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Adverse Effects
ACTIVITY:
Herbicide
(2,6-Dinitroaniline)
CAS Name:
N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)benzenamine
Structure:
Reports
available from
The National Technical Information Service
(NTIS)
Order from NTIS by: phone at 1-800-553-NTIS (U.S. customers);
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| Order
No. |
Title |
Abstract |
NTIS/PB87-113494
9p |
1985
- Pesticide Fact Sheet Number 52: Fluchloralin.
Environmental
Protection Agency, Washington, DC. Office of Pesticide
Programs. |
The
document contains up-to-date chemical information, including
a summary of the Agency's regulatory position and rationale,
on a specific pesticide or group of pesticides. A Fact Sheet
is issued after one of the following actions has occurred.
(1) Issuance or reissuance of a registration standard, (2)
Issuance of each special review document, (3) Registration
of a significantly changed use pattern, (4) Registration
of a new chemical, or (5) An immediate need for information
to resolve controversial issues relating to a specific chemical
or use pattern. |
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=9585264&dopt=Abstract
Environ Mol Mutagen 1998;31(3):257-62
Fluchloralin
is cytotoxic and genotoxic and induces apoptosis in
mammalian cells.
Sinha S, Panneerselvam N, Shanmugam
G.
Cancer Biology Division, School of Biological Sciences,
Madurai Kamaraj University, India.
The genotoxic and cytotoxic effects of a widely used
herbicide, fluchloralin, were assessed using cultured
mammalian cells. Treatment of
cells for 8-12 hr with fluchloralin resulted in a significant
increase in the frequency of metaphase cells with chromosomal
damage. At higher concentrations,
the herbicide also induced an increase in the frequency
of sister chromatid exchange. A 50% loss in viability
was observed when cells were exposed to the herbicide
for 72 hr. To understand the mechanism of cell death
caused by fluchloralin, its effect on DNA synthesis
and its ability to induce apoptosis were investigated.
Even short (6 hr) treatment of cells with fluchloralin
resulted in a 30-50% inhibition of DNA synthesis.
Agarose gel electrophoresis of DNA from herbicide-treated
cells and cytochemical staining indicate the induction
of apoptosis by fluchloralin.
PMID: 9585264 [PubMed - indexed for
MEDLINE]
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- From Toxline at Toxnet
Toxicol
Lett 1983 Aug;18(1-2):13-8
Subacute
toxicity of Basalin in rats.
Gupta PK, Singh YP, Parihar NS.
Subacute and acute toxicity of the herbicide N-propyl-N-(2-chloroethyl)-2,6-dinitro-4-trifluromethyl-aniline
(33245-39-5) (Basalin) was investigated. Some male albino-rats
received graded doses from 0.5 to 4 grams per kilogram
(g/kg) of the compound, orally administered as a single
dose. Median lethal doses (LD50) were calculated. Other
rats received 60, 120, 240, 480, or 960 milligrams (mg)/kg
or 1.92g/kg Basalin, orally administered 6 days a week
for 13 weeks, and cumulative LD50 were determined. Animals
receiving 60 and 120mg/kg Basalin were killed; liver,
kidney, heart, spleen, brain, lung, testes, and adrenal
glands were weighed, sectioned, and examined for structural
changes. Blood total leukocyte count, erythrocyte sedimentation
rate, packed cell volume, and blood glucose were measured.
The oral LD50 for Basalin in male
rats was 1.65g/kg. No animals receiving Basalin
at a dose of 1.92g/kg or more daily for 1 week survived.
Animals developed hyperexcitability
and tremors; these were followed by convulsions and
death. The cumulative LD50 after 13 weeks was
135mg/kg. Basalin had a slow and steady cumulative effect,
reaching a maximum after 10 weeks. In
animals receiving 60 or 120mg/kg of the herbicide for
13 weeks, liver weight was significantly increased whereas
that of spleen, heart, testes, and adrenal glands was
significantly decreased. Total leukocytes, hemoglobin,
and erythrocyte sedimentation rate were increased in
a dose dependent manner. Blood glucose showed a 10 percent
decrease at 120mg/kg Basalin. The 60mg/kg dose did not
produce significant pathological change in the organs
examined. However, 120mg/kg provoked infiltration of
mononuclear cells in liver tissue. Spermatids
in seminiferous tubules were reduced at this dose; a
few tubules were coalescing and filled with binucleate
spermatogonial cells. The authors conclude that
oral administration of Basalin as a single dose or with
repeated administration produces a dose dependent toxicity.
