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ボスカリド

Boscalid

HCID 213013
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
188425-85-6
標準SMILES
O=C(Nc1ccccc1-c1ccc(Cl)cc1)c1cccnc1Cl
InChIKey
WYEMLYFITZORAB-UHFFFAOYSA-N
分子式
C18H12Cl2N2O
平均分子量
343.2 g/mol
単同位体質量
342.0326684

概要

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 a xenobiotic, an environmental contaminant, an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical. It is a member of biphenyls, a pyridinecarboxamide, a member of monochlorobenzenes and an anilide fungicide. It is functionally related to a nicotinic acid.

名称と識別子

優先名称
Boscalid
IUPAC
2-chloro-N-[2-(4-chlorophenyl)phenyl]pyridine-3-carboxamide
現地名
ボスカリド
英語名
Boscalid
分子式
C18H12Cl2N2O
分子量
343.21

名称と別名

Boscalid188425-85-6NicobifenEnduraEmeraldCantusPristineBAS 510FBas 5102-chloro-N-(4'-chlorobiphenyl-2-yl)nicotinamideDTXSID6034392UNII-32MS8ZRD1V
名称をさらに表示
ボスカリド標準品ボスカリド2-クロロ-N-(4'-クロロビフェニル-2-イル)ニコチンアミドCS_N-11328-100MG_ボスカリドボスカリド STANDARDボスカリド Standard, 100 µg/mL in Methanolニコビフェンカンタス2-クロロ-N-(4′-クロロビフェニル-2-イル)ニコチンアミド2-クロロ-N-{4'-クロロ-[1,1'-ビフェニル]-2-イル}ピリジン-3-カルボキサミドN-(4′-クロロ-1,1′-ビフェニル-2-イル)-2-クロロピリジン-3-カルボアミド2-クロロ-N-(4′-クロロ-2-ビフェニリル)ニコチンアミドBoscalid 100mg [188425-85-6]2-CHLORO-N-(4'-CHLORO-2-BIPHENYLYL)NICOTINAMIDEboscali50%Boscalid80%Boscalid70%BoscalidBoscalid >Jingqinhe Ling
Bas-51032MS8ZRD1VEmerald8115BAS 510 FHSDB 7499DTXCID4014392CHEBI:818222-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl)pyridine-3-carboxamide

物性

構造計算による物性

XLogP
4.9
極性表面積
42 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
3
重原子数
23
形式電荷
0
複雑度
398

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
pHpH = 5.5 at 23 °C (1% solution)
Pesticides · 6 件

Pesticides

Fungicides

Active substance -> EU Pesticides database: Approved

Pesticides -> Fungicides

Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

LogPlog Kow = 2.96
OdorOdorless
Density1.381 at 20 °C
Color/FormWhite crystalline
Solubility · 3 件

In water, 4.6 mg/L at 20 °C

Solubility in n-heptane, <10 g/L, 20 °C

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 °C

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point142.8 to 143.8 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 1.7% (3 of 178) of reports.

H411 (98.3%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 178 reports by companies from 3 notifications to the ECHA C&L Inventory.

H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 2 件

Boscalid is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

Reg. (EU) 2022/708, 08/44/EC, Reg (EU) 2023/918, Reg (EU) 2026/372, Reg. (EU) 2018/917, Reg. (EU) 2019/707, Reg. (EU) 2020/869, Reg. (EU) 2021/745, Reg. (EU) No 540/2011

Hazards Summary · 1 件

In high-dose animal studies, causes changes in thyroid and liver; [RTECS] Suggestive evidence of carcinogenicity, but not sufficient to assess human carcinogenic potential. Practically nontoxic to terrestrial animals and moderately toxic to aquatic animals for acute exposures; Ecological risks are low; Slowly degradable with low mobility in most soils; Exposure of aquatic animals is limited by chemical's tendency to sorb to sediments. [Reference #1]

Special Reports · 1 件

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]

FIFRA Requirements · 5 件

Tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), in or on the following raw agricultural commodities:[Table#7160]

化学と産業

薬理情報

Biological Half-LifeIn 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.
Metabolism/Metabolites · 2 件

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/

Absorption, Distribution and Excretion · 2 件

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/

用途と製造

Uses · 5 件

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
188425-85-6
PubChem CID
213013
DTXSID
DTXSID6034392
ChEMBL
CHEMBL1076544
ChEBI
CHEBI:81822
UNII
32MS8ZRD1V
EC Number
606-143-0
Nikkaji
J1.989.940C
Vapor Pressure · 2 件

0.00000001 [mmHg]

