Nitrofen

BENZENE. 2,4-DICHLORO-1-(4-NITROPHENOXY)-ETHER. 2,4-DICHLOROPHENYL P-NITROPHENYL NITROFENE (FRA) 

It is prohibited to place on the market or use plant protection products containing nitrofen. The authorizations for plant protection products containing nitrofen had to be withdrawn from the 1st of January 1988 according to Council Directive 87/181/EEC of 9 March 1987. There is sufficient evidence to provide a strong presumption that human exposure to nitrofen may result in the development of cancer. Hazard to non-target organisms. (Reference (EPS) UNEP/FAO - PIC Circulars XIV. XV, XVI, XVII - 12/2001,6/2002, 12/2002,6/2003., ) 

FAO PLANT PRODUCTION PROTECTION PAPER, 56,, 1983 FAO PLANT PRODUCTION PROTECTION PAPER, 61,, 1983 

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Nitric acid, 98 Nitric oxide, 98 Nitrilotriacetic acid, 98 p-Nitroaiiiline, 99 Nitrobenzene, 99 Nitrocarbono SA, 146 Nitrocellulose, 99 p-Nitrochlorobenzene, 99 Nitroethane, 99 Nitrofen, 99 Nitrogen, 99 Nitrogen dioxide, 99 Nitrogen oxides, 99 Nitrogen trifluoride, 99 Nitroglycerin, 100 Nitrokemia 200 Rt., 167 Nitromethane, 100 5-Nitro-o-anisidine, 99 5-Nitro-o-toluidine, 100 Nitrophenols, 100... 

In Japan, bifenox is the only registered diphenyl ether herbicide. The tolerance and/or maximum residue limits (MRLs) are established at 0.1 mg kg for cereals such as rice grain, barley and wheat, and 0.05mgkg for potatoes (Ministry of Health, Labour and Welfare, Japan). Ibe California Department of Food and Agriculture (CDFA) established the minimum detectable quantity of diphenyl ether herbicides at 0.1 mgkg for bifenox, nitrofen and oxyfluorfen. ... 

Chlornitrofen and nitrofen conditions for GC/MS column, cross-linked methyl silicone capillary (12 m x 0.22-mm i.d., 0.33- am film thickness) column temperature, 60 °C (1 min), 18 °C min to 265 °C inlet, transfer line and ion source temperature, 260, 200 and 200 °C, respectively He gas column head pressure, 7.5 psi injection method, splitless mode solvent delay, 3 min electron ionization voltage, 70 eV scan rate, 0.62 s per scan cycle scanned mass range, m/z 100-400. The retention times for chlornitrofen and nitrofen were 11.8 and 11.3 min, respectively. The main ions of the mass spectrum of chlornitrofen were at m/z 317, 319 and 236. Nitrofen presented a fragmentation pattern with the main ions at m/z 283, 202 and 285. ... 

Okumura et al reported State regulatory programs for pesticide residues in food crops analyzed by the CDFA. In the multiresidue analysis of several organochlorine pesticides including diphenyl ether herbicides, bifenox, nitrofen and oxyfluorfen, HPLC has also been used. 

Bifenox, nitrofen and oxyfluorfen HPLC conditions withpost-columnfluorescence reactor system column, C-18 reversed-phase (25cmx4.6-mm i.d.) temperature, 40 °C flow rate, 1 mL min flow composition, acetonitrile-water (1 4, v/v) (2 min), with increase in acetonitrile at 5%min to 90% acetonitrile to acetonitrile-water... 

The recoveries of nitrofen and oxyflourfen from green bean, bell pepper, lettuce and carrot fortified with 0.25 mg kg were obtained using GC/MS. The average recoveries ranged from 106 to 127% and the LOD was 0.05 mg kg ... 

In the HPLC method for the regulatory system of the CDFA, the MDCs are O.lmgkg" for each of bifenox, nitrofen and oxyfluorfen. In the determination of acifluorfen residues in soybeans using PLE and CL, the recovery of acifluorfen fortified with 0.1 mgkg was between 70 and 72%. ... 

A 100-mL volume of benzene is added to the 20 g of air-dried soil and the mixture is shaken vigorously for 2h. After extraction twice with 100 mL of benzene, the combined extract is filtered through filter paper and the filter cake is washed with an additional 20 mL of benzene. The benzene extracts are dried over anhydrous Na2S04 and concentrated to dryness using a vacuum rotary evaporator. The residue is dissolved in an appropriate volume followed by GC/ECD analysis. For the monitoring of pesticide residues in soil, methanol for bifenox and oxyfluorfen and acetonitrile for nitrofen were recommended as the solvents for efficient extraction. ... 

