Dichlofluanid
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Dichlofluanid
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CAS No:
1085-98-9
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Formula:
C9H11Cl2FN2O2S2
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Chemical Name:
Dichlofluanid
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Synonyms:
Methanesulfenamide,1,1-dichloro-N-[(dimethylamino)sulfonyl]-1-fluoro-N-phenyl-;Sulfamide,N-[(dichlorofluoromethyl)thio]-N′,N′-dimethyl-N-phenyl-;1,1-Dichloro-N-[(dimethylamino)sulfonyl]-1-fluoro-N-phenylmethanesulfenamide;Bayer 47531;Dichlofluanid;Euparen;N-[(Dichlorofluoromethyl)thio]-N′,N′-dimethyl-N-phenylsulfamide;BAY 47531;N-Phenyl-N-(fluorodichloromethylsulfenyl)-N′,N′-dimethylsulfamide;Dichlofluanide;N,N-Dimethyl-N′-phenyl-N′-(fluorodichloromethylthio)sulfamide;N′-(Dichlorofluoromethylthio)-N,N-dimethyl-N′-phenylsulfamide;Oiparen;N,N-Dimethyl-N′-phenyl-N′-(dichlorofluoromethylthio)sulfamide;Elvaron;Pecudin;Eparen;Diclofluanide;Chlormethionate;Preventol A 4;Preventol A 4S;Coatcide TW;Euparen WG;Lichenicide 246;N,N-Dimethyl-N′-(dichlorofluoromethylthio)-N′-phenylsulfamide;NSC 218451;129428-96-2;12698-56-5;56590-61-5;79235-99-7;90416-56-1;1135443-43-4
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CAS No:
Description
ChEBI: A member of the class of sulfamides that is sulfamide in which the hydrogens attached to one of the nitrogens are replaced by methyl groups, while those attached to the other nitrogen are replaced by a phenyl and a [dichloro(fluoro)methyl]sulfanediyl group A fungicide introduced in 1965 and used in the cultivation of fruit and vegetables, as well as in wood preservatives, it is no longer approved for use in the European Union.
Dichlofluanid is a member of the class of sulfamides that is sulfamide in which the hydrogens attached to one of the nitrogens are replaced by methyl groups, while those attached to the other nitrogen are replaced by a phenyl and a [dichloro(fluoro)methyl]sulfanediyl group. A fungicide introduced in 1965 and used in the cultivation of fruit and vegetables, as well as in wood preservatives, it is no longer approved for use in the European Union. It has a role as an acaricide and an antifungal agrochemical. It is a member of sulfamides, an organofluorine compound, an organochlorine compound and a phenylsulfamide fungicide. It derives from a sulfamide.
Dichlofluanid Basic Attributes
333.23
333.23
214-118-7
76A92XU36Y
218451
DTXSID5041851
WHITE POWDER|White, crystalline powder
Characteristics
74.3
3.45
1.5752 (rough estimate)
105-105.6 °C
154°C (rough estimate)
2 °C
1.6000 (estimate)
In water 1.3 mg/l (20 deg C). In dichloromethane >200, toluene 145, xylene 70, methanol 15, isopropanol 10.6, hexane 2.6 (all in g/l, 20 deg C).
APPROX 4°C
1.5 x 10 -5 Pa (20 °C)
Oral-rat LD50: 500 mg/kg; Oral-Mouse LD50: 1250 mg/kg
Decomposes toxic halide, nitrogen oxide, sulfur oxide gas by heating
Safety Information
III
6.1(b)
2588
3
20-36-43-50/53-20/21/22-11-50
24-37-60-61-36-26-16-36/37
WO6475000
Xn,N,F
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
DECOMP BY STRONGLY ALKALINE MEDIA & BY POLYSULFIDES
P261-P273-P280-P302 + P352 + P312-P304 + P340 + P312-P501
H302 + H332-H311-H317-H319-H410
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
VETTORAZZI FG; STATE OF THE ART OF THE TOXICOLOGICAL EVALUATION CARRIED OUT BY THE JOINT FAO/WHO EXPERT COMMITTEE ON PESTICIDE RESIDUES. III. MISCELLANEOUS PESTICIDES USED IN AGRICULTURE AND PUBLIC HEALTH; RESIDUE REV 66: 137-84 (1977). A REVIEW ON PESTICIDE CHEMICALS EXAMINED BY FAO/WHO JOINT MEETINGS FROM 1963-1975.
|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P333+P313, P337+P313, P363, P391, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 346 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P261, P264, P271, P272, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P333+P313, P337+P313, P363, P405, and P501
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.
