Boscalid
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Boscalid
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CAS No:
188425-85-6
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Formula:
C18H12Cl2N2O
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Chemical Name:
Boscalid
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Synonyms:
3-Pyridinecarboxamide,2-chloro-N-(4′-chloro[1,1′-biphenyl]-2-yl)-;2-Chloro-N-(4′-chloro[1,1′-biphenyl]-2-yl)-3-pyridinecarboxamide;Boscalid;Nicobifen;BAS 510F;Filan;Cantus;Endura;F 510;2-Chloro-N-(4′-chlorobiphenyl-2-yl)nicotinamide;Emerald (fungicide);Emerald;2-Chloro-N-[2-(4-chlorophenyl)phenyl]pyridine-3-carboxamide
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CAS No:
Description
Boscalid is a pyridinecarboxamide obtained by formal condensation of the carboxy group of 2-chloronicotinic acid with the amino group of 4'-chlorobiphenyl-2-amine. A fungicide active against a broad range of fungal pathogens including Botrytis spp., Alternaria spp. and Sclerotinia spp. for use on a wide range of crops including fruit, vegetables and ornamentals. It has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor, an environmental contaminant, a xenobiotic and an antifungal agrochemical. It is a member of biphenyls, a pyridinecarboxamide, a member of monochlorobenzenes and an anilide fungicide. It derives from a nicotinic acid.|Boscalid has been investigated for the treatment of OSDI, Glaucoma, Staining, Schirmers, and Disease Severity, among others.
Characteristics
41.99000
5.38070
white powder
1.368 g/cm3
143 °C
447.7ºC at 760 mmHg
224.6ºC
1.666
Solubility in acetone, 16-20 g/100 mL; acetonitrile, 4-5 g/100 mL; methanol, 4-5 g/100 mL; ethylacetate, 6.7-9 g/100mL; dichloromethane, 20-25 g/100 mL; toluene, 2-2.5 g/100 mL; 1-octanol, <1 g/100 mL, all at 20 deg C
0-6ºC
3.28E-08mmHg at 25°C
Odorless
pH = 5.5 at 23 °C (1% solution)
Henry's Law constant = 5.178X10-5 Pa- cu m/mol /5.3X10-11 atm-cu m/mol/ at 25 °C
Does not dissociate
171.67 Ų [M+H]+ [CCS Type: TW]|178.57 Ų [M-H]-
White powder; faintly smoky odor; mp: 143.3 to 143.6 °C; density: 1.394 g/cu cm /Technical grade/|Stable to hydrolysis at pH 4, 5, 7 and 9; stable to aqueous photolysis
Safety Information
III
UN1294 3
R11
36/37-62
US4587550
F; Xn
Stable under recommended storage conditions.
P273
H411
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.
USEPA; Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Boscalid, Reason for Issuance: New Chemical (July 2003).[Available from, as of June 24, 2016: https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-128008_01-Jul-03.pdf]
|H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501|Aggregated GHS information provided by 288 companies from 3 notifications to the ECHA C&L Inventory.|H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]
Eye/face protection: Safety glasses with side-shields conforming to EN166. 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: Impervious clothing. 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).
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.
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.|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.
Not irritating in Primary Eye Irritation Test. Not irritating to skin in a Primary Dermal Irritation Test. /From table/
SEDIMENT: The US Geological Survey conducted a study of 34 fungicides and an additional 57 current-use pesticides in bed sediments and suspended solids collected from areas of intense fungicide use within three geographic areas across the United States. Sampling sites were selected near or within agricultural research farms using prophylactic fungicides at rates and types typical of their geographic location. Boscalid was detected in 53% of sediments collected within highly agricultural areas(1,2).
