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Fluorodifen

CAS No. 15457-05-3

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Adverse Effects

ACTIVITY: Herbicide (nitrophenyl ether)

CAS Name: 2-nitro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene

Note: WHO: believed obsolete or discontinued

Structure:


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=2631624&dopt=Abstract

Ann Ist Super Sanita 1989;25(4):577-82

Genotoxicity of selected herbicides.

Pinter A, Torok G, Surjan A, Csik M, Borzsonyi M, Kelecsenyi Z.

Twenty-two herbicides were studied in 67 tests for induction of DNA damage, gene mutation and chromosomal changes in vitro and in vivo. Triazine and urea-type herbicides were found to be inactive in all but one test. Of 4 thiocarbamates, molinate and vernolate caused chromosomal changes, namely increased incidence of sister chromatid exchanges and chromosomal aberrations in vitro and increased frequency of micronucleated polychromatic erythrocytes in mouse bone marrow. These compounds, however, did not cause gene mutation and only molinate gave equivocal positive result in bacterial repair test. Out of 11 miscellaneous herbicides, ethofumesate, alachlor, dichlorprop and fluorodifen proved to be positive only in one or two tests. In the light of clastogenicity of some thiocarbamates, serious consideration should be given to start animal carcinogenicity studies with these chemicals.

PMID: 2631624 [PubMed - indexed for MEDLINE]


From Toxline at Toxnet

Environmental Protection Agency Vol:EPA/600/8-88/050 (1987) 27 p

Health effects assessment for Nitrophenols

EPA working group

Available data regarding the environmental fate of the nitrophenols pertain primarily to 4- nitrophenol. It is assumed that the environmental fate is similar for 2-, 3- and 4-nitrophenol. Monitoring data indicate that 4-nitrophenol is removed from the atmosphere by wet and dry deposition (U.S. EPA, 1985). Direct photolysis or reaction with photochemically generated hydroxyl radicals are also potential removal mechanisms. The estimated atmospheric removal half- life of the nitrophenols that is due to rainfall is 3 weeks and the estimated hydroxyl reaction half- life of 2-nitrophenol is 9 days (U.S. EPA, 1985). The half-lives of 2- and 3-nitrophenols in water could not be located in the available literature. U.S. EPA (1985) reported that 4-nitrophenol reacts quite rapidly with hydroxyl radicals in water in the presence of sunlight and that the nitrophenols are capable of undergoing significant biodegradation in various ambient surface waters. The observed photolysis half-life of 4-nitrophenol in aqueous solution is reported to vary from 16 hours to 5.7 days at pH 5, 6.7 days at ph 7 and 13.7 days at pH 11.5 (U.S. EPA, 1985). The soil half- life of 4-nitrophenol was estimated using a decay rate constant of 0.105/day measured in a model soil ecosystem. Soil microorganisms are capable of degrading the nitrophenols and the nitrophenols may be susceptible to leaching in certain soil types, although biodegradation may occur rapidly enough to prevent extensive leaching (U.S. EPA, 1985). Pertinent guidelines and standards including EPA ambient water and air quality criteria, drinking water standards, HAs, AADIs and ACGIH, NIOSH or OSHA occupational exposure limits could not be located in the available literature. The U.S. EPA (1980) defined organoleptic detection thresholds for nitrophenols of 0.24-389 mg/2 based upon the Soviet literature. U.S. EPA (1980) stated that the absence of chronic toxicity data precluded derivation of water criteria for the nitrophenols. The tolerance for the herbicide fluorodifen and its metabolites (including 4-nitrophenol) on peanut hulls, peanuts and peanut vine hay is 0.2 ppm (CFR, 1982). For soybean forage, soybeans, and seed and pod vegetables and their forages, the tolerance is 0.1 ppm (CFR, 1982).


From Toxline at Toxnet

CROP PROT; 5 (3). 1986. 203-208.

