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.
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 DT
50 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.
