Tolylfluanid

347.26

347.26

211-986-9

382277YXSG

DTXSID8042478

Colorless crystals

74.3

3.90 at 20 deg C

1.52 g/cu cm

96 °C

Decomposes on distillation

175.1ºC

1.606

In water, 0.9 mg/L at 20 deg C

0-6°C

2 x 10 -5 Pa (20 °C)

Oral-Rat LD50: 1000 mg/kg; Oral-Mouse LD50: 1000 mg/kg

Combustion produces toxic chloride, fluoride, nitrogen oxide and sulfur oxide gases

Odorless

Henry's Law constant = 7.6X10-7 atm-cu m/mol at 25 °C /Estimated/

175.32 Ų [M+Na]+

Hydroxyl radical reaction rate constant = 1.8X10-11 cu cm/molecule-sec at 25 °C /Estimated/

III

6.1(b)

2588

3

23-36/37/38-43-48/20-50/53-50-48/23-26

24-26-37-38-45-60-61-63-36/37/39-28

WO6560000

T,N,T+

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Hydrolysis DT50 (22 deg C) 12 days (pH 4), 29 hr (pH 7), <10 min (pH 9). Under environmental conditions, hydrolysis occurs much more rapidly than photolysis.

P260-P273-P280-P284-P305 + P351 + P338-P310

H315-H317-H319-H330-H335-H372-H400

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Incompatible with liquid insecticides and with alkaline substances (e.g. Bordeaux mixture, lime sulfur).

WHO/FAO; Joint Meeting on Pesticide Residues on Tolylfluanid (731-27-1). Available from http://www.inchem.org/pages/jmpr.html as of November 18, 2004

|Danger|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P260, P261, P264, P270, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P310, P312, P314, P320, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Warning|P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 403 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P307+P311, P310, P314, P320, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501

moderately toxic

LD50 Rat oral >5000 mg/kg|LD50 Rat dermal >5000 mg/kg|LD50 Mouse oral >1,000 mg/kg|LD50 Guinea pig oral 250-500 mg/kg|For more Non-Human Toxicity Values (Complete) data for TOLYLFLUANID (11 total), please visit the HSDB record page.

Tolylfluanid's former production and use as a fungicide(1) may have resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3200(SRC), determined from a log Kow of 3.90(2) and a regression-derived equation(3), indicates that tolylfluanid is expected to have slight mobility in soil(SRC). Volatilization of tolylfluanid from moist soil surfaces is not likely(SRC) given an estimated Henry's Law constant of 7.6X10-7 atm-cu m/mole(SRC), calculated from a vapor pressure of 1.50X10-6 mm Hg at 20 °C(2) and a water solubility 9.00X10-1 mg/L(2). Tolylfluanid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Adsorption to soil is expected to attenuate volatilization(SRC). The average half-life of tolylfluanid in soil has been reported as 2 days(4) and may be due to chemical hydrolysis(2).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3200(SRC), determined from a log Kow of 3.90(2) and a regression-derived equation(3), indicates that tolylfluanid is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not likely(3) based upon an estimated Henry's Law constant of 7.6X10-7 atm-cu m/mole(SRC), calculated from a vapor pressure of 1.50X10-6 mm Hg at 20 °C(2) and a water solubility 9.00X10-1 mg/L(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 60 and 660 days, respectively(SRC). Volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 32 years if adsorption is considered(4). According to a classification scheme(5), an estimated BCF of 540(SRC), from a log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Tolylfluanid is expected to undergo hydrolysis based on half-lives of 12 days at pH 4, 29 hours at pH 7, and <10 minutes at pH 9(2). The half-life of tolylfluanid in water has been reported as less than 14 days(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tolylfluanid, which has a vapor pressure of 1.50X10-6 mm Hg at 20 deg(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tolylfluanid 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 22 hours(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase tolylfluanid may be removed from the air by wet and dry deposition(SRC).

Tolylfluanid is expected to undergo hydrolysis based on half-lives of 12 days at pH 4, 29 hours at pH 7, and <10 minutes at pH 9(1). A hydrolysis half-live of 2 days has also been reported(2).

An estimated BCF of 540 was calculated for tolylfluanid(SRC), using a log Kow of 3.90(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not altered physically or chemically once released into the environment.

The Koc of tolylfluanid is estimated as 3200(SRC), using a log Kow of 3.90(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that tolylfluanid is expected to have slight mobility in soil.

