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オルトスルファムロン

Orthosulfamuron

HCID 11091168
ノートを作成反応を作成見積依頼を出す
印刷プレビュー
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
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基本情報

CAS
213464-77-8
標準SMILES
COc1cc(OC)nc(NC(=O)NS(=O)(=O)Nc2ccccc2C(=O)N(C)C)n1
InChIKey
UCDPMNSCCRBWIC-UHFFFAOYSA-N
分子式
C16H20N6O6S
平均分子量
424.4 g/mol
単同位体質量
424.11650355

概要

Orthosulfamuron is an N-sulfonylurea and sulfuric amide resulting from the formal condensation of sulfuric acid with the primary amino group of 1-(4,6-dimethoxypyrimidin-2-yl)urea and with the primary amino group of 2-amino-N,N-dimethylbenzamide (1 mol eq. of each). An acetolactate synthase inhibitor, it is used as a pre- and post-emergent herbicide for the treatment of grasses and broad-leaved weeds in rice crops. It has a role as an EC 2.2.1.6 (acetolactate synthase) inhibitor and a herbicide. It is a tertiary carboxamide, an aromatic ether, a sulfuric amide and a N-sulfonylurea.

名称と識別子

優先名称
Orthosulfamuron
IUPAC
2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethylbenzamide
現地名
オルトスルファムロン
英語名
Orthosulfamuron
分子式
C16H20N6O6S
分子量
424.43

名称と別名

Orthosulfamuron213464-77-8KelionPercutioOrthosulfamuron [ISO]RO0AIV9EYNDTXSID4034788IR 5878UNII-RO0AIV9EYNHSDB 78882-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylamino]-N,N-dimethylbenzamideBENZAMIDE,2-
名称をさらに表示
オルトスルファムロンfamuronOrthosuLOrthosulfamuron,NAAzoxynil sulfonamideOrthosulfamuron solutionC15748500 OrthosulfamuronPhenolphthalein Impurity 4Orthosulfamuron@100 μg/mL in Acetone
ORTHOSULFAMURON [MI]DTXCID2014788CHEBI:1410681-(4,6-Dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)phenylsulfamoyl]urea(1-(4,6-dimethoxypyrimidin-2-yl)-3-1-(4,6-DIMETHOXYPYRIMIDIN-2-YL)-3-(2-(DIMETHYLCARBAMOYL)PHENYLSULFAMOYL)UREA2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]sulfamoyl}amino)-N,N-dimethylbenzamide2-((((((4,6-DIMETHOXY-2-PYRIMIDINYL)AMINO)CARBONYL)AMINO)SULFONYL)AMINO)-N,N-DIMETHYLBENZAMIDE

データベース識別子

物性

構造計算による物性

XLogP
1.6
極性表面積
160 Ų
水素結合供与体数
3
水素結合受容体数
9
回転可能結合数
7
重原子数
29
形式電荷
0
複雑度
657

実験および物理化学的性質

Pesticides · 4 件

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticide (Orthosulfamuron) -> USDA PDB

Pesticide

LogPlog Kow = 1.31 (pH 7); 2.02 (pH 4); <0.3 (pH 9)
Density1.48 at 22.0 °C
Color/FormVery fine white powder with a tendency to form clumps
Solubility · 2 件

In n-heptane 0.23, xylene 129.8 (both in mg/L, 20 °C). In acetone 19.5, ethyl acetate 3.3, 1,2-dichloromethane 56.0, methanol 8.3 ( all in g/L, 20 °C)

In water, 629 mg/L at 20 °C (pH 7); 26.2 mg/L at 20 °C (pH 4); 38,900 mg/L at 20 °C (pH 8.5)

Boiling PointDecomposes before boiling
Melting Point157 °C
Vapor Pressure8.4X10-7 mm Hg at 20 °C at 25 °C

物理化学的性質

融点
160 · 160–162°C
比重(密度)
1.466 · 1.466±0.06 g/cm3(Predicted)

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 · 4 件

Warning

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

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

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 4 件

Commission Regulation (EU) No 188/2011

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

06/806/EC, Reg. (EU) 2017/840

REACH registered substance: Orthosulfamuron (EC: 606-744-8)

FIFRA RequirementsTolerances are established for residues of orthosulfamuron 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)- phenylsulfamoyl] urea) per se in or on the following commodities: [Table#7688]
Hazard Classes and CategoriesAquatic Acute 1 (100%)

安全と保護具

Fire Fighting Procedures · 1 件

Fire-Fighting Measures. Recommended extinguishers: Water, CO2, Foam, Chemical powders, according to material involved in fire. ... Risks arising from combustion: Avoid inhaling the fumes which at high temperatures may contain toxic fumes such as CO(x), NO(x) and SO(x). Protective equipment: Wear breathing protection (respirator) and standard protection equipment according to the materials involved in the fire. /Strada WG Herbicide/

Storage Conditions · 2 件

Store in cool, dry place ... Adequately ventilated premises.