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From Science
Direct
Toxicology
Letters; Volume 95, Supplement 1 , July 1998,
Pages 144-145
Basalin
induced neurotoxic effects in broiler chicks
Sushma
Rishi and Uma Arora
Dept.
of Pharmacology, CCS Haryana Agricultural University
Hisar 125 004 India
Basalin, a formulation of fluchloralin (N-(2-chloroethyl)-2-6-dinitro-N-propyl-4-(trifluoromethyl)-aniline),
is being very widely used as herbicide in large number
of important crops. But very limited data on its toxicological
profile is available. Its adverse effects on central
nervous system and locomotor alterations in sheep given
5 mg/kg orally have been reported. Preliminary studies
in our laboratory indicated alteration in gait in chicken
given Basalin orally @ 200-500 mg/kg followed by ataxia
at higher doses. Since chicken is a suitable model for
neurotoxicity assay, present studies were conducted
on one week old broiler chicks given Basalin daily for
four weeks through feed at different dose levels of
50 mg/kg (Gr I), 100 mg/kg (Gr II) and 150 mg/kg (Gr
III). Each group contained ten chicks. The control chicks
(Gr C) were given equal amount of normal feed. Activities
of brain, liver and plasma acetylcholinesterase (ACHE),
carboxylesterase (CE) and brain neurotoxicesterase (NTE)
were estimated, the tissue esterases after four weeks
treatment and plasma esterases at weekly intervals.
The locomoter activity was determined using inclined
plane at alternate days. Histopathological examinations
of brains and spinal cords of four birds from each group
were conducted after four weeks treatment. The
data on all these experiments indicated inhibition of
all tissue and plasma esterases in a dose dependent
manner, which were significant in chicks of Gr III receiving
maximum dose for four weeks. (Brain NTE 70%, brain and
liver ACHE 85.71 and 85.45% respectively and liver CE
85.58% of control activity). The plasma ACHE and CE
activities were significantly inhibited in this group
after two weeks onwards (ACHE90.8-90.3%, CE 84.9-84.5%
of control). Alteration in gait in Gr III chicks
was observed after three weeks treatment and was correlated
with NTE inhibition. Histopathological
examinations of brain and spinal cords of chicks receiving
maximum dose revealed increased number of Schwann cells
in brain and small numbers of myelinated nerve fibers
in spinal cord. The studies thus indicated possibility
of neuropathic effects of Basalin on prolonged exposure
or at higher doses.
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From Toxline at Toxnet
Mutat
Res 1995 Aug;344(1-2):69-72
Genotoxicity
of the herbicide fluchloralin on human lymphocytes in
vitro: chromosomal aberration
and micronucleus tests.
Panneerselvam N, Sinha S, Shanmugam G.
Cancer Biology Division, School of Biological Sciences,
Madurai Kamaraj University, India.
The genotoxic effect of fluchloralin (33245-39-5) in
cultured human blood lymphocytes was investigated. Venous
blood samples were obtained from healthy donors and
lymphocyte cultures were established. Cell cultures
were treated with 2.5, 5.0, or 10 micrograms/milliliter
(microg/ml) fluchloralin for 24 or 48 hours. Following
treatment, slides were prepared and cells were scored
for chromatid aberrations. In a micronuclei (MN) test,
cell were exposed up to 50microg/ml fluchloralin for
up to 48 hours. Cell microslides were prepared and scored
for MN frequency. Treatment of the lymphocytes for 24
to 48 hours resulted in a significant dose dependent
increase in the total number of chromatid type aberrations.
The frequency of chromatid aberrations was high compared
to isochromatid breaks at all dose levels. The increase
in the frequency of isochromatid breaks was notable
after 48 hours of treatment. Gap formation was high
at all concentrations. Multiple aberrated cells showed
a dose dependent increase at both time points. The frequency
of occurrence of MN in cultured human blood lymphocytes
following fluchloralin treatment was noted. The induction
of MN formation was similar and significant at 24 and
48 hours of treatment at 2.5 to 10microg/ml.
At the higher concentrations there was a statistically
dose related increase in the frequency of micronucleated
binucleate cells. The authors
conclude that fluchloralin at higher concentrations
have the ability to damage the human genome.
|
From Science
Direct
Pesticide
Biochemistry and Physiology; Volume 6, Issue 3 , June
1976, Pages 229-238
Persistence
and metabolism of dinitroaniline herbicides in soils
P.
C. Kearney (1), J. R. Plimmer, W. B. Wheeler (2) and
A. Kontson
1 Agricultural Environmental Quality Institute, Agricultural
Research Service, U.S. Department of Agriculture, Beltsville,
Maryland 20705.
2 Pesticide Research Laboratory, Department of Food
Science, University of Florida, Gainesville, Florida
32601.
The persistence, binding, and metabolism of six dinitroaniline
herbicides, including trifluralin, profluralin, dinitramine,
butralin, fluchloralin, and chlornidine, added to Matapeake
silt loam were determined after 3, 5, and 7 months.
