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Flutolanil

Flutolanil structure

Flutolanil 

structure
  • CAS No:

    66332-96-5

  • Formula:

    C17H16F3NO2

  • Chemical Name:

    Flutolanil

  • Synonyms:

    Benzamide,N-[3-(1-methylethoxy)phenyl]-2-(trifluoromethyl)-;N-[3-(1-Methylethoxy)phenyl]-2-(trifluoromethyl)benzamide;3′-Isopropoxy-2-trifluoromethylbenzanilide;Flutolanil;Moncut;ProStar;Moncoat;84461-35-8;1135441-60-9

  • Categories:

    Agrochemicals  >  Fungicides

Description

COLOURLESS-TO-WHITE CRYSTALS.


COLOURLESS-TO-WHITE CRYSTALS.


Flutolanil is a member of the class of benzamides, obtained by formal condensation of the carboxy group of 2-(trifluoromethyl)benzoic acid with the amino group of 3-(ispropyloxy)aniline. A fungicide used to control a range of pathogens especially Rhizoctonia spp. on rice, turf and other crops. It has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical. It is a member of benzamides, an aromatic ether, a member of (trifluoromethyl)benzenes and a benzanilide fungicide.

Flutolanil Basic Attributes

323.31

323.31

613-921-3

2USL6Y9JZ4

1265

DTXSID8024109

White, crystalline solid|Colorless crystals

2924299033

Characteristics

38.3

3.7

1.3 g/cm3

102 °C

339.1ºC at 760 mmHg

158.9ºC

1.543

Solubility in water, g/100ml at 20°C: 0.001 (none)

0-6°C

Vapour pressure at 20°C: negligible

Oral-Rat LD50: 10000 mg/kg; Oral-Mouse LD50: 10000 mg/kg

Flammable; burning produces toxic nitrogen oxides and chloride gases

Henry's Law constant = 7.1X10-7 atm-cu m/mol at 25 °C (est VP/WSOL)

175.45 Ų [M+H]+ [CCS Type: TW]

Pale yellowish/greyish powder (technical)|Hydroxyl radical reaction rate constant = 1.5X10-14 cu cm/mole-sec at 25 °C (est)

Safety Information

CV5581320

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

Stable under recommended storage conditions.

P273, P391, P501

H401

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.

Incompatible materials: Strong oxidizing agents.

Combustible. Liquid formulations containing organic solvents may be flammable.

|Warning|H400 (79.49%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 156 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]|Not Classified

Eye/face protection: 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: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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: Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. 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.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. 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: Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. 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.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

In a study ... reported in 1986, the acute ocular irritancy of flutolanil (purity, 97.5%) was investigated in six male New Zealand white rabbits, which received a dose of 0.1 g instilled into the conjunctival sac. There was no evidence of an initial pain response. Conjunctival redness (score=1) was seen in all animals at 1 hr, and the redness was still present at 48 hr in four animals. All eyes were normal by 72 hr.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

NO open flames.

Avoid inhalation of dust and mist.

Protective gloves.

Wear safety spectacles.

SEDIMENTS: In 2007 flutolanil was detected in sediments from the southern and northen basins of Lake Biwa in Japan at concentrations ranging between less than 1 to 5 ug/kg(1).

URBAN/SUBUBAN: In July 1991 flutolanil was detected in ambient air samples from Kitakyushu, Japan at a concentration of 0.46 ng/cu m(1).

Flutolanil was detected in 36 out of 123 drainage samples from 24 golf courses in Tokyo from 1994 to 1996, the maximum concentration found was 0.037 mg/L(1).