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. /Residential users/

化学と産業

薬理情報

Mechanism of Action · 1 件

Orthosulfamuron is a systemic post-emergence herbicide belonging to the sulfamoylurea class of herbicides. Sulfamoylurea herbicides act through inhibition of branch-chain amino acid biosynthesis in plants. Orthosulfamuron's specific mode of action is through the inhibition of the plant enzyme, acetolactate synthase, also known as acetohydroxy acid synthase (ALS/AHAS). Inhibition of ALS/AHAS blocks the branched-chain amino acid biosynthesis of valine, leucine, and isoleucine, which are involved in the plant growth process.

Biological Half-Life · 1 件

In a series of rat metabolism studies, [14C-U-phenyl] IR5878 or [14C-5-pyrimidinyl] IR5878 in 0.5% aqueous carboxymethycellulose (radiochemical purity >97%) was administered by gavage to Sprague Dawley rats. In the preliminary study, 2 rats/sex received a single 250 mg/kg dose. In the main study, 4 rats/sex/dose received a single dose of 5 or 1000 mg/kg or 14 daily doses at 5 mg/kg (non-radioactive) followed by a single radioactive dose (5 mg/kg) on day 15. Additionally, a biliary excretion study was performed where 4 males and 7 females received a single dose at 5 mg/kg. ... The half-life was similar regardless of sex, dose, or number of doses (8.9-13.3 hr), with the exception of the females treated with a single 5 mg/kg dose of [14C-5- pyrimidinyl] IR5878 (16.7 hr). ...

Metabolism/Metabolites · 1 件

...HPLC and HPLC-MS analyses were used to identify parent and a total of 10 metabolites in excreta from rats treated with [14C] IR5878. Six to 7 metabolites were identified after treatment with each radiolabeled compound, and 3 of these metabolites were common to treatment with both radiolabeled compounds. Parent and identified metabolites in excreta accounted for 71-86% of the dose in all animals, and overall recovery was 95-99% of the dose. Unidentified compounds accounted for 1-16% of the dose, but no single compound accounted for > or = 5% of the dose. The parent was found in the 5 mg/kg animals (single and multiple doses) at 1-6% dose and in the 1000 mg/kg animals at 33-56% dose in urine and feces. The predominant metabolite was 1-(4- methoxy-6-hydroxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)phenylsulfamoyl]urea (O-desm IR5878). It was found at 53-64% dose in all animals treated at 5 mg/kg/day and at 14-20% dose in all animals treated at 1000 mg/kg; it was found in similar quantities in the urine and feces. 2-sulfoamino-N,N-dimethylbenzamide (DBS acid) was a primary metabolite in all animals treated with [14C-U-phenyl] IR5878 and was found primarily in the feces at 8-12% dose. In all animals treated with [14C-5-pyrimidinyl] IR5878, a fraction was isolated (primarily in feces) that contained (4,6-dimethoxy-5-O-glucuronidyl pyrimidin-2-yl)urea (Pyr-O-Glucur DOP urea) and 1- (4,6-dimethoxy-5-O-glucuronidyl pyrimidin-2-yl)-3-[2- (dimethylcarbamoyl)phenylsulfamoyl]urea (Pyr-O-Glucur IR5878). This fraction represented 9-18% dose. Additionally, 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(methylcarbamoyl)phenylsulfamoyl] urea (N-desm IR5878) was found at 5-8% dose in the urine of animals treated with 1000 mg/kg [14C-5-pyrimidinyl] IR5878. All other identified metabolites each accounted for <5% dose. Identification of IR5878 metabolites indicates that metabolism mainly occurs through O- and/or N-demethylations. Additionally, hydrolytic cleavage of the sulfamoylurea linkage yields DOP urea, and hydroxylation of the pyrimidinyl ring occurs followed by glucuronic acid or sulfate conjugation. The metabolic profile of the liver, kidney, and bile was also evaluated. In the liver and kidneys of all animals treated with [14C-U-phenyl] IR5878, the parent and O-desm IR5878 were found in the highest concentrations. In the liver and kidneys of all animals treated with [14C-5- pyrimidinyl] IR5878, O-desm IR5878 and an unidentified fraction were generally found in the highest concentrations, as well as 2-amino-N,N-dimethylbenzamide (DB amine) in the male kidney. In the bile, O-desm IR5878 and an unidentified fraction were found in the highest concentration. Other identified compounds (same as found in the excreta) were not detected in the liver, kidney, or bile or were generally found at relatively low concentrations.

