101-27-9O=C(Nc1cccc(Cl)c1)OCC#CCClMCOQHIWZJUDQIC-UHFFFAOYSA-NBarban is a crystalline solid. Water solubility is 11 ppm at 20 °C. Used as a selective herbicide.
101-27-9DTXSID3041617CHEMBL1076452、CHEMBL1570161CHEBI:33421Herbicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Herbicides, Other
Pesticide
Crystalline solid
COLORLESS
Crystals from n-hexane + benzene
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
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
Corrosive
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
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)
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.)
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).
... Interfering with cell division ... is believed to be the primary mode of action.
Weak anticholinesterase inhibitor.
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)
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.
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."
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./
불러오는 중…
When heated to decomposition it emit very toxic fumes of /hydrogen chloride and nitrogen oxides/.
Technical decomposes at 224 °C.
Crystalline solid; melts at 75°C (167°F);insoluble in water [11 mg/L at 25°C (77°F)];slightly soluble in hexane; soluble in benzeneand chlorinated hydrocarbons.
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.
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.
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)/
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.
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/
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.
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.
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.
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)/
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.
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).
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.
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.
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.
/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).
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)
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).
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).
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.
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).
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/
(1975) 1.82X10+6 G (CONSUMPTION)
(1976) GREATER THAN 2.27X10+6 G
Barban was reported as having 52,000 lb AI/yr national use from 1987 through 1989.
100% AS AN HERBICIDE ON WHEAT (1975)
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)
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).
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.
용도Barban is used as a selective herbicide forwild oats.
일반 설명Crystalline solid. Water solubility is 11 ppm at 20°C. Used as a selective herbicide.
정의ChEBI: 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.