Toxicity

practically nontoxic

IDENTIFICATION AND USE: Flutolantil is a solid. It acts against Basidiomycetes. It is used as a foliar fungicide for the control of Typhula on barley and sheath blight on rice, as well as a seed dressing against Rhizoctonia solani on potatoes and cucurbits. HUMAN EXPOSURE AND TOXICITY: Flutolanil exhibits estrogenic activities in human breast cancer cells. Negative results were seen in assays for clastogenicity in human lymphocytes. ANIMAL STUDIES: Conjunctival redness was seen in rabbits at 1 hr, and the redness was still present at 48 hr in four animals. All eyes were normal by 72 hr. Flutolanil was not carcinogenic in mice, rats and dogs. Flutolanil showed no specific reproductive effects in a two-generation study of reproductive toxicity in rats. The only sign of general toxicity, increased liver weight, occurred at similar frequency in both generations of parents. Flutolanil has been tested for genotoxicity in a range of assays in vitro and in an assay for micronuclei in bone marrow of mice treated in vivo. Negative results were seen in assays for bacterial reverse mutation, bacterial DNA repair, mammalian gene mutation, unscheduled DNA synthesis in rat hepatocytes, and chromosomal effects (micronucleus induction) in vivo. A weak positive result was reported in an assay for chromosomal aberration in Chinese hamster lung cells in the presence of metabolic activation. ECOTOXICITY STUDIES: In D. magna flutolanil significantly reduced the size of the first brood at concentrations less than half of those for LC50 (8 days). Sublethal effects induced by flutolanil on zebrafish embryos were noted, including growth inhibition, abnormal spontaneous movement, slower heart rate, complete hatching failure, and morphological deformities. In addition, flutolanil could cause notochord deformation and short body length of larvae.

LD50 Rat oral 10 g/kg|LD50 Rat dermal >5 g/kg|LD50 Rat ip >10 g/kg|LD50 Rat sc >10 g/kg|For more Non-Human Toxicity Values (Complete) data for Flutolanil (7 total), please visit the HSDB record page.

/AQUATIC SPECIES/ We investigated acute and subchronic toxicities of 30 agricultural chemicals commonly used in Japan in D. magna. Acute toxicity of the agricultural chemicals was determined using the concentrations yielding 50% immobility of D. magna after 24 hr and 48 hr exposure as end points. D. magna was cultivated with the chemical and algae until the first brood production. Lethal toxicity and the number of survival broods were determined within 13 days. All insecticides among the agricultural chemicals exhibited the strongest acute toxicity (LC50 from 0.00053 to 0.037 mg/L). More than 50% of the herbicides and fungicides did not exhibit acute toxicity at 10 mg/L. Chlornitrofen, pencycuron, and fenitrothion showed significantly lower LC50 values at 8 days than at 24 hr and 48 hr. Isoprothiolane, flutolanil, and thiophanatemethyl significantly delayed the first brood at concentrations less than half of those for LC50 (8 days). Thiobencarb, iprodione, flutolanil, mepronil, and thiophanatemethyl significantly reduced the size of the first brood at concentrations less than half of those for LC50 (8 days). In this study, chlornitrofen, pencycuron, and fenitrothion were suggested to have slow-acting toxicity. Also, thiobencarb, iprodione, flutolanil, mepronil, and thiophanatemethyl were suggested to have parthenogenetic toxicity.|/AQUATIC SPECIES/ In this study, we applied various developmental stages of zebrafish to address the potential environmental risk and aquatic toxicity of bromothalonil and flutolanil. This results demonstrated that the acute toxicity of bromothalonil to the three phases of zebrafish were 4.34 (embryo) <3.27 (12 hr old larvae) <2.52 mg/L (adult fish) and that of flutolanil were 5.47 (embryo) <4.09 (72 hr old larvae) <3.91 (12 hr old larvae) <2.70 mg/L (adult). Sublethal effects induced by both bromothalonil and flutolanil on zebrafish embryos were noted, including growth inhibition, abnormal spontaneous movement, slower heart rate, complete hatching failure, and morphological deformities. In addition, both bromothalonil and flutolanil could cause notochord deformation and short body length of larvae. This study provides a foundation for future investigation into the mechanism of bromothalonil and flutolanil toxicity in zebrafish.|/PLANTS/ There is growing evidence that the application of biocontrol organisms (e.g., Pseudomonas and Bacillus spp., arbuscular mycorrhizal fungi-AMF) is a feasible option to reduce incidence of plant pathogens in an integrated control strategy. However, the utilization of these microorganisms, in particular AMF, may be threatened by the application of fungicides, a widely-used measure to control Rhizoctonia solani in various crops among /them,/ potato. Prior to their application, it is thus important to determine the impact of fungicides on AMF. The present study investigated, under in vitro controlled conditions, the impact of azoxystrobin (a systemic broad-spectrum fungicide), flutolanil (a systemic Basidiomycota-specific fungicide), and pencycuron (a contact Rhizoctonia-specific fungicide) and their respective formulations (Amistar, Monarch, and Monceren) on the growth and development of the AMF Rhizophagus irregularis MUCL 41833 (spore germination, root colonization, extra-radical mycelium development, and spore production) at doses used to control R. solani. Results demonstrated that azoxystrobin and its formulation Amistar, at threshold values for R. solani control (estimated by the half maximal inhibitory concentration, IC50, on a dry weight basis), did not affect spore germination and potato root colonization by R. irregularis, while the development of extra-radical mycelium and spore production was reduced at 10 times the threshold value. Flutolanil and its formulation Monarch at threshold value did not affect spore germination or extra-radical development but decreased root colonization and arbuscule formation. At threshold value, pencycuron and its formulation Monceren, did not affect spore germination and intra- or extra-radical development of R. irregularis. These results suggest that azoxystrobin and pencycuron do not affect the AMF at threshold concentrations to control R. solani in vitro, while flutolanil (as formulation) impacts the intraradical phase of the fungus. These fungicides and R. irregularis thus have the potential to be used in parallel against Rhizoctonia disease in potato.

