Tolclofos-methyl

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

For more Preventive Measures (Complete) data for Tolclofos-methyl (6 total), please visit the HSDB record page.

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection: Handle with gloves.

Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 761-1540(2) indicate that tolclofos-methyl is expected to have low mobility in soil(SRC). Volatilization of tolclofos-methyl from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 1.5X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 4.3X10-4 mm Hg(2), and water solubility, 1.1 mg/L(3). Tolclofos-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Tolclofos-methyl had field half-lives of 26-30 days(3). Tolclofos-methyl, applied to soil and exposed to sunlight outdoors from May-Jun had a degradation half-life of 1-2 days(4).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 761-1540(2), indicate that tolclofos-methyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.5X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 4.3X10-4 mm Hg(2), and water solubility, 1.1 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 hours and 10 days, respectively(SRC). Tolclofos-methyl has a reported hydrolysis half-life of 90 days at pH 6.1(5). According to a classification scheme(6), BCFs of 281-1383 measured in fish(7), suggest bioconcentration in aquatic organisms is high to very high. Tolclofos-methyl is rapidly biodegraded(4).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tolclofos-methyl, which has a vapor pressure of 4.3X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tolclofos-methyl 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 6 hours(SRC), calculated from its rate constant of 6.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Tolclofos-methyl does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Tolclofos-methyl was detected in 3 of 122 head lettuce and 1 of 82 potato samples collected Jan 1995 to Dec 1996 in a Danish national commodity survey, it was not detected in grapefruit, lemon, mandarin, clementine, orange, apple, pear, quince, apricot, cherries, peach, nectarine, plum, grape, strawberry, black berry, boysenberry, elderberry, raspberry, rowanberry, bilberry, red and black currant, gooseberry, banana, fig, kiwi, pomegranate, beetroot, carrot, celeriac, horseradish, parsnip, parsley root, radish, garlic, onion, tomato, pepper, eggplant, cucumber, melon, squash, corn, broccoli, cauliflower, Brussel sprout, cabbage, kale, spinach, chive, dill, marjoram, rosemary, thyme, bean, pea, celery, leek, rhubarb, mushroom or sunflower seed(1). Tolclofos-methyl was not detected in 1579 food samples (cabbage, grape leaf, lettuce, melokhia, spinach, watercress, artichoke, beans, cauliflower, cantaloupe, cucumber, eggplant, peas, okra, onion, pepper, squash, tomato, carrot, sweet potato, taro, apple, apricot, banana, dates, fig, grape, guava, lemon, lime, mango, orange, peach, pear, plum, pomegranate, strawberry) collected throughout 1996 from 8 Egyptian local markets located in 6 governorates(2). Tolclofos-methyl was detected at 0.08 and 0.32-2.26 mg/kg in 1 of 20 banana and 4 of 95 tangerine samples collected Sep 2000 to Jun 2001 from agricultural cooperatives located near Valencia, Spain(3). It was not detected (detection limit 0.01 mg/kg) in 15 chard, 20 onion, 15 pepper, 15 lemon and 20 orange samples(3). Tolclofos-methyl was detected at 2.0 ng/g in 1 of 173 agricultural product samples from a local market in Japan(4). Tolclofos-methyl was detected at 18.25-404.5, 13.14-119.4 and 23.15-3673 ug/kg in 102 of 118, 22 of 24 and 9 of 10 fresh, red and dried ginseng samples tested(5). Tolclofos-methyl was not detected (detection limit 0.002 mg/kg) in 20 milk, 17 egg and 17 fish samples collected from the market in China(6). Tolclofos-methyl was not detected (detection limit 0.3 ug/kg) in six commercial honey and five raw citrus honey samples collected directly from Spanish beekeepers(7).

In a total market basket survey conducted in Belgium from 1991 to 1993 tolclofos-methyl was not detected in many food commodities (potatoes, onions, cauliflower, beans, mushrooms, peas, spinach, cucumbers, peppers, leeks, tomato, Belgian endive, carrots currents, apples, oranges, banana, lemon, strawberry, pineapple, grapes, kiwi, melon, nectarines, pear, peach, wheat flour, rice, tea, water, wine and bran)(1). Tolclofos-methyl was detected in the following commodities(1):[Table#8517]