CHEMICAL WEED CONTROL IN DIRECT-SEEDED IRRIGATED RICE ORYZA-SATIVA IN THE LAKE CHAD BASIN NIGERIA

OKAFOR LI

Abstract:
BIOSIS COPYRIGHT: BIOL ABS. RRM LUFFA-ECHINATA SORGHUM-AETHIOPICUM ECHINOCHLOA-COLONA ELEUSINE-INDICA DIGITARIA-SANGUINALIS ORYZA-LONGISTAMINATA CYPERUS-ROTUNDUS CYPERUS-ESCULENTUS PROPANIL OXADIAZON FLUORODIFEN BENTAZONE THIOBENCARB DYMRON HERBICIDES GRAIN YIELD


From Toxline at Toxnet

J AGRIC FOOD CHEM; 31 (6). 1983. 1201-1207.

Diphenyl ether herbicides and related compounds: Structure-activity relationships as bacterial mutagens.

DRAPER WM, CASIDA JE

Pest. Chem. Toxicol. Lab., Dep. Entomol. Sci., Univ. Calif., Berkeley, Calif. 94720, USA.

HEEP COPYRIGHT: BIOL ABS. Several 4-nitrodiphenyl ether herbicides and related compounds or their nitroso, hydroxyamino or amino derivatives are mutagens or promutagens in the Salmonella typhimurium (strain TA100)/microsome (S9) assay. Six of eleven 4-nitrodiphenyl ethers examined with no 3-substituent are direct-acting mutagens (4-9 revertants/nmol) and 10 of 11 of the analogous 4-aminodiphenyl ethers (including those of the herbicides fluorodifen, nitrofen and CNP) are mutagens (1-30 revertants/nmol) but only on metabolic activation (+S9). Herbicides with a 3-substituent (i.e., acifluorfen, acifluorfen-methyl, bifenox, bifenox free acid, chlomethoxynil and oxyfluorfen) and their amino derivatives are generally not detected as mutagens (| S9). Nitroso- and (hydroxyamino)nitrofen, nitroso-CNP, nitrosooxyfluorfen and nitrosoacifluorfen are direct-acting mutagens (2-7 revertants/nmol). Rats reduce orally administered nitrofen, CNP, oxyfluorfen, acifluorfen-methyl and bifenox, presumably via nitroso and hydroxyamino intermediates, to the amino compounds that are excreted in the feces. (This study may be related to teratogenesis and carcinogenesis.)


From Toxline at Toxnet

ABST PAP AM CHEM SOC 185:PEST 97,1983

STRUCTURE-ACTIVITY RELATIONSHIPS FOR BACTERIAL MUTAGENESIS BY NITRODIPHENYL ETHERS

DRAPER WA, CASIDA JE

Taxonomic Name: SALMONELLA TYPHIMURIUM,TA100

Test Object: BACTERIA

Name of Agent (CAS RN):

MICROSOMES,RAT LIVER,S9
P-NITRODIPHENYL ETHER ( 620-88-2 )
4-CHLORO-P-NITRODIPHENYL ETHER ( 1836-74-4 )
4-FLUORO-P-NITRODIPHENYL ETHER ( 2561-25-3 )
4-METHYL-P-NITRODIPHENYL ETHER ( 3402-74-2 )
4-CYANO-P-NITRODIPHENYL ETHER ( 17076-68-5 )
3-METHYL-P-NITRODIPHENYL ETHER ( 2303-25-5 )
3,5-DIMETHYL-P-NITRODIPHENYL ETHER ( 1630-17-7 )
BIFENOX ( 42576-02-3 )
BIFENOX FREE ACID ( 59024-05-4 )
ACIFLUORFEN ( 50594-66-6 )
ACIFLUORFEN METHYL ESTER ( 50594-67-7 )
NITROFEN ( 1836-75-5 )
OXYFLUORFEN ( 42874-03-3 )
CHLOMETHOXYNIL ( 32861-85-1 )
FLUORODIFEN ( 15457-05-3 )
P-AMINODIPHENYL ETHER ( 139-59-3 )
4-CHLORO-P-AMINODIPHENYL ETHER ( 101-79-1 )
4-FLUORO-P-AMINODIPHENYL ETHER ( 36160-82-4 )
4-METHYL-P-AMINODIPHENYL ETHER ( 41295-20-9 )
4-CYANO-P-AMINODIPHENYL ETHER ( 17076-69-6 )
3-METHYL-P-AMINODIPHENYL ETHER ( 56705-84-1 )
3,5-DIMETHYL-P-AMINODIPHENYL ETHER ( 86823-17-8 )
2-AMINO-5-(2,4-DICHLOROPHENOXY)BENZOIC ACID METHYL ESTER ( 59216- )
75-0
2-AMINO-5-(2,4-DICHLOROPHENOXY)BENZOIC ACID ( 59216-76-1 )
2-AMINO-5-(2-CHLORO-4-(TRIFLUOROMETHYL)PHENOXY)BENZOIC ACID ( 742 )
74-36-5
2-AMINO-5-(2-CHLORO-4-(TRIFLUOROMETHYL)PHENOXY)BENZOIC ACID METHYL ESTER ( 58105-66-1 )
4-(2,4-DICHLOROPHENOXY)BENZENAMINE ( 14861-17-7 )
4-(2-CHLORO-4-(TRIFLUOROMETHYL)PHENOXY)-2-ETHOXYBENZENAMINE ( 643 )
78-95-6
4-(2,4-DICHLOROPHENOXY)-2-METHOXYBENZENAMINE ( 59683-60-2 )
2-(4-AMINOPHENOXY)-5-(TRIFLUOROMETHYL)BENZENAMINE ( 24219-88-3 )
4-(2-NITRO-4-(TRIFLUOROMETHYL)PHENOXY)BENZENAMINE ( 24219-87-2