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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
その他の操作
ノートを作成反応を作成見積依頼を出す
CAS
213464-77-8
PubChem CID
11091168
DTXSID
DTXSID4034788
ChEMBL
CHEMBL3561054
ChEBI
CHEBI:141068
UNII
RO0AIV9EYN
EC Number
606-744-8
Nikkaji
J3.178.741F
蒸気圧
1.1 · <1.1 × 10-4 (Pa at 25 °C)
貯蔵温度
Refrigerator, under inert atmosphere
溶解性
有機溶媒への溶解度 (g/lat 20°C) キシレン 0.13
酸解離定数(Pka)
Dissociation constant (pKa at 20 °C) Predicted to have five overlapping dissociation constants: 1.4, 0.7, 3.5, 9.6, 11.5
色
ホワイトからオフホワイト
水溶解度
水に対する溶解度 (g/lat 20℃) 0.026 (pH4、緩衝液) 0.63 (pH7、緩衝液) 39 (pH8.5、緩衝液)
BRN
11343666 · 11343666
Henry's Law Constant
1.3 · 1.3×104 mol/(m3Pa) at 25℃, HSDB (2015)
安定性
湿気に敏感
主な用途
農業環境
InChI
1S/C16H20N6O6S/c1-22(2)14(23)10-7-5-6-8-11(10)20-29(25,26)21-16(24)19-15-17-12(27-3)9-13(18-15)28-4/h5-9,20H,1-4H3,(H2,17,18,19,21,24)
InChIKey
UCDPMNSCCRBWIC-UHFFFAOYSA-N
SMILES
COc1cc(OC)nc(NC(=O)NS(=O)(=O)Nc2ccccc2C(=O)N(C)C)n1
LogP
0.3 · 0.3-2.02 at 20℃ and pH4-9
表面張力
71.4 mN/m · 71.4mN/m at 37.7mg/L and 22℃
EPAの化学物質情報
2 · Benzamide, 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]amino]-N,N-dimethyl- (213464-77-8)
Cleanup Methods · 3 件

ACCIDENTAL RELEASE MEASURES. Measures for personal safety: use a mask, gloves and protective clothing ... ; Environmental measures: If the product has entered a waterway and/or drainage system, or has contaminated the ground and/or vegetation, notify the competent authorities; Cleaning methods: Rapidly recover the product and prevent it from entering into drainage systems, if possible. In so doing wear protective clothing ... After the product has been recovered, rinse the area and contaminated materials involved with water. Dispose unrecoverable product, rinsate, or rinsate solids as hazardous substance. /Strada WG Herbicide/

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/

Disposal Methods · 5 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Disposal Considerations. Recover, if possible. Send non-recoverable product, rinsate or rinsate solids to authorized disposal plants or for incineration under controlled conditions. In so doing, comply with the local and national regulations currently in force. /Strada WG Herbicide/

Do not contaminate arable land and/or water when disposing of equipment wash water or rinsate. /Strada WG Herbicide/

Wastes resulting from the use of this product must be disposed of on site or at an approved waste disposal facility. /Strada WG Herbicide/

For more Disposal Methods (Complete) data for Orthosulfamuron (6 total), please visit the HSDB record page.

Preventive Measures · 5 件

Use this product only in accordance with its labeling, and with the Worker Protection Standard, 40 CFR part 170. /Strada WG Herbicide/

Do not apply this product in a way that will contact workers or other people, either directly or through drift. Only protected handlers may be in the area during application. /Strada WG Herbicide/

Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. /Strada WG Herbicide/

Users should wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Users should remove clothing/PPE immediately if pesticide gets inside. Then wash skin thoroughly and put on clean clothing. /Strada WG Herbicide/

For more Preventive Measures (Complete) data for Orthosulfamuron (16 total), please visit the HSDB record page.