Toxicity
IDENTIFICATION AND USE: Boscalid is a solid. It is used as fungicide, plant health product, seed treatment/protectant. HUMAN EXPOSURE AND TOXICITY: Boscalid may be genotoxic and cytotoxic in vitro in human peripheral blood lymphocytes. ANIMAL STUDIES: Boscalid has a low toxicity in animal studies. In subchronic and chronic feeding studies in rats, mice and dogs, boscalid generally caused decreased body weights and body weight gains and effects on the liver (increase in weights, changes in enzyme levels and histopathological changes) as well as on the thyroid (increase in weights and histopathological changes). In a developmental toxicity study in rats, no developmental toxicity was observed in the fetuses at the highest dose tested. In a developmental toxicity study in rabbits, an increased incidence of abortions or early delivery was observed at the limit dose. The does and fetuses were equally sensitive to the test material. In a 2-generation reproduction study in rats, the NOAEL for parental toxicity was based on decreased body weight and body weight gain as well as hepatocyte degeneration. No reproductive toxicity was observed in this study at the highest dose tested. There was quantitative evidence of increased susceptibility in the developmental neurotoxicity study in rats, where decreases in pup body weights and body weight gains were seen in the absence of any maternal toxicity. In a two-year chronic toxicity study and a two-year carcinogenicity study in male and female rats, the combined data showed that, for thyroid follicular cell adenomas, males had a significant increasing trend, when compared with controls. There was no treatment-related increase in thyroid follicular cell carcinomas. The increase in thyroid follicular cell adenomas appeared to be treatment-related in males. Regarding females, combined data from the two rat studies indicated that there was an increasing trend for thyroid follicular cell adenomas. No carcinomas were observed in female. Boscalid was tested in five mutagenicity studies and was found to be negative in all of them. ECOTOXICITY STUDIES: Boscalid is categorized as practically nontoxic to birds in both an acute and subacute studies. Boscalid was harmless to adult Galendromus occidentalis. Boscalid use does not represent a risk to plants. Commercial producers of honey bee queens (Apis mellifera L.) have reported unexplained loss of immature queens during the larval or pupal stage. Many affected queen-rearing operations are situated among the almond orchards of California and report these losses in weeks after almond trees bloom. Almond flowers are a rich foraging resource for bees, but are often treated with fungicides, insecticides, and spray adjuvants during bloom. Anecdotal reports by queen producers associate problems in queen development with application of the fungicide Pristine (boscalid and pyraclostrobin). Chemical analysis revealed that low concentrations of pyraclostrobin (50 ppb), but no boscalid, were detectable in royal jelly secreted by nurse bees feeding on treated pollen.
LD50 Rat oral >5,000 mg/kg (Technical boscalid) /From table/|LD50 Rat dermal >2,000 mg/kg (Technical boscalid) /From table/
/BIRDS and MAMMALS/ Risk to Avian Species (Acute/Chronic). Boscalid is categorized as practically nontoxic to birds in both an acute and subacute exposure basis, no acute levels of concern (LOC) are exceeded for birds feeding on any of the modeled food items (short grass, tall grass, broadleaf plants insects and seeds). However, chronic exposure to boscalid at the proposed application rate for strawberries, i.e., 5 applications of 0.350 lbs a.i./A with a 7-day reapplication interval, results in the chronic risk level of concern being exceeded for birds feeding on short grasses (RQ=1.08). Exposure to boscalid on other avian food items (tall grasses, broadleaf plants/insects, and seeds) at this application rate did not result in any exceedance of either acute or chronic LOCs. Based on maximum estimated concentrations on short grass the chronic risk LOC would be exceeded for approximately 4 days; however, if mean foliar residues were used to estimate exposure, chronic avian LOCs would not have been exceeded since mean foliar residues are roughly half maximum exposure values.|/AQUATIC SPECIES/ The presence of fungicides in the marine environment may pose risks to marine organisms, but little is known about fungicide effects on these organisms, especially invertebrates. The present study investigated the effects of the commonly used boscalid fungicide Filan on life history traits, feeding rate, and energy reserves (lipid, glycogen, and protein content) of the marine amphipod Allorchestes compressa over 6 wk under laboratory conditions. Amphipods were exposed to 3 concentrations of Filan (1 ug, 10 ug, and 40 ug active ingredient [a.i.]