IDENTIFICATION AND USE: Tolclofos-methyl is agricultural fungicide. HUMAN STUDIES: Tolclofos-methyl induced weak responses in vitro in human estrogenicity assays. Negative results were reported for in vitro unscheduled DNA synthesis assay conducted in human carcinoma cells (HeLa). ANIMAL STUDIES: Tolclofos-methyl was minimally irritating to eyes and not irritating on skin when tested in rabbits. It was not a skin sensitizer when tested in guinea pigs. After acute exposure of rats, mice, and dogs to tolclofos-methyl, animals showed decreased spontaneous motor activity, dyspnea, piloerection, urinary incontinence and ataxia. Recovery was complete by day 10. Brain cholinesterase activity was lower 16 days after treatment in dogs given 1000 mg/kg bw than in animals given lower doses. In dogs at 2000 ppm, plasma cholinesterase activity was decreased by 19-26% in females throughout the study, but no significant decreases were seen in erythrocyte cholinesterase activity in animals of each sex or in plasma cholinesterase activity in males. Brain cholinesterase activity was unaffected by treatment. In rabbits treated dermally erythrocyte cholinesterase activity was lower than in controls in males, but there was no dose-effect relationship. Plasma cholinesterase activity was lower (by 22-29%) than in controls in animals of each sex at 300 and 1000 mg/kg bw per day. The relative weights of the kidneys were increased (by 20%) in females at 1000 mg/kg bw per day. Tolclofos-methyl was not teratogenic in rabbits at doses up to and including 3000 mg/kg bw per day, which was toxic to dams. Tolclofos-methyl was not embryotoxic, fetotoxic or teratogenic in rats at doses up to and including 50 mg/kg bw per day. An in vitro reverse mutation assay with Salmonella typhimurium TA98, 100, 1535, 1537, 1538 was negative with and without metabolic activation. In vivo genotoxicity studies in rats and mice were negative as well.

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of August 9, 2018: http://actor.epa.gov/dashboard/]

Tolclofos-methyl was detected at 0.003 ug/L in catchment water from a paddy in 1992, monitoring data was collected May-Nov each year from 1990 to 1993(1). Less than 1% of tolclofos-methyl was found in leachate samples collected 3-37 days after standard application to a golf course in Japan(2).

The Koc of tolclofos-methyl was reported to range from 761-1540(1). According to a classification scheme(2), this Koc range suggests that tolclofos-methyl is expected to have low mobility in soil(SRC). A Koc of 3620 was reported in sediment(3).

Measured sorption coefficient for tolclofos-methyl in five soils(1).[Table#8518]

URBAN/SUBURBAN: Tolclofos-methyl was detected at 0.05 ng/cu m in atmospheric samples collected Apr 23-24, 1992 from Kitakyushu City, Japan; it was not detected (detection limit 0.04 ng/cu m) in samples collected Jul 21-22, 1991 in the same city(1).

/EPIDEMIOLOGY STUDIES/ The medical records of 20 workers in Japan were reviewed. All workers had been engaged continuously in packaging operations since manufacture of technical-grade tolclofos-methyl began in 1988, for an average of 4 hr/day. No occupation-related problems were observed or reported. Plasma and erythrocyte cholinesterase activities were not measured.

/ENDOCRINE MODULATION/ The estrogenic potential of four pesticides (endosulfan, prochloraz, tolchlofos-methyl and propamocarb) was compared in parallel with 17beta-estradiol (E2) by reporter constructs in transient transfected MCF-7BUS and in stable transfected MVLN cells. Similar detection limit and half maximum effect concentration was determined for E2, whereas the maximum effect concentration of E2 was much higher in MCF-7BUS (10 nM) than in MVLN (150 pM), with the induced response being approximately six times the level in MVLN cells. Alone the four pesticides elicited the same relative response in the two bioassays, and similar data was obtained upon co-exposure with E2 for endosulfan and propamocarb. In contrast to the transient MCF-7BUS system, endosulfan further increased the E2 induced response in MVLN cells, whereas propamocarb did not induce the E2 response in MVLN cells as observed in MCF-7BUS cells. In conclusion, high agreement between the two reporter assays was observed, although some performance characteristics have to be considered.