Allowable TolerancesTolerances are established for residues of orthosulfamuron 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)- phenylsulfamoyl] urea) per se in or on the following commodities: [Table#7687]
Personal Protective Equipment (PPE) · 3 件

Applicators and other handlers must wear the following: Long-sleeved shirt and long pants. Shoes plus socks. Chemical-resistant gloves made of any waterproof material. Protective eyewear. /Strada WG Herbicide/

... Restricted entry interval (REI) of 12 hours. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, is: coveralls, chemical resistant gloves, (made of any waterproof material), protective eyewear, and shoes plus socks. /Strada WG Herbicide/

When handlers use closed systems, enclosed cabs, or aircraft in a manner that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides (40 CFR 170.240(d)(4-6), the handler PPE requirements may be reduced or modified as specified in the WPS. /Strada WG Herbicide/

毒性情報

Ecotoxicity Values · 5 件

LC50; Species: Oncorhynchus mykiss (Rainbow trout, juvenile); Conditions: freshwater, static; Concentration: >122 mg/L for 96 hr /98.56% a.i./

LC50; Species: Lepomis macrochirus (Bluegill sunfish, juvenile); Conditions: freshwater, static; Concentration: >142 mg/L for 96 hr /98.56% a.i./

EC50; Species: Daphnia magna (Water flea, neonate); Conditions: freshwater, static; Concentration: >97.3 mg/L for 48 hr; Effect: immobilization (lethality) /98.54% a.i./

LC50; Species: Procambarus clarkia (Crayfish, juvenile); Conditions: freshwater, static; Concentration: >129 mg/L for 96 hr /98.56% a.i./

For more Ecotoxicity Values (Complete) data for Orthosulfamuron (27 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that orthosulfamuron is expected to have very high mobility in soil(SRC). Volatilization of orthosulfamuron from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.4X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, 8.4X10-7 mm Hg(3), and water solubility, 629 mg/L(3). Orthosulfamuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). No biodegradation data were located for orthosulfamuron in soil but aerobic degradation is expected to be the major route of dissipation in alkaline paddy water(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that orthosulfamuron is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.4X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 8.4X10-7 mm Hg(4), and water solubility, 629 mg/L(4). Orthosulfamuron is expected to undergo hydrolysis in the environment and has reported half-lives of 8 hours, 24 days and 228 days at pH 4, 7 and 9, respectively, at 25 °C(4). According to a classification scheme(5), an estimated BCF of 3.4(SRC), from its log Kow of 1.31(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Orthosulfamuron's major route of degradation in acidic to neutral rice paddy water is hydrolysis, with a half-life of hours to days(7). Aerobic biodegradation is the major route of degradation in alkaline rice paddy water, with a half-life of weeks to months(7). Both routes of degradation are expected at similar rates in paddy water at neutral pH(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), orthosulfamuron, which has a vapor pressure of 8.4X10-7 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase orthosulfamuron is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 35 minutes(SRC), calculated from its rate constant of 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase orthosulfamuron may be removed from the air by wet or dry deposition(SRC). Orthosulfamuron contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Ecotoxicity Excerpts · 5 件

/BIRDS and MAMMALS/ Chronic studies of the reproductive toxicity of orthosulfamuron in mallard duck and bobwhite quail administered orthosulfamuron TGAI for approximately 21 weeks. ...Results of both studies showed no treatment-related effects on adult bird mortality, food consumption, body weight, clinical signs, or reproductive endpoints at the highest dietary concentration tested (NOAEC = 1280 mg a.i./kg diet). In addition, no clinical signs or treatment-related effects in offspring survival or body weight were observed at the highest dietary concentration tested in these studies (1280 mg a.i/kg diet).

/AQUATIC SPECIES/ The acute toxicity of technical grade orthosulfamuron to freshwater fish was evaluated in two species, with 96-hour LC50 values of >122 mg a.i./L in rainbow trout and >142 mg a.i./L in bluegill sunfish. No mortalities were observed in controls or treated groups for both studies. Based on these results, orthosulfamuron is categorized as practically nontoxic to freshwater fish on an acute exposure basis.