/L), with 5 replicates per treatment. Lipid content and reproduction were the most sensitive measures of effect, with lipid content reduced by 53.8% at the highest concentration. Survival, growth, and other energy reserves of amphipods were also negatively affected by Filan, and the effects were concentration dependent. Antennal deformities were incidentally observed on the amphipods at a concentration of 40 ug a.i./L. The results of the present study indicate comprehensive effects of the boscalid fungicide Filan on A. compressa at environmentally relevant concentrations. The decline or absence of A. compressa in marine ecosystems could impair the ecosystem function because of their important role in trophic transfer and nutrient recycling. The authors' results suggest that even though the use of fungicides is often regarded as posing only a minor risk to aquatic organisms, the assessment of their long-term effects is critical.|/AQUATIC SPECIES/ Boscalid is moderately toxic to aquatic animals; however based on estimated exposure concentrations, the proposed uses of boscalid are not likely to represent a threat to either acute or chronic ecological risk to freshwater fish and invertebrates or to estuarine/marine fish at a maximum proposed multiple application rates as high as six applications of 0.350 lbs. a.i./A. However, the acute risk level of concern for endangered species is exceeded for estuarine/marine invertebrates. While boscalid is not expected to adversely affect aquatic animals whose lives are primarily spent in open water, bottom-dwelling (benthic) fauna may be more likely to encounter boscalid based on the chemical's persistence and tendency to sorb to sediments. Modeling of benthic exposure, based on a closed farm pond scenario over a 36-year period, did not exceed the chronic risk level of concern for sediment-dwelling animals.|/OTHER TERRESTRIAL SPECIES/ A laboratory evaluation of fenbuconazole, myclobutanil propiconazole, boscalid, fenhexamid and pyraclostrobin revealed these fungicides to be harmless to adult Galendromus occidentalis /mite/. None of these fungicides affected adversely fecundity and egg viability. Elemental sulphur also had no effect on adults and fecundity. However, 72.4% of the young larvae perished after hatching. The six novel fungicides are safer alternatives to sulphur in perennial crops in British Columbia.|For more Ecotoxicity Excerpts (Complete) data for BOSCALID (10 total), please visit the HSDB record page.
Boscalid's production may result in its release to the environment through various waste streams; its use as a fungicide(1) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9500(SRC), determined from a structure estimation method(2), indicates that boscalid is expected to be immobile in soil(SRC). Volatilization of boscalid from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 5.11X10-11 atm-cu m/mole(3). Boscalid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.4X10-10 mm Hg at 20 °C(3). Biodegradation half-lives in soil ranging from 96 to 578 days(4) indicate that biodegradation is not an important environmental fate process in soil(SRC).|TERRESTRIAL FATE: Boscalid is generally persistent in the field based on terrestrial dissipation studies employing both cropped and bare plots in the US and Canada(1). The DT50 dissipation rate ranged from 27 to 372 days, generally being greater than 100 days(1).|TERRESTRIAL FATE: The aim of this study was to analyze the environmental fate of the fungicide boscalid in a sandy soil. Boscalid was applied in spring 2010/11 to a cropland site in western Germany. Three years after second application 65 undisturbed soil samples were taken. Boscalid was extracted using accelerated solvent extraction (ASE). Boscalid contents in the plough horizon ranged between 0.12 and 0.53 with a field mean of 0.20 +/- 0.09 ug/kg. These contents were considerably lower compared to calculation using literature DT50 values, whereby a concentration of 16.89 ug kg/L was expected assuming a literature DT50 value of 345 days. Therefore, the measured field boscalid concentration only yields 1.2% of the expected value. To test whether the unknown extraction efficiency, losses from spray drift and interception can explain the mismatch between calculated and measured concentrations all these uncertainties were taken into account into calculations, but field concentrations and DT50 were still lower as expected. Leaching to deeper horizons was also studied but could not explain the discrepancy either. Moreover, a short-term incubation experiment using (14)C-labelled boscalid revealed also shorter DT50 values of 297-337 compared to the 345 days taken from literature. However, this DT50 value is still considerably larger compared to the 104-224 days that were calculated based on the field experiment. Our results indicate that boscalid dissipation under field conditions is much faster at agricultural sites with sandy soil type than expected from laboratory incubation experiments.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9500(SRC), determined from a structure estimation method(2), indicates that boscalid is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 5.11X10-11 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 42(SRC), from its log Kow of 2.96(4) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation half-lives in soil ranging from 96 to 578 days(6) indicate that biodegradation is not an important environmental fate process in water(SRC).|For more Environmental Fate (Complete) data for BOSCALID (6 total), please visit the HSDB record page.
