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Butachlor

Butachlor structure

Butachlor 

structure
  • CAS No:

    23184-66-9

  • Formula:

    C17H26ClNO2

  • Chemical Name:

    Butachlor

  • Synonyms:

    Acetamide,N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-;Acetanilide,N-(butoxymethyl)-2-chloro-2′,6′-diethyl-;N-(Butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide;CP 53619;2′,6′-Diethyl-N-butoxymethyl-2-chloroacetanilide;2′,6′-Diethyl-N-butoxymethyl-α-chloroacetanilide;2-Chloro-2′,6′-diethyl-N-(butoxymethyl)acetanilide;Butachlor;Machete;Machete (herbicide);N-(Butoxymethyl)-2-chloro-2′,6′-diethylacetanilide;Machette;2-Chloro-2′,6′-diethyl-N-(butoxymethyl)acetoanilide;Butaclor;Hiltachlor;Delchlor;Delchlor 5G;Bilchlor;NSC 221683;Machet;Dingcaoan;130661-11-9

  • Categories:

    Organic Chemistry  >  Amides

Description

Machette [also known as butachlor] belongs to the chloroacetanilide group herbicides. Butachlor, together with other chloroacetanilide-class herbicides including acetochlor, alachlor, metachlor, and propachlor, are the most consumed chemicals all over the world in agriculture. Butachlor [N-[butoxymethyl]-2-chloro-2’,6’-diethyl acetanilide] is a widely recommended herbicide for application in rice cultivation. It is a systemic selective pre-emergent herbicide applied on rice, tea, wheat, beans a


Butachlor is an aromatic amide that is 2-choro-N-(2,6-diethylphenyl)acetamide in which the amide nitrogen has been replaced by a butoxymethyl group. It has a role as a herbicide, an environmental contaminant and a xenobiotic. It is an aromatic amide, an organochlorine compound and a tertiary carboxamide. It derives from a N-phenylacetamide.

Butachlor Basic Attributes

311.85

311.85

245-477-8

94NU90OO5K

221683

DTXSID3034402

Amber liquid|Light yellow oil

2924299032

Characteristics

29.5

4.5

Light yellow-purple Liquid

1.070 g/cm3 @ Temp: 25 °C

<-5 °C

156 °C @ Press: 0.5 Torr

100 °C

1.528

In water, 20 mg/l at 20 deg C

0-6°C

approx. 0 mm Hg Solubility in water: 24 ppm

Oral-Rat LD50: 1740 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

Faint, sweet odor

5.10e-08 atm-m3/mole|Henry's Law constant = 5.1X10-8 atm-cu m/mol at 25 °C

184.3 Ų [M+Na]+

Stable to UV light. Decomposes at temperatures greater than or equal to 165 °C|Hydroxyl radical reaction rate constant = 5.7X10-11 cu cm/molecule sec @ 25 °C /Estimated/

No corrosion to No. 316 and No. 304 stainless steel, aluminum, and heresite, but corrodes steel and black iron

Safety Information

UN30829/PG3

3

22-50/53

60-61

AE1200000

Xn,N

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

Stable to UV light. Stable indefinitely

P273

H302-H400

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P311, P321, P330, P333+P313, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 74 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P330, P333+P313, P337+P313, P363, P391, P403+P233, P405, and P501

Rubber gloves, respirator, boots, long sleeved shirt or jacket, long pants.|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticide, liquid/|If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/

Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/

Avoid contact with mouth, skin or eyes, washing all parts with plenty of soap and water after handling. Keep away from children. Store in cool, dry place away from feed and foodstuffs.|Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/|Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/|If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine pesticides, solid, toxic/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organochlorine pesticide, liquid/

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

In a field study in Thailand in which 4.0 kg/ha was applied to cultivated fields containing clay loam soil (8-10% slope) and clay soil (25-28% slope) during the rainy season, the maximum concn of butachlor in runoff was 61.5 and 15.5 ug/L, respectively(1). 52.2% of the butachlor in the runoff was in the water phase(1). The highest amounts of herbicide was lost 1-3 days after application(1).

Toxicity

moderately

LD50 Rat oral 1740 mg/kg|LD50 Rat oral 2000 mg/kg /Technical butachlor/|LD50 Rabbit dermal >13,000 mg/kg /Technical butachlor/|LD50 Mouse oral 4747 mg/kg|For more Non-Human Toxicity Values (Complete) data for BUTACHLOR (6 total), please visit the HSDB record page.

