Art. -Nr.: HY-146145

Metyltetraprole

Name: Metyltetraprole
Brand: MedChemExpress
SKU: HY-146145
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Metyltetraprole is a QoI fungicide containing a tetrazolinone pharmacophore that binds to the Qo site of the cytochrome bc1 complex (complex III), blocks D-Panthenol (HY-B1391) oxidation, and inhibits mitochondrial electron transport, while retaining antifungal activity against QoI-resistant isolates and exhibiting broad-spectrum antifungal effects. Metyltetraprole is used in the study of wheat Septoria leaf blotch, net blotch, cucumber downy mildew, and powdery mildew.

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Reinheit : 99.53%
CAS. Nr.: 1472649-01-6
Formel: C₁₉H₁₇ClN₆O₂
Molecular Weight:396.83

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

Metyltetraprole Chemical Structure

CAS. Nr.: 1472649-01-6

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Biologische Aktivität
- Beschreibung
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

In Vitro

Metyltetraprole (0.000061-1 ppm; 5 days) exhibits equally potent in vitro activity against both wild-type and G143A mutant Zymoseptoria tritici strains, with an EC₅₀ of 0.002 ppm for both^[2].
Metyltetraprole (1 ppm; 20 min) binds to the Q_o site of the cytochrome bc₁ complex in the submitochondrial fraction of Zymoseptoria tritici^[2].
Metyltetraprole is slightly more sensitive to QoI-R strains that may carry the G143A mutation than to QoI-S strains of Pyrenophora tritici-repentis, whereas no effect is observed in Ramularia collo-cygni^[3].
Metyltetraprole (0.0003-3 mg/L; 3 days for P. tritici-repentis and 7 days for V. effusa) retains potent inhibitory activity against QoI-resistant Pyrenophora tritici-repentis and Venturia effusa isolates carrying non-wild-type cytochrome b haplotypes, with resistance factors ranging from 0.7 to 2.9^[4].
Metyltetraprole (0.0001-10 mg/L; 2 h and 18 h) retains potent inhibitory activity against Puccinia horiana carrying the L299F, N256S + L299F, and L275F + L299F cytochrome b substitutions, with resistance factors ranging from 0.7 to 2.9^[4].
Metyltetraprole exhibits potent inhibitory activity against Saccharomyces cerevisiae CIII with a K_i of 0.92 nM and an IC₅₀ of 0.001 μM, but shows significantly lower activity against porcine CIII with a K_i of 298.87 nM and an IC₅₀ of 0.312 μM^[5].
Metyltetraprole binds to the Q_o site in Saccharomyces cerevisiae CIII, but binds to the Q_i site in porcine CIII, indicating species-specific differences in the binding site^[5].
Metyltetraprole acts as a Pm-type inhibitor at the Qo site in Saccharomyces cerevisiae CIII, whereas in porcine CIII, it functions as a dual-target inhibitor that binds to both the Qo and Qi sites^[5].
Metyltetraprole maintains its binding mode and retains a favorable binding energy of -49.20 kcal/mol with the G143A mutant of Saccharomyces cerevisiae CIII, resulting in a low resistance factor of 1.6^[5].
Metyltetraprole (0.0001-3 mg/L) effectively inhibits the in vitro growth of Zymoseptoria tritici (EC₅₀ 0.0022 mg/L), Ramularia collo-cygni (EC₅₀ 0.0020 mg/L), Parastagonospora nodorum (EC₅₀ 0.0025 mg/L), and Ustilago maydis (EC₅₀ 0.040 mg/L)^[6].
Metyltetraprole (0.0001-3 mg/L) effectively inhibits the growth of Pyrenophora teres in vitro (EC₅₀ 0.0048 mg/L), while showing lower activity against basidiomycetes and oomycetes^[6].
Metyltetraprole (0.0001-3 mg/L) retains potent antifungal activity against field isolates of Zymoseptoria tritici and Pyrenophora teres that are resistant to other fungicide classes, with EC₅₀ values ranging from 0.0025 to 0.0088 mg L⁻¹ for Z. tritici and from 0.007 to 0.015 mg L⁻¹ for P. teres^[6].