Boscalid is stable to hydrolysis at pH 5, 7 and 9 as indicated by no change to ring-labeled bocalid at a concentration of 3 mg active ingredient/L maintained in sterile aqueous buffer solutions for 30 days(1). Boscalid is stable to photolysis in water(2); 3 ug/L active ingredient remained unchanged following exposure to continuous irradiation using a xenon lamp for 15 days(1).
An estimated BCF of 42 was calculated in fish for boscalid(SRC), using a log Kow of 2.96(1) and a regression-derived equation(1). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Accumulation is expected to be greatest in non-edible versus edible tissue and should depurate rapidly once organism is no longer exposed(4).
The Koc of boscalid is estimated as 9500(SRC), using a log Kow of 2.96(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that boscalid is expected to be immobile in soil(SRC). Boscalid is expected to sorb to aquatic sediments(4).|Buffer zones such as ponds and ditches are used to reduce field-scale losses of pesticides from subsurface drainage waters to surface waters. The objective of this study was to assess the efficiency of these buffer zones, in particular constructed wetlands, focusing specifically on sorption processes. We modelled the sorption processes of three herbicides [2-methyl-4-chlorophenoxyacetic acid (2,4-MCPA), isoproturon and napropamide] and three fungicides (boscalid, prochloraz and tebuconazole) on four substrates (two soils, sediment and straw) commonly found in a pond and ditch in Lorraine (France). A wide range of Freundlich coefficient (K fads) values was obtained, from 0.74 to 442.63 mg(1 - n) L (n) kg(-1), and the corresponding K foc values ranged from 56 to 3,725 mg(1 - n) L (n) kg(-1). Based on potential retention, the substrates may be classified as straw >> sediments > soils. These results show the importance of organic carbon content and nature in the process of sorption. Similarly, the studied pesticides could be classified according to their adsorption capacity as follows: prochloraz >> tebuconazole-boscalid > napropamide >> MCPA-isoproturon. This classification is strongly influenced by the physico-chemical properties of pesticides, especially solubility and K oc. Straw exhibited the largest quantity of non-desorbable pesticide residues, from 12.1 to 224.2 mg/L for all pesticides. The presence of plants could increase soil-sediment sorption capacity. Thus, establishment and maintenance of plants and straw filters should be promoted to optimize sorption processes and the efficiency of ponds and ditches in reducing surface water pollution.
The Henry's Law constant for boscalid is 5.11X10-11 atm-cu m/mole(1). This Henry's Law constant indicates that boscalid is expected to be essentially nonvolatile from water surfaces(2). Boscalid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.4X10-10 mm Hg(1).
GROUNDWATER: Boscalid was not reported in groundwater samples taken from Italy in the regions of the Po River, Arno River, unspecified rivers in Tuscany, or the Fuscino Plain); research was conducted from 1997 through 2013(1).|SURFACE WATER: The US Geological Survey conducted a study of 33 fungicides and an additional 57 current-use pesticides applied to streams, ponds, and shallow groundwater located in areas of intense fungicide use within three geographic areas across the United States. Sampling sites were selected near or within farms using prophylactic fungicides at rates and types typical of their geographic location. Boscalid was detected in 72% of samples(1,2).|SURFACE WATER: Boscalid was reported at a maximum concentration of 2,000 ng/L in an unspecified surface water sample taken from Italy (Po River, Arno River, unspecified rivers in Tuscany, or surface waters of the Fuscino Plain); research was conducted from 1997 through 2013(1).