Dinitramine was rapidly degraded during the first 5
months, while butralin and chlornidine
were less persistent than fluchloralin, profluralin,
and trifluralin after 7 months. The latter three herbicides
were similar in persistence and binding properties.
The parent herbicide was the major extractable product
detected in soil at each sampling time. Degradation
products were identified by cochromatography on thin-layer
plates, retention times on gas-liquid and high-pressure
liquid chromatography, and mass spectral analysis. Dealkylated
and cyclic derivatives of the parent herbicide were
detected as metabolites. The cyclic products included
benzimidazole derivatives of dinitramine, trifluralin,
and fluchloralin; a morpholine derivative of chlornidine;
and a quinoxaline derivative of fluchloralin. A unique
metabolite of butralin was derived from the parent material
by the loss of one nitro substituent.
|
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12068946&dopt=Abstract
Bull Environ
Contam Toxicol 2002 May;68(5):766-70
Persistence
and effect of butachlor and basalin on the activities of phosphate
solubilizing microorganisms in wetland rice soil.
Debnath A, Das AC, Mukherjee D.
Department of Agricultural Chemistry and Soil Science, Bidhan
Chandra Krishi Viswavidyalaya, Mohanpur, India.
PMID: 12068946 [PubMed - indexed for MEDLINE]
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11852643&dopt=Abstract
Pest Manag
Sci 2002 Feb;58(2):179-82
Photolysis
of fluchloralin in aqueous methanol.
Saha T, Bhattacharyya A.
Pesticide Residue Laboratory, Department of Agricultural Chemicals,
Bidhan Chandra Krishi Viswavidyalaya, Mohanpur-741252, West
Bengal, India.
The photodegradation of fluchloralin by UV irradiation or sunlight
in aqueous methanolic solution has been examined. In the presence
of titanium dioxide five photoproducts were obtained, but only
four in its absence. One photoproduct,
2, 2'-azoxy-bis(alpha,alpha,alpha-trifluoro-6-nitro-p-toluidine)
is reported for the first time as a metabolite of fluchloralin.
In natural sunlight the rate of degradation was higher than
in UV light and titanium dioxide had almost no effect on the
rate of degradation.
PMID: 11852643 [PubMed - indexed for MEDLINE]
From Toxline at Toxnet
JOURNAL OF ENVIRONMENTAL SCIENCE AND HEALTH PART B PESTICIDES
FOOD CONTAMINANTS AND AGRICULTURAL WASTES; 29 (6).
1994. 1137-1152.
Cytotoxicity of the herbicide Basalin
(Fluchloralin) in Helianthus and Linum.
SAXENA S, SRIVASTAVA S
Dep. Genetics, Univ. Delhi, South Campus, Benito Juarez Road,
New Delhi-110021, India.
BIOSIS COPYRIGHT: BIOL ABS. The herbicide Basalin (Fluchloralin:
N-propyl-N (2 chloroethyl)-2,6-dinitro-n-trifluoromethyl aniline)
was found to reduce the germination percentage in both Helianthus
annuus L. and Linum usitatissimum L.. Treatment with Basalin
also decreased the mitotic index and increased the total chromosomal
abnormalities in these crops. Chromosomal
abnormalities arising due to mitotic spindle disruption were
commonly observed.
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2509191&dopt=Abstract
Ecotoxicol
Environ Saf 1989 Oct;18(2):145-8
Effects
of three pesticides on MSX-induced ammonia photoproduction by
the cyanobacterium Nostoc linckia.
Mishra AK, Pandey AB, Kumar HD.
Department of Botany, Banaras Hindu University, India.
Three pesticides (2,4-D, basalin, aldrin) inhibited L-methionine-DL-sulfoximine
(MSX)-induced photoproduction of ammonia by the nitrogen-fixing
cyanobacterium Nostoc linckia. Combinations of pesticides and
MSX were inhibitory except at low concentrations (100 and 500
micrograms/ml) of 2,4-D which stimulated NH+4 production. Similar
results were obtained when pesticides were added 6 hr after
the addition of MSX, but the inhibition was weaker. When MSX
was added to the culture 6 hr after the addition of pesticides,
the pesticides stimulated NH+4 photoproduction. Similar results
were obtained on nitrogenase activity of the organism.
PMID: 2509191 [PubMed - indexed for MEDLINE]
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2725440&dopt=Abstract
Neurotoxicol
Teratol 1989 Jan-Feb;11(1):45-50
The
behavioral effects of pesticides in male mice.
Mitchell JA, Long SF, Wilson MC, Kallman
MJ.
Department of Pharmacology, School of Pharmacy, University of
Mississippi, University 38677.