Avoid contact with eyes and skin and inhalation of spray mist
Toxicity
moderately toxic
If dichlofluanid were used as an acaricide and fungicide(1), it may result in its direct release to the environment. (SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1100(SRC), determined from a structure estimation method(2), indicates that dichlofluanid will have low mobility in soil(SRC). Based on limited data, dichlofluanid is expected to biodegrade in soil(SRC). Dichlofluanid, added to a sandy loam and a silt loam was lost due to mineralization of this compound(3). Volatilization of dichlofluanid should not occur from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.7X10-7 atm-cu m/mole(SRC), using a recommended regression equation(4), or from dry soil surfaces(SRC), based on a measured vapor pressure of 1.57X10-7 mm Hg(SRC), determined using a fragment constant method(5). Dichlofluanid may degrade in alkaline soils(SRC); degradation has been shown for this compound in alkaline solution giving N',N'-dimethyl-N-phenylsulphamide as a product of this reaction(6).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1100(SRC), determined from a structure estimation method(2), indicates that dichlofluanid may adsorb to suspended solids and sediment in water(SRC). Based on limited soil study data, dichlofluanid may biodegrade in water(SRC). Dichlofluanid, added to a sandy loam and a silt loam was lost due to mineralization of this compound(3). Dichlofluanid should not volatilize from water surfaces based on an estimated Henry's Law constant of 6.7X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated BCF value of 70(1,SRC), from an estimated log Kow(5,SRC), suggests that dichlofluanid may moderately bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(6). Dichlofluanid may degrade in alkaline waters(SRC); degradation has been shown for this compound in alkaline solution giving N,N'-dimethyl-N-phenylsulphamide as a product of this reaction(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlofluanid, which has a measured vapor pressure of 1.57X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dichlofluanid 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 about 1 day(3,SRC). Particulate-phase dichlofluanid may be physically removed from the air by wet and dry deposition(SRC).
DICHLOFLUANID IS DEGRADED BY UV LIGHT IN METHANOL, BENZENE & ACETONE SOLN. PRODUCTS FROM ACETONE INCL N,N-DIMETHYL-N'-PHENYL SULFAMIDE, PHENYLISOCYANATE, PHENYL ISOTHIOCYANATE & DIMETHYL AMIDOSULFONYL CHLORIDE. GAS CHROMATOGRAPHY & MASS SPECTROMETRY INDICATED PRESENCE OF BIS(DICHLOROFLUOROMETHYL)DISULFIDE, 1-(DICHLOROFLUOROMETHYLTHIO)PROPAN-2-ONE & 1-(DICHLORO FLUOROMETHYL SULFONYL) PROPANE-2-ONE. IN VITRO TESTS AGAINST BOTRYTIS CINEREA SHOWED THAT ULTRAVIOLET IRRADIATION DECREASED THE ACTIVITY OF DICHLOFLUANID AND THAT SYNERGISM DID NOT OCCUR.|The rate constant for the vapor-phase reaction of dichlofluanid with photochemically produced hydroxyl radicals has been estimated as 1.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Dichlofluanid degrades in alkaline solution giving N',N'-dimethyl-N-phenylsulphamide(2).
An estimated BCF value of 70 was calculated for dichlofluanid(SRC), using an estimated log Kow of 2.72(1,SRC) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms may be an important fate process(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for dichlofluanid can be estimated to be about 1100(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that dichlofluanid has low mobility in soil(SRC). Dichlofluanid added to a sandy loam and a silt loam was found mainly in the 0-10 cm soil layers of both soils during a three year period(3).
The Henry's Law constant for dichlofluanid is estimated as 6.7X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that dichlofluanid will volatilize slowly from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 100 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 730 days(2,SRC). Dichlofluanid's estimated values for vapor pressure, 1.57X10-7 Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces will not occur(SRC).
Dichlofluanid was detected but concentrations were not reported during the 1989(1), 1990(2), 1994(3) and the 1978-1982(4) and 1983-1986(5) regulatory and incidence/level monitoring of both domestic and imported foods, primarily raw agricultural products. Dichlofluanid was detected in 8 of 19,851 samples of domestic and imported food and feed commodities at concentrations up to and greater than 2 ppm(6).
