch BA, Shull LR, Hammock BD.

Department of Entomology, University of California, Davis.

Male mice were treated with structurally diverse herbicides to study their effect on liver xenobiotic-metabolizing enzymes. Chlorfiurecol, trifluralin, alachlor, propham, MCPP and 2,4-DP caused increases in phase I (cytochrome P-450, ethoxycoumarin O-deethylase, and/or aminopyrine N-demethylase) and phase II (microsomal epoxide hydrolase and cytosolic glutathione S-transferase) activities. MCPP and 2,4-DP also increased cytosolic epoxide hydrolase and carnitine acetyltransferase activities suggestive of peroxisome proliferation. Benthiocarb and molinate increased only some phase II enzyme activities. Dicamba, at the dose employed, caused mortality and decreases in some of the enzymes monitored. Most of the herbicides tested induced xenobiotic-metabolizing enzyme activities, the pattern of induction being dependent on herbicide structure.

PMID: 1755024 [PubMed - indexed for MEDLINE]

From Toxline at Toxnet

IARC Monogr Eval Carcinog Risks Hum 1991;53:515-34


No Authors listed.

Exposure data: Trifluralin is a selective pre-emergence herbicide used for control of annual grasses and certain broadleaf weeds. It was first registered for use in 1963. Trifluralin has been formulated as emulsifiable concentrates, granules and liquids. Exposure to trifluralin may occur during its production and application and, at much lower levels, from consumption of residues in food and water. N-Nitrosodi-n-propylamine has been detected in technical trifluralin, and levels of nitrosamines in trifluralin have been restricted in some countries.
Carcinogenicity in humans: Use of trifluralin was associated with an increase risk for non- Hodgkin's lymphoma in a study in the USA. A study of ovarian cancer in Italy did not suggest an association with exposure to trifluralin. Both results were based on small numbers of exposed subjects. A larger US study showed no association with the occurrence of leukaemia.
Carcinogenicity in experimental animals: One technical grade of trifluralin (possibly contaminated with N- nitrosodi-n-propylamine) was tested for carcinogenicity in mice and rats by administration in the diet. In female mice, it induced an increased of hepatocellular carcinomas; in the same study, an increase in the incidence of lung adenomas or carcinomas was observed in females. An increased incidence of squamous-cell carcinomas of the forestomach was noted in female mice at the lower but not at the higher dose. In rats, an increase in the combined incidence of follicular-cell adenomas and carcinomas of the thyroid was noted at the lower but not at the higher dose in females. Another preparation of trifluralin was tested for carcinogenicity in mice by administration in the diet. No increase in tumour incidence was observed. Other relevant data: In a single study, trifluralin was embryolethal and increased the incidence of skeletal variants in mice at doses that caused some maternal toxicity. No data were available on the genetic and related effects of trifluralin in humans. A commercial trifluralin formulation induced chromosomal aberrations in bone-marrow, embryonal cells and the male germ line in mice. Chromosomal aberrations were also induced in plants. Aneuploidy was induced in several lower eukaryotes. There was little evidence for the induction of gene mutation in any test system.
Evaluation: There is inadequate evidence in humans for the carcinogenicity of trifluralin. There is limited evidence in experimental animals for the carcinogenicity of technical-grade trifluralin. Overall evaluation: Trifluralin is not classifiable as to its carcinogenicity to humans (Group 3).


Food Addit Contam 1989;6 Suppl 1:S79-85

WHO drinking water quality guidelines for selected herbicides.

Kello D.

Toxicology and Food Safety, Environment and Health Service, World Health Organization, Copenhagen, Denmark.

Following the successful introduction of its Guidelines for Drinking-Water Quality in 1984, the WHO Regional Office for Europe was approached by the Government of Italy to develop, as a matter of urgency, recommendations for guidelines levels of certain herbicides found in drinking water supplies. Realizing the extent of the problem, the Regional Office for Europe organized two consultations to develop drinking water quality guidelines for the following 11 herbicides most commonly used in Italy: alachlor, metolachlor, pyridate, atrazine, molinate, simazine, bentazon, pendimethalin, trifluralin, MCPA and propanil. The presence of these and other herbicides in ground and surface water has been reported in several countries. Although the main purpose of these guidelines is to provide guidance to the Government of Italy in making risk management decisions, the information given was also intended to assist the other countries of the European Region in setting standards or in developing alternative control procedures where the implementation of standards is not feasible. The purpose of this paper is to review the process of health risk assessment used in the development of the WHO drinking water quality guidelines for selected herbicides. It will also reveal the major dilemmas and concerns expressed by the participating experts during the process of scientific deliberations, in the interests of understanding the complex issues involved in reaching the bare figures of the recommended guidelines.

PMID: 2599158 [PubMed - indexed for MEDLINE]


Mutat Res 1988 Dec;203(6):427-44

The TX; Y test for the detection of nondisjunction and chromosome breakage in Drosophila melanogaster. I. Analysis of spontaneous events and results of male exposure.

