Dinocap

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 = 5.3×106 mPa, a Kow LogP = 4.54, and is almost insoluble (<0.1 mgL1) in water (5).

Chemical Properties

Dinotefuran is a dark red viscous liquid with irritating odor, melting point -22.5℃, boiling point 138~140℃(0.05mmHg), it will be decomposed when it exceeds 200℃ under normal pressure. Vapor pressure 3.33×10-3 mPa(25℃), KowlgP=4.54(20℃).Henry's constant 1.36×10-3Pa- m3/mol(calculated). Relative density 1.10 (20°C). Solubility in water 0.151mg/L. Solubility in other solvents, 2,4-isomer: in acetone, 1,2-dichloroethane, ethyl acetate, n-heptane, methanol, and xylene >250g/L; 2,6-isomer: in acetone, 1,2-dichloroethane, ethyl acetate, and xylene >250g/L, n-heptane 8.5~10.2g/L, methanol 20.4~25.3g/L. Decompose rapidly at light, decompose above 32℃, stable to acid, hydrolyze ester group in alkaline environment. Flash point 67℃.

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.

General Description

Dark oily liquid. Nearly insoluble in water. Used as a fungicide and acaricide.

Air & Water Reactions

Nearly insoluble in water. Hydrolysis of the ester group occurs with alkaline pHs.

Reactivity Profile

A dinitrophenyl derivative.

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®

Safety Profile

Poison by ingestion and intravenous routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Questionable carcinogen with experimental neoplastigenic data. See NITRATES. When heated to decomposition it emits toxic fumes of NOx.

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).