The Henry's Law constant for tolylfluanid is estimated as 7.6X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.50X10-6 mm Hg(1), and water solubility, 9.0X10-1 mg/L(1). This Henry's Law constant indicates that tolylfluanid may volatilize from water surfaces(2). 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)(2) is estimated as 60 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 660 days(SRC). Volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 32 years if adsorption is considered(3). Tolylfluanid's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Tolylfluanid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Tolylfluanid was found in food samples tested during 1989, 1990, and 1994 FDA regulatory monitoring(1-3). Additional information was not provided. During the Danish National Pesticide Monitoring Program conducted from January 1995 to December 1996, tolylfluanid was detected in 2 out of 33 pear samples, 5 out of 72 strawberry samples, 2 out of 21 black currant samples, 2 out of 38 and 1 out of 48 tomato samples, and 1 out of 41 cucumber samples(4). The general limit of determination for analytes in this study was 0.05 mg/kg(4). Tolylfluanid was detected (mean, max, limit of detection) in 2.7% of lettuce samples (0.007 ppm, 0.85 ppm, 0.01 ppm), in 5.1% of tomato samples (0.014 ppm, 0.85 ppm, and 0.01 ppm), in 3.0% of lamb's lettuce samples (0.173 ppm, 13.44 ppm, 0.01 ppm), in 13.6% of currant samples (0.017 ppm, 0.3 ppm, and 0.01 ppm), in 7.8% of apple samples (0.01 ppm, 0.55 ppm, 0.003 ppm), in 5.4% of strawberry samples (0.034 ppm, 1.44 ppm, 0.01 ppm), and in 46.0% of pear samples (0.091 ppm, 0.86 ppm, 0.003 ppm) during a Belgian Total Diet Study(5). Tolylfluanid concentrations in the peels of pears previously treated with the fungicide were 2.9 mg/kg after 0 days, 2.8 mg/kg after 99 days, 2.4 mg/kg after 142 days, 1.6 mg/kg after 171 days, 1.3 mg/kg after 197 days, and 1.1 mg/kg after 210 days in cold storage under a controlled atmosphere(6). Concentrations in the pulp under these conditions were 0.1 mg/kg after 0 and 99 days(6). Tolylfluanid was not detected in the pulp after 99 days of cold storage(6). Tolylfluanid was detected in 1 out of 775 fresh pears at a concentration of 0.50 ppm during a study of pesticide residues in Canadian imported commodities (1992-1994)(7). A Sweedish pesticide risk reduction study listed tolylfluanid as a pesticide frequently reported as a residue in domestic fruit and vegetables between 1990 and 1994(8).

Occupational exposure to tolylfluanid may occur through inhalation and dermal contact with this compound at workplaces where tolylfluanid is produced or used. Monitoring data indicate that the general population may have been exposed to tolylfluanid via ingestion of food. (SRC)

