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Barban

HCID 7551
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Basic information

CAS
101-27-9
Standard SMILES
O=C(Nc1cccc(Cl)c1)OCC#CCCl
InChIKey
MCOQHIWZJUDQIC-UHFFFAOYSA-N
Molecular formula
C11H9Cl2NO2
Average molar mass
258.1 g/mol
Monoisotopic mass
257.0010339

Overview

Barban is a crystalline solid. Water solubility is 11 ppm at 20 °C. Used as a selective herbicide.

Names & identifiers

Preferred name
Barban
IUPAC
4-chlorobut-2-ynyl N-(3-chlorophenyl)carbamate
English name
BARBAN
Molecular formula
C11H9Cl2NO2
Molecular weight
258.1

Names & synonyms

BARBAN101-27-9BarbamateBarbaneCarbyneChlorinatCarbinNeobanCarbyne (herbicide)4-Chlorobut-2-ynyl 3-chlorophenylcarbamateFisons B254-Chloro-2-butynyl m-chlorocarbanilate
Show more names
OataxA 980a-980C-847S 847s-847
4-chlorobut-2-yn-1-yl (3-chlorophenyl)carbamate4-Chloro-2-butynyl 3-chlorocarbanilate4-Chloro-2-butynyl N-(3-chlorophenyl)carbamateCaryneCaswell No. 068CS-847DTXSID3041617Carbamic acid, (3-chlorophenyl)-, 4-chloro-2-butynyl ester

Database identifiers

CAS
101-27-9
PubChem CID
7551
DTXSID
DTXSID3041617
ChEMBL
CHEMBL1076452、CHEMBL1570161
ChEBI
CHEBI:33421
UNII
33306K781F
EC Number
202-930-4
Nikkaji
J4.988C

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
38.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
16
Formal charge
0
Complexity
295

Experimental & physicochemical properties

SpringerMaterials PropertiesFusion temperature
Pesticides · 4 items

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Other

Pesticide

LogPlog Kow = 3.41 /Estimated/
OdorODORLESS SOLID
Density1.403 g/cu cm at 25 °C
Color/Form · 3 items

Crystalline solid

COLORLESS

Crystals from n-hexane + benzene

Solubility · 2 items

At 25 °C g/100 g solvent: benzene 32.7 g; n-butylbenzene 11.3 g; n-dodecane less than 0.1 g; n-hexane 0.14 g; isopropylbenzene less than 7.0 g; kerosene 0.39 g; toluene 25.7 g; 2,2,4-trimethylpentane more than 0.3 g; xylene 27.9 g; water 0.0011 g

In water, 1.1X10+1 mg/L at 25 °C

Corrosivity · 2 items

Liq concn may cause corrosion of tin plate & mild steel at the liq-air interface; aluminum, phenolic-lined cans or glass are recommended for storage

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

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

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 2 items

2002/2076

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Carbamic acid, (3-chlorophenyl)-, 4-chloro-2-butynyl ester: Human health tier I assessment
DOT LabelClass 9
Fire HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards SummaryAn irritant and potent human skin sensitizer; [HSDB]
Reactive GroupCarbamates
RCRA Requirements · 1 item

U280; As stipulated in 40 CFR 261.33, when barban, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

... Interfering with cell division ... is believed to be the primary mode of action.

Weak anticholinesterase inhibitor.

Metabolism/Metabolites · 6 items

When barban was orally administered to rats, hydroxylation and side-chain oxidation occurred. Chloro-aniline, 2-amino-4-chlorophenol and 4-amino-2-chlorophenol were excreted free & in conjugated form. Side-chain oxidation was only of minor importance in metabolism of barban. In addition to aniline & m-chloroaniline, hydroxycarbamate was found in blood & all organs. Urine contained p-aminophenol.

Plant metabolism of carbanilate herbicides has been shown to involve aryl hydroxylation and conjugation instead of hydrolysis. /Carbanilate Herbicides/

After treatment with barban, plants formed a water-soluble 3-chloroaniline compound. Related carbamates were found to form similar products. Another metabolite detected, also in a bound state, was 2-chloro-4-amino-phenol ... .

