Tecnazene is a fungicide that acts by inhibiting fungal growth. As a chlorinated nitrobenzene, its mechanism of action likely involves disruption of fungal cell membranes or interference with cellular respiration. It is used to control sprouting and fungal diseases in stored potatoes and other crops. Specific molecular targets are not well-characterized in the available literature.

Tecnazene demonstrates fungicidal activity in vitro against various fungal pathogens. It is effective in controlling post-harvest fungal diseases in potatoes and other crops. The compound's activity is related to its ability to inhibit fungal growth and development. Specific in vitro data, including IC50 values against various fungal strains, are not extensively provided in the available literature.

Tecnazene demonstrates in vivo activity as a fungicide and plant growth regulator. It is used as a post-harvest treatment for potatoes to control fungal diseases and inhibit sprouting. The compound is applied to stored crops to extend their shelf life and prevent spoilage. Specific in vivo efficacy data, including application rates and crop types, are not extensively provided.

In vitro antifungal assays for Tecnazene involve measuring inhibition of fungal growth. Fungal strains (e.g., Fusarium, Penicillium) are cultured on agar plates or in liquid medium containing varying concentrations of Tecnazene. Fungal growth is measured by colony diameter or by optical density. IC50 values are calculated from concentration-response curves.

For in vitro cell-based assays, fungal cells are cultured and treated with Tecnazene at various concentrations. Fungal viability is assessed using standard assays (e.g., CFU counting, metabolic activity assays). The compound's effects on fungal cell morphology and membrane integrity can also be studied using microscopy.

In vivo animal studies for Tecnazene are primarily conducted for toxicological assessment rather than therapeutic efficacy. Rodent models are used to assess acute and subchronic toxicity. Tecnazene is administered orally at various doses. Clinical signs of toxicity are monitored. Histological examination of tissues is performed. LD50 values are determined from dose-response studies.

Absorption, Distribution and Excretion
The absorption, distribution, metabolism, and excretion of [14C]tinakrazine in rats have been studied. Previous studies on the metabolism of unlabeled tinakrazine have also been conducted in rats, rabbits, guinea pigs, and pigeons. Tinakrazine is extensively metabolized in all species. In animals, the nitro group is reduced to 2,3,5,6-tetrachloroaniline and 4-amino-2,3,5,6-tetrachlorophenol. These metabolites are excreted unchanged in the urine, or phenol is excreted as an ether glucuronide or sulfate conjugate. The nitro group can be replaced by glutathione to generate another major metabolite, S-(2,3,5,6-tetrachlorophenyl)-N-acetylcysteine, which is also excreted in the urine. …In vivo distribution tracking of [14C]tinakrazine and its metabolites was performed in male and female rats administered a dose of 1 mg/kg body weight. At 24 hours, the highest tissue concentrations of 14C were observed in the kidneys, liver, and nasal cavity of both male and female rats. At 7 days, 14C residues were low, but generally slightly higher in male rats, with the highest concentrations found in abdominal fat (0.032 mg/kg, calculated as tinacine), kidneys (0.016 mg/kg), lungs (0.016 mg/kg), blood (0.014 mg/kg), and heart (0.013 mg/kg). In female rats, the highest concentrations were found in abdominal fat, blood, and ovaries, at 0.011 mg/kg. At 7 days, the proportion of total dose in tissues was 0.13% in males and 0.05% in females. Based on 24-hour and 48-hour autoradiography and 7-day liquid scintillation counts, the concentration of 14C in tissues appeared to decrease over time.
After a single oral dose of 0.1-3.0 g/rat, 60-78% of the drug is excreted in feces and 35-38% in urine within 3 days (mainly in conjugate form). After an oral dose of 0.01 g, 22-30% of the drug is recovered in feces.
Metabolism/Metabolites
The metabolic pathway of the drug was determined after a single oral dose of 1 mg/kg [U-14C]-2,3,5,6-tetrachloronitrobenzene (terconazine) in male and female rats, and after a single oral dose of 135 mg/kg in surgically prepared rats with bile duct cannulation. In female rats, radioactivity was mainly excreted in urine (82%). In male rats, approximately equal amounts of radioactivity were excreted in urine and feces (the latter mainly through bile). The main metabolic pathway is conjugation with glutathione (GSH) accompanied by nitro substitution. GSH conjugates and their related metabolites are excreted via bile, ultimately in the urine as thiouric acid conjugates. Cysteine conjugates are metabolized by β-lyase to thiols, which are then methylated to anisole, followed by S-oxidation. 4. A novel tetrachloromethyl disulfide metabolite is also generated.
After administration of 2,3,5,6-tetrachloronitrobenzene to rabbits, some nitro reduction reactions occurred in the intestines. Very small amounts of tetrachloroaniline, thiouric acid, free 4-amino-2,3,5,6-tetrachlorophenol, sulfate, and glucuronide were excreted in the urine.
In rats, S-(2,3,5,6-tetrachlorophenyl)glutathione was generated. /Excerpt from table/
After administration of 1-3 g ticarzine to rabbits, the excretion rate of thiouric acid conjugates was 11% within 48 hours. Other excreted metabolites include ether glucuronide (12%), 2,3,5,6-tetrachloroaniline (10%), unconjugated 4-amino-2,3,5,6-tetrachlorophenol (2%), and ether sulfate (1%). For more complete metabolite/metabolite data on TECNAZENE (7 metabolites in total), please visit the HSDB record page.