Flutolanil's production may result in its release to the environment through various waste streams; its use as an agricultural fungicide(1), specifically a fungicide for seed treatment and protection(2) will result in its direct release to the environment(SRC). Flutolanil is an active ingredient in many formulated pesticide products used on numerous crops, nurseries and turf(3).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 418 to 1340(2) indicate that flutolanil is expected to have moderate to low mobility in soil(SRC). Volatilization of flutolanil from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.1X10-7 atm-cu m/mole(3) derived from its vapor pressure, 1.33X10-5 mm Hg(4), and water solubility, 8.01 mg/L(5). Flutolanil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Utilizing aerobic soil metabolism studies, flutolanil soil biodegradation half-lives of 190 to 320 days(2) suggest that biodegradation is not an important environmental fate process in soil(SRC).|FIELD STUDIES: Flutolanil is not expected to biodegrade rapidly. However, soil adsorption, slow soil biodegradation, aquatic metabolism, and dilution will aid in its dissipation in the environment; therefore, it is not considered persistent(1). Flutolanil is slowly degraded in soils, primarily by microbial processes, with reported half-lives ranging from to 190 to 320 days in flooded and upland soils(2,3).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 418 to 1340(2) indicate that flutolanil is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.1X10-7 atm-cu m/mole(3) derived from its vapor pressure, 1.33X10-5 mm Hg(4), and water solubility, 8.01 mg/L(5). According to a classification scheme(6), BCF values of 9.3(2) to 270(7) suggest that bioconcentration in aquatic organisms is low to high(SRC). Utilizing an aquatic aerobic metabolism study, a half-life of 1 year was reported(2) suggesting that biodegradation is not an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), flutolanil, which has a vapor pressure of 1.33X10-5 mm Hg mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase flutolanil 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 3 hours(SRC), calculated from its rate constant of 1.5X10-14 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method(3). Particulate-phase flutolanil may be removed from the air by wet and dry deposition(SRC). Flutolanil contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Flutolanil has an aqueous photolysis half-life of 277 days(5); however it is resistant to photolysis on soil(6).

