N-(ジクロロフルオロメチルチオ)-N-(ジメチルアミノスルホニル)アニリン

Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Fungicides

Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

Pesticides -> Fungicides

WHITE POWDER

White, crystalline powder

INSOL IN WATER; 1.5% IN METHANOL; 7% IN XYLENE

SOL IN ACETONE

In water 1.3 mg/l (20 °C). In dichloromethane >200, toluene 145, xylene 70, methanol 15, isopropanol 10.6, hexane 2.6 (all in g/l, 20 °C).

0.00000011 [mmHg]

Vapor pressure = 1X10-6 mm Hg @ 20 °C

1.57X10-7 mm Hg at 25 °C

LIGHT-SENSITIVE BUT DISCOLORATION DOES NOT AFFECT ITS BIOLOGICAL ACTIVITY

STABLE IN STORAGE FOR AT LEAST ONE YR WHEN WORKED UP WITH A SMALL QUANTITY OF INERT MATERIAL; PRACTICALLY NON-VOLATILE

DECOMP BY STRONGLY ALKALINE MEDIA & BY POLYSULFIDES

Positive

2.17

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P317, P321, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P317, P321, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

2002/2076

Dichlofluanid: HSNO Approval: HSR002837 Approved with controls

Technical product may cause skin sensitization; May cause lung damage if swallowed; Causes fluorosis in animals after repeated oral administration; No evidence of reproductive toxicity; Not likely to be carcinogenic in humans; Workers should wear suitable protective clothing, including gloves and footwear. [ToxPlanet: CPS&Q: Biocidal Products] An eye irritant; May cause skin sensitization; [eChemPortal: ESIS]

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.

Skin Sens. 1 (100%)

Acute toxicity - category 4

Acute toxicity (Inhalation: Dusts and mists) - Category 4

Acute Tox. 4

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.

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.

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 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).

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).

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).

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).

MUTAGENICITY; DNA REPAIR-DEFICIENT BACTERIAL TESTS: QUESTIONABLE.

IN 2-YR FEEDING TRIALS ON MALE & FEMALE RATS, THE "NO EFFECT" LEVEL WAS 1500 MG/KG DIET.

LD50 OF EUPAREN IN RAT IS 4630 MG/KG, IN MOUSE 1905 MG/KG, & IN GUINEA PIG 805 MG/KG. CUMULATION COEFFICIENT @ ADMIN RATE OF 1/20 LD50 IS 3.7 IN MICE & 3.3 IN GUINEA PIGS. THRESHOLD DOSE WAS DETERMINED TO BE 5.4 MG/KG IN 10 MO CHRONIC EXPT.

BY USING RECOMBINATION-DEFICIENT (REC) STRAINS OF BACILLUS SUBTILIS, DICHLOFLUANIDE PROVED A POSITIVE MUTAGEN BUT IS NOT YET SPECIFIED AS TO TYPE OF MUTAGENICITY.

For more Non-Human Toxicity Excerpts (Complete) data for DICHLOFLUANID (10 total), please visit the HSDB record page.

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).

If dichlofluanid were used as an acaricide and fungicide, it may result in its direct release to the environment. If released to the atmosphere, dichlofluanid will exist in both the vapor and particulate phases in the ambient atmosphere, based on a measured vapor pressure of 1.57X10-7 mm Hg at 25 °C. Vapor-phase dichlofluanid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals with a half-life of about 1 day. Particulate-phase dichlofluanid may be physically removed from the air by wet and dry deposition. An estimated Koc of 1100 suggests that dichlofluanid will have low mobility in soil. Volatilization from dry and moist soil surfaces should not be significant. Based on limited data, this compound is expected to biodegrade in both soil and water. Dichlofluanid, added to a sandy loam and a silt loam was lost due to mineralization of this compound. Dichlofluanid may degrade in alkaline soils and water; degradation has been shown for this compound in alkaline solution giving N',N'-dimethyl-N-phenylsulphamide as a product of this reaction. Dichlofluanid may adsorb to sediment or particulate matter in water. This compound is not expected to volatilize from water surfaces given an estimated Henry's Law constant of 6.7X10-7 atm-cu m/mole. Moderate bioconcentration in aquatic organisms may occur based on an estimated BCF value of 70. The general population may be exposed to dichlofluanid through the ingestion of contaminated food. (SRC)

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.

Used as fungicide and acaricide; [HSDB] Used in wood preservatives and treatments, e.g., pre-treatment of lumber and brush application to wood;; [CPSS&Q: Biocidal Products]

Applying Wood Preservatives [Category: Other]

ACARICIDE; FUNGICIDE

Fungicidal preventative and curative action. Secondary acaricidal action.

PRODUCED BY THE REACTION OF DICHLOROFLUOROMETHANESULFENYL CHLORIDE WITH N,N-DIMETHYL-N'-PHENYLSULFAMIDE, WHICH IS FORMED BY REACTING SULFURYL CHLORIDE WITH, IN TURN, DIMETHYLAMINE AND ANILINE...

Prepn: E Klauke et al, Belg Pat 609,868 corresp to US Pats 3,285-929, 3,341,403 (1962, 1966, 1967, all to Bayer).

Dimethylsulphamyl chloride + aniline + dichlorofluoromethanesulphenyl chloride (sulphonamide formation/dehydrochlorination)

Dust, wettable powder, water dispersable granule

Wettable powder, dustable powder, water dispersible granules, fumigant (smoke)

Mixtures (dichlofluanid + oxadixyl; copper oxychloride; cymoxanil; tebuconazole)

Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

Pesticides -> Fungicides

...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.