From Toxline at Toxnet

Source: Agr. Chem.; 25(3): 21-2, 24, 47 1970

New pesticides for 1970.

ANON

HAPAB The status and availability of a number of new and recently introduced pesticides are reviewed. Newly registered herbicides include Igran 80W (Geigy), Ro-Neet (Stauffer), Tandex (Niagara), Preforan and Marolan (Ciba) and Solo (Uniroyal). Five herbicides have received expanded registrations: Evik (Geigy), Royal MH30 (Uniroyal) and Stauffer's Tillam, Prefar and Sutan 6E. Temporary labels were granted for the herbicides Bladex (Shell), CP52223 (Monsanto) and Kerb 75W (Rohm and Haas). Herbicides awaiting registration and in test stages are: VCS 438 (Velsicol), CP53619 (Monsanto), Nopalmate (Pennwalt), Dowco 221 (Dow), ER5461 (Esso Research), Bay 94337 (Chemagro) Alar and Uni-F 523 (Uniroyal). New insecticides being tested or awaiting registration cited are: Lannate (E. I. duPont), Torak (Hercules), Phosvel (Velsicol), Biothin (American Cyanamid) and Chemagro's Bay 93820, 37289, 68138 and 37344. Those insecticides receiving new registrations are: Temik 10G (Union Carbide), Cygon 267 and Cygon Systemic 25 (American Cyanamid), and the pyrethrums Pyrenone (Niagara), Prentox Pyronyl 60-6 (Prentiss) and SBP-1382. Omite (Uniroyal) had its label expanded to cover a wider range of uses. Dyfonate 20G (Stauffer) is a new 20% granular formulation of Dyfonate 10G (a 10% formulation). American Cyanamid has improved their Cythion for ULV (0.92 oz/acre) control of mosquitos. Uniroyal is awaiting registration of its new systemic fungicide, Plantvax. Bay 78175 (Chemagro) is being tested as a broad spectrum soil and seed treatment fungicide. Miller Chemical and Fertilizer Company has introduced Nu-Film 17, a residue control agent which increases the residual life and effectiveness of such insecticides as Sevin, morestan, guthion, difolatan, malathion, daconil, polyram and others. 1970


From Toxline at Toxnet

Source: Dissertation Abstr. Intern.; 31(3): 1020B 1970

The persistence and movement of p-nitrophenyl-alpha,alpha,alpha-trifluoro-o-nitro-p-tolyl ether in plants and soils.

Walter J

HAPAB Microfilm and Xerox copies of the thesis are available from University Microfilms at $4.00 and $6.00, respectively (order No. 70-16,771). 1970

CAS Registry Numbers:
15457-05-3


 
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