| Identification | Back Directory | [Name]
DINOBUTON | [CAS]
973-21-7 | [Synonyms]
TALAN
ACREX
akrex
DESSIN
mc1053
oms1056
sytasol
uc19786
ds18302
kasebon
DINOFEN
DRAWINOL
DINOBUTON
ent27,244
ACARELTE UO
'LGC' (1613)
Dinofen liquid
dinobuton (bsi,iso)
Isophen (pesticide)
Union Carbide 19786
Dinobuton(content>10%)
DINOBUTON PESTANAL, 250 MG
HDWLUGYOLUHEMN-UHFFFAOYSA-N
Dinobuton liquid(content>2%)
dinitro-sec-butylphenylisopropylcarbonate
isopropyl2,4-dinitro-6-sec-butylphenylcarbonate
2,4-dinitro-6-sec-butylphenylisopropylcarbonate
2,4-dinitro-6-sek.butyl-isopropylphenylcarbonat
2-sec-butyl-4,6-dinitro-phenoisopropylcarbonate
(2-sek.butyl-4,6-dinitrofenyl)-isopropylkarbonat
2-SEC-BUTYL-4,6-DINITROPHENYLISO-PROPYLCARBONATE
ISO-PROPYL-2,4-DINITRO-6-SEC-BUTYLPHENOLCARBONATE
(2-butan-2-yl-4,6-dinitrophenyl) propan-2-yl carbonate
(2-butan-2-yl-4,6-dinitro-phenyl) propan-2-yl carbonate
carbonicacid,2-sec-butyl-4,6-dinitrophenylisopropylester
2-(1-methyl-2-propyl)-4,6-dinitrophenylisopropylcarbonate
isopropyl-2-(1-methyl-n-propyl)-4,6-dinitrophenylcarbonate
1-methylethyl2-(1-methylpropyl)-4,6-dinitrophenylcarbonate
2-(1-Methylpropyl)-4,6-dinitrophenyl-1-methylethylcarbonate
carbonic acid (2,4-dinitro-6-sec-butyl-phenyl) isopropyl ester
carbonicacid,1-methylethyl2-(1-methylpropyl)-4,6-dinitrophenylester
dinobuton (ISO) 2-(1-methylpropyl)-4,6-dinitrophenyl isopropyl carbonate | [EINECS(EC#)]
213-546-1 | [Molecular Formula]
C14H18N2O7 | [MDL Number]
MFCD00055423 | [MOL File]
973-21-7.mol | [Molecular Weight]
326.3 |
| Chemical Properties | Back Directory | [Melting point ]
61-62℃ | [Boiling point ]
464.35°C (rough estimate) | [density ]
1.2731 (rough estimate) | [refractive index ]
1.5110 (estimate) | [form ]
neat | [Water Solubility ]
Insoluble in water | [Merck ]
13,3315 | [BRN ]
2065340 | [Henry's Law Constant]
6.2×102 mol/(m3Pa) at 25℃, HSDB (2015) | [CAS DataBase Reference]
973-21-7 | [EPA Substance Registry System]
Dinobuton (973-21-7) |
| Hazard Information | Back Directory | [Uses]
Miticide. | [Description]
Dinobuton is a dinitrophenol multi-use pesticide which is not approved for use in the UK nor the EU. It has a low aqueous solubility but soluble in most organic solvents. Limited information is available regarding its environmental fate but is reported as being non-mobile. It is moderately toxic to mammals, birds and bees but considered highly toxic to fish. Limited data is available on its toxicity to humans but some reports suggest it is a possible cardiovascular, liver and kidney toxicant | [Definition]
ChEBI:Dinobuton is a C-nitro compound. | [Production Methods]
The commercial production of dinobuton involves synthesising a dinitrophenol-based compound through a series of organic reactions that introduce key functional groups responsible for its fungicidal and acaricidal activity. The process typically starts with the preparation of a sec-butyl-substituted aromatic intermediate, which is then nitrated to form the dinitrophenol core. This is followed by carbonate esterification, linking the dinitrophenol moiety to the sec-butyl group via a carbonate bridge. | [Mechanism of action]
Non-systemic, rapid contact action. Uncoupler of oxidative phosphorylation via disruption of proton gradient. | [Metabolic pathway]
Dinobuton is metabolised in plants and animals via common metabolic
pathways. The primary reaction is hydrolytic cleavage of the
carbonate-dinitrophenyl linkage to yield dinoseb. Further reduction of
the nitro-groups of dinoseb yields the corresponding monoamino and
diamino analogues. Acetylation and deamination via hydroxylation/
elimination, and oxidation of the sec-butyl moiety also occurred. N- and
O-Conjugation as glucosides and glucuronides occurred in both plants
and animals. The metabolic pathways of dinobuton are presented in
Scheme 1. | [Degradation]
There is limited information on the hydrolytic stability of dinobuton (1).
Marchenko and Vakulenko (1983) reported that the hydrolysis DT50 values
of dinobuton in pH 2, 7 and 11 buffer solutions at 22 °C were 15 days,
17 days and 4 hours, respectively. In vitro studies showed the rapid
hydrolysis of dinobuton to dinoseb [ 2-sec-butyl-4,6-dinitrophenol (2)] by
tissue homogenates of spider mites and animal tissues. Once generated,
dinoseb was stable to hydrolytic and photolytic degradation under acidic
condition but was readily degraded under alkaline conditions (Brestkin
et al., 1978; Molnar, 1935). Uncharacterised complex polar materials
were reported as photodecomposition products of dinoseb (Matsuo and
Casida, 1970). Grechko et al. (1986) reported that the DTW for dinobuton
in aqueous solution under UV light irradiation (365 nm) was <30 min. | [Pesticide Type]
Acaricide; Fungicide; Insecticide |
|
|