The rate constant for the vapor-phase reaction of flutolanil with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Flutolanil is not expected to undergo hydrolysis in the environment as it is expected to be hydrolytically stable at pH 5, 7, and 9(2,3). Flutolanil contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Flutolanil has an aqueous photolysis half-life of 277 days at pH 7 and 25 °C(5) and was found to be stable to photodegradation on soil(3). Flutolanil was not decomposed under deaerated conditions in aqueous solution. However, the compound was degraded in ethanolic aqueous solution under UV irradiation and photolysis was accelerated in the presence of photosensitizers(6).

19.50|A BCF value of 20 was measured for flutolanil in carp (Cyprinus carpio)(1). Flutolanil, present at 0.1 and 0.001 ppm, resulted in whole fish BCF values of 13-26 and 9.3-24, respectively, in Japanese carp (C. carpio)(2). An edible BCF of 13, a nonedible BCF of 270, and a whole body BCF of 150 was reported for flutolanil in bluegill sunfish (Lepomis macrochirus) exposed for 28 days in the EPA bioconcentration guideline 165-4/OPPTS 950.1730 test(2,3). The depuraton half-life in blugill sunfish was reported as 0.3 days(2). According to a classification scheme(4), BCF values of zero to 30 are low and from 100 to 1,000 are high(SRC).

A Koc of 418 was determined for flutolanil using soil columns with turf grass soils(1). Flutolanil has reported Koc values ranging between 457 and 1340 calculated from guideline studies using several soils such as sand, loam, clay, and sediment, and an average Koc from 10 soils of 780.7(2). According to a classification scheme(3), these Koc values suggests that flutolanil is expected to have moderate to low mobility in soil(SRC).

The Henry's Law constant for flutolanil is estimated as 7.1X10-7 atm-cu m/mole(1) derived from its vapor pressure, 1.33X10-5 mm Hg(2), and water solubility, 8.01 mg/L(3). This Henry's Law constant indicates that flutolanil is expected to be essentially nonvolatile from water surfaces(4). Flutolanil's estimated Henry's Law constant indicates that volatilization from moist soil surfaces in not expected(SRC). Flutolanil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2).

SURFACE WATER: In 2007, flutolanil was detected in waters from the southern and northen basins of Lake Biwa in Japan at concentrations ranging between less than 1 to 0.06 ug/L(1). Flutolanil was detected at concentrations of less than 0.01 to 0.068 ug/L in surface river water samples collected at 4 monitoring sites near the mouth of the Shinano River in Japan between April and September 1996(2,3). A survey conducted from April 1993 to March 1994 detected flutolanil in 32 out of 105 river water samples in the Lake Biwa basin, Japan, from May to February at concentrations of 0.04 to 0.11 ng/mL(4). Monitoring studies in Japan conducted between 1989 and 1993 detected flutolanil in river waters near golf courses at concentrations of 0.9006 mg/L(5). At a location in Singapore, flutolanil was detected, but not quantified, in golf course waters such as artificial lakes, ponds, and rain waters, dates were not provided(6).|SEAWATER: In June and July of 2005 flutolanil was detected in the coastal waters of southern Japan receiving effluents from a wastewater reservoir containing runoff from rice paddy fields, maximum concentrations in both the reservoir and the coastal waters were 0.1 ug/L(1).|RAIN/SNOW: In Utsunomiya, Japan, where fungicides are typically applied from July to September in rice fields, flutolanil was detected in rainwater during July, August, and September 1999 and in July 2000 at concentrations ranging from 0.4 to 9.5 ug/cu m; flutolanil was not detected in the rainwater from October 1999 through June 2000(1).

Results from an agricultural product monitoring effort in Japan during April 1995 through March 2000 reported flutolanil in 4 out of 51 rice samples at concentrations less than 0.01 ug/g(1). Mean concentrations for flutolanil of 65.9, 90.8, 85.2, 92.8, 84.2, 98.8, 72.1, 92.2, 101.1, and 87.9 ppm(ug/g) were quantified in brown rice, potato, cabbage, lettuce, carrot, cucumber, shiitake mushroom, apple, strawberry, and banana, respectively. Samples were collected from retail produce sources in Japan prior to 1994(2). Flutolanil was detected in 1 out of 173 agricultural product samples from a local market in Japan at a concentration of 31.1 ng/g; dates were not provided(3).