The effects of four fungicides commonly used for the control of fungal diseases in vines and grapes in the course of winemaking were tested. The concentration of fungicide residues was monitored throughout the process to establish their kinetics of dissipation. In all cases the percentages of dissipation were >68%, which shows the detoxificant effect of the winemaking process. On the other hand, the effect of the fungicide residues on the aroma composition of Tempranillo red wines was tested. To evaluate possible modifications on the aroma profile of wines, seven odorant series (ripe fruits, fresh fruits, lactic, floral, spicy, vinous, and herbaceous) were built from the odor activity values (OAVs) obtained for each volatile compound. Ripe fruits and fresh fruits were the major aromatic attributes in all Tempranillo red wines. These two odorant series registered the highest variations in their total OAVs with respect to the control wine, especially with the application of boscalid + kresoxim-methyl into vines, leading to a decrease in the ripe fruit and fresh fruit nuances of the resulting wines. Moreover, when the effect of these fungicides on the aroma of Tempranillo red wines was compared throughout two years (2012 and 2013), wines elaborated from grapes treated in the field with boscalid + kresoxim-methyl in 2013 displayed the highest variation in aroma profile with respect to control wine. During alcoholic fermentation, dissipation half-lives of 4.7 and 5.7 days in 2012 and 2013, respectively, were exhibited for boscalid + kresoxim-methyl(1).|Azoxystrobin, boscalid, cyprodinil, fenhexamid, and pyrimethanil are new generation fungicides extensively employed in order to combat diseases affecting vineyards worldwide. Owing to their physico-chemical characteristics, residues of these compounds on grapes are transferred to must and wine. In this study, a survey of the occurrence of these fungicides in international wines was carried out by using rapid antibody-based assays. Results are discussed as a function of wine type and sample geographical origin. 44.4% of the samples contained at least one of the targets (>10 ug/L). Fungicide residue occurrences were 22.4%, 19.2%, 18.8%, 6.8%, and 1.2% for pyrimethanil, boscalid, fenhexamid, cyprodinil, and azoxystrobin, respectively, while residue contents higher than 100 ug/L were found in 8.4% of the samples. This study shows that contamination of commercial wines with pesticides is an issue of worldwide relevance with potential implications for consumer health and international trade.|Crops grown under plastic-clad structures or in greenhouses may be prone to an increased frequency of pesticide residue detections and higher concentrations of pesticides relative to equivalent crops grown in the open field. To test this we examined pesticide data for crops selected from the quarterly reports (2004-2009) of the UK's Pesticide Residue Committee. Five comparison crop pairs were identified whereby one crop of each pair was assumed to have been grown primarily under some form of physical protection ('protected') and the other grown primarily in open field conditions ('open'). For each pair, the number of detectable pesticide residues and the proportion of crop samples containing pesticides were statistically compared (n=100 samples for each crop). The mean concentrations of selected photolabile pesticides were also compared. For the crop pairings of cabbage ('open') vs. lettuce ('protected') and 'berries' ('open') vs. strawberries ('protected') there was a significantly higher number of pesticides and proportion of samples with multiple residues for the protected crops. Statistically higher concentrations of pesticides, including cypermethrin, cyprodinil, fenhexamid, boscalid and iprodione were also found in the protected crops compared to the open crops. The evidence here demonstrates that, in general, the protected crops possess a higher number of detectable pesticides compared to analogous crops grown in the open. This may be due to different pesticide-use regimes, but also due to slower rates of pesticide removal in protected systems. The findings of this study raise implications for pesticide management in protected-crop systems.|Greenhouse studies were conducted to evaluate the dissipation rate kinetics and estimate the behavior of selected pesticides after washing, peeling, simmering, and canning of tomato expressed as processing factor (PF). Two varieties (Marissa and Harzfeuer) were treated by six fungicides: azoxystrobin, boscalid, chlorothalonil, cyprodinil, fludioxonil, and pyraclostrobin at single and double dose and risk assessment defined as hazard quotient was performed. The QuEChERS method was used for sample preparation followed by liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS). The dissipation of fungicides approximately fitted to a first-order kinetic model, with half-life values ranging from 2.49 and 2.67 days (cyprodinil) to 5.00 and 5.32 days (chlorothalonil) for Marissa and Harzfeuer variety, respectively. Results from processing studies showed that treatments have significant effects on the removal of the studied fungicides for both varieties. The PFs were generally less than 1 (between 0.01 and 0.90) and did not depend on variety. The dietary exposure assessed based on initial deposits of application at single and double dose on tomatoes and concentration after each process with PF correction showed no concern to consumer health. Our results would be a useful tool for monitoring of fungicides in tomatoes and provide more understanding of residue behavior and risk posed by these fungicides.
