나이트로펜(나이트로펜)

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Protox-Inhibiting

Pesticide (Nitrofen) -> USDA PDB

log Kow = 4.64

4.64

3.4/5

4.64

1.33 at 90 °C

1.3 g/cm³

Crystalline solid

White solid

Crystals

Yellow crystalline solid

Free-flowing solid, dark brown color

less than 1 mg/mL at 70 °F (NTP, 1992)

In water, 1.0 mg/L at 22 °C

In water, 0.7-1.2 ppm at 22 °C

Soluble in ethanol 40, n-hexane 280, benzene 2000 (all in g/kg at 20 °C)

0.001 mg/mL at 22 °C

Solubility in water, g/100ml at 22 °C: 0.0001

356 to 374 °F at 0.25 mmHg (NTP, 1992)

BP: 180-190 °C at 0.25 mm Hg

at 101.3kPa: 368 °C

158 to 160 °F (NTP, 1992)

70-71 °C

70 °C

70-71 °C

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)

Hazard Traits - Bioaccumulation; Carcinogenicity; Environmental Persistence; Reproductive Toxicity

Nitrofen: HSNO Approval: HSR004593 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Combustible. Finely dispersed particles form explosive mixtures in air.

A skin and respiratory tract irritant; May have effect on the CNS and liver and possibly carcinogenic to humans; Animal tests show that this substance possibly causes malformations in human babies. [ICSC] Increase congenital malformations in rodent experiments at levels that were not overtly toxic to mothers; [REPROTOX] May cause skin irritation; [HSDB] May cause skin and eye irritation; [CAMEO] Caused convulsions and coma in a woman who ingested 10 ml/kg; [MSDSonline] See Fluthiacet-methyl.

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Nitrofen (1836-75-5) is listed as reasonably anticipated to be a human carcinogen. First listed in the Third Annual Report on Carcinogens (1983).[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]

Weisburger EK; Carcinogenicity tests on pesticides; Chamvers, JE and JD Yarbrough (ed); Effects of chronic exposures to pesticides on animal systems. XII, 250 pages, Raven Press, New York, NY, USA. 165-76 (1982) ISBN 0-89004-756-1. Carcinogenicity tests on pesticides, incl nitrofen, were presented.

DHEW/NCI; Bioassay of Nitrofen for Possible Carcinogenicity (1979) Technical Rpt Series No. 184 DHEW Pub No. (NIH) 79-1740

DHEW/NCI; Bioassay of Nitrofen for Possible Carcinogenicity (1978) Technical Rpt Series No. 26 DHEW Pub No. (NIH) 78-826

Manson JM; Environ Health Perspect 70: 1337-47 (1986). A review with 30 refs on the mechanism of nitrofen.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Rest. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Landfill: The dichloro aromatic constituent of the nitrofen molecule precludes rapid degradation in the environment. Burial away from water supplies is the preferred method of disposal. Large quantities should be incinerated. Recommendable method: Incineration.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for NITROFEN (7 total), please visit the HSDB record page.

Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: P3 filter respirator for toxic particles.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

DO NOT SMOKE WHILE USING. KEEP CONCENTRATE AWAY FROM FIRE & SPARKS. NO HAZARDS WITH WP.

Avoid contact with eyes, skin, and mucous membranes of respiratory tract. Prevent drifting during use. Keep away from children.

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for NITROFEN (12 total), please visit the HSDB record page.

... The aim of this study was to examine whether antenatal treatment with vitamin A can increase lung growth and reduce the incidence of CDH in a nitrofen-treated rat model. The animals were randomly assigned to four groups: control, vitamin A, nitrofen, and nitrofen/vitamin A (NIP/Vit A). The incidence of CDH /congenital diaphragmatic hernia/ in the NIP/Vit A group (54%) was markedly lower than that in the nitrofen-treated group (85%). Although lung weight was decreased in the nitrofen-treated and NIP/vitamin A groups, the fetal lung weight-to-body weight ratio was slightly increased in the NIP/vitamin A group, compared to the nitrofen-treated group. The mRNA levels of lung surfactant proteins were decreased in the NIP/vitamin A group. We conclude that antenatal treatment with vitamin A reduced the incidence of CDH without lung maturation in the nitrofen-induced rat model.