/FIELD STUDIES/ The effects of pesticide contamination on the population size and denitrification activity of denitrifying bacteria (DNB) were studied with three types of paddy soil (Huangsong paddy soil, red earth paddy soil and purple paddy soil) treated with carbofuran, carbendazim and butachlor for four weeks. The results showed that the population size of DNB in purple paddy soil, Huangsong paddy soil and red earth paddy soil varied in the range of 59.04 x 10(4)-157.59 x 10(4), 42.89 x 10(4)-108.97 x 10(4) and 32.14 x 10(4)-75.30 x 10(4) cfu.g-1 dried soil, respectively, which was positively related to the quantity of consumed nitrate in paddy soils. The population size and denitrification activity of DNB were increased by adding carbofuran (1 mg.kg-1 dried soil) or butachlor (1 mg.kg-1 dried soil), but decreased significantly by adding 10 mg.kg-1 dried soil of butachlor, 5 mg.kg-1 dried soil of carbofuran, and 10 mg.kg-1 dried soil of carbendazim on 7th d, 14th d and 7th d, respectively.

Butachlor's production may result in its release to the environment through various waste streams; its former use(1) as a preemergence herbicide(2) may have resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6700(SRC), determined from a log Kow of 4.5(2) and a regression-derived equation(3), indicates that butachlor is expected to be immobile in soil(SRC). Volatilization of butachlor from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 5.10X10-8 atm-cu m/mole(4). Butachlor is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.90X10-6 mm Hg(4). Half-lives for butachlor in soil reported from biodegradation studies range from approximately 1.6 days to 11.4 days(5).|TERRESTRIAL FATE: Field half-lives of butachlor in soil have been measured to be 11 to 18 days, 4 to 8 days, and 10 to 18 days(1). When butachlor was applied to Ray silt and Wabash silty loam soil in Missouri at their normal preplant application time, the field half-lives were 9.4 and 14.4 days, respectively(2). Dissipation followed first order kinetics(2). Despite moist field conditions (near saturation at time of application and 2.25 cm of rain on the 3rd day), <1% of the herbicide was found below 4 cm(2). Therefore leaching does not appear to make a significant contribution to field dissipation. In a field study in Thailand, butachlor applied to cultivated fields containing clay loam and clay soils during the rainy season was detectable by GC for 180 days after application(3). In a study of butachlor persistance in Indian soils using plant bioassays, butachlor persisted for 40 days in a sandy clay loam soil, 60 days in sandy and clayey soils, and lost its activity rapidly in an organic soil(4). Under natural conditions of paddy fields, the half-life of butachlor was determined to be 1.65-2.48 days and 5.79-6.30 days when applied as an emulsion and granules, respectively(5). The half-lives in soil were found to be 2.67-5.33 and 4.95-6.30 days, respectively for these formulations(5). When butachlor was applied to 4 Chinese paddy soils, the half-life ranged from 3.17 to 3.61 days(1). In rice fields, leaching occurred in the silty loam and loamy silt soils, but not in the clay loam and red loam soils where it remained in the upper 5-cm(6). However, no residues were found in the soil profile or ground water after the rice growing season(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6,700(SRC), determined from a log Kow of 4.5(2) and a regression-derived equation(3), indicates that butachlor 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 5.10X10-8 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 1500(SRC), from an estimated log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Butachlor degraded rapidly when applied to water at the recommended rates; its half-life in water was 1.11-1.12 days(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butachlor, which has a vapor pressure of 2.990X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase butachlor 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 6.8 hours(SRC), calculated from its rate constant of 5.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase butachlor may be removed from the air by wet and dry deposition(SRC). Butachlor does not absorb UV light >290 nm and therefore direct photolysis is not expected(4).

The rate constant for the vapor-phase reaction of butachlor with photochemically-produced hydroxyl radicals has been estimated as 5.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Butachlor is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(3).

An estimated BCF of 1500 was calculated for butachlor(SRC), using a log Kow of 4.5(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

724.44 L/kg|Adsorbed by soil colloids.|The Koc of butachlor is estimated as 6700(SRC), using a log Kow of 4.5(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that butachlor is expected to be immobile in soil(SRC).