Male Swiss mice, 25-30 g, were utilized to define some of the
behavioral effects of the herbicides Lasso [alachlor 43%; (A)],
Basalin [fluchloralin 45%; (F)],
Premerge 3 [dinoseb 51%; (D)], and the fungicide Maneb-80 [maneb
80%; (M)]. These compounds were tested for their effects on
locomotor activity and for their ability to establish a conditioned
taste aversion following oral or dermal exposure. Individual
and grouped (N = 5) activity measures were assessed immediately
following the dermal administration of the commercially available
pesticide formulations. Grouped activity measures were also
assessed following the oral administration of the compounds.
Total activity was significantly (p less than 0.05) increased
over vehicle controls in both grouped and individual subjects
by A, F, and D following dermal administration. Grouped activity
measures were also increased by A, F, D, and M following the
oral administration of the compounds. Similar subjects were
tested in a conditioned taste aversion paradigm using a normally
preferred 0.3% saccharin solution. Animals were given 30 min
access to the saccharin solution followed immediately by the
administration of the pesticide or control solution. Twenty-four
hours later, animals were given the choice of 2 solutions, one
containing water and the other the 0.3% saccharin solution.
The percent saccharin consumed and the total fluid intake were
calculated for each group (N = 8/group). A, F, and D produced
a significant aversion to (N = 8/group) the saccharin following
both oral and dermal administration. Oral administration of
M, but not dermal exposure, also resulted in a flavor aversion.
Total fluid intake, however, was not altered by any of the treatments.(ABSTRACT
TRUNCATED AT 250 WORDS)
PMID: 2725440 [PubMed - indexed for MEDLINE]
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=4041637&dopt=Abstract
- Bull
Environ Contam Toxicol 1985 Sep;35(3):285-90
Identification
of fluchloralin in imported dried fruit.
Barry TL, Petzinger G, Stenson M.
PMID: 4041637 [PubMed - indexed for MEDLINE]
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=6857720&dopt=Abstract
Toxicol
Lett 1983 May;16(3-4):249-52
Effect
of chronic herbicide intoxication on in vivo activities of certain
enzymes in the liver of freshwater fish Nemachelius denisonii
(day).
Rashatwar SS, Ilyas R.
Effect of 120 days of continuous exposure of three sublethal
concentrations (1/2, 1/4 and 1/8 fractions of 96 h LC50) of
Basalin on alkaline phosphatase (Alk P), acid phosphatase (Acid
P), lactic dehydrogenase (LDH), succinic dehydrogenase (SDH),
glutamic oxaloacetic transaminase (GOT), and glutamic pyruvic
transaminase (GPT) activities in the liver of Nemacheilus denisonii
were studied. Alk P, Acid P, LDH, and GPT activities were significantly
inhibited, but GOT activities were not significantly altered.
More inhibition was observed with the higher concentration,
but Acid P, LDH, and GPT activities were significantly inhibited
in all three sublethal concentrations.
PMID: 6857720 [PubMed - indexed for MEDLINE]
From Science Direct
Pesticide Biochemistry and Physiology; Volume 7, Issue 1 ,
February 1977, Pages 73-82
Metabolism of trifluralin, profluralin,
and fluchloralin by rat liver microsomes*1
J. O. Nelson (a), P. C. Kearney (b),
J. R. Plimmer (b) and R. E. Menzer (a)
a Department of Entomology, University of Maryland, College
Park, Maryland 20742, USA
b Agricultural Environmental Quality Institute, Agricultural
Research Service, U.S. Department of Agriculture, Beltsville,
Maryland 20705, USA
Three structurally related [14C]dinitroaniline herbicides,
trifluralin, profluralin, and fluchloralin, were extensively
metabolized in vitro by both normal and phenobarbital-induced
rat liver microsomes. Identification of the metabolites in the
ethyl acetate extracts indicated that aliphatic hydroxylation,
N-dealkylation, reduction of a nitro group, and cyclization
were the predominant metabolic routes for these herbicides in
vitro. Of particular interest was the formation of a benzimidazole
metabolite.
*1 Scientific article
No. A2194, contribution No. 5169, of the Maryland Agricultural
Experiment Station, Department of Entomology. Investigation
supported in part by a cooperative agreement from the Pesticide
Degradation Laboratory, Agricultural Environmental Quality
Institute, Agricultural Research Service, U. S. Department
of Agriculture, and is a contribution to Regional Project
NE-53. Mention of proprietary products does not imply endorsement
or approval by the U.S. Department of Agriculture to the exclusion
of other suitable products.
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1063644&dopt=Abstract
Environ
Qual Saf Suppl 1975;3:277-81
Degradation
and metabolism of fluchloralin in soil.
Otto S.
PMID: 1063644 [PubMed - indexed for MEDLINE]
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