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Propineb

Alias: LH-3012; LH 3012; Propineb
Cat No.:V13261 Purity: ≥98%
Propineb (Zinc propylenebis) is a compound extensively used against fruit and vegetable diseases and has broad spectrum (a wide range) activity against plant fungal diseases.
Propineb
Propineb Chemical Structure CAS No.: 12071-83-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Propineb (Zinc propylenebis) is a compound extensively used against fruit and vegetable diseases and has broad spectrum (a wide range) activity against plant fungal diseases.
Propineb (CAS#: 12071-83-9), also known as Zinc propylene bis(dithiocarbamate), is a broad-spectrum dithiocarbamate fungicide widely used in agriculture to protect crops from fungal diseases. It is a zinc-containing compound that acts as a protectant foliar fungicide with long residual activity. Propineb is effective against a variety of fungal pathogens, including those causing downy mildew, blight, and rust in fruits, vegetables, and ornamental plants. The compound is commonly used on crops such as potatoes, tomatoes, grapes, strawberries, and citrus fruits. Its molecular formula is C5H8N2S4Zn, with a molecular weight of 289.74 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Propineb acts as a multi-site inhibitor, disrupting fungal enzyme functions and inhibiting spore germination. It contains dithiocarbamate groups that can chelate metal ions and react with sulfhydryl groups of essential enzymes in fungal cells, leading to metabolic disruption and cell death. The compound also facilitates acetylcholine signaling and has been studied for its effects on the nervous system. Its protective action prevents the establishment and spread of fungal pathogens by killing conidia and germinating conidia upon contact.
ln Vitro
In vitro, Propineb exhibits broad-spectrum antifungal activity against a range of plant pathogenic fungi. It inhibits mycelial growth and spore germination in a dose-dependent manner. The compound is effective against Oomycetes, Ascomycetes, and Deuteromycetes. Its activity is primarily protective rather than curative, making it most effective when applied before infection occurs. The zinc content of the molecule contributes to its antifungal properties and its stability in formulations.
ln Vivo
Prozine (propylene bizinc) causes particular goiterogenic effects in rats and has a moderate to low acute toxicity. Reproductive system failure, carcinogenesis, teratogenesis, and deformities of the live organism are linked to prolonged exposure, oral administration, or inhalation [2].
In vivo, Propineb is used as a protective foliar fungicide in agricultural crops. It provides long-lasting protection against fungal diseases such as downy mildew, black rots, and scab. The compound is applied as a spray and forms a protective barrier on the plant surface, preventing fungal spore germination and penetration. Its long residual activity reduces the frequency of applications needed. In animal studies, Propineb has been shown to have moderate to low acute toxicity but has a specific goitrogenic effect in rats with long-term exposure.
Enzyme Assay
The in vitro antifungal activity of Propineb is assessed using the agar dilution or broth microdilution method. The compound is dissolved in an appropriate solvent and incorporated into agar media or liquid growth medium at various concentrations. Fungal spores or mycelial plugs are inoculated onto the medium, and the inhibition of radial growth or mycelial biomass is measured after incubation at 25-28°C for 3-7 days. The EC50 (effective concentration for 50% inhibition) is calculated from dose-response curves. For cell-free assays, the compound's ability to inhibit key fungal enzymes (e.g., dehydrogenases) can be measured spectrophotometrically using appropriate substrates.
Cell Assay
For cellular assays, fungal cultures of target pathogens (e.g., Phytophthora infestans, Plasmopara viticola) are grown in liquid media. Cells are treated with various concentrations of Propineb (typically 1-100 µg/mL) for defined periods. Fungal viability is assessed by measuring the reduction of triphenyltetrazolium chloride (TTC) or by fluorescence staining with FDA/PI. The effect on spore germination is evaluated by counting germinated spores under a microscope after 6-24 hours of incubation. The disruption of membrane integrity can be assessed by measuring electrolyte leakage or by using fluorescent dyes such as propidium iodide.
Animal Protocol