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

In Vivo

Metyltetraprole (0.1‑100 µg/L; immersion; 7 consecutive days) does not exhibit obvious developmental toxicity in zebrafish at the highest tested concentration of 100 µg/L (survival rate 94‑97%, malformation rate ≤ 5%); however, the 100 µg/L group induces significant hyperactivity in zebrafish during the first dark cycle and alters the expression of mitochondrial electron transport chain-related genes mt‑nd3 and uqcrc2^[1].
Metyltetraprole (0.1-10 µg/L; immersion; 7 consecutive days) alters the expression of mitochondrial electron transport chain genes, in which mt-nd3 is upregulated at 1 µg/L, while uqcrc2 expression decreases in a dose-dependent manner^[1].

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

Animal Model:

AB × Tübingen strain (embryos/larvae)^[1]
Dosage:

0.1, 1, 10, and 100 µg/L
Administration:

immersion; continuous; from ~6 hpf until 7 days post-fertilization
Result:

Showed a significant difference in combined survival rates between the DMSO control and Metyltetraprole concentrations (Log-rank Mantel-Cox test, Chi-square = 30.98, d.f. = 5).
Observed high overall survival of 94-97% across all groups.
Recorded few deformities in each group (> 5%), with no significant reoccurring deformities (< 3%).
Detected no significant effect on ROS levels at any concentration tested [F(4,15) = 0.9010].
Found no differences in transcripts cat, sod1, sod2, cox5a1, cox4i1, cycl1, mt-nd1, mt-nd2, ndufs3, uqcrb, uqcrc2, uqcrc2b, and uqcrh among groups.
Observed significant upregulation of mt-nd3 in fish exposed to 1 µg/L Metyltetraprole.
Revealed a reduction in uqcrc2 expression with increasing concentration of Metyltetraprole via regression analysis.
Induced hyperactivity in larval zebrafish following 100 µg/L Metyltetraprole during the first dark period [F(4,145) = 7.960].

Animal Model:

AB × Tübingen strain (embryos)^[1]
Dosage:

0.1, 1, and 10 µg/L
Administration:

immersion; continuous; from 6 hpf until 7 days post-fertilization
Result:

Observed significant upregulation of mt-nd3 in fish exposed to 1 µg/L MTP.
Revealed a dose-dependent change in uqcrc2 expression in 7-day old larval zebrafish exposed to 0.1, 1, or 10 µg/L MTP, with a regression analysis revealing a reduction in uqcrc2 expression with increasing concentration of MTP.

Animal Model:

Rat^[7]
Dosage:

1000 mg/kg bw per day
Administration:

dermal; 28-day study
Result:

Reported a systemic dermal no observed adverse effect level (NOAEL) of 1000 mg/kg bw per day.

Animal Model:

Dog^[7]
Dosage:

100 mg/kg bw per day
Administration:

oral; 13-week study
Result:

Reported a short-term oral LOAEL of 100 mg/kg bw per day based on liver effects and decreased thymus weight.

Animal Model:

Mice^[7]
Dosage:

82.2 mg/kg bw per day
Administration:

oral; 18-month study
Result:

Reported a long-term and carcinogenic NOAEL of 82.2 mg/kg bw per day based on increased liver weight and malignant lymphomas.

Animal Model:

Rat^[7]
Dosage:

83.9 mg/kg bw per day
Administration:

oral; 2-year study
Result:

Reported a carcinogenic NOAEL of 83.9 mg/kg bw per day.

Animal Model:

Rat^[7]
Dosage:

409 mg/kg bw per day (parental and offspring NOAEL); 1385 mg/kg bw per day (reproductive NOAEL)
Administration:

oral; multigeneration study
Result:

Reported parental and offspring NOAELs of 409 mg/kg bw per day and a reproductive NOAEL of 1385 mg/kg bw per day.

Animal Model:

Rat^[7]
Dosage:

500 mg/kg bw per day (developmental NOAEL); 1000 mg/kg bw per day (maternal NOAEL)
Administration:

oral; teratogenicity study
Result:

Reported a developmental NOAEL of 500 mg/kg bw per day and a maternal NOAEL of 1000 mg/kg bw per day.

Animal Model:

Rabbit^[7]
Dosage:

100 mg/kg bw per day
Administration:

oral; teratogenicity study
Result:

Reported maternal and developmental NOAELs of 100 mg/kg bw per day.

