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.
B, Marcos R, Yanikoglu A, Creus A.
of Biology, Faculty of Arts and Sciences, Akdeniz University,
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.
14706518 [PubMed - indexed for MEDLINE]
November 24,2004, US EPA released these documents
in a Proposed
pesticide tolerance for residues of trifluralin in mint
August 30, 2004 - Trifluralin
Risk Assessment Overview (10 pages)
7, 2004 - Trifluralin:
Human Health Risk Assessment (55 pages)
2, 2003 - Toxicology
Disciplinary Chapter for the Tolerance Reassessment Eligibility
Decision Document Trifluralin (PC Code: 036101)
31, 2004 - Report
of the Food Quality Protection Act (FQPA) Tolerance Reassessment
Progress and Risk Management Decision (TRED) for Trifluralin
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)
12, 2004 -
Review of "Dissipation of Transferable Residues of
Benefin and Trifluralin on Turf Treated with a Formulation
of the Pesticides" (15 pages)
2, 2003 - Report
of the Hazard Identification Assessment Review Committee -
Trifluralin (P.C. Code 036101) - (32 pages)
5, 2004 - Residential
Exposure Assessment and Recommendations for the Tolerance
Reassessment Evaluation Decision (TRED) Document for
Trifluralin (50 pages)
8, 2004 - Trifluralin.
Anticipated Residues, Acute, Probabilistic, Chronic and
Cancer Dietary Exposure Assessments for the Reregistration
Eligibility Decision (68 pages)
9, 2004 - Trifluralin:
Health Effects Division (HED) Metabolism Assessment Review
Committee (MARC) Decision Document. Meeting Date:
4 February 2004. PC Code: 036101 (4 pages)
4, 2004 - Trifluralin:
Residue Chemistry Chapter for the Tolerance Reassessment
Evaluation Decision (TRED) Document (75 pages)
3, 2003 - Trifluralin
- Drinking Water Assessment for Tolerance Reassessment
Eligibility Decision (PC Code: 036101; DP Barcode:
D296624 (109 pages)
9, 2004 -
Review of Trifluralin Incident Reports DP Barcode
D300064, Chemical# 036101 (11 pages)
of Fish Diseases 1979, 2,
dysplasia in young fish exposed to the herbicide trifluralin
A. COUCH, J. T. WINSTEAD, D. J. HANSEN and L. R. GOODMAN
Breeze Environmental Research Laboratory, Gulf Breeze,
Florida^ USA and ^Department of Biology, University of
Southern Mississippi, USA
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.
(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
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,
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,
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
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.
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
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. firstname.lastname@example.org
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
Formation of non-extractable pesticide residues: observations
on compound differences, measurement and regulatory issues.
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
[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,
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,
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
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
similar to naphthalene dioxygenase genes in trifluralin-degrading
Mde L, Henriques JA, Gaylarde CC, Greer CW.
Department of Biology and Chemistry, UNIJUI, RS, Brazil.
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.
[PubMed - in process]
Bull Environ Contam
Toxicol. 2004 May;72(5):962-9.
Trifluralin residues in runoff and infiltration water from tomato
Kentucky State University, Land Grant Program, Department of Plant
and Soil Science, 218 Atwood Research Facility, Frankfort, KY
PMID: 15266692 [PubMed - indexed for MEDLINE]
Arch Environ Contam
Toxicol. 2003 Jul;45(1):30-6.
organic contaminants, including toxaphene and trifluralin, in
cotton field soils from Georgia and South
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,
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.
[PubMed - indexed for MEDLINE]
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]
Abiotic reduction of dinitroaniline herbicides.
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.
[PubMed - indexed for MEDLINE]
J Environ Qual 2002
in surface water, sediment, and rainfall of the northeastern Pantanal
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. email@example.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]
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
PMID: 12146622 [PubMed - indexed for MEDLINE]
Toxicol Sci 2002
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. firstname.lastname@example.org
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
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,
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),
simazine [2-chloro-4,6-bis(ethylamino)-1,3,5-triazine], and trifluralin
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
comparison of crop and non-crop plants as sensitive indicator
species for regulatory testing.
McKelvey RA, Wright JP, Honegger JL.
Laboratory for Health and Environmental Sciences, PO Box 50, 1090
Elkton Rd, Newark, DE 19714-0050, USA. email@example.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
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. firstname.lastname@example.org
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
PMID: 11926182 [PubMed - indexed for MEDLINE]
exhibited by trifluralin-induced bicellular pollen on diploid
and tetraploid maize crosses.
National Institute of Agrobiological Resources, Ministry of Agriculture,
Forestry and Fisheries, Ibaraki, Japan. email@example.com
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
pesticide use in California: pesticide prioritization, use densities,
and population distributions for a childhood
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. firstname.lastname@example.org
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
of soil aggregate size on atrazine and trifluralin leaching.
SM, Portal JM, Schiavon M.
Centre de Pedologie
Biologique, CNRS FRE 2111, H. Poincare University, B.P. 5, 54501
Vandoeuvre-les-Nancy Cedex, France..
[PubMed - indexed for MEDLINE]
Environ Toxicol 2001;16(1):9-19
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. email@example.com
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]
Laboratory study on the interaction between herbicides
and sediments in water systems.
GG, Williams B.
