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Cyclanilide

HCID 11097730
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
113136-77-9
Standard-SMILES
O=C(O)C1(C(=O)Nc2ccc(Cl)cc2Cl)CC1
InChIKey
GLWWLNJJJCTFMZ-UHFFFAOYSA-N
Summenformel
C11H9Cl2NO3
Durchschnittliche Molmasse
274,1 g/mol
Monoisotopische Masse
272,9959485

Überblick

Cyclanilide is a monocarboxylic acid that is cyclopropanecarboxylic acid that is substituted by a 3,5-dichlorophenylcarbamoyl group at position 1. It is a plant growth regulator which is used as a cotton harvest aid. It has a role as a fungicide and a plant growth regulator. It is an anilide, a dichlorobenzene, a monocarboxylic acid and a member of cyclopropanes.

Namen und Bezeichner

Bevorzugter Name
Cyclanilide
IUPAC
1-[(2,4-dichlorophenyl)carbamoyl]cyclopropane-1-carboxylic acid
Englischer Name
CYCLANILIDE
Summenformel
C11H9Cl2NO3
Molmasse
274.1

Namen und Synonyme

Cyclanilide113136-77-91-((2,4-Dichlorophenyl)carbamoyl)cyclopropanecarboxylic acidFinishCyclanilide [ISO]1-[(2,4-dichlorophenyl)carbamoyl]cyclopropane-1-carboxylic AcidRPA 90946DTXSID5032600UNII-E5WZ0SSS5VE5WZ0SSS5VHSDB 70181-(2,4-dichlorophenylcarbamoyl)cyclopropancarboxylic acid
Weitere Namen anzeigen
RPA 090946Cyclanilide StandardChlorpyrifos Impurity 57Cyclanilide 10.0 μg/ml Acetonitrile
CYCLANILIDE [HSDB]EINECS Annex I Index 616-110-00-2DTXCID30126001-((2,4-dichlorophenyl)carbamoyl)cyclopropane-1-carboxylic acidCHEBI:148439EC 419-150-71-(((2,4-Dichlorophenyl)amino)carbonyl)cyclopropanecarboxylic acid1-[(2,4-Dichlorophenyl)aminocarbonyl]-1-cyclopropanecarboxylic acid

Datenbank-Bezeichner

CAS
113136-77-9
PubChem CID
11097730
DTXSID
DTXSID5032600
ChEMBL
CHEMBL1904079

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,8
Polarare Oberfläche (TPSA)
66,4 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
3
Schwere Atome
17
Formalladung
0
Komplexität
344

Experimentelle und physikochemische Eigenschaften

pHpH = 3.8 (1% w/v water, 21 °C)
Pesticides · 4 Einträge

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Anilide

Pesticide (Cyclanilide) -> USDA PDB

LogPlog Kow = 3.25, unstated pH
Density1.4691 - 1.482 g/ml @ 20 °C
Color/FormPowdery solid
Solubility · 2 Einträge

Low solubility in water, soluble in organic solvents.

Solubility (g/100 ml): acetone 5.29; acetonitrile 0.50; dichloromethane 0.17; ethylacetate 3.18; hexane <0.0001; methanol 5.91; 1-octanol 6.72; 2-propanol 6.82.

CorrosivityNon-corrosive to non-metallic packing materials
Melting Point195.5 °C
Vapor Pressure0.00000001 [mmHg]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

H302 (93.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

Regulation (EC) No 1107/2009 (amended)

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

01/87/EC, Reg. (EU) 2022/801, Reg. (EU) No 1022/2011, Reg. (EU) No 540/2011

REACH registered substance: 1-(2,4-dichlorophenylcarbamoyl)cyclopropancarboxylic acid (EC: 419-150-7)

Hazards SummaryEnd-use product corrosive to eyes and causes severe skin burns that resolve by day 10; [HSDB] See Ethephon.
FIFRA Requirements · 2 Einträge

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 026201; Type of Pesticide: fungicide; Use Site: non-food use (cotton); Year: 1997.

Tolerances are established for residues of the plant growth regulator, cyclanilide, (1-(2,4-dichlorophenylaminocarbonyl)-cyclopropane carboxylic acid) determined as 2,4-dichloroaniline (calculated as cyclanilide) in or on the following food commodities and processed feed: cattle, fat; cattle, meat; cattle, mbyp (except kidney); cattle, kidney; cottonseed; cotton gin byproducts; goats, fat; goats, meat; goats, mbyp (except kidney); goats, kidney; horses, fat; horses, meat; horses, mbyp (except kidney); horses, kidney; hogs, fat; hogs, meat; hogs, mbyp (except kidney); hogs, kidney; milk; sheep, fat; sheep, meat; sheep, mbyp (except kidney); sheep, kidney.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesIn the rat metab study radioactive cyclanilide was rapidly absorbed after oral admin. The principal route of elimination was by renal excretion of the parent compound & amino acid conjugates. Methylation was a minor metabolic pathway.
Absorption, Distribution and ExcretionIn the rat metab study radioactive cyclanilide was rapidly absorbed after oral admin. The principal route of elimination was by renal excretion of the parent compound & amino acid conjugates. Methylation was a minor metabolic pathway.