The 4-chloro-2-butynyl moiety of barban is the most reactive position of the molecule and is implicated in the formation of plant metabolites.

For more Metabolism/Metabolites (Complete) data for BARBAN (6 total), please visit the HSDB record page.

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Absorption, Distribution and Excretion · 1 item

When barban was orally administered to rats ... chloroaniline, 2-amino-4-chlorophenol and 4-amino-2-chlorophenol were excreted free and in conjugated form. ... In addition to aniline and m-chloroaniline, hydroxycarbamate was found in blood and all organs. Urine contained p-aminophenol.

Uses & manufacturing

Uses · 6 items

No active product registrations in the US; [NPIRS] Used formerly as selective post-emergence herbicide; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

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Related reactions

2 records
New reaction record
HRID 662995 reaction equation
HRID 662995As productTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 825162 reaction equation
HRID 825162As productTest data from https://doi.org/10.1039/C8SC04228D

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Corrosive

Flash Point122 °F (Closed cup)
Boiling PointDegrades before boiling
Decomposition · 2 items

When heated to decomposition it emit very toxic fumes of /hydrogen chloride and nitrogen oxides/.

Technical decomposes at 224 °C.

Melting Point75-76 °C

Physicochemical properties

Melting point
75 · 75-76℃
Boiling point
340.8 · 340.8±32.0 °C(Predicted)
Density
1.403 · 1.403
refractive index
1.607 · 1.6070 (estimate)
storage temp.
0 · 0-6°C
form
Powder/Solid
pka
12.3 · 12.30±0.70(Predicted)
color
White
Water Solubility
11 mg/L · 11mg/L(25 ºC)
Merck
13 · 13,962
BRN
2376181 · 2376181
Henry's Law Constant
8.4 · 8.4×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
EWG's Food Scores
5 · 5
FDA UNII
33306 K781F · 33306K781F
Pesticides Freedom of Information Act (FOIA)
Carbyne
EPA Substance Registry System
Barban (101-27-9)
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
302 · H302-H317-H410
Precautionary statements
264 · P264-P270-P261-P272-P280-P273-P301+P312-P330-P302+P352-P333+P313-P362+P364-P391-P501
Hazard Codes
Xn,N
Risk Statements
22 · 22-43-50/53
Safety Statements
24 · 24-36/37-60-61
RIDADR
3077 · UN3077 9/PG 3
WGK Germany
3 · 3
RTECS
7700000 · FD7700000
HS Code
29242990 · 29242990
Hazardous Substances Data
101 · 101-27-9(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in rats: 600 mg/kg (Bailey, White)
FIFRA Requirements · 2 items

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 4-Chloro-2-butynyl meta-chlorocarbanilate is found on List B. Case No: 2025; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 4-Chloro-2-butynyl meta-chlorocarbanilate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

A time-limited tolerance, with an expiration date of January 1, 1998, is established for negligible residues of the herbicide barban (4-chloro-2-butynyl m-chlorocarbanilate) in or on the raw agricultural commodities barley, flax, seed, lentils, mustard, seed, pea, safflower seed, soybean, sugar beet, sugar beet tops, sunflower, seed, and wheat.

Reactivity Profile · 1 item

BARBAN is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Air and Water ReactionsHydrolyzed by strong acid or base.
EPA Hazardous Waste NumberU280; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Safety & protection

Fire FightingExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
First AidExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Fire Fighting Procedures · 4 items

If material /is/ on fire or involved in /a/ 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. /Carbamate pesticide, liquid, nos, (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec/

Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, liquid nos (compounds and preparations) (insecticides, other than agricultural, nec)/

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. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/

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 foam, dry chemical, or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

Storage Conditions · 2 items

Aluminum, phenolic-lined cans, or glass are recommended for lengthy storage

Do not store near or contaminate feed or foodstuffs. Do not ... store near heat or open flame.

Cleanup Methods · 1 item

A system for removing pesticides from the wash water produced by pesticide applicators as they clean their equipment has been developed. The first step is the flocculation/coagulation and sedimentation of the pesticide-contaminated wash water. The supernatant from the first step is then passed through activated carbon columns. /Pesticides/

Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Disposal Methods · 1 item

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.