A lactating goat was given 14C-ring-labelled tolylfluanid at a dose of 10 mg/kg bw per day by gavage for 3 days. Blood was taken 0.25, 0.5, 1, 2, 3, 4, 6, 8 and 24 hr after the first dose. Milk was sampled before dosing and 8 hr after dosing. Urine and feces were collected at 24-hr intervals. The goat was killed 50 hr after the first dose (2 hr after the last dose), and the liver, kidney, muscle and fat were removed, weighed and sampled for radioactivity. The plasma concentration peaked at 2.2 ug/mL 50 min after dosing. By 50 hr after the first dose, the highest concentrations were seen in kidney (37 mg/kg), followed by liver (20 mg/kg). Low concentrations were found in fat (1.5 mg/kg) and muscle (0.53 mg/kg). The main route of excretion was urine (49% of the administered dose). Fecal excretion accounted for 10% of the administered dose, and only 0.24% was found in milk. ... Approximately 62% of the administered dose was recovered|Six Wistar (Bor:WISW SPF Cpb) rats were dosed orally and one was dosed by intravenous injection with ring-labelled tolylfluanid at 4 mg per rat, corresponding to a dose of 20 mg/kg bw. The rat treated intravenously was killed 5 min after dosing, and those treated orally were killed 2, 4, 8, 24, 48 and 72 hr after dosing. After oral administration, the radioactivity was absorbed relatively rapidly, as radioactivity was detected in all body tissues except compact bone 2 hr after treatment. The kidney, liver and intestinal tract had markedly higher concentrations than other tissues. After intravenous injection, the pattern was quite different, with high concentrations in all tissues, including fat, probably due to the presence of unchanged parent compound, which is relatively lipophilic. After oral administration, the distribution pattern was that of a hydrophilic substance, with no evidence of storage in a particular organ or tissue. ...The presence of high concentrations in the renal medulla and renal papillary area 2 hr after oral dosing indicated rapid, extensive renal excretion. Rapid fecal excretion also appeared to occur. Over the 24 hr after dosing, the concentrations in tissues and organs decreased rapidly, while depletion was much slower during the subsequent 48 hr. A slightly increased concentration of radioactivity in the infraorbital gland may have indicated some elimination in lachrymal fluid.|Groups of BOR: WISW (SPF Cpb) Wistar rats were given phenyl ring-labelled tolylfluanid at 2 mg/kg bw or at 1 mg/kg bw in combination with unlabelled tolylfluanid at 99 mg/kg bw by gavage. Another group of rats received unlabelled tolylfluanid at 2 mg/kg bw per day for 14 days and then a dose of 2 mg/kg bw of radiolabelled tolylfluanid by gavage. The plasma concentration peaked after about 1 h. By 24 h, the plasma 14C concentration had decreased by about 10-fold after 100 mg/kg bw and by about 100-fold after 2 mg/kg bw. The distribution volume in steady state was more than 14 times the body volume, indicating that 14C had been distributed rapidly into peripheral compartments. The short mean residence time in the central compartment of 14 hr indicated rapid redistribution into plasma before excretion. The radioactivity was rapidly excreted, 87-100% of the administered dose being excreted within 48 hr. The main route of excretion was the urine, particularly in females, which excreted < 85% of the administered dose by this route. The tissue concentrations of 14C at 48 hr were low after 100 mg/kg bw. Sex differences were seen in some tissues, with higher concentrations in erythrocytes, kidney, brain and skin in females and higher concentrations in thyroid in males.|A dose of 2 or 20 mg/kg bw of 14C-ring-labelled tolylfluanid was given orally to male and female Wistar rats. A further group of rats of each sex was pretreated for 14 days with non-radioactive tolylfluanid at a dose of 2 mg/kg bw before receiving radioactive compound. Tolylfluanid was quickly and almost completely absorbed (> 95%); the peak plasma concentration was reached within 1.5 hr. Within 48 hr, 75-80% of the radioactivity was excreted in urine, 14-25% in feces and 0.06% in expired air. In animals with biliary fistula, biliary secretion accounted for about 14% of the total elimination. Total residual radioactivity represented 0.07-0.2% of the total administered dose. Higher concentrations of radioactivity were found in liver and kidney (three to seven times the mean body concentration), and lower concentrations were found in perirenal fat, brain, gonads and thyroid (three to nine times less than the mean body concentration). Renal clearance was 3.1-4 mL/min, which corresponds to normal renal plasma flow in rats. No effect of dose was observed on pharmacokinetics.|Single doses of tolylfluanid labelled with 14C at the fluoridichloromethylsulfenyl group were administered orally to rats. At doses of 0.1-20 mg/kg bw, 50-60% of the administered activity was eliminated in urine and 20-30% in feces within 48 hr. ... In rats with biliary fistula given 0.5 mg/kg bw by intraduodenal administration, about 6% of the total radioactivity was eliminated in bile. When tolylfluanid was administered orally at a dose of 5 mg/kg bw, however, 16% of the activity was exhaled within 48 hr, and the maximal plasma concentration (about 1.5 ppm) was attained after 2 hr. ... Of the administered activity, 6% was retained (excluding gastrointestinal tract) for 8 hr after administration, 2% for 48 hr, 1% for 6 days and 0.5% for 12 days. The highest concentrations were found in the thyroid gland, with 5 ppm 1 day after administration and 1 ppm after 10 days. Whole-body autoradiography after intravenous injection of 10 mg/kg bw confirmed this observation.