The Henry's Law constant for butachlor is 5.10X10-8 atm-cu m/mole(1). This Henry's Law constant indicates that butachlor is expected to be essentially nonvolatile from moist soil or water surfaces(2). Butachlor is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.90X10-6 mm Hg(1).|The rate of volatilization from a glass surface was 3.1X10-7 g/hr(1). Little butachlor volatilization occurred from dry soil surfaces exposed to a constant 3.2 kph, 21 degC air stream; the volatilization half-lives for Ray silt and Wabash silty clay soil were 116 and 217 days, respectively(2). In contrast, the volatilization half-lives from continuously moist soil under similar exposure conditions were 22 and 62 days(2). Therefore, significant volatilization losses would occur from wet, exposed soil under windy conditions. Such conditions would be transitory in the field as it would lead to drying of the soil surface and a reduction in volatilization(3).

DRINKING WATER: Butachlor was not detected in EPA's National Pesticide Survey(1). In this survey, water samples from 783 rural domestic wells and 566 community water system wells, nationwide were tested.|SURFACE WATER: Butachlor residues in the River Koise and its tributaries in Japan in 1985 were detected mainly before the rainy season from May to early June(1). Concns were not reported. Butachlor was detectable in water in the Ishikari River in Japan from early May to mid July and reached a maximum level of 4.4 ppb on May 21, approximately one week after its application on paddy fields(2).

Occupational exposure to butachlor occur through dermal contact with this compound at workplaces where butachlor is produced. In the past, the general population may have been exposed to butachlor via dermal contact with this compound and other products containing butachlor. Current general population exposure in the United States is expected to be low or non-existent since butachlor is no longer used in the US. (SRC)

Drug Information

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)|Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)

In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Soild Organochlorines/|The results of dermal penetration studies with rhesus monkeys indicate that butachlor is poorly absorbed through the skin. ... Employing a 6-hr topical exposure period, only 0.02 % of the dose was systemically absorbed during exposure to a granular formulation, and 5 % of the dose was absorbed when an EC (emulsifiable concentrate) formulation was applied.|Approximately 85 % of an orally administered dose is eliminated in 48 hr; 60 % of the excretedmaterial is found in the feces and 40 % in urine.|... Following a 24-hr exposure, an average butachlor quantity of approximately 5.00% of the applied dose (1.01 micrograms) was absorbed by the skin. The mean peak penetration rate was 0.7% of the applied dose per hour. The skin retained 1.40 to 8.10% of the applied butachlor.

... Butachlor ... yielded 20-60 mol% formaldehyde on incubation with the mouse liver microsomal mixed function oxidase system under standard conditions.|The metabolism of butachlor was studied in rat liver and kidney homogenates. In vitro incubation of butachlor with liver fractions (S9, microsome and cytosolic fractions) formed a considerable amount of butachlor glutathione conjugate, while the conjugating activity was not efficient for the kidney S9 fraction. There is a sex difference in the distribution of glutathione S-transferase in the liver. ... More enzyme activity was detected in the female liver microsome, while this is not the case in its cytosolic fraction. Further biotransformation of butachlor glutathione conjugate to mercapturate was not observed in the liver S9 fraction. This metabolite was further transformed to butachlor acetyl cysteine conjugate in the presence of acetyl CoA, but to butachlor cysteine conjugate in the absence of acetyl CoA.|Butachlor metabolism in rats is complex due to extensive biliary excretion, intestinal microbial metabolism, and enterohepatic circulation of metabolites. Metabolism in rats follows three major pathways: initial conjugation with glutathione followed by mercapturic acid pathway metabolism; cytochrome P-450-mediated hydroxylation of the aromatic ring, its ethyl groups and the N- butoxymethylene group; and cleavage of the amide bonds via aryl amidase to form 2,6-diethyl aniline, which is further oxidized to 4-amino-3,5-diethylphenol.|... Butachlor is metabolized to CDEPA to a much greater extent by rat liver microsomes (0.045 nmol/min/mg) than by human liver microsomes (< 0.001 nmol/min/mg).|Butachlor has known human metabolites that include 2-Chloro-N-(2,6-diethylphenyl)acetamide.

