| Identification | Back Directory | [Name]
BARBAN | [CAS]
101-27-9 | [Synonyms]
Oatax
A 980
a-980
C-847
S 847
s-847
Neoban
Caryne
CS-847
Karbin
Carbin
BARBAN
Carbine
Carbyne
Barbane
Barbamate
Chlorinat
fisonsb25
BARBANATE
ENT 28201
NSC 29168
CARBYNE(R)
Fisons B25
BARBAMATE(R)
BARBAN PESTANAL.
A 980 (herbicide)
Carbyne【pesticide】
carbyne(herbicide)
BARBAN, 100MG, NEAT
Carbyne (Herbicide)
Barban 100mg [101-27-9]
barban (ansi,bsi,wssa,iso)
chloro-2-butynylm-chlorocarbamate
Chloro-2-butynyl m-chlorocarbamate
4-chloro-2-butynyl3-chlorocarbanilate
4-Chloro-2-butynyl 3-chlorocarbanilate
2-Butynyl 4-chloro-m-chlorocarbanilate
2-butynyl-4-chloro-m-chlorocarbanilate
4-CHLORO-2-BUTYNYL-M-CHLOROCARBANILATE
4-Chlorobut-2-ynyl-m-chlorocarbanilate
4-chloro-2-butyn-1-om-chlorocarbanilate
4-chloro-2-butynylmeta-chlorocarbanilate
4-Chloro-2-butynyl3-Chlorophenylcarbamate
4-CHLOROBUT-2-YNYL-3-CHLOROPHENYLCARBAMATE
4-Chloro-2-butynyl 3-chlorophenylcarbamate
2-Butyn-1-ol, 4-chloro-, m-chlorocarbanilate
4-chloro-2-butynyl-N-(3-chlorphenyl)carbamate
m-chloro-carbanilicaci4-chloro-2-butynylester
m-chlorocarbanilicacid,4-chloro-2-butynylester
4-CHLORO-2-BUTYNYL N-(3-CHLOROPHENYL)CARBAMATE
4-Chlorobut-2-yn-1-yl (3-chlorophenyl)carbamate
n-(3-chlorophenyl)carbamatede4-chloro2-butynyle
carbanilicacid,m-chloro-,4-chloro-2-butynylester
3-CHLOROCARBANILIC ACID 4-CHLORO-2-BUTYNYL ESTER
(4-Chlor-but-2-in-yl)-N-(3-chlor-phenyl)-carbamat
m-Chlorocarbanilic acid, 4-chloro-2-butynyl ester
(4-Cloro-but-2-in-il)-N-(3-cloro-fenil)-carbammato
(3-chlorophenyl)-carbamicaci4-chloro-2-butynylester
(3-chlorophenyl)carbamicacid4-chloro-2-butynylester
(4-Chloor-but-2-yn-yl)-N-(3-chloor-fenyl)-carbamaat
N-(3-Chloro phenyl)carbamate de 4-chloro 2-butynyle
CARBANILICACID,META-CHLORO-,4-CHLORO-2-BUTYNYLESTER
Carbanilic acid, m-chloro-, 4-chloro-2-butynyl ester
4-[N-(3-Chlorophenyl)carbamoyloxy]-1-chloro-2-butyne
(3-Chlorophenyl)carbamic acid 4-chloro-2-butynyl ester
carbamicacid,(3-chlorophenyl)-,4-chloro-2-butynylester
n-(3-chlorophenyl)carbamatede4-chloro2butynyle(french)
Carbamic acid, (3-chlorophenyl)-, 4-chloro-2-butynyl ester
4-chlorbut-2-ynyl N-(3-chlorophenyl)carbamate,barban (ISO)
barban (ISO) 4-chlorbut-2-ynyl N-(3-chlorophenyl)carbamate
(4-chloor-but-2-yn-yl)-n-(3-chloor-fenyl)-carbamaat (dutch)
Carbamic acid, N-(3-chlorophenyl)-, 4-chloro-2-butyn-1-yl ester | [EINECS(EC#)]
202-930-4 | [Molecular Formula]
C11H9Cl2NO2 | [MDL Number]
MFCD00045297 | [MOL File]
101-27-9.mol | [Molecular Weight]
258.1 |
| Chemical Properties | Back Directory | [Melting point ]
75-76℃ | [Boiling point ]
340.8±32.0 °C(Predicted) | [density ]
1.403 | [refractive index ]
1.6070 (estimate) | [storage temp. ]
0-6°C | [form ]
Powder/Solid | [pka]
12.30±0.70(Predicted) | [color ]
White | [Water Solubility ]
11mg/L(25 ºC) | [Merck ]
13,962 | [BRN ]
2376181 | [Henry's Law Constant]
8.4×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [EPA Substance Registry System]
Barban (101-27-9) |
| Hazard Information | Back Directory | [Description]
Barban 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. | [Chemical Properties]
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. | [Chemical Properties]
Whitecrystallinesolid;meltsat75°C(167°F);insoluble in water, dissolves in benzene,toluene, and ethylene dichloride; hydrolyzedby acids and alkalies; alkaline hydrolysis liberates terminal chlorine atom. | [Uses]
Barban is used as a selective herbicide forwild oats. | [Uses]
Selective herbicide for wild oats. | [Definition]
ChEBI: 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. | [Production Methods]
The commercial production of barban involves a multi-step synthesis starting with the preparation of key intermediates from readily available precursors. First, phosgene is reacted with 3-chloroaniline in a controlled chlorination and carbamoylation process to form 3-chlorophenyl isocyanate or the corresponding carbamoyl chloride intermediate, typically conducted in an inert solvent like toluene. Concurrently, 2-butyne-1,4-diol is chlorinated using thionyl chloride in the presence of a base such as pyridine, yielding 1,4-dichloro-2-butyne through a straightforward substitution at the primary alcohol groups, often performed at reflux temperatures to ensure complete conversion. These two intermediates are then coupled in a final esterification step, where the carbamoyl chloride or isocyanate derivative reacts with the dichlorobutynyl alcohol under basic conditions to form the target ester linkage, followed by purification via distillation or crystallisation to achieve the required purity. | [General Description]
Crystalline solid. Water solubility is 11 ppm at 20°C. Used as a selective herbicide. | [Air & Water Reactions]
Hydrolyzed by strong acid or base. | [Reactivity Profile]
BARBAN(101-27-9) 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. | [Health Hazard]
Moderately toxic by ingestion and inhalation;absorption through skin may be very slowand, therefore, almost nontoxic by dermalroute; used as a herbicide, rather than as apesticide; toxic symptoms are those of othercarbamate esters;
LD50 oral (rat): 600 mg/kg
LD50 skin (rabbit): >20,000 mg/kg. | [Mechanism of action]
Herbicidal action is due to anti-mitotic effects, reducing plant cellular division and so retarding shoot growth. Inhibition of microtubule organisation. | [Pesticide Type]
Herbicide |
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