DINOCAP

The Uses of DINOCAP

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 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.