Preventive Measures · 4 items

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

/When handling/ do not get in eyes, or on skin or clothing.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Allowable Tolerances · 1 item

A time-limited tolerance, with an expiration date of January 1, 1998, is established for negligible residues of the herbicide barban (4-chloro-2-butynyl m-chlorocarbanilate) in or on the raw agricultural commodities barley, flax, seed, lentils, mustard, seed, pea, safflower seed, soybean, sugar beet, sugar beet tops, sunflower, seed, and wheat.

Personal Protective Equipment (PPE) · 6 items

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Possible allergic reaction in man by skin contact should be avoided by the use of plastic protective clothing.

Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, nec, liquid)/

Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/

Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/

Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec); Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

Toxicology

Treatment · 1 item

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects · 1 item

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

Ecotoxicity Values · 5 items

LC50 Goldfish 1.3 ppm (96 hr) /Conditions of bioassay not specified in source examined/

LC50 Guppies 1.3 ppm (96 hr) /Conditions of bioassay not specified in source examined/

LC50 Rainbow trout 0.6 mg/L (96 hr test) /Conditions of bioassay not specified in source examined/

LC50 Bluegill 1.2 mg/L (96 hr) /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for BARBAN (8 total), please visit the HSDB record page.

Environmental Fate · 5 items

Decomposes within 28-38 days of the last plant spraying.

TERRESTRIAL FATE: RESULTANT AVG PERSISTENCE @ RECOMMENDED RATES: DOWN TO TRACE AMT WITHIN 3 WK IN MOST SOILS.

Terrestrial fate: Duration of residual activity in soil 2-3 months (at 3 kg/ha).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a water solubility of 11 mg/L(2) and a regression-derived equation(3), indicates that barban is expected to have low mobility in soil(SRC). Volatilization of barban from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 3.8X10-7 mm Hg(4), and water solubility mg/L(2). Barban is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Barban was found to disappear more rapidly in non-autoclaved soil than in autoclaved soil(5) and appeared to be stable in the presence of anaerobic microorganisms(6); however, specific details were not available.

For more Environmental Fate (Complete) data for BARBAN (7 total), please visit the HSDB record page.

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Barban is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Ecotoxicity Excerpts · 1 item

/FIELD STUDIES/ At the application level of 5 kg/ha (20 ppm) on the soil Psuedogley-Parabraunerde cretaceous clay, barban killed 40 percent of ammonium oxidizers, based upon the assumption of initial inhibition(1). The estimated rate of application of barban for > 25 percent inhibition in soil (ammonium oxidation) was 100 to 250 kg/ha at 0.5 to 2 applications per year. The estimated rate of application of barban for > 25 percent inhibition in soil (nitrite oxidation) was 1 to 2 kg/ha at 0.5 to 2 applications per year(2).

Signs and Symptoms · 1 item

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

Acute Toxicity LinkChemical: BARBAN
Soil Adsorption/Mobility · 1 item

The Koc of barban is estimated as 1,200(SRC), derived from its water solubility of 11 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that barban is expected to have slight mobility in soil. Using TLC and aluminum oxide sorbent, the Rf value of barban was determined to be 0.5(4). The phenylcarbamate herbicides are much more water soluble than the substituted anilines(5). In spite of this, however, they are very immobile in soil systems. These compounds have been shown to be activated by adsorption to soil organic matter. Compounds in this group include barban. The mechanism of adsorption to soil organic matter is thought to involve hydrogen bonding between the carboxyl groups of the organic matter and the nitrogen and carbonyl oxygen of the carbamate(5).

Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Barban... is a potent skin sensitizing agent in man.