Vitamin A (vit A) alleviates the effects of nitrofen in exposed rat pups. The present study examines the effects of early exposure to vitamin A on the neural-crest-related cardiovascular, thymic, parathyroid, and thyroid malformations previously reported in the rat model of congenital diaphragmatic hernia (CDH). Pregnant rats were exposed on gestational day 9.5 to 100 mg 2-4-dichlorophenyl-p-nitrophenyl ether (nitrofen) alone or followed by 15,000 IU vit A. Controls were treated only with oil or oil + vit A. The fetuses were recovered near term and diaphragmatic, lung, heart, and thymic malformations were sought after dissection. The parathyroids and thyroid were histologically investigated. The hearts were also examined for protein, DNA, and proportion of proliferating cells. None of the control fetuses had malformations, whereas 41% of nitrofen and 27% of nitrofen + vit A fetuses had CDH. Anomalies of the heart outflow tract and pharyngeal arteries were seen in 64% and 43%, respectively, in both groups. Heart and thymic hypoplasia, which were severe in the nitrofen group with significant decreases of total DNA and percent proliferating cells, were significantly improved in the nitrofen + vit A group. The hypoplastic thymus was malformed in 53% and 27% of fetuses, respectively, and the parathyroids were abnormal in 48% and 35%, respectively. Only minimal anomalies of the thyroid were found. The significant improvement of heart and thymic hypoplasia associated with vit A was not seen for the other variables studied, but there was a trend in this direction for all of them. Vit A definitely improved heart hypoplasia induced by nitrofen by stimulating myogenesis. It also improved thymic hypoplasia, but had limited beneficial effects on malformations of the cardiac outflow tract and pharyngeal derivatives that accompany CDH in rats exposed to nitrofen.

... DIURON & SIMETRYNE DECR ACTIVITY OF NITROFEN, BUT THERE WAS A POSSIBILITY THAT CLOSURE OF LEAF STOMATA BY /THEM/ ... MIGHT DECR NITROFEN UPTAKE & ITS ACTIVITY.

EC50; Species: Scenedesmus subspicatus (Green Algae); Conditions: freshwater, static; Concentration: 1800 ug/L for 49-79 min, population decrease /100% purity formulation/

LC50; Species: Ceriodaphnia dubia (Water Flea) neonate age <12 hr; Conditions: freshwater, static, 25 °C, pH 8.18, hardness 57.07 mg/L CaCO3, alkalinity 81.00 mg/L CaCO3; Concentration: 216.8 ug/L for 48 hr />99% purity/

LC50; Species: Gammarus fasciatus (Scud) immature organism; Conditions: freshwater, static, 15 °C, pH 7.4, hardness 44 mg/L CaCO3; Concentration: 4000 ug/L for 24 hr (95% confidence interval: 2700-5700 ug/L) /100% purity formulation/

LC50; Species: Gammarus fasciatus (Scud) immature organism; Conditions: freshwater, static, 15 °C, pH 7.4, hardness 44 mg/L CaCO3; Concentration: 3100 ug/L for 96 hr (95% confidence interval: 1700-5600 ug/L) /100% purity formulation/