Occupational exposure to boscalid may occur through inhalation and dermal contact with this compound at workplaces where boscalid is produced or used. Monitoring data indicate that the general population may be exposed to boscalid via ingestion of some fruits and wines, dermal contact with spray in the vicinity of farms applying boscalid and contact with contaminated surface water or sediments in agricultural regions using this fungicide. (SRC)|Concerns about pesticide drift from neighbouring vineyards affecting children attending school on a farm adjacent to an urban suburb of Cape Town, Western Cape in South Africa were investigated. The study involved a before-after design, measuring levels of environmental exposure before and during pesticide application activities on the neighbouring farms. Samples were collected in air, dust and grass cuttings at the preschool and primary school located on the farms during September-December in 2010 and tested for pesticides using multi-pesticide methods. Eleven different pesticides were detected in the various samples. Six of these chemicals (endosulfan, dimethomorph, penconazole, cyprodinil, boscalid and bromopropylate) were on the spraying schedules of the two farms neighbouring the schools and the timing and location of detection were generally consistent with farm application. Three pesticides detected (chlorpyrifos, cypermethrin, permethrin) are agents commonly used in household applications and one (pyriproxifen) is used in pet treatment agents. Kresoxim-methyl, the other pesticide detected, is likely to come from drift from other farms in the area. The concentration of pesticides was all lower than 0.1 ug/cu m in air and 0.1 ug/kg in dust and grass apart from permethrin and cypermethrin. The findings confirm the presence of drift onto the school premises and concentrations found in this study were generally low in comparison to that detected in other studies. Regular monitoring to track the effectiveness of containment and mitigation measures that reduce drift is recommended.
Drug Information
Dermal Penetration (rat). Maximum % absorption: 0.01 mg/sq cm = 10.93 (24 hour exposure, 24 hour sacrifice) 0.10 mg/sq cm = 3.76 (24 hour exposure, 24 hour sacrifice) 1.00 mg/sq cm = 1.48 (10 hour exposure, 72 hour sacrifice /From table/|In the rat, Boscalid was readily absorbed and excreted following single oral 50 mg/kg; at single 500 mg/kg or 15 doses of 500 mg/kg, absorption was saturated. Excretion mainly by feces (80-98%). Biliary excretion 40- 50% of fecal activity at 50 mg/kg, 10% at 500 mg/kg. Urine, about 16% at 50 mg/kg, 3-5% at 500 mg/kg. Absorption about 56% at 50 mg/kg and 13-17% at 500 mg/kg. Excretory patterns similar by gender or radiolabel position. /From table/
Three ... groups of Wistar rats were treated and sampled ... for qualitative analyses of metabolites. ... Metabolites were separated by HPLC. Primary identification was by mass spectrometry (MS). ... The most important metabolites were hydroxyl or O-glucuronide metabolites on the diphenyl ring (usually para to the amide nitrogen), and S-glucuronide conjugation products displacing the chlorine on the pyridine ring of the parent compound. The sulfur originated from glutathione (GSH) addition to the ring. GSH was often cleaved to cysteine in bile or feces, or further degraded in feces to a thiol, which in turn was sometimes conjugated as a glucuronide). Tissue residues (liver, kidney, and plasma) were scant ... Some parent BAS 510 F was found in kidneys and plasma. Thus BAS 510 F was effectively metabolized and efficiently excreted.|/In the rat,/ metabolites (hydroxylation and conjugation products) were consistent with Phase I oxidation reactions followed by Phase II conjugation with glucuronic acid or sulfate, or by conjugation of the parent with glutathione with cleavage to sulfate metabolites. /From table/
In the rat, the predominant route of excretion of BAS 510 F is fecal with urinary excretion being minor. The half-life of BAS 510 F is less than 24 hours.