Regulatory information

RCRA Requirements · 1 item

U280; As stipulated in 40 CFR 261.33, when barban, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

FIFRA Requirements · 2 items

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 4-Chloro-2-butynyl meta-chlorocarbanilate is found on List B. Case No: 2025; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 4-Chloro-2-butynyl meta-chlorocarbanilate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

A time-limited tolerance, with an expiration date of January 1, 1998, is established for negligible residues of the herbicide barban (4-chloro-2-butynyl m-chlorocarbanilate) in or on the raw agricultural commodities barley, flax, seed, lentils, mustard, seed, pea, safflower seed, soybean, sugar beet, sugar beet tops, sunflower, seed, and wheat.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Safety data

wgk
3
rtecs
FD7700000
ridadr
UN3077 9/PG 3
hs_code
29242990
Toxicity
LD50 orally in rats: 600 mg/kg (Bailey, White)
risk_code
22-43-50/53
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn,N
safety_code
24-36/37-60-61
Hazard statements
H302-H317-H410
Precautionary statements
P264-P270-P261-P272-P280-P273-P301+P312-P330-P302+P352-P333+P313-P362+P364-P391-P501
Hazardous Substances Data
101-27-9(Hazardous Substances Data)

For barban (USEPA/OPP Pesticide Code: 017601) there are 0 labels match. /SRP: Not registered for current 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./

Selective post-emergence herbicide /Former use/

For postemergence control of ... canarygrass in barley, flax, lentils, mustard (grown for oil), peas, safflower, sugar beets, wheat, semi-dwarf wheat, sunflower and soybeans. For postemergence control of Italian ryegrass in barley, flax, lentils, mustard (grown for oil), peas, safflower, sugar beets, wheat, semi-dwarf sunflower, and soybeans in California and Oregon. /Former use/

U.S. Production · 2 items

(1975) 1.82X10+6 G (CONSUMPTION)

(1976) GREATER THAN 2.27X10+6 G

Consumption Patterns · 2 items

Barban was reported as having 52,000 lb AI/yr national use from 1987 through 1989.

100% AS AN HERBICIDE ON WHEAT (1975)

Methods of Manufacturing · 3 items

Condensation of 4-chloro-2-butyn-1-ol with m-chlorophenylisocyanate

By the reaction of 3-chlorophenyl isocyanate with 2-butyne-1,4 diol, followed by chlorination with thionyl chloride in an inert solvent.

US patent 2906614 (1959 to Spencer Chem)

Formulations/Preparations · 3 items

An emulsifiable concentrate (125 and 250 g active ingredient/L)

Carbyne is a 1 lb barban/gal emulsifiable concentrate (12.0% active ingredient).

With esters of mecoprop, dichlorprop, and MCPB as dualweed, with esters of mecoprop and MCPB as neobyne and with esters of metoxuron and simazine as wheatclene, (Dualweed, Neobyne, wheatclene, discontinued by FBC Limited).

Use ClassificationHERBICIDES
General Manufacturing Information · 5 items

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

... A selective post-emergence herbicide controlling wild oats at the 1.5-2.5 leaf stage, and broad beans, field flax, lentils, lucerne, mustard, oil seed rape, safflower, soyabeans, sugar beet, sunflowers, wheat, Russian wild rye and other grasses.

Compatible with MCPA in combination sprays.

Discontinued 1980 by Gulf Oil.

Compatible with Hoelon 3EC, Avenge, Glean and bromoxynil in combination sprays.

Applications · 4 items

DescriptionBarban is an obsolete post-emergence carbonate herbicide. It has a moderate aqueous solubility, is volatile and would not normally be expected to leach to groundwater. It is not persistent in soiI systems and is unlikely to be persistent in water systems. It has a moderate mammalian toxicity with a low potential for bioaccumulation. There are gaps in biodiversity toxicity data but it is reported to be moderately toxic to most aquatic species.

UsesBarban is used as a selective herbicide forwild oats.

UsesSelective herbicide for wild oats.

General DescriptionCrystalline solid. Water solubility is 11 ppm at 20°C. Used as a selective herbicide.

Upstream & downstream products

Upstream raw materials

2-Butyne-1,4-diol3-Chloroaniline

Additional notes

DefinitionChEBI: A carbamate ester that is 4-chlorobut-2-yn-1-yl ester of N-(3-chlorophenyl)carbamic acid. A herbicide, it is no longer approved for use within the European Community.