For more Ecotoxicity Values (Complete) data for NITROFEN (10 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7,800(SRC), determined from a structure estimation method(2), indicates that nitrofen is expected to be immobile in soil(SRC). Volatilization of nitrofen from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 7.95X10-6 mm Hg(3), and water solubility, 1 mg/L(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Nitrofen is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). A 2% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is slow in soil(SRC). After 16 weeks of incubation in laboratory experiments, 15 and 38% of the initial concentration (10 ppm) of nitrofen remained in sandy loam (0.7% organic matter, pH 7.0) and muck (36.7% organic matter, pH 7.0) soils, respectively, 94% and 82% nitrofen remained in the same soils that were sterilized(6). Nitrofen shows greater persistence in the field than is suggested by laboratory data, possibly due to cooler temperatures in the field(6). The half-life of nitrofen in flooded soil was 10 days at 30 °C(7), much shorter then that in upland soil even when the water content was at field capacity(7,8). Nitrofen applied to the surface of three Saskatchewan soils in a 3-year field experiment declined to 46, 40, and 38% of the initial concentration after 12 months in sandy loam, heavy clay, and silty clay soil, respectively(9). Substantial residues remained in all three soils after 2 growing seasons. Minimal leaching occurred to the 5-10 cm soil layer(9).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7,800(SRC), determined from a structure estimation method(2), indicates that nitrofen is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.0X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 8X10-6 mm Hg(4), and water solubility, 1 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 21 and 160 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 454 months if adsorption is considered(6). According to a classification scheme(7), BCFs of 1550(8) to 5370(9), suggest bioconcentration in aquatic organisms is very high(SRC). In a river die-away test using Asahi River (Japan) water, 1% of the nitrofen remained after 50 days incubation at 20 °C(10). Nitrofen is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Nitrofen photodegraded 65% in one week and 88% in 4 weeks when exposed to sunlight(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nitrofen, which has a vapor pressure of 7.95X10-6 mm Hg at 40 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase nitrofen is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 14 days(SRC), calculated from its rate constant of 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase nitrofen may be removed from the air by wet or dry deposition(SRC). Nitrofen contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Survey results of domestic and imported produce for nitrofen during fiscal year 1970 to 1976 showed that one of 864 samples of beans, 15 of 3857 samples of root vegetables, and 36 of 5631 samples of leafy vegetables contained detectable residues(1). In the Total Diet Program (a sampling of US food consumption) of the US FDA conducted during 1973-1974, nitrofen was detected in one of 30 composite samples of leafy vegetables at a level of 0.039 mg/kg(2,3). According to the fiscal year 1977 and 1978 Total Diet Studies, there was no detectable dietary intake of nitrofen for infants and toddlers(4). In the adult Total Diet Study for fiscal year 1979 in which 20 market basket samples of 12 food groups were analyzed from all parts of the country, only one sample of leafy vegetables contained 6 ppb of nitrofen was identified which would result in an average daily intake of 0.0151 ug/day(5). Nitrofen was qualitatively detected in domestic and imported agricultural commodities in the FDA's pesticide residue monitoring program, fiscal year 1978 to 1982(6). Nitrofen was not detected (detection limit 0.100 ppm) in 6970 samples representing 81 varieties of fruits and vegetables in the H.E.B. Food Stores of San Antonio, TX pesticide residue screening program conducted 1989 to 1991(7).

Nitrofen was not detected in cereals, sugars and confectionaries, oils and fats, beans, fruits, vegetables, seasonings and beverages, meats and eggs or prepared foods collected in a market basket survey June 1982, Osaka Prefecture, Japan(1). Nitrofen was not detected in samples of rice from Japan or broccoli and cauliflower from Finland(2).

... NO RESIDUES OF NITROFEN & ITS METABOLITE ... WERE FOUND IN MILK, URINE, OR FECES OF A COW FED 5 PPM OF THE HERBICIDE.

Nitrofen was not detected in 178 individual human breast milk samples from women living throughout Belgium, taken two to eight weeks after delivery(1).

In the adult Total Diet Study for fiscal year 1979 in which 20 market basket samples of 12 food groups were analyzed from all parts of the country, only one sample of leafy vegetables contained 6 ppb of nitrofen was identified which would result in an average daily intake of 0.0151 ug/day(1).

Abdominal pain. Cough. Diarrhoea. Dizziness. Headache. Laboured breathing. Sore throat. Vomiting.

Redness. Pain.

Redness. Pain.

See Inhalation.

Pregnant rats were exposed to nitrofen or vehicle on gestational day 9 (D9). Embryos were sacrificed on D15, D18 and D21 and divided into nitrofen- and control group. Pulmonary RNA was extracted and mRNA levels of EDNRA and EDNRB were determined by real-time PCR. Immunohistochemistry for protein expression of both receptors was performed. mRNA levels of EDNRA and EDNRB were significantly increased in the nitrofen group on D15, D18 and D21. Immunohistochemistry revealed increased pulmonary vascular expression of EDNRA and EDNRB /Endothelin Receptors A and B/ compared to controls.