7.2X10-4 mPa /5.4X10-10 mm Hg/ at 20 °C

Henry's Law ConstantHenry's Law constant = 5.178X10-5 Pa- cu m/mol /5.3X10-11 atm-cu m/mol/ at 25 °C

物理化学的性質

融点
142.8 · 142.8-143.8°.
沸点
447.7 · 447.7±45.0 °C(Predicted)
比重(密度)
1.381 · 1.381
闪点
4 °C · 4 °C
貯蔵温度
2 · Inert atmosphere,2-8°C
水溶解度
Practically insoluble in water
溶解性
DMSO: Slightly Soluble,Methanol: Slightly Soluble
酸解離定数(Pka)
10.75 · 10.75±0.70(Predicted)
外見
すっきり&_&しっかり
色
White to Almost white
Merck
14 · 14,1352
Henry's Law Constant
1.9 · 1.9×104 mol/(m3Pa) at 25℃, MacBean (2012)
主な用途
農業環境
InChI
InChI=1S/C18H12Cl2N2O/c19-13-9-7-12(8-10-13)14-4-1-2-6-16(14)22-18(23)15-5-3-11-21-17(15)20/h1-11H,(H,22,23)
InChIKey
WYEMLYFITZORAB-UHFFFAOYSA-N
SMILES
C1(Cl)=NC=CC=C1C(NC1=CC=CC=C1C1=CC=C(Cl)C=C1)=O
LogP
4.31 · 4.310 (est)
EPAの化学物質情報
Boscalid (188425-85-6)

化学的性質

化学的特性Light Beige Solid

Tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), and metabolites 2-chloro-N-(4'-chloro-5-hydroxy-biphenyl-2-yl) nicotinamide and glucuronic acid conjugate of 2-chloro-N-(4'-chloro-5-hydroxy-biphenyl-2-yl) nicotinamide, calculated as the stoichiometric equivalent of boscalid in or on the following food commodities:[Table#7161]

Time-limited tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Compliance with the tolerance level specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl). This tolerance will expire and is revoked on the date specified in the following table:[Table#7162]

Tolerances are established for the indirect or inadvertent residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), in or on the following commodities:[Table#7163]

Pesticide Fact Sheet for Boscalid: Reason for Issuance: New Chemical; Date Issued: July 2003.

Toxic Combustion ProductsSpecial hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas.
Hazard Classes and CategoriesAquatic Chronic 2 (98.3%)
State Drinking Water Guidelines(ME) MAINE 152.6 ug/L
Skin, Eye, and Respiratory IrritationsNot irritating in Primary Eye Irritation Test. Not irritating to skin in a Primary Dermal Irritation Test. /From table/

安全と保護具

Fire Fighting Procedures · 2 件

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.

Storage Conditions · 2 件

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

Cleanup Methods · 1 件

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.

Disposal Methods · 2 件

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.

Preventive Measures · 5 件

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.

Allowable Tolerances · 4 件

Tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), in or on the following raw agricultural commodities:[Table#7156]

Tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), and metabolites 2-chloro-N-(4'-chloro-5-hydroxy-biphenyl-2-yl) nicotinamide and glucuronic acid conjugate of 2-chloro-N-(4'-chloro-5-hydroxy-biphenyl-2-yl) nicotinamide, calculated as the stoichiometric equivalent of boscalid in or on the following food commodities:[Table#7157]

Time-limited tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Compliance with the tolerance level specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl). This tolerance will expire and is revoked on the date specified in the following table:[Table#7158]

Tolerances are established for the indirect or inadvertent residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), in or on the following commodities:[Table#7159]

Personal Protective Equipment (PPE) · 4 件

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).

毒性情報

Ecotoxicity Values · 1 件

EC50; Species: Danio rerio (Zebra Danio) age 6-8 hr postfertilization embryo; Conditions: freshwater, renewal, 26 °C; Concentration: 1.1337 uM for 120 hr; Effect: multiple effects: increased mortality, deformation; decreased hatch /formulation/

Environmental Fate · 5 件

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.

Food Survey Values · 4 件

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.

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Toxicity Summary · 1 件

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.

Ecotoxicity Excerpts · 5 件

/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.

Animal Concentrations · 2 件

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 an 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.