/AQUATIC SPECIES/ The acute toxicity of technical grade orthosulfamuron to estuarine/marine fish was evaluated in the sheepshead minnow. The study reported a 96-hour LC50 >123 mg a.i./L, indicating that orthosulfamuron was practically nontoxic to estuarine/marine fish on an acute exposure basis. No sublethal effects were observed in sheepshead minnow exposed up to 123 mg a.i./L.

/AQUATIC SPECIES/ Acute toxicity tests with estuarine/marine invertebrates exposed to technical grade orthosulfamuron were conducted in eastern oyster and mysid shrimp. No effect on shell deposition or increased mortality were observed in an acute toxicity (96-hour) test in the eastern oyster exposed to orthosulfamuron TGAI, yielding a 96-hour EC50 >97 mg a.i./L. These results indicate that orthosulfamuron is characterized as slightly toxic to estuarine/marine mollusks. An acute toxicity study of orthosulfamuron in the mysid shrimp reported a 96-hour LC50 >122 mg a.i./L, indicating that orthosulfamuron is practically nontoxic to estuarine/marine invertebrates on an acute exposure basis; no sublethal effects were observed.

For more Ecotoxicity Excerpts (Complete) data for Orthosulfamuron (12 total), please visit the HSDB record page.

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of orthosulfamuron can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that orthosulfamuron is expected to have very high mobility in soil.

Artificial Pollution SourcesOrthosulfamuron's production may result in its release to the environment through various waste streams; its use as a herbicide(1) will result in its direct release to the environment(SRC).
Environmental BiodegradationAEROBIC: Moderate biodegradation occurs in water(1). Aerobic biodegradation is the major route of degradation in alkaline rice paddy water, with a half-life of weeks to months(1).
Environmental Bioconcentration · 1 件

An estimated BCF of 3.4 was calculated in fish for orthosulfamuron(SRC), using a log Kow of 1.31(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for orthosulfamuron is estimated as 7.4X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 8.4X10-7 mm Hg(1), and water solubility, 629 mg/L(1). This Henry's Law constant indicates that orthosulfamuron is expected to be essentially nonvolatile from water or moist soil surfaces(2). Orthosulfamuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Non-Human Toxicity Excerpts · 5 件

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90-day subchronic oral toxicity study, IR5878 (98.0% a.i.) was administered to ten Han Wistar rats/sex/dose in the diet at dose levels of 0, 250, 1500, and 9000 ppm (equivalent to 0, 19, 113, and 706 mg/kg bw/day, respectively, for males and to 0, 22, 131, and 773 mg/kg bw/day, respectively, for females). Concurrently, a recovery group of five Han Wistar rats/sex/dose were administered either 0 or 9000 ppm (equivalent to 0 or 706 mg/kg bw/day, respectively, for males and to 0 or 773 mg/kg bw/day, respectively, for females) during the 90-day study period and were then maintained for an additional four weeks on the control diet. There were no compound-related effects on mortality, body weights, body weight gains, food consumption, neurological observations and measurements, hematology, clinical chemistry, or gross pathology. Compared to controls, an increase in dorsal hair loss was seen in females, but this finding is common. Other treatment-related effects (transient increases in liver weight and hepatocellular hypertrophy in high-dose males compared to controls) indicate a minimal, adaptive response in the liver following exposure to IR5878 that is not considered adverse. The LOAEL was not identified in this study (>706 mg/kg/day for males and >773 mg/kg/day for females). The NOAEL is the highest dose tested in this study (9000 ppm), which was equivalent to 706 mg/kg/day for males and 773 mg/kg/day for females.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90-day subchronic oral toxicity study, IR5878 (98.0% a.i.) was administered to ten CD-1 mice/sex/dose in the diet at dose levels of 0, 250, 1250, and 6000 ppm (equivalent to 0, 36, 187, and 865 mg/kg bw/day, respectively, for males and to 0, 47, 228, and 1096 mg/kg bw/day, respectively, for females). There were no compound-related effects on clinical signs, mortality, body weights, clinical chemistry, gross pathology, or histopathology. Compared to controls, slight decreases in food consumption, MCH, and MCV in high-dose females and slight decreases in the lymphocyte count of high-dose males were noted, but these changes were not biologically significant. The LOAEL was not identified in this study (>865 mg/kg/day for male mice and >1096 mg/kg/day for females). The NOAEL is the highest dose tested in this study (6000 ppm), which was equivalent to 865 mg/kg/day for male mice and 1096 mg/kg/day for females. Dosing in this study is considered adequate because the highest dose tested is sufficiently close to the limit dose of 1000 mg/kg/day.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 28-day dermal toxicity study, Orthosulfamuron (IR5878; 98.56% a.i.) was moistened with deionized water and applied by semi-occlusive dressing to the shaved intact skin of 10 Sprague-Dawley rats/sex/dose at dose levels of 0 or 1000 mg/kg bw/day (limit dose), 6 hours/day for 7 days/week during a 4-week period. No adverse compound-related effects were observed in mortality, clinical signs, dermal effects, body weight, body weight gain, food consumption, food conversion efficiency, hematology, clinical chemistry, ophthalmology, absolute or relative organ weights, or gross and histological pathology. The LOAEL was not determined. The NOAEL is 1000 mg/kg/day (limit dose).