... The present studies were performed to begin to address the cellular mechanisms of these nitrofen-induced effects. Heart fibroblasts were isolated and treated with varying doses of nitrofen in vitro. Experiments were performed to determine the effects of this herbicide on important cellular processes including migration, proliferation and apoptosis. These studies illustrated a dose-dependent decrease in collagen gel contraction and proliferation in response to nitrofen. Assays were also performed to determine the effects of nitrofen on fibroblast gene expression. Increased expression of collagen type I and specific integrins were seen following nitrofen exposure. These studies illustrate that nitrofen has direct effects on cardiac fibroblast proliferation and extracellular matrix remodeling, cellular events important in valvuloseptal development.

Lactate dehydrogenase (LDH) release test, 3H-thymidine (3H-TdR) and 3H-leucine (3H-Leu) incorporation tests and flow cytometric analysis (FCM) of cell cycle were employed to elucidate cellular and molecular mechanism of nitrofen-induced toxicity in cultured keratinocytes. The results showed that cell morphologic damages were observed after exposure to 1.0 mmol/L and 10.0 mmol/L nitrofen. LDH release increased in a dose- and time-dependent manner. Depressions in 3H-TdR and 3H-Leu incorporation were found even at 0.01 mmol/L, and increased with the exposure dose. Cell cycle was analyzed from the DNA- histogram with propidium iodide stain. The results showed that there was no pronounced alteration in cell cycle after cells exposed to 0.01 and 0.1 mmol/L nitrofen. At dose of 1.0 mmol/L, S phase cells increased 2 times of that of control. With the increase of dose, G2/M phase cells became to increase about 5 times of that of the control. At 1.0 mmol/L, time course of cell cycle after exposure was observed. At the beginning of exposure, cells in S phase and G2/M phase were about 8.7% and 11%. Following 24 hr incubation with nitrofen, cells in S phase increased to 18.0% with almost no change in G2/M. 72 hr after exposure, G2/M phase cells increased to 63.3%. The above results demonstrated that S phase and G2/M phase blockage in cultured keratinocytes after exposed to nitrofen seems of importance in the mechanism of nitrofen-induced toxicity.

... Nitrofen induces a time-dependent cell death of P19 cells that is associated with increases in TUNEL-positivity and caspase-3 cleavage suggesting that nitrofen induces P19 cell apoptosis. In addition, the increase in TUNEL-positive cells was inhibited with zVAD-fmk, suggesting that nitrofen induces a caspase-dependent apoptosis. Nitrofen treatment was associated with increased p38 MAP kinase activity, though pretreatment of cells with multiple p38 inhibitors did not affect nitrofen-mediated caspase-3 cleavage, suggesting caspase-3 cleavage is p38-independent. Nitrofen induced a dose-dependent increase in reactive oxygen species (ROS), which was accompanied by a decrease in the ratio of reduced/oxidized glutathione, indicating that nitrofen alters the cellular redox state of these cells. Furthermore, pretreatment of cells with N-acetyl cysteine gave a dose- and time-dependent reduction of caspase-3 cleavage, supporting the observations that caspase-3 cleavage is cell-redox-dependent. Therefore, nitrofen induces P19 cell apoptosis that is cell-redox-dependent and is associated with increases in p38 activity and ROS and may play a role in nitrofen-mediated birth defects.

For more Mechanism of Action (Complete) data for NITROFEN (8 total), please visit the HSDB record page.