There is considerable and ongoing debate as to the harm inflicted on bees by exposure to agricultural pesticides. In part, the lack of consensus reflects a shortage of information on field-realistic levels of exposure. Here, we quantify concentrations of neonicotinoid insecticides and fungicides in the pollen of oilseed rape, and in pollen of wildflowers growing near arable fields. We then compare this to concentrations of these pesticides found in pollen collected by honey bees and in pollen and adult bees sampled from bumble bee colonies placed on arable farms. We also compared this with levels found in bumble bee colonies placed in urban areas. Pollen of oilseed rape was heavily contaminated with a broad range of pesticides, as was the pollen of wildflowers growing nearby. Consequently, pollen collected by both bee species also contained a wide range of pesticides, notably including the fungicides carbendazim, boscalid, flusilazole, metconazole, tebuconazole and trifloxystrobin and the neonicotinoids thiamethoxam, thiacloprid and imidacloprid. In bumble bees, the fungicides carbendazim, boscalid, tebuconazole, flusilazole and metconazole were present at concentrations up to 73 nanogram/gram (ng/g). It is notable that pollen collected by bumble bees in rural areas contained high levels of the neonicotinoids thiamethoxam (mean 18 ng/g) and thiacloprid (mean 2.9 ng/g), along with a range of fungicides, some of which are known to act synergistically with neonicotinoids. Pesticide exposure of bumble bee colonies in urban areas was much lower than in rural areas. Understanding the effects of simultaneous exposure of bees to complex mixtures of pesticides remains a major challenge.

Ongoing Test Status · 1 件

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 July 7, 2016: http://actor.epa.gov/dashboard/]

Soil Adsorption/Mobility · 2 件

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.

Human Toxicity Excerpts · 2 件

/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.

Artificial Pollution SourcesBoscalid'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).
Environmental Biodegradation · 2 件

AEROBIC: A biodegradation half-life in soil ranging from 96 to 578 days and a dissipation half-life range of 27 to 372 days(1) indicate that boscalid is not expected to biodegrade rapidly under aerobic conditions(SRC).

ANAEROBIC: Boscalid is stable in soil under anaerobic conditions(1).

法規制情報

FIFRA Requirements · 5 件

Tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), in or on the following raw agricultural commodities:[Table#7160]

Tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), and metabolites 2-chloro-N-(4'-chloro-5-hydroxy-biphenyl-2-yl) nicotinamide and glucuronic acid conjugate of 2-chloro-N-(4'-chloro-5-hydroxy-biphenyl-2-yl) nicotinamide, calculated as the stoichiometric equivalent of boscalid in or on the following food commodities:[Table#7161]

Time-limited tolerances are established for residues of the fungicide boscalid, including its metabolites and degradates, in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. Compliance with the tolerance level specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl). This tolerance will expire and is revoked on the date specified in the following table:[Table#7162]

Tolerances are established for the indirect or inadvertent residues of the fungicide boscalid, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only boscalid, 3-pyridinecarboxamide, 2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl), in or on the following commodities:[Table#7163]

Pesticide Fact Sheet for Boscalid: Reason for Issuance: New Chemical; Date Issued: July 2003.

State Drinking Water Guidelines(ME) MAINE 152.6 ug/L

安全データ

wgk
2
rtecs
US4587550
ridadr
UN1294 3/PG 2
毒性
LD50 in rats (mg/kg): >5000 orally; >2000 dermally (U.S. EPA)
hs_code
2933.39.2100
risk_code
11-38-48/20-63-65-67-51/53
hazard_code
F,Xn,N
safety_code
36/37-62-61
hazard_class
9
packing_group
III
Hazard Classifications
Aquatic Chronic 2
ストレージクラス
11 - Combustible Solids
有毒物質データの
188425-85-6(Hazardous Substances Data)

Used as a broad spectrum carboxamide fungicide to control diseases in turf, field, row, orchard, and vineyard crops; [Merck Index]

Farming (Pesticides) [Category: Industry]

For boscalid (USEPA/OPP Pesticide Code: 128008) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Fungicide, plant health product, seed treatment/protectant.

This is a man-made compound that is used as a pesticide.

Methods of Manufacturing · 3 件

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).

Formulations/Preparations · 5 件

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.

Household ProductsInformation on 2 consumer products that contain Boscalid in the following categories is provided:
Use Classification · 2 件

Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

General Manufacturing InformationThe 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.
応用分野 · 2 件

用途ミトコンドリア複合体Ⅱ阻害剤菌核病菌や灰色かび病菌など子嚢菌やその近縁の不完全菌

使用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. Bos calid is used in the agriculture to protect crops from gray mold, powdery mildew and other fungus.

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補足説明 · 1 件

定義ChEBI: 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., <ital Alternaria spp. and Sclerotinia spp. for use on a wide range of crops including fruit, vegetables and ornamentals.

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.

/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.