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of orthosulfamuron with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 35 minutes at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Orthosulfamuron is expected to undergo hydrolysis in the environment and has reported half-lives of 8 hours, 24 days and 228 days at pH 4, 7 and 9, respectively, at 25 °C(2). Orthosulfamuron's major route of degradation in acidic to neutral rice paddy water is hydrolysis, with a half-life of hours to days(3). Orthosulfamuron contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human ExposureOccupational exposure to orthosulfamuron may occur through inhalation of dust and dermal contact with this compound at workplaces where orthosulfamuron is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 件

Orthosulfamuron's production may result in its release to the environment through various waste streams; its use as a herbicide will result in its direct release to the environment. If released to air, a vapor pressure of 8.4X10-7 mm Hg at 25 °C indicates orthosulfamuron in both the vapor and particulate phases in the atmosphere. Vapor-phase orthosulfamuron will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 35 minutes. Particulate-phase orthosulfamuron will be removed from the atmosphere by wet or dry deposition. Orthosulfamuron contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, orthosulfamuron is expected to have very high mobility based upon an estimated Koc of 10. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 7.4X10-10 atm-cu m/mole. Orthosulfamuron's major route of degradation in acidic to neutral rice paddy water is hydrolysis, with a half-life of hours to days. Aerobic biodegradation is the major route of degradation in alkaline rice paddy water, with a half-life of weeks to months. Both routes of degradation are expected at similar rates in paddy water at neutral pH. If released into water, orthosulfamuron is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3.4 suggests the potential for bioconcentration in aquatic organisms is low. Orthosulfamuron is expected to undergo hydrolysis in the environment and has reported half-lives of 8 hours, 24 days and 228 days at pH 4, 7 and 9, respectively, at 25 °C. Occupational exposure to orthosulfamuron may occur through inhalation of dust and dermal contact with this compound at workplaces where orthosulfamuron is produced or used. (SRC)

法規制情報

FIFRA RequirementsTolerances are established for residues of orthosulfamuron 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)- phenylsulfamoyl] urea) per se in or on the following commodities: [Table#7688]

安全データ

wgk
3
ストレージクラス
11 - Combustible Solids
有毒物質データの
213464-77-8(Hazardous Substances Data)
Absorption, Distribution and Excretion · 1 件