In analyses at fortification levels of 1 and lOmgkg of chlornitrofen, nitrofen and chlomethoxyfen in soil, the recoveries varied from 96 to 103% for GC/ECD (2 m x 3-mm i.d. spiral glass column packed with 1.5% silicone GE SE-30 temperature of column, injector and detector, 220, 230 and 220 °C, respectively) the LOD was 0.1 mgkg. In the method reported by Bao et a/. using a combination of disk SPE with GC/ITDMS, the recovery of oxyfluorfen at fortification levels ranging from 0.01 to 0.4mgkg was between 100 and 102% the LOD was 0.004mgkg. ... 

Niki and Kuwatsuka reported a method involving trifluoroacetylation of the amino derivatives of chlornitrofen, nitrofen and chlomethoxyfen. A 1-mL volume of 10 M NaOH solution was added to 50 g of soil and the mixture was extracted with 100 mL of benzene. After separation and drying over anhydrous Na2S04, the benzene solution was trifluoroacetylated by adding successively 1 mL of 0.1% trifluoroacetic anhydride in benzene and 1 mL of 0.1% triethylamine in benzene. The mixture was shaken for 30 s and diluted to 10 mL with benzene. To remove the excess of trifluoroacetic anhydride, about 2 mL of water were added to the mixture and shaken for 30 s. The benzene layer was dried over anhydrous Na2S04 and injected for gas chromatography/flame ionization detection (GC/FID). 

The GC/FID conditions were as follows column, 1.5% OV-17 (2 m x 3-mm i.d.) glass column N2 carrier gas flow rate, 45mLmin temperature of injection port, column and detector, 240,235 and 235 °C, respectively. The recoveries of these amino derivatives with fortification level ranging from 0.5 to lO.Omgkg" were 62-101% for chlornitrofen, 62-101% for nitrofen and 58-101% for chlomethoxyfen, and satisfactory recoveries from soil were obtained at high concentrations, but the recoveries at lower concentration averaged about 66% for the least recovered compound. Interference from other substances in the soil extracts derived from the acetylation reaction was negligible. 

Gray LE Jr, Kavlok RJ, Ostby J, et al. 1986. An evaluation of figure-eight maze activity and general behavioral development following prenatal exposure to forty chemicals Effects of cytosine arabinoside, dinocap, nitrofen, and vitamin A. Neurotoxicology 7(2) 449-462. 

D 2,4,5-T Alachlor Amifrole Atrazine Metribuzine Nitrofen Trifluralin... 

Pendimethalin Aminonitrofen, see Nitrofen p-(4-Amino-3-nitrophenyl)glucopyranoside, see 2-Nitroaniline... 

Dichloroallyl mercaptan, see Diallate 2,4 -Dichloro-4 -aminodiphenyl ether, see Nitrofen Dichloroaniline, see Iprodione... 

Nitrophenol, see Benzene, EPN, Fluorodifen. Nitrobenzene, Nitrofen, Parathion... 

CASRN 1836-75-5 molecular formula C13H7F3N2O5 FW 284.10 Chemical/Physical. When nitrofen as an aqueous suspension was irradiated using UV light (A. = 300 nm), 2,4 -dichloro-4 -aminodiphenyl ether formed as the major products (>80% of total product formation). In addition, 4-nitrophenol and 2,4-dichlorophenol formed as minor products (<10%). In cyclohexanone, the major photooxidation product was aminonitrofen (Ruzo et al., 1980). 

Yamada-Okabe T, Sakai H, Kashima Y, Yamada-Okabe H (2005) Modulation at a cellular level of the thyroid hormone receptormediated gene expression by 1,2,5,6,9,10-hexabromocyclodo-decane (HBCD), 4,4 -diiodobiphenyl (DIB), and nitrofen (NIP). Toxicol Lett 55 127-133 Zahm SH, Blair A (1993) Cancer among migrant and seasonal farmworkers An epidemiologic review and research agenda. Am J Ind Med 24 753-766 Zahm SH, Ward MH (1998) Pesticides and childhood cancer. Environ Health Perspect 106 893-908... 

Daston GP, Rehnherg BP, Carver B, et ah Punctional teratogens of the rat kidney. II. Nitrofen and ethylenethiourea. Fundam Appl Toxicol 11(3) 401 15, 1988... 

Alfonso LF, Arnaiz A, Alvarez FJ, Qi BQ, Dies-Pardo JA, Vallisi-Soler A, Tovar JA (1996) Lung hypoplasia and surfactant system immaturity induced in the fetal rat by prenatal exposure to nitrofen. Biol Neonate 69 94-100... 

Costlow R, Manson J (1981) The heart and diaphragm target organs in the neonatal death induced by nitrofen. Toxicology 20 209-227... 

Francis BM. 1989. Relative developmental toxicities of nine diphenyl ethers related to nitrofen. Environ Toxicol Chem 8(8) 681-688. 

A foreign compound, which may act in this way is the herbicide nitrofen (2,4-dichloro-4 -nitro diphenyl ether), which causes a variety of malformations lethal to the neonate. There is no growth retardation or embryolethality at doses, which are teratogenic, however (Fig. 6.27), and therefore this exhibits the first type of dose-response relationship (see above). The... 

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