CAS No. 33245-39-5
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Adverse Effects

ACTIVITY: Herbicide (2,6-Dinitroaniline)

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


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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.


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]

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.

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.

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.


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]


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


Cytotoxicity of the herbicide Basalin (Fluchloralin) in Helianthus and Linum.


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.


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]


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]

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]


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.


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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