Occupational exposure to flutolanil may occur through inhalation and dermal contact with this compound at workplaces where flutolanil is produced or used. Limited monitoring data indicate exposure may occur via ingestion of imported foods containing flutolanil residues, and inhalation and dermal contact with soil and water in areas where this fungicide is applied (e.g. golf courses). (SRC)

Drug Information

In a study performed in 1992, [aniline ring-U-14C]flutolanil (specific activity; 20 mCi/mmol; radiochemical purity, >99%) suspended in a vehicle consisting of 1% Tween 80 and 0.5% carboxymethyl cellulose was given orally to groups of three male and three female CD (Sprague-Dawley-derived) rats. Unlabelled flutolanil (purity, 99.9% or 97.6%) was also used in preparation of the solutions. The animals received either a single dose of 20 mg/kg bw [14C]flutolanil; consecutive doses of 20 mg/kg bw per day of unlabelled flutolanil for 14 days followed by single dose of [14C]flutolanil on day 15; or a single dose of 1000 mg/kg [14C]flutolanil. After administration, urine was collected three times on day 1, then daily; and feces and cage wash were collected daily. After sample collection on day 7, the animals were killed, and blood and 12 tissue samples were obtained. The radioactivity in the samples was determined by liquid scintillation counting after appropriate processing. Volatile 14C production was not determined as an earlier study showed that <0.1% of the dose had been exhaled. The total recovery was acceptable at the lower dose but was <90% at the higher dose. Most of the radioactivity was excreted within 24 hr, approximately half the urinary excretion occurring within 12 hr, indicating relatively rapid absorption. The extent of absorption, as determined by urinary excretion, varied with dose and repeated dosing, indicating saturation of absorption by large doses. There was evidence of induction of flutolanil metabolism by repeated dosing. Similar results were found in the two sexes. The concentration and distribution of radioactivity in blood and tissues at 7 days was minimal, representing <0.2% of that administered to any animal, indicating no significant potential for bioaccumulation. The tissue concentrations varied considerably between animals in the same group. The only tissue in which consistent concentrations were found was the liver, in which the mean was about 10 times those in blood. The amount of radioactivity in the livers was higher in females in all groups than in males (2.4 +/- 1.1 versus 0.68 +/- 0.38 ug/g at 1000 mg/kg bw; 0.23 +/- 0.04 versus 0.12 +/- 0.01 ug/g after repeated doses).|In a study in which flutolanil was given in the diet to Sprague-Dawley rats for 4 weeks, analyses of brain, liver, blood, kidney and fat showed low concentrations in animals receiving >2000 ppm. The highest concentrations of residues were found in adipose tissue and liver. There was minimal retention of flutolanil. The lowest dose of 400 ppm was equal to 36 mg/kg bw per day in males and 41 mg/kg bw per day in females. Comparison of the results at 400 ppm with those at 20 mg/kg bw in /another study/ indicated that flutolanil that has no significant propensity to accumulate. The increase in residue concentration with increasing dose indicated that the saturation of absorption seen after administration by gavage does not occur after dietary intake.|An analysis of tissue samples from the study in rats given repeated doses showed that flutolanil was present only in fat and at low concentrations: 0.2 ppm at 2,000 ppm and 0.6 ppm at 10,000 ppm, which are similar to those found after a single dose. As the analytical method was only for the parent compound, any metabolites that might have contributed to the residues after a single dose would not have been detected. However, as the metabolites formed from flutolanil are relatively polar and are excreted primarily in urine, the findings from the study with repeated doses indicate that flutolanil has little if any potential to bioaccumulate.

0.25 Days

Fresh air, rest.


