| Identification | Back Directory | [Name]
DINOCAP | [CAS]
131-72-6 | [Synonyms]
SIALITE
4-DNOPC
KARATHAN
KARATHANE
CR1639(R)
MILDEX(R)
2;4-DNOPC
CROTOTHANE
KARATHANE(R)
CROTOTHANE(R)
ISOCOTHANE(R)
Meptyldinocap
Meptyldinocap [iso]
Meptyldinocap Solution
2,6-DINITRO-4-OCTYLPHENYLCROTONATE
Meptyldinocap@100 μg/mL in Methanol
2-METHYLHEPTYL-4,6-DINITROPHENYL CROTONATE
2-(1-METHYLHEPTYL)-4,6-DINITROPHENYL CROTONATE
Meptyldinocap Solution in Acetonitrile, 100μg/mL
(E)-2,4-dinitro-6-(octan-2-yl)phenyl but-2-enoate
Crotonic acid 2-(1-methylheptyl)-4,6-dinitrophenyl
(RS)-2-(1-Methylheptyl)-4,6-dinitrophenyl crotonate
(E)-2-(1-Methylheptyl)-4,6-dinitrophenyl 2-butenoate
2-(1-Methylheptyl)-4,6-dinitrophenyl (2E)-2-butenoate
2(OR 4)-ISO-OCTYL-4,6-(OR 2,6)-DINITROPHENYL 2-BUTENOATE
(E)-2-Butenoic acid 2-(1-methylheptyl)-4,6-dinitrophenyl ester
2-Butenoic acid, 2-(1-methylheptyl)-4,6-dinitrophenyl ester, (E)-
2-Butenoic acid, 2-(1-methylheptyl)-4,6-dinitrophenyl ester, (2E)- | [EINECS(EC#)]
679-522-1 | [Molecular Formula]
C18H24N2O6 | [MDL Number]
MFCD00054268 | [MOL File]
131-72-6.mol | [Molecular Weight]
364.39 |
| Chemical Properties | Back Directory | [Boiling point ]
473.7±45.0 °C(Predicted) | [density ]
1.175±0.06 g/cm3(Predicted) | [vapor pressure ]
7.5 x 10-5 Pa (25 °C) | [storage temp. ]
0-6°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [Water Solubility ]
<0.1 mg l-1 | [color ]
Light yellow to yellow | [Henry's Law Constant]
8.6×101 mol/(m3Pa) at 25℃, Maniere et al. (2011) | [Major Application]
agriculture
environmental | [InChI]
1S/C18H24N2O6/c1-4-6-7-8-10-13(3)15-11-14(19(22)23)12-16(20(24)25)18(15)26-17(21)9-5-2/h5,9,11-13H,4,6-8,10H2,1-3H3/b9-5+ | [InChIKey]
NIOPZPCMRQGZCE-WEVVVXLNSA-N | [SMILES]
CCCCCCC(C)c1cc(cc(c1OC(=O)\C=C\C)[N+]([O-])=O)[N+]([O-])=O | [LogP]
6.477 (est) | [EPA Substance Registry System]
(E)-2-(1-Methylheptyl)-4,6-dinitrophenyl 2-butenoate (131-72-6) |
| Hazard Information | Back Directory | [Description]
Meptyldinocap is a protectant, curative and eradicant fungicide. It has a low aqueous solubility, it is volatile and, based on its chemical properties, is unlikely to leach to groundwater. It is not persistent in soil and will usually degrade in water systems quickly. It is moderately toxic to mammals and bioaccumulation may be a concern. Whilst it is not highly toxic to birds, it is more toxic to many aquatic species including fish and algae. | [Uses]
Dinocap is a contact fungicide which provides both protective and
curative activities against powdery mildews, fruit rots, stem rots, leaf
spots, brown rots, etc., in a wide range of crops including pome fruits,
stone fruits, citrus, vines, hops, ornamentals and berries. | [Definition]
ChEBI: 2,4-dinitro-6-(octan-2-yl)phenyl (E)-but-2-enoate is an enoate ester obtained by formal condensation of the carboxy group of 3-methylacrylic acid with the phenolic hydroxy group of 2,4-dinitro-6-(octan-2-yl)phenol. It is a C-nitro compound and an enoate ester. | [Production Methods]
The industrial synthesis of meptyldinocap begins with the preparation of the dinitrophenol core, typically derived from 2,4-dinitrophenol. This compound is then alkylated with 1-methylheptyl bromide to introduce the hydrophobic side chain, enhancing lipophilicity and plant surface adhesion. The resulting intermediate undergoes esterification with crotonic acid (2-butenoic acid) under acidic conditions, forming the final ester linkage. The reaction is carried out in organic solvents like toluene or acetonitrile, with temperature and pH carefully controlled to ensure high yield and minimal by-product formation. | [Mechanism of action]
Protectant, curative and eradicant activity by inhibiting spore germination. Uncoupler of oxidative phosphorylation | [Metabolic pathway]
Dinocap is a mixture 2,4- and 2,6-dinitro isomers of octylphenyl crotonate.
Limited data are available in the open literature. Information presented in
this summary is abstracted from the data evaluation published by the
Pesticide Safety Directorate (PSD). Degradation and metabolism studies
were conducted mainly with the 2,4-dinitro isomer. Hydrolytic cleavage
of the crotonate to yield the corresponding phenol is the primary pathway
in soil, plants and animals. β-Hydroxylation and/or carboxylation of the
octyl moiety is a minor pathway in animals (Scheme 1). | [Degradation]
The hydrolytic degradation of dinocap [1,(2,4-dinitro-6-octylphenyl
crotonate)] was examined at 25 °C. The estimated DT50 values of
[14C-phenyl]dinocap in pH 5, 7 and 9 buffer solution were 229 days, 56
days and 17 hours, respectively. Cleavage of the crotonate moiety yielded
2,4-dinitro-6-octylphenol(2) as the major product. | [Pesticide Type]
Fungicide |
|
| Company Name: |
BOC Sciences
|
| Tel: |
1-631-485-4226; 16314854226 |
| Website: |
https://www.bocsci.com |
| Company Name: |
Alfa Chemistry
|
| Tel: |
1-516-6625404 |
| Website: |
https://www.alfa-chemistry.com |
|