Foureman PA.

Department of Zoology, University of Wisconsin, Madison 53706.

The translocation X; Y test is a selective system in Drosophila melanogaster designed to detect and distinguish among sex chromosome nondisjunction, chromosome breakage, and X-Y interchange. In the test, only exceptional progeny survive. This enables the investigator to score thousands of progeny with relative ease. The distribution of spontaneous events occurring in individual TX; Y males are analyzed in this paper. Evidence is obtained suggesting that the clusters of two products arising from a single nondisjunction can significantly affect the distribution of recovered chromosome gain or chromosome loss events. Non-parametric statistical methods are therefore recommended for the analysis of TX; Y data. In addition, use of the TX; Y test following exposures of pre-adult males to X-rays, heat shock, cold shock, colchicine, dimethyl sulfoxide (DMSO), and trifluralin are presented. Significant increases in nondisjunction (both gain and loss) were obtained following exposures to heat shock, cold shock, DMSO and trifluralin. Significant increases in chromosome breakage and X-Y interchange were obtained after exposures to X-rays and heat shock. These results indicate that the TX; Y test is an efficient method for detecting aneuploidy. Further work is needed, however, to fully validate this system for the routine screening of aneuploidy-inducing agents.

PMID: 3143067 [PubMed - indexed for MEDLINE]


Bull Environ Contam Toxicol 1988 Oct;41(4):569-73

No Abstract available

Loss of trifluralin from clay and loam soils containing aged and freshly applied residues.

Smith AE, Aubin AJ, Derksen DA.

Agriculture Canada, Research Station, Regina, Saskatchewan.

PMID: 3224176 [PubMed - indexed for MEDLINE]

TERATOLOGY 23:33-55,1981



No abstract available


Environ Mutagen 1985;7(3):349-67

Chemical mutagenesis testing in Drosophila. IV. Results of 45 coded compounds tested for the National Toxicology Program.

Yoon JS, Mason JM, Valencia R, Woodruff RC, Zimmering S.

Results from Drosophila mutagenicity tests of 45 chemical compounds assayed for the National Toxicology Program are presented. Nine compounds were judged positive and four equivocal in the sex-linked recessive lethal test. The nine positive compounds were acetin, allyl glycidyl ether, cyclophosphamide, 1,2-dibromo-3-chloropropane, 2,3-dibromo-1-propanol, dimethylcarbamyl chloride, 1,2-epoxy-butane, lasiocarpine, and N-nitrosopiperidine. The results for chloral hydrate, maleic hydrazide, propantheline bromide, and trifluralin were equivocal. Of the nine compounds positive in recessive lethal induction, only two--allyl glycidyl ether and dimethylcarbamyl chloride--failed to induce translocations. The remaining 32 were judged to be nonmutagenic under the conditions used.

PMID: 3930235 [PubMed - indexed for MEDLINE]


Natl Cancer Inst Carcinog Tech Rep Ser. 1978;34:1-96.

Bioassay of trifluralin for possible carcinogenicity.

National Toxicology Program.

A bioassay for possible carcinogenicity of technical-grade trifluralin was conducted using Osborne-Mendel rats and B6C3F1 mice. Analysis of the technical product established the presence of 84 to 88 ppm dipropylnitrosoamine. The product was administered in the feed, at either of two concentrations, to groups of 50 male and 50 female animals of each species. Fifty animals of each sex were placed on test as controls for the rat bioassay, while 20 of each sex were utilized as controls for the mouse study. The time-weighted average high and low dietary concentrations of trifluralin were, respectively, 8,000 and 4,125 ppm for male rats, 7,917 and 4,125 ppm for female rats, 3,744 and 2,000 ppm for male mice, and 5,192 and 2,740 ppm for female mice. After a 78-week treatment period, there was an additional observation period of 33 weeks for rats and 12 weeks for mice. For female mice the association between increased dosage and elevated incidence of hepatocellular carcinomas was significant (0/20, 12/47, and 21/44 of the control, low dose, and high dose, respectively) as was the relationship between dose and incidence of alveolar/bronchiolar adenomas. Significance of incidence for both types of tumors was supported by tests for significance at each dose level. Squamous-cell carcinomas of the stomach were observed in dosed female mice, but not in controls. Although incidences of these tumors were not statistically significant, they are unusual lesions in B6C3F1 mice and are considered to be treatment-related. Neoplasms observed in treated rats were types that have occurred spontaneously in this strain and were apparently unrelated to trifluralin treatment. Evaluation of the results of this bioassay indicates that technical-grade trifluralin is a carcinogen in female B6C3F1 mice, being associated in these animals with an elevated incidence of hepatocellular carcinomas, alveolar/bronchiolar adenomas and squamous-cell carcinomas of the forestomach. Sufficient evidence was not provided for the carcinogenicity or tumorigenicity of trifluralin in male B6C3F1 mice or in Osborne-Mendel rats of either sex.

PMID: 12844173 [PubMed]

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