Tecnazene  (Synonyms: 1,2,4,5-テトラクロロ-3-ニトロベンゼン)

Tecnazene is a dinitroaromatic fungicide and plant growth regulator. Tecnazene binds irreversibly to human skin tissues and exhibits acute toxicity in Rattus norvegicus (brown rat). Tecnazene exerts sprouting-inhibiting and antifungal activities by inhibiting the sprouting of potato tuber buds and blocking the growth and reproduction of fungi that cause dry rot. Tecnazene has significant antifungal and sprouting-inhibiting activities, and shows high toxicity to aquatic organisms such as freshwater fish and crustaceans. Tecnazene is used for sprouting inhibition and dry rot control during potato storage^[1].

Tecnazene is mainly applied in the agricultural field as a dual-effect pesticide for sprouting inhibition and dry rot control during potato storage. It is also used in studies on the in vitro human skin permeation properties of highly lipophilic chlorinated aromatic compounds, as well as in the calibration and optimization of transdermal absorption and diffusion models^[2].
In in vitro human skin permeation assays, the percutaneous absorption rate of Tecnazene reaches 22-33% under occlusive conditions and 2.2-6.1% under non-occlusive conditions^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Tecnazene is metabolized in organisms via pathways such as glutathione conjugation and nitro substitution, and can form metabolites including mercapturic acid conjugates and tetrachloroanisole. It undergoes rapid bioconcentration and rapid excretion in aquatic organisms^[3].
Tecnazene shows high toxicity to aquatic organisms such as freshwater fish and crustaceans, with a 96-hour LC₅₀ of 270-2340 μg/L^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

260.89

C₆HCl₄NO₂

117-18-0

Solid

White to off-white

ClC1=C(C(Cl)=C(C=C1Cl)Cl)[N+]([O-])=O

Room temperature in continental US; may vary elsewhere.

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

• [1]. Pouretedal H R, et al. Prediction of toxicity of nitroaromatic compounds through their molecular structures[J]. Journal of the Iranian Chemical Society, 2011, 8(1): 78-89.

  [2]. Bhatt V D, et al. Permeation of tecnazene through human skin in vitro as assessed by HS-SPME and GC-MS[J]. Environmental science & technology, 2008, 42(17): 6587-6592.

  [3]. Lappin G J, et al. Metabolism of 2, 3, 5, 6-tetrachloronitrobenzene (tecnazene) in rat[J]. Xenobiotica, 1996, 26(1): 65-77.

  [4]. Whale G, et al. The toxicity of tecnazene, a potato sprouting inhibitor, to freshwater fauna[J]. Chemosphere, 1988, 17(6): 1205-1217.