/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 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. 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 (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/GENOTOXICITY/ The aim of this study was to investigate the genotoxic and cytotoxic potential of the Signum fungicide and its active ingredients (boscalid and pyraclostrobin) on human peripheral blood lymphocytes using the cytokinesis-block micronucleus (CBMN) assay. Micronuclei (MNi), nucleoplasmic bridges (NPBs), nuclear bud (NBUDs) formations, and the cytokinesis-block proliferation index (CBPI) were evaluated in treated lymphocytes in Go (cells were treated and then kept in culture without stimulation for 24 hr) and proliferation phases (cells were treated after 44 hr culture in medium containing phytohemagglutinin). MN formation in lymphocytes treated in G0 statistically increased at doses of 2, 6, and 25 ug/mL signum; 0.5 and 2 ug/mL boscalid; and 0.5, 1.5, and 2 ug/mL pyraclostrobin; while NPB formation increased at a dose of 0.25 ug/mL pyraclostrobin. All concentrations of each fungicide did not statistically increase NBUD formation, while the cytotoxicity increased the dependent on concentration in lymphocytes treated in G0 . Doses of 0.5, 1, 1.5, and 3 ug/mL signum; 0.5, 1, and 1.5 ug/mL boscalid; and 0.75 ug/mL pyraclostrobin statistically increased the MN formation in proliferating lymphocytes. NPB formation increased in proliferating lymphocytes at doses of 1, 1.5, 2, and 3 ug/mL signum and at a dose of 0.75 ug/mL pyraclostrobin. In addition, a dose of 0.75 ug/mL pyraclostrobin increased NBUD frequencies. Cytotoxicity increased with increasing concentrations of each fungicide. It is concluded that signum, boscalid, and pyraclostrobin may be genotoxic and cytotoxic in vitro human peripheral blood lymphocytes in consideration of each of the two protocols.|/ALTERNATIVE and IN VITRO TESTS/ Nonpersistent pesticides are considered less harmful for the environment, but their impact as endocrine disruptors has not been fully explored. The pesticide Switch was applied to grape vines, and the maximum residue concentration of its active ingredients was quantified. The transactivation potential of the pesticides Acorit, Frupica, Steward, Reldan, Switch, Cantus, Teldor, and Scala and their active compounds (hexythiazox, mepanipyrim, indoxacarb, chlorpyrifos-methyl, cyprodinil, fludioxonil, boscalid, fenhexamid, and pyrimethanil) were tested on human estrogen receptor alpha (ERalpha), androgen receptor (AR) and arylhydrocarbon receptor (AhR) in vitro. Relative binding affinities of the pure pesticide constituents for AR and their effect on human breast cancer and prostate cancer cell lines were evaluated. Residue concentrations of Switch's ingredients were below maximum residue limits. Fludioxonil and fenhexamid were ERalpha agonists (EC50 -values of 3.7 and 9.0 uM, respectively) and had time-dependent effects on endogenous ERalpha-target gene expression (cyclin D1, progesterone receptor, and nuclear respiratory factor 1) in MCF-7 human breast cancer cells. Fludioxonil, mepanipyrim, cyprodinil, pyrimethanil, and chlorpyrifos-methyl were AhR-agonists (EC50 s of 0.42, 0.77, 1.4, 4.6, and 5.1 uM, respectively). Weak AR binding was shown for chlorpyrifos-methyl, cyprodinil, fenhexamid, and fludioxonil. Assuming a total uptake which does not take metabolism and clearance rates into account, our in vitro evidence suggests that pesticides could activate pathways affecting hormonal balance, even within permitted limits, thus potentially acting as endocrine disruptors.
2-chloro-N-(4-chlorobiphenyl-2-yl)nicotinamide
Boscalid Use and Manufacturing
Boscalid can be synthesized by reaction of 2-amino-4'-chlorobiphenyl in aqueous xylene with 2-chloro-3-pyridinecarbonyl chloride.|2-Halopyridinecarboxamides of primary aromaticity in /the/ ortho-position-substituted monoamine, were prepared by reacting 2-halopyridinecarbonyl chloride with the corresponding aromatic monoamine in a solvent mixture containing water and greater than 1 solvent non-mixable with water; whereby the reaction mixture comprises a base in a quantity of 0-<10 mol% based on the 2-halopyridinecarbonyl chloride. Thus a mixture of water and 2-amino-4'-chlorobiphenyl in xylene was heated at 65 °C under stirring followed by /the/ addition of 2-chloro-3-pyridinecarbonyl chloride and stirring for 10 minutes at 95 °C to give 93% /boscalid/.|Preparation: K. Eicken et al., European Patent Office patent 545099; eidem, United States of America patent 5589493 (1993, 1996 both to BASF).
Boscalid is a fungicide belonging to the class of carboxamides. Boscalid acts by inhibiting spore germination, germ tube elongation and is also effective on all other stages of fungal development. Boscalid is used in the agriculture to protect crops from gray mold, powdery mildew and other fungus.