Rinse skin with plenty of water or shower.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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 ... . /Poisons 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 severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/GENOTOXICITY/ Flutolanil has been tested for genotoxicity in a range of assays in vitro and in an assay for micronuclei in bone marrow of mice treated in vivo. Negative results were seen in assays for... clastogenicity in human lymphocytes...|/ALTERNATIVE and IN VITRO TESTS/ Endocrine disruptors, when absorbed into the body, interfere with the normal function by mimicking or blocking the hormone system. To investigate compounds mimicking estrogen in the drinking water source of the residence of Seoul, the Pal-dang reservoir was monitored over a period of 5 years, between 2000 and 2004. Nine kinds of pesticide (carbaryl, DBCP, diazinon, fenitrothion, fenobucarb, flutolanil, iprobenphos, isoprothiolane and parathion) were found to exist in the river water sample. These compounds were detected at low concentrations in the water samples. The total concentration and those of each of these pesticides were below the permissible limits of the National Institute of Environmental Research (NIER), Korea. The estrogenic potencies of the nine pesticides were examined using an E-screen assay with MCF-7 BUS estrogen receptor (ER)-positive human breast cancer cells, with ER-negative MDA MB 231 cell lines also used to compare the results. From this, flutolanil and isoprothiolane were confirmed to have estrogenic activities as shown by the increasing MCF-7 BUS cell growth on their addition. In addition, the estrogen receptor alpha (ERalpha) protein, estrogen receptor-regulated progesterone receptor (PR) and pS2 mRNA levels on the addition of flutolanil and isoprothiolane were measured with MCF-7 BUS cells. It was observed that the levels of ERalpha protein decreased and those of the PR and pS2 genes increased on the addition of either flutolanil or isoprothiolane at concentrations of 1x10(-4) M, in the same manner as with the addition of 17beta-estradiol, which was used as the positive control. From these results, it was confirmed that flutolanil and isoprothiolane exhibit estrogenic activities, suggesting they might act through estrogen receptors.

flutolanil

Flutolanil Use and Manufacturing

Methods of Manufacturing

Preparation method One o-trifluoromethyl benzoyl chloride can use o-trifluoromethyl chlorobenzene as raw material, after Grignard reaction, and then carbonylation with dry ice reaction, and then hydrolyzed to obtain o-trifluoromethyl benzoic acid, the acid by acid chloride Chemically prepared o-trifluoromethyl benzoyl chloride. O-trifluoromethyl benzoyl chloride was added to tetrahydrofuran under ice cooling, and reacted with m-isopropoxyaniline for 2h in the presence of triethylamine and room temperature to obtain fludioxanil. Preparation method Diflubenzin can also be prepared by reacting 3-(2-trifluoromethylbenzoylamino)phenol with 2-chloropropane.

Uses

Agricultural fungicide.

Prostar 50WP (Bayer Environmental Science): Active ingredient: Flutolanil 50.3%.|Prostar 70 WP (Bayer Environmental Science): Active ingredient: Flutolanil 70.0%.|Sysstar WDG (Bayer Environmental Science): Active ingredient: Flutolanil 51.42%; Thiophanate-methyl 28.58%.|Prostar 70 WDG Fungicide (Bayer Environmental Science): Active ingredient: Flutolanil 70.0%.|For more Formulations/Preparations (Complete) data for Flutolanil (18 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Flutolanil as unlikely to present an acute hazard in normal use; Main Use: fungicide, other than for seed treatment.

Agrochemicals -> Fungicides|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)

Flutolanil has known environmental transformation products that include Flutolanil M-11, Flutolanil M-2 HFT, Flutolanil M-3 HIP, Flutolanil M-4/DIP, Flutolanil M-5 HDP, Flutolanil M-6/MDP, and Flutolanil M-7 HMD.

Computed Properties

Molecular Weight:323.31
XLogP3:3.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:323.11331324
Monoisotopic Mass:323.11331324
Topological Polar Surface Area:38.3
Heavy Atom Count:23
Complexity:398
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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