Verwendung und Herstellung

Uses · 6 Einträge

A plant growth regulator applied at the end of the cotton season to promote boll opening, defoliation, and inhibition of terminal foliar regrowth; Formulated with ethephon and sold as FINISH Harvest Aid for Cotton; [Reference #1]

Farming (Pesticides) [Category: Industry]

For Cyclanilide (USEPA/OPP Pesticide Code: 026201) 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./

Plant growth regulator and used as a cotton harvest aid.

Fungicide; non-food use in cotton

Type of Pesticide: fungicide; Use Site: non-food use (cotton); Year: 1997.

Formulations/Preparations · 2 Einträge

USEPA/OPP Pesticide Code 026201; Trade Names: RPA 90946, EXP 31039B, component of.

Cyclanilide Technical ... is a 98.5% manufacturing use product.

Anwendungen · 1 Eintrag

VerwendenCyclanilide is a plant growth regulator that functions by interactting with auxin-regulated processes. Cyclanilide is commonly used on cotton plants to either suppress vegetative growth or accelerate senescence. Cyclanilide is also used as a bioregulator of deciduous fruit trees.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEBI
CHEBI:148439
UNII
E5WZ0SSS5V
EC Number
419-150-7
Nikkaji
J3.180.206G
Henry's Law Constant
Henry's Law constant = 7.31X10-10 atm-cu cm/mol @ 25 °C
Physical DescriptionWhite solid with no characteristic odor; [Reference #1]
Stability/Shelf Life · 2 Einträge

Stable in non-metallic packaging.

Stable for 14 days at 54 °C; stable for 30 days at 50 °C; stable for 90 days at 35 °C; stable for 1 yr at room temp; stable for 14 days of continual exposure to artificial sunlight (23 °C); stable to metals over the range of 30-150 °C; degraded between 40-90 °C in the presence of metal ions.

Physikochemische Eigenschaften

Schmelzpunkt
196 ℃ · approximate 196℃
Siedepunkt
513.2 · 513.2±50.0 °C(Predicted)
Dichte
1.4691 · 1.4691-1.4820 g/cm3
storage temp.
Sealed in dry,Room Temperature
Wasserlöslichkeit
Practically insoluble in water
Löslichkeit
DMSO (Slightly), Methanol (Slightly, Sonicated)
pka
3.39 · 3.39±0.20(Predicted)
Farbe
White to Light yellow
Henry's Law Constant
1.4 · 1.4×104 mol/(m3Pa) at 25℃, MacBean (2012)
InChI
InChI=1S/C11H9Cl2NO3/c12-6-1-2-8(7(13)5-6)14-9(15)11(3-4-11)10(16)17/h1-2,5H,3-4H2,(H,14,15)(H,16,17)
InChIKey
GLWWLNJJJCTFMZ-UHFFFAOYSA-N
SMILES
C1(C(NC2=CC=C(Cl)C=C2Cl)=O)(C(O)=O)CC1
CAS Datenbank
113136 · 113136-77-9
EPA chemische Informationen
Cyclanilide (113136-77-9)
Hazard Classes and Categories · 3 Einträge

Acute Tox. 4 (93.3%)

Acute toxicity - category 4

Acute Tox. 4 *

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Allowable Tolerances · 1 Eintrag

Tolerances are established for residues of the plant growth regulator, cyclanilide, (1-(2,4-dichlorophenylaminocarbonyl)-cyclopropane carboxylic acid) determined as 2,4-dichloroaniline (calculated as cyclanilide) in or on the following food commodities and processed feed: cattle, fat: 0.10 ppm; cattle, meat: 0.02 ppm; cattle, mbyp (except kidney): 0.2 ppm; cattle, kidney: 2.0 ppm; cottonseed: 0.60 ppm; cotton gin byproducts: 25.0 ppm; goats, fat: 0.10 ppm; goats, meat: 0.02 ppm; goats, mbyp (except kidney): 0.20 ppm; goats, kidney: 2.0 ppm; horses, fat: 0.10 ppm; horses, meat: 0.02 ppm; horses, mbyp (except kidney): 0.2 ppm; horses, kidney: 2.0 ppm; hogs, fat: 0.10 ppm; hogs, meat: 0.02 ppm; hogs, mbyp (except kidney): 0.2 ppm; hogs, kidney: 2.0 ppm; milk: 0.04 ppm; sheep, fat: 0.10 ppm; sheep, meat: 0.02 ppm; sheep, mbyp (except kidney): 0.2 ppm; sheep, kidney: 2.0 ppm.