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Tecnazene has a molecular formula of C6HCl4NO2 and a molecular weight of 260.88. It is a white to light yellow to light orange powder or crystal. It is practically insoluble in water but soluble in ethanol, benzene, chloroform, and carbon disulfide. It has a melting point of 98-101°C and a boiling point of 304°C. It should be stored at room temperature.

Non-Human Toxicity Values
Rat intraperitoneal LD50: 3500 mg/kg
Rat oral LD50: 250 mg/kg
Rat oral LD50: 7500 mg/kg body weight

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Tecnazene has low acute toxicity in animals but may cause skin and eye irritation. As a chlorinated nitrobenzene compound, it may have potential for chronic toxicity and environmental persistence. The compound is primarily used as an agricultural fungicide and is not approved as a therapeutic agent for human use. Standard toxicology assessments would be required for safety evaluation.

2,3,5,6-Tetrachloronitrobenzene is a pale yellow crystal. (NTP, 1992)
Ttecnabenzene is a C-nitro compound with the structure nitrobenzene, in which the four hydrogen atoms attached to the ortho and para positions of the nitro group are replaced by chlorine atoms. It was once a fungicide used to control dry rot, but is no longer approved for use in the European Union. It is an antifungal pesticide. It is a C-nitro compound, a tetrachlorobenzene compound, and an aromatic fungicide. Its structure is similar to that of 1,2,4,5-tetrachlorobenzene.

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Tecnazene (CAS#: 117-18-0) is a fungicide and plant growth regulator. It is a chlorinated nitrobenzene compound used as a post-harvest fungicide for potatoes and other crops. Tecnazene is practically insoluble in water but soluble in organic solvents. It is used to control sprouting and fungal diseases in stored crops. The compound is primarily used in agricultural applications and is not approved as a therapeutic agent for human use.

C6HCL4NO2

260.88

258.876

117-18-0

8330

Colorless crystals

1.8±0.1 g/cm3

304.0±0.0 °C at 760 mmHg

98-101 °C(lit.)

143.1±26.5 °C

0.0±0.6 mmHg at 25°C

1.620

3.73

0

2

0

13

195

0

C1=C(C(=C(C(=C1Cl)Cl)[N+](=O)[O-])Cl)Cl

XQTLDIFVVHJORV-UHFFFAOYSA-N

InChI=1S/C6HCl4NO2/c7-2-1-3(8)5(10)6(4(2)9)11(12)13/h1H

1,2,4,5-tetrachloro-3-nitrobenzene

NSC-10235; NSC 10235; Tecnazene

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)