THE FATE OF /LABELED/ NITROFEN IN ... PLANTS/ ... WAS STUDIED ... /BY INVESTIGATORS/, WHO REPORTED THAT RAPE ... REDROOT PIGWEED ... & GREEN FOXTAIL ... LEAVES TREATED WITH 2 DROPS OF (14)C-NITROFEN ... UNDER HIGH LIGHT CONDITIONS, PRODUCED SEVERAL LABELED CMPD OF DIFFERENT MOLECULAR SIZE & CHROMATOGRAPHIC PROPERTIES. THEY THEORIZED THAT AT LEAST 2 OF THESE CMPD WERE LIPID-NITROFEN CONJUGATES OR NITROFEN POLYMERS, WHILE THE OTHERS MIGHT BE FORMED BY CLEAVAGE OF NITROFEN AT THE ETHER LINKAGE. IDENTIFICATION OF THE DERIVATIVES WERE NOT POS ... . ALL RADIOACTIVITY RECOVERED FROM PLANTS GROWN UNDER CONDITIONS OF LOW LIGHT INTENSITY & HIGH TEMP WAS FOUND ONLY IN THE (14)C-NITROFEN PEAK. HOWEVER, 2 RADIOACTIVE CMPD, IN ADDITION TO (14)-C NITROFEN, WERE DETECTED IN PLANT EXTRACTS 2 DAYS AFTER TREATMENT UNDER HIGHER LIGHT INTENSITY & LOWER TEMP. ... /IT WAS/ ... PROPOSED THAT A LIGHT-CONTROLLED BIOCHEM PROCESS APPARENTLY CAUSES (14)-C-NITROFEN TO POLYMERIZE OR ENABLES IT TO COMBINE WITH UNIDENTIFIED CELL LIPIDS.

... NITROFEN IN FRESH RUMEN FLUID IN VITRO /SHOWED/ ... A METABOLITE RAPIDLY PRODUCED WHICH WAS ... P-AMINOPHENYL 2,4-DICHLOROPHENYL ETHER, A REDUCED COMPD OF NITROFEN.

Rat liver homogenates incubated with amino derivatives of nitrofen, an NADPH-generating system and erythrocytes from rats or humans metabolized the amino derivatives to methemoglobin forming metabolites. ... (14)C Labelled nitrofen was administered orally to a sheep at a dose of 40 mg/kg body weight. ... The predominant metabolites were 2,4-dichlorophenyl 4-aminophenyl ether, 2,4-dichloro-5-hydroxyphenyl-4-nitrodiphenyl ether, 2,4-dichlorophenol, 2-chlorophenyl-4-nitrophenyl ether & conjugates.

Oral exposure of pregnant Long Evans rats on day 11 of gestation to nitrofen which was uniformly labeled with (14)C in the nitrophenyl ring, resulted in the accumulation of radioactivity in maternal fat with lesser amounts found in liver, kidney, other tissues, and in the embryonic compartment. High performance liquid chromatography of embryo placental extracts revealed 4 metabolites in addition to the parent cmpd: 4'-amino and 4'-acetylamino derivatives plus 2 hydroxylated derivatives. A similar metabolic profiles was observed in maternal blood and liver.

For more Metabolism/Metabolites (Complete) data for NITROFEN (6 total), please visit the HSDB record page.

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

Chemicals used to destroy pests of any sort. The concept includes fungicides (FUNGICIDES, INDUSTRIAL); INSECTICIDES; RODENTICIDES; etc.

... NO RESIDUES OF NITROFEN & ITS METABOLITE ... WERE FOUND IN MILK, URINE, OR FECES OF A COW FED 5 PPM OF THE HERBICIDE.

... STUDIED /NITROFEN/ ABSORPTION & TRANSLOCATION USING RAPE, REDROOT PIGWEED, & GREEN FOXTAIL. ... FOUND ONLY SLIGHT TRANSLOCATION OF FOLIARLY APPLIED (14)C-NITROFEN & DIFFERENT ANATOMICAL EFFECTS BETWEEN THE WEEDS & RAPE. ... NITROFEN HAD ALMOST NO EFFECT ON TOPS OF BARNYARD GRASS WHEN HERBICIDE WAS APPLIED TO SOIL ONLY UNDER WEED SEEDS. LOW TRANSLOCATION & LACK OF LIGHT UNDER SOIL MAY BE REASONS FOR THIS ... WEEDS ABSORB THE CHEM DURING THEIR GERMINATION & ELONGATION THROUGH TREATED SOILS, & AFTER EXPOSURE TO SUNLIGHT THEY DIE.

NOT READILY ABSORBED FROM SOIL INTO PLANTS. ... NOT SIGNIFICANTLY TRANSLOCATED IN CROPS OR WEEDS.