Drug Information
3. 3= Moderately toxic: probable oral lethal dose (human) 0.5-5 g/kg, between 1 ounce & 1 pint (or 1 lb) for 70 kg person (150 lb).
When applied to strawberries, dichlofluanid disappearance followed first order kinetics in the first 21 days.
FOLLOWING TREATMENT FRUIT CONTAINS RESIDUES OF BOTH UNCHANGED COMPD & ITS METABOLITE, N,N'-DIMETHYL-N-PHENYL DIAMINO SULFIDE.|STUDIES ON METABOLIC FATE OF DICHLOFLUANID IN STRAWBERRIES SHOW IN VITRO REACTIONS WITH CELL THIOLS. IN PLANTS TREATED WITH (14)C-DICHLOFLUANID, NO PARENT CMPD DETECTED IN FRUIT. 83% WERE UNIDENTIFIED, VERY POLAR METABOLITES; 3% WAS THIAZOLIDINE-2-THIONE-4-CARBOXYLIC ACID.
METABOLITE WAS SLIGHTLY MORE TOXIC & LESS CUMULATIVE THAN EUPAREN.
Bay 47531
Dichlofluanid Use and Manufacturing
Prepared with aniline as raw material.
Fungicide.
Not marketed in the US.
Dust, wettable powder, water dispersable granule|Wettable powder, dustable powder, water dispersible granules, fumigant (smoke)|Mixtures (dichlofluanid + oxadixyl; copper oxychloride; cymoxanil; tebuconazole)
...INTRODUCED IN 1965 BY BAYER AG...|IT IS RECOMMENDED THAT TOLERANCE OF 1.3 MG/KG BE ESTABLISHED FOR EUPAREN & ITS METABOLITE ON GRAPES & THAT 0 TOLERANCE LEVEL BE SET IN STRAWBERRIES. RESIDUE IN EXCESS OF 10 PPM WILL ALTER TASTE OF FRUIT.|...A MEMBER OF THE ARYL(DICHLOROFLUOROMETHYLTHIO) CMPD... A PROTECTIVE FUNGICIDE WITH A BROAD RANGE OF ACTIVITY USED FOR CONTROL OF VENTURIA SPP ON APPLES & PEARS, BOTRYTIS SPP & DOWNY MILDEWS. HAS SOME EFFECT ON POWDERY MILDEWS...|FOR CONTROLLING BOTRYTIS ON STRAWBERRIES, RASPBERRIES, CURRANTS, & VINE GRAPES, ROSE MILDEW & OTHER FUNGAL DISEASES ON ORCHARD FRUITS, GARDEN CROPS, & ORNAMENTALS. SUPRESSION OF MITES, DOWNY POWDER, POWDERY MILDEW.|For more General Manufacturing Information (Complete) data for DICHLOFLUANID (9 total), please visit the HSDB record page.
DETERMINATION OF DICHLOFLUANID IN FORMULATIONS BY GLC.|A THIN-LAYER CHROMATOGRAPHIC METHOD IS DESCRIBED FOR DETERMINATION OF EUPAREN AND ITS METABOLITE, N',N'-DIMETHYL-N-PHENYLDIAMIDE SULFATE, IN STRAWBERRIES AND GRAPES. LIMIT OF THIN-LAYER CHROMATOGRAPHY SENSITIVITY IS 0.02 MG/KG FOR EUPAREN AND 0.06 MG/KG FOR ITS METABOLITE N',N'-DIMETHYL-N-PHENYLDIAMINE SULFATE.|Product analysis by HPLC or by reaction with sodium methoxide and, ultimately, titration of the chloride. Residues determined by GLC.|FDA Method 242.1. Organonitrogen Residues General Method for Nonfatty Foods Including Acetone Extraction and Isolation in Organic Phase. Analysis by GC/ECD.
Agrochemicals -> Fungicides|Fungicides|Pesticides -> Fungicides|Environmental transformation -> Pesticides (parent, predecessor)
Dichlofluanid has known environmental transformation products that include N,N-Dimethylaminosulfanilide and N,N-Dimethylsulfamide.|Dichlofluanid has known environmental transformation products that include dimethylaminosulfanilide.
Computed Properties
Molecular Weight:333.2
XLogP3:3.6
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:331.9623035
Monoisotopic Mass:331.9623035
Topological Polar Surface Area:74.3
Heavy Atom Count:18
Complexity:367
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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