In a series of rat metabolism studies, [14C-U-phenyl] IR5878 or [14C-5-pyrimidinyl] IR5878 in 0.5% aqueous carboxymethycellulose (radiochemical purity >97%) was administered by gavage to Sprague Dawley rats. In the preliminary study, 2 rats/sex received a single 250 mg/kg dose. In the main study, 4 rats/sex/dose received a single dose of 5 or 1000 mg/kg or 14 daily doses at 5 mg/kg (non-radioactive) followed by a single radioactive dose (5 mg/kg) on day 15. Additionally, a biliary excretion study was performed where 4 males and 7 females received a single dose at 5 mg/kg. Pharmacokinetic analyses of the absorption and distribution were performed, including blood kinetics, along with identification of the metabolites in the excreta. Absorption was rapid in all groups, regardless of sex, dose, or number of doses. Tmax values were 12 min for the 5 mg/kg repeated dose group, 24 min-1 hr for the single 5 mg/kg dose group, and 1- 4 hr for the single 1000 mg/kg dose group. Following a single 5 mg/kg dose of [14C-U-phenyl] IR5878, 76-82% of the dose was absorbed and found in the urine/cage wash, bile, and carcass, indicating extensive absorption. The half-life was similar regardless of sex, dose, or number of doses (8.9-13.3 hr), with the exception of the females treated with a single 5 mg/kg dose of [14C-5- pyrimidinyl] IR5878 (16.7 hr). Within 12 hr of administration of the radiolabeled dose (5 or 1000 mg/kg single dose or multiple 5 mg/kg doses), approximately half of the dose was excreted, and excretion was almost complete at 72 hr post-dose. At 72 hr post-dose, overall recovery of the radioactive dose from both sexes was 92-100%. The majority of the dose was recovered in the feces (43-73%); 18-46% of the dose was found in the urine; and cage wash accounted for 1-5% dose. Minimal radioactivity was detected in the carcass and GI tract (<0.8% dose). In a preliminary study, <0.02% of the radioactive dose was isolated in the expired air; therefore, this route of excretion was not analyzed. A difference in the excretion profile was generally not noted based on sex, dose, or number of doses. Regardless of sex, dose, or number of doses, the distribution of radioactivity in tissues was similar. Comparison of the concentrations of radioactivity in tissues on the basis of radiolabel was not possible due to contrasting sampling times and/or Tmax; a time course of tissue distribution was not performed. Excluding the GI tract, concentrations of radioactivity were highest in the liver, kidney, lung, and whole blood, with the lung having the lowest concentrations. At 5 mg/kg (single or multiple doses), these tissue concentrations were 1.74-23.83 ug equiv./g vs 2.41-5.10 ug equiv./g in whole blood. At 1000 mg/kg in all treated rats, these tissue concentrations were 161-435 ug equiv./g vs 305-495 ug equiv./g in whole blood. As relatively little radioactivity remained in the carcass at 72 hr post-dose (.0.70% dose), bioaccumulation is not suspected under the test conditions.

用途と製造

Uses · 4 件

For orthosulfamuron (USEPA/OPP Pesticide Code: 108209) 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./

Herbicides (pyrimidinylsulfonylurea herbicides)

For use on rice

Early post-emergence control of annual and perennial broad-leaved weeds, sedges and barnyard grass, in dry-seeded rice, water-seeded rice, transplanted rice, cereals, pastures and sugar cane.

Methods of ManufacturingOrthosulfamuron can be synthesized by reaction of N,N-dimethyl 2-sulfamoylchloride benzcarbamate with 2-amino-4,6-dimethoxypyrimidine in the presence of a base.
Formulations/Preparations · 5 件

Orthosulfamuron Technical (Isagro S.P.A.) 99% Orthosulfamuron

IR5878 50 WG (Isagro S.P.A.) 50% Orthosulfamuron

IR5878 0.5 GR (Isagro S.P.A.) 0.5% Orthosulfamuron

Strada XT (Isagro S.P.A.) 50% Orthosulfamuron, 75% Quinclorac

Orthosulfamuron is formulated as both a water dispersible granule (IR5878 50 WG) and a granule (IR5878 0.5 GR).

応用分野

使用Orthosulfamuron can be used in biological study and agricultural use of herbicidal composition comprising erlukuilincaotong, cyhalofop-butyl and sulfonylurea herbicide, and its application in controlling annual weed of rice field.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90-day oral toxicity study, IR5878 (98.0% a.i.) was administered to four beagle dogs/sex/dose in capsules at dose levels of 0, 150, 450, or 1000 mg/kg bw/day for 13 weeks. There were no compound-related effects on mortality, clinical signs, body weight, food consumption, ophthalmologic examinations, hematology, urinalyses, or gross pathology. Total protein levels in the low-, mid-, and high-dose male groups were marginally lower than control males on week 13. Other treatment-related effects indicate an adaptive response in the liver following exposure to IR5878. Compared to controls, alkaline phosphatase levels were significantly increased in the high-dose male and female groups at weeks 6 and 13. Absolute and relative liver weights in the high-dose female group were 22% and 28% greater, respectively, than controls. In the high-dose male group, relative liver weights were increased 28%, compared to controls. Minimal hypertrophy of centrilobular hepatocytes was found in the liver of one high-dose male and two high-dose females, but this histopathological alteration was not found in the livers of any other subjects. The LOAEL for male and female Beagle dogs is 1000 mg/kg/day, based on increased alkaline phosphatase levels, increased absolute and relative liver weights, and histopathological changes (hypertrophy and centrilobular hepatocytes) in the liver. The NOAEL for male and female dogs is 450 mg/kg/day.

For more Non-Human Toxicity Excerpts (Complete) data for Orthosulfamuron (14 total), please visit the HSDB record page.