/ENDOCRINE MODULATION/ A number of pesticides are used in agricultural production with some having estrogenic activities, such as endocrine-disrupting chemicals that may affect wildlife and humans. This study aimed to detect the estrogenic effects of some mixed agricultural chemicals in agricultural production. The assay to measure estrogenic activity was evaluated by the cell proliferative activity of MtT/Se cells, which respond well to estrogen. To evaluate MtT/Se cells we went down to the molecular level of estrogen receptor (ER)-alpha and ER-beta expression. The proportion of ER-alpha to ER-beta was 3.55:1, as determined by semi-quantitative real-time polymerase chain reaction (PCR). These results showed that ER-alpha was dominant in MtT/Se cells on the transcriptional level, therefore implying that the estrogenic activity detected by these cells may be mainly mediated by ER-alpha. It was found that diazinon, tolclofos-methyl, pyriproxyfen, prothiofos and thiabendazole had estrogenic activity. Several pesticides are often present in agricultural products. Therefore, we evaluated the estrogenic activity of a mixture of two pesticides. The REC(10) levels of prothiofos/pyriproxyfen and thiabendazole/orthophenylphenol were increased up to 10-fold. We concluded that those two pesticide combinations showed a significantly higher estrogenic effect in comparison to the results of the respective pesticides when tested individually.

/ENDOCRINE MODULATION/ Twenty-four pesticides were tested for interactions with the estrogen receptor (ER) and the androgen receptor (AR) in transactivation assays. Estrogen-like effects on MCF-7 cell proliferation and effects on CYP19 aromatase activity in human placental microsomes were also investigated. Pesticides (endosulfan, methiocarb, methomyl, pirimicarb, propamocarb, deltamethrin, fenpropathrin, dimethoate, chlorpyriphos, dichlorvos, tolchlofos-methyl, vinclozolin, iprodion, fenarimol, prochloraz, fosetyl-aluminum, chlorothalonil, daminozid, paclobutrazol, chlormequat chlorid, and ethephon) were selected according to their frequent use in Danish greenhouses. In addition, the metabolite mercaptodimethur sulfoxide, the herbicide tribenuron-methyl, and the organochlorine dieldrin, were included. Several of the pesticides, dieldrin, endosulfan, methiocarb, and fenarimol, acted both as estrogen agonists and androgen antagonists. Prochloraz reacted as both an estrogen and an androgen antagonist. Furthermore, fenarimol and prochloraz were potent aromatase inhibitors while endosulfan was a weak inhibitor. Hence, these three pesticides possess at least three different ways to potentially disturb sex hormone actions. In addition, chlorpyrifos, deltamethrin, tolclofos-methyl, and tribenuron-methyl induced weak responses in one or both estrogenicity assays. Upon cotreatment with 17beta-estradiol, the response was potentiated by endosulfan in the proliferation assay and by pirimicarb, propamocarb, and daminozid in the ER transactivation assay. Vinclozolin reacted as a potent AR antagonist and dichlorvos as a very weak one. Methomyl, pirimicarb, propamocarb, and iprodion weakly stimulated aromatase activity. Although the potencies of the pesticides to react as hormone agonists or antagonists are low compared to the natural ligands, the integrated response in the organism might be amplified by the ability of the pesticides to act via several mechanism and the frequent simultaneous exposure to several pesticides.

Tolclofos-methyl was not detected (detection limit 5-10 ng/g) in pale chub (Zacco platypus), ayu sweetfish (Plecoglossus altivelis) or dark chub (Zacco temminckii) samples collected Apr 1992-Mar 1993 from seven rivers flowing into Lake Biwa, Japan(1).

For tolclofos-methyl (USEPA/OPP Pesticide Code: 128905) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

For control of soilborne diseases caused by Rhizoctonia, Sclerotium, and Typhula on bulbs, cereals, coffee, cotton, peanuts, potatoes, sugar beets, vegetables, ornamentals, turf, and lawns.

... Used as a seed treatment and a soil fungicide.

Agricultural fungicide.

Toclofos-methyl is produced by reaction of 2,6-dichloro-p-cresol with (O,O-dimethyl) chlorothiophosphate in the presence of a base.

Preparation: T. Kato et al., Germany patent 2501040; United Kingdom patent 1467561 (1975, 1977 both to Sumitomo).

ST Pre-mix #2 (Albaugh, LLC): Active ingredient: fludioxonil 1.79%; metalaxyl 11.23%; and tolclofos-methyl 6.95%.

Tolclofos-methyl Technical Fungicide (Valent USA, LLC): Active ingredient: tolclofos-methyl 97.0%.

Rizolex Flowable Fungicide (Valent USA, LLC): Active ingredient: tolclofos-methyl 42.0%.

Premix Partners: Thiram

For more Formulations/Preparations (Complete) data for Tolclofos-methyl (6 total), please visit the HSDB record page.