| Identification | Back Directory | [Name]
Terbacil | [CAS]
5902-51-2 | [Synonyms]
SINBAR
Dup-732
GEONTER
TERBACIL
DPX-D732
Turbacil
dupont732
SINBAR(R)
Sinbar 80W
Du Pont 732
compound732
Compound 732
Herbicide 732
TerbacilStandard
TERBACIL, 1GM, NEAT
terbacil SINBAR WDG
DUPONT HERBICIDE 732
High purity Terbacil
experimentalherbicide732
Terbacil 1g [5902-51-2]
Experimental Herbicide 732
Butyl-5-chloro-6-methyluracil
TerbacilSolution,1000mg/L,1ml
Terbacil@100 μg/mL in Methanol
Terbacil@1000 μg/mL in Methanol
terbacil WP or SINBAR WDG
terbacil (bsi,iso,ansi,wssa,jmaf)
3-t-butyl-5-chloro-6-methyluracil
Chloro-3-tert-butyl-6-methyluracil
3-tert.Butyl-5-chlor-6-methyluracil
3-tert-butyl-5-chloro-6-methyl-uraci
5-Chloro-3-tert-butyl-6-methyluracil
3-TERT-BUTYL-5-CHLORO-6-METHYLURACIL
Uracil, 3-tert-butyl-5-chloro-6-methyl-
TERBACIL PESTANAL (3-TERT.-BUTYL- 5-CHLO
TERBACIL [3-TERT-BUTYL-5-CHLORO-6-METHYLURACIL]
3-tert-Butyl-5-chloro-6-methyl-1H-pyrimidine-2,4-dione
5-Chloro-3-(1,1-dimethylethyl)-6-methyl-pyrimidinedione
3-tert-Butyl-5-chloro-6-methyl-2,4(1H,3H)-pyrimidinedione
3-tert-Butyl-5-chloro-6-methylpyrimidine-2,4(1H,3H)-dione
3h)-pyrimidinedione,5-chloro-3-(1,1-dimethylethyl)-6-methyl-4(1h
5-Chloro-3-(1,1-dimethylethyl)-6-methyl-2,4(1H,3H)-pyrimidinedione
2,4(1H,3H)-Pyrimidinedione, 5-chloro-3-(1,1-dimethylethyl)-6-methyl- | [EINECS(EC#)]
227-595-1 | [Molecular Formula]
C9H13ClN2O2 | [MDL Number]
MFCD00055344 | [MOL File]
5902-51-2.mol | [Molecular Weight]
216.66 |
| Chemical Properties | Back Directory | [Melting point ]
175-177° | [density ]
1.3400 | [refractive index ]
1.5388 (estimate) | [storage temp. ]
0-6°C | [form ]
Solid | [pka]
8.79±0.40(Predicted) | [color ]
Off-white | [Water Solubility ]
0.71g/L(25 ºC) | [Merck ]
13,9230 | [BRN ]
643054 | [Henry's Law Constant]
5.2×104 mol/(m3Pa) at 25℃, HSDB (2015) | [NIST Chemistry Reference]
Terbacil(5902-51-2) | [EPA Substance Registry System]
Terbacil (5902-51-2) |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless crystals. Mp 175C. Soluble
in dimethylacetamide and cyclohexanone; partially
soluble in xylene and butyl acetate. | [Uses]
Herbicide. | [Uses]
Nonselective herbicide used to control herbaceous and woody plants on noncrop
land. | [Uses]
Terbacil is also absorbed by plant roots and inhibits
photosynthesis. It is used for the selective control of many
annual and some perennial weeds in apples, citrus, peaches,
and sugarcane. Application rates range from 0.5 to 8 kg/ha. | [Definition]
ChEBI: Terbacil is an organohalogen compound and a member of pyrimidines. | [Production Methods]
Terbacil is produced commercially through a multi-step chemical synthesis that constructs its uracil-based herbicidal structure. The synthesis typically begins with the preparation of substituted aniline or phenol derivatives, which are then reacted with cyanoacetic acid or similar intermediates to form a uracil ring system. This ring is further functionalised with alkyl groups to yield the active compound, 3-tert-butyl-5-chloro-6-methyluracil. | [General Description]
Colorless crystals. Non corrosive. Used as an herbicide. | [Air & Water Reactions]
Water soluble. | [Reactivity Profile]
A uracil derivative. | [Agricultural Uses]
Herbicide: Terbacil is a selective herbicide that treats a broad
spectrum of broadleaf weeds and grasses. It is formulated
as a wettable powder and is applied by aircraft or ground
equipment on terrestrial food and feed crops (e.g., apples,
mint/peppermint/spearmint, sugarcane, and ornamentals),
forestry [e.g., cottonwood (forest/shelterbelt)], terrestrialfood (e.g., asparagus, blackberry, boysenberry, dewberry,
loganberry, peach, raspberry, youngberry and strawberry),
and terrestrial feed (e.g., alfalfa, sainfoin (hay and fodder),
and forage). Not approved for use in EU countries.
Registered for use in the U.S. | [Trade name]
COMPOUND® 732; DuPontTM® 732;
EXPERIMENTAL HERBICIDE 732; GEONTER®;
SINBAR®; TURBSVIL®; ZOBAR®[C] | [Mechanism of action]
Selective, absorbed mainly through the roots. Inhibits photosynthesis (photosystem II). | [Environmental Fate]
Soil. In microbially active soils, tebuthiuron is degraded via demethylation. The average
half-life in soil 12–15 months in areas receiving 60 inches of rainfall a year (Humburg et
al., 1989).
Groundwater. According to the U.S. EPA (1986) terbacil has a high potential to leach
to groundwater.
Plant. The major degradation products of [2-14C]terbacil identified in alfalfa using a
mass spectrometer were (% of applied amount): 3-tert-butyl-5-chloro-6-hydroxymethyluracil
(11.9) and 6-chloro-2,3-dihydro-7-(hydroxymethyl)-3,3-dimethyl-5H-oxa
Photolytic. Acher et al. (1981) studied the dye-sensitized photolysis of terbacil in
aerated aqueous solutions over a wide pH range. After a 2-hour exposure to sunlight,
terbacil in aqueous solution (pH range 3.0–9.2) in the presence of methylene blue (3 ppm)
or riboflavin (10 ppm), decomposed to 3-tert-5-butyl-5-acetyl-5-hydroxyhydantoin.
Deacylation was observed under alkaline conditions (pH 8.0 or 9.2) affording 3-tert-5-
hydroxyhydantoin. In neutral or acidic conditions (pH 6.8 or 3.0) containing riboflavin, a
mono-N-dealkylated terbacil dimer and an unidentified water-soluble product formed.
Product formation, the relative amounts of products formed and the rate of photolysis
were found to be all dependent upon pH, sensitizer, temperature and time (Acher et al.,
1981).
Chemical/Physical. Stable in water (Worthing and Hance, 1991). | [Metabolic pathway]
When rats are administered terbacil orally, the primary
biotransformation products of terbacil in the urine are
derived from hydroxylation of the 6-methyl group and
are identified as the aglycone, glucuronide, and
sulfate. The other conjugated metabolite is the
mercapturic acid conjugate of the 6-methyl substituent.
Minor metabolites are identified as sulfoxides and
sulfone at the 6-methyl substituent of terbacil. | [Pesticide Type]
Herbicide |
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