Department of Environmental
Science and Management, The University of Adelaide, Roseworthy
Campus, Roseworthy, SA 5371, Australia.
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.
Sci Total Environ 2000
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.
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
study on leachability of five herbicides in South
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
J Environ Sci Health
B 2000 Jan;35(1):51-9
of pesticide residues in a cotton crop soil.
Luchini LC, Peres TB, de Andrea MM.
Instituto Biologico, Centro de Protecao Ambiental, Sao Paulo,
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]
Saf 1999 Jun;43(2):213-21
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
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
of carcinogenic action of pesticides inducing
thyroid follicular cell tumors in rodents.
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
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,
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
PMID: 9467199 [PubMed - indexed for MEDLINE]
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,
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]
resistance caused by spontaneous mutation of the cytoskeletal
Anthony RG, Waldin TR, Ray JA, Bright SW,
School of Biological Sciences, Royal Holloway University of London,
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
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,
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
of spray adjuvants on the behavior of trifluralin in the soil.
MK, Mulinski Z, Zbiec I.
Department of General
Chemistry, Agricultural University, Szczecin, Poland.
[PubMed - indexed for MEDLINE]
Rev Environ Contam
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)
[PubMed - indexed for MEDLINE]
Bull Environ Contam
Toxicol 1997 Nov;59(5):750-6
of trifluralin in soil and melon.
O, Maden S, Tuncbilek AS.
Ankara Nuclear Research
and Training Center, Turkish Atomic Energy
Authority, Saray, 06105 Ankara, Turkey.
[PubMed - indexed for MEDLINE]
Bull Environ Contam
Toxicol 1997 Jul;59(1):58-64
of trifluralin in a soil and their uptake by carrots.
O, Gozek K, Khan SU.
Ankara Nuclear Research
and Training Center, Turkish Atomic Energy Authority, Saray, Ankara,
[PubMed - indexed for MEDLINE]
Arch Toxicol 1997;71(3):193-7
vivo genotoxicity of selected herbicides in the mouse bone-marrow
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
From Toxline at Toxnet
Vol. 371, Nos. 1/2, pages 15-21, 30 references, 1996
Evaluation of the Herbicide Trifluralin on Human Lymphocytes Exposed
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
Bull Environ Contam
Toxicol 1996 Apr;56(4):655-62
deformity susceptibilities of marine fishes exposed to herbicide.
Division, National Research Institute of Fisheries Science, Yokosuka,
[PubMed - indexed for MEDLINE]
Mutat Res 1995
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
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,
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
size and the toxicokinetics of trifluralin in rainbow
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
contact dermatitis from the herbicides trifluralin
MT, Andreozzi RJ, Marks JG Jr.
Department of Medicine,
Pennsylvania State University College of Medicine, Hershey.
[PubMed - indexed for MEDLINE]
endpoints and overview of a mouse skeletal
variant assay for detecting exposure to teratogens.
Department of Biological Sciences, DePaul University, Chicago,
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.
M, Montepiani C, Ragozza L, Bartoletti C, Ioannilli E, Del Re
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)).
[PubMed - in process]
From Dart Special at Toxnet
Chemically Induced Birth Defects 1993;2:675-721
International Research and Development Corporation, Mattawan,
Medical Subject Headings (MeSH):
Substance (CAS Registry Number): [Too many
Sodium fluoroacetate (62-74-8)
[Note: the following organofluorines were
Gliftor (8065-71-2) - [Synonym: 1-Chloro-3-fluoro-2-propanol mixt.
N-Methyl-N- 1-naphthyl fluoroacetamide [Nissol] (5903-13-9)
Sarin [Synonym: (+-)-Isopropyl methylphosphonofluoridate] (107-44-8)
hexafluorosilicate [also known as Sodium fluorosilicate] (16893-85-9)
Soman [Synonym: 1,2,2-Trimethylpropyl methylphosphonofluoridate]
Food Chem Toxicol 1992
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.
[PubMed - indexed for MEDLINE]
Toxline at Toxnet
Canadian water quality
guidelines Vol:Appendix XI (1992)
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
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
Toxicol Lett 1991
effect of structurally divergent herbicides on mouse liver
xenobiotic-metabolizing enzymes (P-450-dependent mono-oxygenases,
epoxide hydrolases and glutathione S-transferases) and carnitine
Moody DE, Narloch BA, Shull LR, Hammock
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]
Toxline at Toxnet
Monogr Eval Carcinog Risks Hum 1991;53:515-34
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
drinking water quality guidelines for selected herbicides.
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
PMID: 2599158 [PubMed - indexed for MEDLINE]
Mutat Res 1988
TX; Y test for the detection of nondisjunction
and chromosome breakage in Drosophila melanogaster. I.
Analysis of spontaneous events and results of male exposure.
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
Loss of trifluralin from clay
and loam soils containing aged and freshly applied residues.
AE, Aubin AJ, Derksen DA.
Research Station, Regina, Saskatchewan.
[PubMed - indexed for MEDLINE]
OF ADULT SKELETONS TO DETECT PRENATAL EXPOSURE TO 2,4,5-T OR TRIFLURALIN
Environ Mutagen 1985;7(3):349-67
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.
of trifluralin for possible carcinogenicity.
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
PMID: 12844173 [PubMed]