Animal Model:

Rat^[7]
Dosage:

500 mg/kg bw per day (neurotoxicity NOAEL); 2000 mg/kg bw per day (systemic toxicity NOAEL)
Administration:

oral; acute study
Result:

Reported an acute neurotoxicity NOAEL of 500 mg/kg bw per day and a systemic toxicity NOAEL of 2000 mg/kg bw per day.

Chemical Information

CAS. Nr. 1472649-01-6
Appearance Solid
Molecular Weight 396.83
Formel C₁₉H₁₇ClN₆O₂
Color White to off-white
SMILES

O=C1N(C)N=NN1C2=CC=CC(C)=C2COC3=NN(C4=CC=C(Cl)C=C4)C=C3
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 100 mg/mL (252.00 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.5200 mL

12.5999 mL

25.1997 mL

5 mM

0.5040 mL

2.5200 mL

5.0399 mL

10 mM

0.2520 mL

1.2600 mL

2.5200 mL

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.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 5 mg/mL (12.60 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 5 mg/mL (12.60 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 5 mg/mL (12.60 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (290 KB)
SDS (251 KB)
- English - EN (251 KB)
- Français - FR (251 KB)
- Deutsch - DE (251 KB)
- Norwegian - NO (251 KB)
- Español - ES (251 KB)
- Swedish - SV (251 KB)
- Italian - IT (251 KB)
- Korean - KR (251 KB)
- Portuguese - PT (251 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Casine T, et al. Toxicity Assessment of Metyltetraprole, a Novel Fungicide Inhibitor, to Embryo/Larval Zebrafish (Danio rerio). Toxics. 2025 Jul 28;13(8):634.

[2]. Matsuzaki Y, et al. Discovery of metyltetraprole: Identification of tetrazolinone pharmacophore to overcome QoI resistance. Bioorg Med Chem. 2020 Jan 1;28(1):115211. [Content Brief]

[3]. Matsuzaki Y, et al. Antifungal activity of metyltetraprole against the existing QoI-resistant isolates of various plant pathogenic fungi: Metyltetraprole against QoI-R isolates. Pest management science. 2020 May;76(5):1743-1750.

[4]. Matsuzaki Y, et al. Metyltetraprole activity against plant pathogens with relatively rare cytochrome b haplotypes for azoxystrobin resistance. J Gen Plant Pathol 88, 318–324 (2022).

[5]. Wang YX, et al. Cryo-EM Structures Reveal the Unique Binding Modes of Metyltetraprole in Yeast and Porcine Cytochrome Complex Enabling Rational Design of Inhibitors. Journal of the American Chemical Society. 2024 Dec 11;146(49):33903-33913.

[6]. Suemoto H, et al. Metyltetraprole, a novel putative complex III inhibitor, targets known QoI-resistant strains of Zymoseptoria tritici and Pyrenophora teres. Pest management science. 2019 Apr;75(4):1181-1189. [Content Brief]

[7]. Álvarez F, et al. Peer review of the pesticide risk assessment of the active substance metyltetraprole. EFSA journal. European Food Safety Authority. 2026 Apr;24(4):e9971.

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

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.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.5200 mL	12.5999 mL	25.1997 mL	62.9993 mL
	5 mM	0.5040 mL	2.5200 mL	5.0399 mL	12.5999 mL
	10 mM	0.2520 mL	1.2600 mL	2.5200 mL	6.2999 mL
	15 mM	0.1680 mL	0.8400 mL	1.6800 mL	4.2000 mL
	20 mM	0.1260 mL	0.6300 mL	1.2600 mL	3.1500 mL
	25 mM	0.1008 mL	0.5040 mL	1.0080 mL	2.5200 mL
	30 mM	0.0840 mL	0.4200 mL	0.8400 mL	2.1000 mL
	40 mM	0.0630 mL	0.3150 mL	0.6300 mL	1.5750 mL
	50 mM	0.0504 mL	0.2520 mL	0.5040 mL	1.2600 mL
	60 mM	0.0420 mL	0.2100 mL	0.4200 mL	1.0500 mL
	80 mM	0.0315 mL	0.1575 mL	0.3150 mL	0.7875 mL
	100 mM	0.0252 mL	0.1260 mL	0.2520 mL	0.6300 mL

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Metyltetraprole