In a metabolism study in rats, tolylfluanid was administered in single doses of 2 or 100 mg/kg bw, was readily absorbed and rapidly hydrolyzed within 48 hours. Absorption and excretion were independent of dose, sex and pretreatment. About 86-100% of the dose was recovered in 48 hours, with 56-80% of the dose being excreted in urine, 12-36% in the feces, and /about/ 0.48% found in the carcass. Urinary metabolite common to both sexes were dimethylaminosulfonylamino-benzoic acid (RNH 0166; 46-78%), and 4-methylamino-benzoic acid (RNH 0416; 3-6%). Fecal compounds identified were unchanged tolylfluanid (1-19%), dimethylaminosulfotoluidid (DMST; 5-8%), RNH 0166 (3-12%) and RNH 0416 (<1%). The data indicate that tolylfluanid hydrolyzed to DMST, which is then transformed to the major metabolite RNH 0166, which can be further demethylated to the minor metabolite, RNH 0416.|Series of metabolism studies showed that metabolic profile /is/ dependent upon label position. With [dichlorofluoromethyl-14C]-tolylfluanid labeling major urinary metabolite was thiazolidine-2-thione-4carbonic acid resulting from cleavage of the side chain and accounted for 73-74% and 50-63%, respectively by iv and oral routes. Benzene ring label resulted in metabolite 4-(dimethylamino-sulfonylamino) benzoic acid which accounted for 90% of urinary metabolic activity and 70% of fecal radioactivity.|[fluorodichloromethyl-14C]Tolylfluanid was administered orally or intravenously to rats at a single dose of 5 or 10 mg/kg bw. The main metabolite in the urine of treated rats was thiazolidine-2-thioxo-4-carbonic acid, which accounted for 74% of the radioactivity in urine 8 hr after intravenous administration and for 50-63% after oral administration. Tolylfluanid was not detected in urine.|After administration of a single oral dose of 20 mg/kg bw of [14C-benzene ring]tolylfluanid to male Wistar rats, 90% of the radioactivity in urine and 70% of that in feces was due to one metabolite, 4-dimethylaminosulfonylaminobenzoic acid. A minor metabolite (6% of total radioactivity) was not characterized.|For more Metabolism/Metabolites (Complete) data for TOLYLFLUANID (7 total), please visit the HSDB record page.

The plasma concentration fell in a biphasic manner /in goats after 14C-ring-labelled tolylfluanid at a dose of 10 mg/kg bw per day by gavage for 3 days/, with a half-life of 1.6 hr during the first 6 hr after dosing and a half-life of 9.1 hr in the terminal phase. The mean residence time was 7.3 hr.|...Urinary elimination /of tolylfluanid/ took place with a half-life of 2-3 hr during the first 24 hr and then more slowly, with a half-life of about 40 hr from the third day.

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/HUMAN EXPOSURE STUDIES/ ...Six male volunteers received a cotton-wool pad containing dry tolylfluanid on the skin of the forearm for 24 hr. No signs of irritation were observed. In a similar study, no irritation was seen on the skin of 10 male volunteers after a 24-hr exposure.|/CASE REPORTS/ ...Two cases of allergic skin disease were associated with /occupational/ exposure to tolylfluanid. Both cases resolved when the workers were not handling tolylfluanid. In the first case, prurient, pustular lesions on both forearms were seen after packing of tolylfluanid formulations; in the second case, exanthema /(eruption of skin occurring as a symptom of a disease)/ of the face and throat was seen after the worker had spent time in the packing hall. No other abnormalities were found that could be related to exposure to tolylfluanid.

Euparen M

Nominally 98.1% technical product.|Wettable powder, water dispersible granule.|Selected tradenames: Elvaron M; Euparen M; Euparen Multi. Mixtures: Talat (+fenhexamid); Folicur EM (+tebuconazole) (spray, Germany); Folicur Multi (+tebuconazole) (spray); Hattrick (+tebuconazole) (spray, Czech Republic, Slovakia); Melody Multi (+iprovalicarb) (Germany); Yeomji (+tebuconazole) (spray , Korea).

Technical grade and formulated tolylfluanid are produced by Bayer AG in Germany for use outside the United States. No production of tolylfluanid containing products occurs in the U.S.

Product analysis by hplc ... Residues determined by glc.

Agrochemicals -> Acaricides, Fungicides|Pharmaceuticals|Fungicides, Wood preservatives|Environmental transformation -> Pesticides (parent, predecessor)

Tolylfluanid has known environmental transformation products that include N,N-dimethyl-N'-p-tolysulphamide.|Tolylfluanid has known environmental transformation products that include 4-(dimethylaminosulfonyl-amino)benzoic acid (XI), 4-(methylaminosulfonyl-amino)benzoic acid (XII), DMST (II), Dichlorofluoro-methanesulfonic acid, Dichlorofluoromethane-sulfenic-acid, methylaminosulfotoluidide (IX), thiophosgene I, and thiophosgene II.