(14)C Labelled nitrofen was administered orally to a sheep at a dose of 40 mg/kg body weight. After 99 hr, 76.2% of the applied dose was accounted for in the excreta. After 100 hr, radioactivity was highest in fat (23 mg/kg); the liver, thyroid, mammary gland, adrenal gland, kidney, lung, muscle, skin and spleen contained levels of 1-3 mg/kg.

Oral exposure of pregnant Long Evans rats on day 11 of gestation to nitrofen which was uniformly labeled with (14)C in the nitrophenyl ring, resulted in the accumulation of radioactivity in maternal fat with lesser amounts found in liver, kidney, other tissues, and in the embryonic compartment. The peak concn of radioactivity occurred 7-9 hr after dosing and the half-life of the label in maternal blood was approx 8 days. In the embryonic compartment, radioactivity was first detected at 2 hr after dosing, peaked at 4-6 hr, and declined to half of that initially seen by 24 hr.

Used as pre- or post-emergence herbicide for control of annual broad-leaved and grass weeds in cereals, rice, sugar beets, ornamentals, vegetables, and public easements; No longer produced or marketed in the US; [HSDB]

Prohibited for use in the US, U.K., Federal Republic of Germany, Sweden, and the Russian Federation, and highly restricted in many other countries; [INCHEM] Banned in the EU; [eChemPortal: ESIS]

Farming (Pesticides) [Category: Industry]

For nitrofen (USEPA/OPP Pesticide Code: 038201) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Nitrofen is a contact herbicide for pre and post emergence control of annual grasses and broadleaf weeds on a variety of food and ornamental crops. Nitrofen has been applied in approximately 25 states by growers of rice, broccoli, cauliflower, cabbage, brussel sprouts, onions, garlic, and celery. Nitrofen has also been used in nurseries growing roses and chrysanthemums and on rights-of-way. ... Nitrofen has not been used around homes and gardens.

Formerly as a herbicide /US/

A sample reported ... to be more than 98% pure was found ... to contain the following five impurities at unspecified levels: para-chloronitrobenzene, bis(para-nitrophenyl)ether, 2,4-dichloro-2,2-dinitrophenyl ether, 2-chloro-4-nitrodiphenyl ether and 4-chloro-4-nitrophenyl ether. Four other unidentified impurities were also observed in the mg/kg (ppm) range. Technical nitrofen may also contain 2,7-dichlorodibenzodioxin.

(1976) No Data

(1978) No Data

(1976) No Data

(1978) No Data

(1975) 3.63X10+8 G (CONSUMPTION)

(1978) 4.09X10+8 G (CONSUMPTION)

HERBICIDE FOR VEGETABLES, 89%; HERBICIDE FOR SUGAR BEETS, 11% (1978)

The direct crop use of nitrofen for 1980 was estimated as 882,000 pounds.

NITROFEN 7% AI, GRANULE, COMBINED FORMULATION 5% + ((4-CHLORO-O-TOLYL)OXY)ACETIC ACID ETHYL ESTER 0.7%; 5% AI, GRANULE (FOR UPLAND), COMBINED FORMULATION 6% + ((4-CHLORO-O-TOLYL)OXY)ACETIC ACID BENZYLTRIETHANOLAMINE SALT 0.4%; 25% AI, EMULSIFIABLE CONCENTRATE COMBINED FORMULATION 5% + 4-((4-CHLORO-O-TOLYL)OXY)BUTYRIC ACID 0.6% + 2-AMINO-3-CHLORO-1,4-NAPHTHOQUINONE; 50% AI, WP, COMBINED 0.75-7% + FERTILIZERS. /FROM TABLE/

Granules, emulsifiable concentrate, wettable powder.

Mixed formulations: (nitrofen plus) diniterb; neburon; linuron.

Trade Names: Mezotox, Niclofen, NIPR, Tokkorn.

Benzene, 2,4-dichloro-1-(4-nitrophenoxy)-: ACTIVE

The WHO Recommended Classification of Pesticides by Hazard identifies nitrofen as an active ingredient believed to be obsolete or discontinued for use as a pesticide.

Effective when left as a thin layer on the soil surface; activity is rapidly lost on incorporation in soil.