Toxikologische Informationen

Ecotoxicity Values · 5 Einträge

LD50 Bobwhite quail 240 mg ai/kg bw (14 day) /Conditions of bioassay not specified./

LC50 Bobwhite quail 2580 ppm (8 day) /Conditions of bioassay not specified./

LC50 Mallard duck 1740 ppm (8 day) /Conditions of bioassay not specified./

LC50 Bluegill sunfish >16 mg ai/L (96 hr) /Conditions of bioassay not specified./

For more Ecotoxicity Values (Complete) data for CYCLANILIDE (9 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 194 to 565(3) indicates that cyclanilide is expected to have moderate mobility in soil(SRC). Volatilization of cyclanilide from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 7.31X10-10 atm-cu m/mole(2). Cyclanilide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.1X10-9 mm Hg(SRC), determined from a fragment constant method(3). Biodegradation may be an important environmental fate process in soil as it has been reported to be readily biodegradable to 2,4-dichloroaniline with a half-life of 95 days for the parent compound(4).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 194 to 565(6) indicate that cyclanilide 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 7.31X10-10 atm-cu m/mole(2). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cyclanilide is relatively stable to hydrolysis(2). Biodegradation may be an important environmental fate process in water as it has been reported to be readily biodegradable in soil at a half-life of 95 days(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyclanilide, which has an estimated vapor pressure of 9.1X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase cyclanilide may be removed from the air by wet and dry deposition(SRC). Cyclanilide is relatively stable to photolysis; the half-life in aqueous solutions under simulated sunlight is approximately 50 to 55 summer Florida days(3). Photodegradation is not a major degradation pathway on soil surfaces(3).

Adverse EffectsDermatotoxin - Skin burns.
Soil Adsorption/MobilityA Koc range of 194 to 565 has been reported for cyclanilide(1). According to a classification scheme(2), this Koc range suggests that cyclanilide is expected to have moderate mobility in soil(SRC).
Artificial Pollution SourcesCyclanilide's production may result in its release to the environment through various waste streams; it's use as a plant growth regulator and cotton harvest aid(1), and fungicide(2) will result in its direct release to the environment(SRC).
Environmental Biodegradation · 2 Einträge

AEROBIC: Cyclanilide, applied at 0.25 ppm, was readily degraded with a half-life of 95 days to 2,4-dichloroaniline, which is further degraded in soil to carbon dioxide(1). Based on field observations, degradation rates are slower during dry and cool autumn and winter seasons but increase with the increased moisture and warmth of the spring and summer seasons(1).

ANAEROBIC: Cyclanilide was not degraded in a water-sediment system(1).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 3 was calculated for cyclanilide(SRC), using a log Kow of 3.25(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 Eintrag

The Henry's Law constant for cyclanilide is 7.31X10-10 atm-cu m/mole(1). This Henry's Law constant indicates that cyclanilide is expected to be essentially nonvolatile from water surfaces(2). Cyclanilide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.1X10-9 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 2 Einträge

Severe ocular reaction (rabbits). /Finish Harvest Aid for Cotton/

Primary skin irritation (rabbits): erythema, edema & necrosis with resolution by day 10. /Finish Harvest Aid for Cotton/

Evidence for CarcinogenicityCancer Classification: Not Likely to be Carcinogenic to Humans
Environmental Abiotic Degradation · 1 Eintrag

Particulate-phase cyclanilide may be removed from the air by wet and dry deposition(SRC). Cyclanilide is relatively stable to hydrolysis(1). The compound is stable to photolysis as shown by continued stability after 14 days of exposure to artificial sunlight at 23 °C(1).

Regulatorische Informationen

FIFRA Requirements · 2 Einträge

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 026201; Type of Pesticide: fungicide; Use Site: non-food use (cotton); Year: 1997.

Tolerances are established for residues of the plant growth regulator, cyclanilide, (1-(2,4-dichlorophenylaminocarbonyl)-cyclopropane carboxylic acid) determined as 2,4-dichloroaniline (calculated as cyclanilide) in or on the following food commodities and processed feed: cattle, fat; cattle, meat; cattle, mbyp (except kidney); cattle, kidney; cottonseed; cotton gin byproducts; goats, fat; goats, meat; goats, mbyp (except kidney); goats, kidney; horses, fat; horses, meat; horses, mbyp (except kidney); horses, kidney; hogs, fat; hogs, meat; hogs, mbyp (except kidney); hogs, kidney; milk; sheep, fat; sheep, meat; sheep, mbyp (except kidney); sheep, kidney.

Sicherheitsdaten

wgk
2
ridadr
2811
hs_code
2924.29.4700
risk_code
22-51/53
hazard_code
Xn,N
safety_code
61
hazard_class
6.1(b)
packing_group
III
Giftige Stoffe Daten
113136-77-9(Hazardous Substances Data)

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl esterDicarboxylic AcidTetrabutylammoniumbromidAnhydrous tolueneAROMA2,4-Dichloranilin