Endura Fungicide (BASF Corporation): Active ingredient: Boscalid 70.0%.|Emerald Fungicide (BASF Corporation): Active ingredient: Boscalid 70.0%.|Boscalid Technical (BASF Corporation): Active ingredient: Boscalid 99.0%.|Pristine Fungicide (BASF Corporation): Active ingredient: Pyraclostrobin 12.8%; Boscalid 25.2%.|For more Formulations/Preparations (Complete) data for BOSCALID (14 total), please visit the HSDB record page.
The WHO Recommended Classification of Pesticides by Hazard identifies boscalid as unlikely to present an acute hazard in normal use; Main Use: fungicide, other than for seed treatment.
Sudden infant death syndrome (SIDS) and sudden intrauterine unexpected death syndrome (SIUDS) are an unresolved teaser in the social-medical and health setting of modern medicine and are the result of multifactorial interactions. Recently, prenatal exposure to environmental contaminants has been associated with negative pregnancy outcomes, and verification of their presence in fetal and newborn tissues is of crucial importance. A gas chromatography-tandem mass spectrometry (MS/MS) method, using a triple quadrupole analyzer, is proposed to assess the presence of 20 organochlorine pesticides, two organophosphate pesticides, one carbamate (boscalid), and a phenol (bisphenol A) in human brain tissues. Samples were collected during autopsies of infants and fetuses that died suddenly without any evident cause. The method involves a liquid-solid extraction using n-hexane as the extraction solvent. The extracts were purified with Florisil cartridges prior to the final determination. Recovery experiments using lamb brain spiked at three different concentrations in the range of 1-50 ng/g were performed, with recoveries ranging from 79 to 106%. Intraday and interday repeatability were evaluated, and relative standard deviations lower than 10% and 18%, respectively, were obtained. The selectivity and sensitivity achieved in multiple reaction monitoring mode allowed us to achieve quantification and confirmation in a real matrix at levels as low as 0.2-0.6 ng/g. Two MS/MS transitions were acquired for each analyte, using the Q/q ratio as the confirmatory parameter. This method was applied to the analysis of 14 cerebral cortex samples (ten SIUDS and four SIDS cases), and confirmed the presence of several selected compounds.|Boscalid is a new-generation fungicide that has been detected in several bee matrices. The objective of this work was to characterize boscalid metabolites in honeybees based on in vivo experimentation, and next to verify the presence of these metabolites into honeybees from colonies presenting troubles. A methodology based on complementary mass spectrometric tools, namely ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry (UHPLC-QToF) or triple quadrupole mass spectrometry (UHPLC-QqQ) was implemented. Honeybees were sprayed with boscalid, at field rate (to induce the metabolization process) and the parent compound with its generated metabolites were then extracted using modified EU-QuEChERS method. The mass characteristics including exact mass, isotopic profile and mass fragments allowed assuming the structure of several metabolites. Some of them were unambiguously identified by comparison with synthesized analytical standards. The metabolites were resulted from hydroxylation and dechlorination of the parent compound as well as the substitution of a chlorine atom with a hydroxyl group. The metabolites were then quantified in bee samples collected from various beehives located in France.Boscalid and three of its metabolites were present in some samples at a level ranged between 0.2 and 36.3 ng/g.|Analytical method. In plants the parent residue is extracted using an aqueous/organic solvent mixture followed by liquid/liquid partitioning and a column clean up. Quantitation is by gas chromatography using mass spectrometry (GC/MS). In livestock the residues are extracted with methanol. The extract is treated with enzymes in order to release the conjugated glucuronic acid metabolite. The residues are then isolated by liquid/liquid partition followed by column chromatography. The hydroxylated metabolite is acetylated followed by a column clean-up. The parent and acetylated metabolite are quantitated by gas chromatography with electron capture detection.
Agrochemicals -> Fungicides|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)
Boscalid has known environmental transformation products that include Boscalid metabolite 1, M510F08, M510F49, M510F50, and M510M47.
Computed Properties
Molecular Weight:343.2
XLogP3:4.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:342.0326684
Monoisotopic Mass:342.0326684
Topological Polar Surface Area:42
Heavy Atom Count:23
Complexity:399
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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