General Description
Dark oily liquid. Nearly insoluble in water. Used as a fungicide and acaricide.
Reactivity Profile
A dinitrophenyl derivative.
Air & Water Reactions
Nearly insoluble in water. Hydrolysis of the ester group occurs with alkaline pHs.
Description
Dinocap is shown in both the 2,4-dinitro and 2,6-dinitro
configurations with 1-methylheptyl and 1-ethylhexyl
chains, respectively, but may also have a 1-propylpentyl
configuration for the “octyl” chain. It is a dark brown
liquid with a bp = 138 to 140 ?C, vp = 5.3×10?6 mPa, a
Kow LogP = 4.54, and is almost insoluble (<0.1 mgL?1) in
water (5).
Uses
Acaricide; fungicide.
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.
Agricultural Uses
Fungicide, Acaricide: Dinocap is a foliar fungicide/miticide used to
control powdery mildew. It is applied to limit mites
in apples and grapes crops outside the U.S., mainly in
Europe, the Middle East and northern Africa. It is also
used to control powdery mildew on fruit, vegetables and
ornamentals. DAS, the registrant of dinocap, intends to
support tolerances for dinocap residues in/on apples and
grapes to permit legal importation of these commodities
into the U.S. Not approved for use in EU countries.
Not currently registered in the U.S. There are 17 global
suppliers.
Trade name
ACTUAL DINOCAP®; ARATHANE®;
CAPRANE®; CR 1639®; CEKUCAP® 25 WP;
CROTOTHANE®; DICAP®; DIKAR®; EZENOAN®;
ISCOTHANE®; ISOCOTHANE®; KARATHANE®[C];
KARATHANE® WD[C]; KARATHENE®[C];
MILDANE®; MILDEX®
Toxicity evaluation
Dinocap shows moderate acute toxicity to mammals
(acute oral LD50 in rats of 1,000 to 5,000 mg/kg) with moderate
dermal irritation but substantial eye irritation in
rabbits (Rohm & Haas MSDS C&P MSDS reference listing;
MDL MSDS database listing). Dinocap is teratogenic
to mice and hamsters at 10 to 100 mg/kg/day (48–51),
although no evidence of teratogenic effects were seen in
rabbits (Rohm & Haas MSDS C&P MSDS reference listing).
Dinocap is classified as “toxic” to fish but is listed as
“nontoxic” to bees (52).