In vivo, Propineb is applied as a foliar spray in field or greenhouse trials. The compound is formulated as a wettable powder or suspension concentrate and applied at recommended rates (typically 1-3 kg active ingredient per hectare). Efficacy is evaluated by assessing disease severity on leaves or fruits at regular intervals after application. The percentage of disease control is calculated by comparing treated plots with untreated controls. In toxicological studies, Propineb is administered orally to rats at various doses (typically 5-500 mg/kg/day) for 28 days to 2 years. Endpoints include body weight, food consumption, clinical chemistry parameters (liver and thyroid function tests), and histopathological examination of tissues, particularly the thyroid gland and liver.
ADME/Pharmacokinetics
Propineb is poorly absorbed after oral administration in mammals, with most of the compound excreted unchanged in feces. The small fraction that is absorbed is metabolized and excreted in urine. In plants, the compound remains on the surface and is not significantly translocated. Its environmental persistence varies depending on soil type, pH, and microbial activity. The compound is relatively stable under dry conditions but may degrade under high moisture and alkaline conditions.
Toxicity/Toxicokinetics
Toxicity Data
LC50 (Rat) > 693 mg/m³/4h
Propineb has moderate to low acute toxicity in mammals. However, long-term exposure has been associated with goitrogenic effects in rats, characterized by thyroid enlargement and altered thyroid hormone levels. The compound can cause skin and eye irritation and may be a sensitizer in some individuals. It is moderately toxic to aquatic organisms and should be used with caution near water bodies. The use of Propineb is regulated in many countries, with maximum residue limits established for food commodities. Proper personal protective equipment should be used during handling and application.
References
[1]. Viviani B, et al. Dithiocarbamate propineb induces acetylcholine release through cytoskeletal actin depolymerization in PC12 cells. Toxicol Lett. 2008 Nov 10;182(1-3):63-8.
[2]. Viviani B, et al. Dithiocarbamate propineb induces acetylcholine release through cytoskeletal actin depolymerization in PC12 cells. Toxicol Lett. 2008 Nov 10;182(1-3):63-8.
[3]. Kazos EA, et al. Determination of dithiocarbamate fungicide propineb and its main metabolite propylenethiourea in airborne samples. Chemosphere. 2007 Aug;68(11):2104-10.
Additional Infomation
Propineb is a polymeric complex formed by zinc and a propene-1,2-bis(dithiocarbamate) anionic ligand. It is a fungicide used to control a variety of fungal diseases, including downy mildew, brown rot, black rot, red spot, leaf spot, and wilt, and is suitable for crops such as grapes, tomatoes, potatoes, berries, citrus, rice, and tea. It is an antifungal pesticide. Propineb is a dithiocarbamate salt, belonging to the macromolecular zinc coordination compounds, containing a propene-1,2-bis(dithiocarbamate) ligand.
Propineb is a widely used agricultural fungicide registered in many countries for the control of fungal diseases in a variety of crops. Its protectant mode of action and long residual activity make it a valuable tool in disease management programs. The compound is often used in combination with other fungicides to broaden the spectrum of activity and delay the development of resistance. Its use is part of integrated pest management strategies to minimize crop losses due to fungal infections. Propineb is not approved for use on all crops, and its application is subject to local regulations.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C5H8N2S4ZN
Molecular Weight
289.75
Exact Mass
287.886
CAS #
12071-83-9
Related CAS #
9016-72-2
PubChem CID
6100711
Appearance
Typically exists as solid at room temperature
Boiling Point
315.4ºC at 760 mmHg
Melting Point
160ºC
Flash Point
144.5ºC
LogP
1.765
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
12
Complexity
148
Defined Atom Stereocenter Count
0
SMILES
CC(NC(S)=S)CN=C([S-])[S-].[Zn+2]
InChi Key
KKMLIVYBGSAJPM-UHFFFAOYSA-L
InChi Code
InChI=1S/C5H10N2S4.Zn/c1-3(7-5(10)11)2-6-4(8)9;/h3H,2H2,1H3,(H2,6,8,9)(H2,7,10,11);/q;+2/p-2
Chemical Name
zinc;N-[1-(sulfidocarbothioylamino)propan-2-yl]carbamodithioate
Synonyms
LH-3012; LH 3012; Propineb
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~33.33 mg/mL (~93.85 mM)
Solubility (In Vivo)
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.

Injection Formulations
(e.g. IP/IV/IM/SC)
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 : PEG300Tween 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 : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
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


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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.4513 mL 17.2563 mL 34.5125 mL
5 mM 0.6903 mL 3.4513 mL 6.9025 mL
10 mM 0.3451 mL 1.7256 mL 3.4513 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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