... The biological half-lives of the three herbicides on exposure at high and low concentrations were 11.6 and 23.1 days for butachlor,

Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposure occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with Valium or phenobarbital. Respiratory depression and even respiratory arrest, especially with concomitant use of Valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. /It is recommended/ that epinephrine not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in the event of hypotension unresponsive to fluid administration, and epinephrine may be necessary in the event of cardiopulmonary arrest. /Organochlorine insecticides/|Persons exceptionally exposed to organochlorine pesticides by any route should be observed for sensory disturbances, incoordination, speech slurring, mental aberrations, and involuntary motor activity that would warn of imminent convulsions. If convulsions occur, place the victim in the left lateral decubitus position with the head down. Move away furniture or other solid objects that may be a source of injury. If jaw movements are violent, place padded tongue blades between the teeth to protect the tongue. Whenever possible, remove dentures and other removable dental work. Aspirate oral and pharyngeal secretions, and, when possible, insert an oropharyngeal airway to maintain an open passage unobstructed by the tongue. Minimize noise and any manipulation of the patient that may trigger seizure activity. Administer oxygen by mask. Maintain pulmonary gas exchange by mechanically assisted ventilation whenever respiration is depressed. /Solid organochlorine insecticides/

2-chloro-2',6'-diethyl-N-(butoxymethyl)acetanilide

Butachlor Use and Manufacturing

Methods of Manufacturing

Acetic acid dehydrates to form ketene, which passes through chlorine to form α-chloroacetyl chloride; aniline and ethylene act to introduce two ethyl groups at the ortho position of the amino group, and then formaldehyde to form a carbon-nitrogen double bond with formaldehyde; the last two intermediates are added And with n-butanol, generate butachlor. See

Uses

Herbicide. It is a kind of high-efficiency and low-toxic pre-emergence herbicide, mainly used to control most annual gramineous and some dicotyledonous weeds in dryland crops; used to control weeds such as barnyardgrass, cattle hair grass, duck tongue in rice; Control of gramineous weeds and annual broadleaf weeds in rice fields

Emulsifiable concentrate, granules.|Trade names: Machete, Butanex, Butataf, Dhanuchlor, Farmachlor, Hiltaklor, Rasayanchlor, Trapp, Wiper, Ban Weed, Butamach, Butanox, Pilarsete, Vibuta. Mixtures: Bandito (+propanil), Sable (+ propanil), Vitanil (+propanil). Discontinued names mixtures: Delcut (+oxadiazon), Kusakarin (+ pyrazolynate)|Lambast|Amichlor|For more Formulations/Preparations (Complete) data for BUTACHLOR (6 total), please visit the HSDB record page.

/Butachlor/ is not marketed in the United States

A method is described for the analysis of water, soil and crops for residues of the herbicide butachlor. Residues are extracted with acetone and light petroleum distillate. The extracts are concentrated and purified on a chromatographic column containing aluminum oxide, silver aluminum oxide and florisil. Finally, they were quantitated by gas chromatography using an electron capture detector. The detection limits of various samples were between 0.001 and 0.015 mg/kg. The avg recoveries ranged from 79.4 to 104.6%.|Method 991.07. Nitrogen- and Phosphorous-Containing Pesticides in Finished Drinking Water. Gas Chromatographic (GC) Method. Capillary GC using a nitrogen-phosphorous detector. Detection limits for 36 pesticides range from 0.13 to 1.0 ug/L.|Method: EPA-TSC/NERL 507, Determination of Nitrogen- and Phosphorus-Containing Pesticides in Water by Gas Chromatography with a Nitrogen-Phosphorus Detector; Analyte: butachlor; Matrix: ground water and finished drinking water; Method Detection Limit: 0.12 ug/L.|Method: EPA-OGWDW/TSC 508.1, Determination of Chlorinated Pesticides, Herbicides, and Organohalides by Liquid-Solid Extraction and Electron Capture Gas Chromatography; Analyte: butachlor; Matrix: drinking water, ground water, and drinking water in any treatment stage; Method Detection Limit: 0.07 ug/L.|For more Analytic Laboratory Methods (Complete) data for BUTACHLOR (6 total), please visit the HSDB record page.

A general method for developing immunoassays to chloroacetanilide herbicides /including butachlor/

Agrochemicals -> Herbicides

Computed Properties

Molecular Weight:311.8
XLogP3:4.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:9
Exact Mass:311.1652068
Monoisotopic Mass:311.1652068
Topological Polar Surface Area:29.5
Heavy Atom Count:21
Complexity:287
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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