Triadimefon - Moligand™, 10 mM in DMSO , CAS No.43121-43-3

CAS: 43121-43-3 Cat. No.: T1495489 Formula: C₁₄H₁₆ClN₃O₂ Molecular Weight: 293.75 EC Number: 256-103-8

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Triadimefon is a triazole fungicide used to control powdery mildew, rusts, and other fungal pests on grains, fruit and vegetable crops, turf, shrubs, and trees. Triadimefon inhibits lanosterol 14α-demethylase, interfering with oxidative demethylation reactions in the ergosterol biosynthesis pathway of fungi, and also blocks gibberellin biosynthesis.

Specifications

Specifications & Purity

Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Isomeric SMILES: CC(C)(C)C(=O)C(N1C=NC=N1)OC2=CC=C(C=C2)Cl
• Molecular Weight: 293.75
• Reaxy-Rn: 619231
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=619231&ln=

Chemical and Physical Properties

• Flash Point(°F): 162 °F
• Flash Point(°C): 72 °C
• Melt Point(°C): 82-83°C

Application Protocols

No manufacturer-validated biological or analytical protocols are provided for this specific item. The following general practices are commonly used for small-molecule library members like triadimefon; adapt to your assay and validate in-house.

• DMSO stock preparation:
  • Weigh the solid quickly at room temperature, cap tightly.
  • Prepare 10–50 mM stocks in anhydrous DMSO; vortex and sonicate briefly to ensure complete dissolution.
  • Optional: Sterile-filter (0.22 µm PTFE) for cell-based assays.
• Working concentrations (general):
  • Enzyme assays: begin with a 10-point half-log dilution series spanning ~0.1 nM to 100 µM as appropriate; maintain constant DMSO across wells.
  • Cell-based yeast/fungal assays: confirm absence of precipitation; keep final DMSO ≤0.5–1%.
• Analytical reference use:
  • For LC–MS calibration, prepare serial dilutions in MeCN or MeCN/H2O with 0.1% formic acid; store aliquots at −20 to −80 °C.
• Stability checks:
  • Evaluate freeze–thaw stability by LC–MS after 3–5 cycles; if degradation observed, use single-use aliquots.
• Documentation:
  • Record batch/lot, exact stock concentration (qNMR or UV where applicable), and storage history to support data reproducibility.

Biological Roles

Note: The following describes general, literature-reported biochemical roles of triadimefon as a research tool compound. It is provided for mechanistic context only and not as a statement of suitability for therapeutic or diagnostic use.

• Mode of action (literature): Triadimefon is a member of the azole class that interacts with fungal sterol 14α-demethylase (CYP51), a cytochrome P450 enzyme in the ergosterol biosynthesis pathway. Binding to the heme iron via the triazole nitrogen perturbs demethylation of lanosterol/obtusifoliol intermediates, altering membrane sterol composition in fungi.
• Selectivity considerations: Azole–CYP interactions are conserved; selectivity across fungal species versus other P450s depends on active-site topology and compound substituents. Triadimefon serves as a comparative scaffold in selectivity profiling experiments (e.g., across fungal CYP51 isoforms).
• Metabolic fate (literature): In biological systems and in vitro, triadimefon can be reduced at the carbonyl to triadimenol, producing stereoisomeric alcohols with differing potencies against CYP51. Oxidative and conjugative metabolism may proceed via aryl ether and ring hydroxylation pathways depending on species.
• Experimental use cases:
  • Positive control in ergosterol-biosynthesis inhibition assays (yeast/fungal cell-based or enzyme assays).
  • Reference inhibitor in P450 spectral binding studies (type II difference spectra) to characterize azole–heme interactions.

Caution: Cytotoxicity and off-target P450 interactions can occur at high concentrations; use appropriate controls and concentration–response designs.

Buffer Applications

This compound is a neutral, sparingly water-soluble small molecule and is not used as a buffering agent. For assay work, prepare DMSO stocks and dilute into pre-selected biological buffers (e.g., phosphate, HEPES, MOPS) while maintaining a suitable final DMSO percentage (commonly ≤0.5–1%). Buffer choice should be driven by the biology of the assay rather than by this compound.

Green Alternatives

Because triadimefon is a solid active organic compound (not a bulk solvent or reagent), “green alternatives” focus on handling and solvent choices for its use rather than replacing the molecule itself.

• Greener solvent choices for stock prep and purification (general guidance):
  • Prefer ethyl acetate, 2-MeTHF, or dimethyl carbonate over chlorinated solvents when solubility and separation permit.
  • Use MeCN–water mobile phases for LC separations instead of MeOH–DCM systems when feasible.
  • For extractions, cyclopentyl methyl ether (CPME) or MTBE can substitute for DCM, balancing safety with performance.
• Process efficiency:
  • Maximize concentration of DMSO stocks (e.g., 50 mM) to reduce solvent volumes and shipping mass.
  • Use microscale assays and 96/384-well formats to reduce chemical consumption and waste.
• Waste minimization:
  • Segregate halogenated from non-halogenated organic waste; recover and recycle solvents where infrastructure exists.

Trade-offs: Chlorinated solvents often deliver superior solubility and rapid evaporation but carry higher environmental and health burdens; greener ethers/esters may require longer evaporation and careful peroxide management (for ethers). Always validate assay compatibility when changing solvents.

Pharmaceutical Uses

Triadimefon is not an excipient or a standard pharmaceutical processing aid. It is provided strictly for research applications (e.g., as a reference small molecule in screening and biochemical studies). No pharmacopeial monograph or formulation role is implied for this item. For any formulation-like work (e.g., preparing dosing solutions for in vitro assays), standard research solvent systems (DMSO stocks diluted into assay media) are recommended, validating solubility and stability under your specific conditions.

Physical Properties

Item-specific specs are not provided for this catalog entry; consult the CoA/SDS for authoritative data. Below are general/literature characteristics of triadimefon to aid planning (do not treat as specifications for this item):

• Physical state/appearance: Typically a crystalline solid; color reported as white to off-white (literature). Item-specific appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Often reported around the upper 70s °C (literature, ≈76–79 °C range).
• Boiling point: Decomposition before boiling under ambient pressure; not typically distilled (literature).
• Density: Not widely reported with high precision; expect typical organic solid packing density ~1.2–1.4 g/cm³ (qualitative literature context).
• Solubility (qualitative):
  • Water: low solubility (sparingly soluble) at room temperature (literature).
  • Organic solvents: good solubility in polar aprotic media (DMSO, DMF, acetone), chlorinated solvents (DCM, CHCl3), and moderate solubility in ethyl acetate and acetonitrile (literature).
• LogP/logD: Reported as moderately lipophilic (literature; logP roughly in the 3–3.5 domain).
• pKa: The 1,2,4-triazole ring is weakly basic/acidic depending on substitution; no strongly ionizable functionality in physiological pH range (literature, qualitative).
• UV absorption: Aromatic and triazole chromophores absorb in UV; exact cutoffs/ε: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable for solid; Not specified for this item; refer to CoA/Spec Sheet.

Note: Values above are literature/general guidance to inform handling and solvent choice; verify with primary data for critical applications.

Quality & Grades

• Supplied grade: Moligand™. This denotes inclusion in Aladdin’s small-molecule/ligand screening collection. Typical expectations for Moligand™ items include:
  • Emphasis on identity confirmation (orthogonal methods such as 1H NMR/MS/HRMS where applicable).
  • Purity suitable for screening and chemical biology workflows; exact assay/purity thresholds are item-specific.
  • Packaging optimized for microgram–gram scale discovery workflows.
• What is specified for this item vs. what is not:
  • Specified: Grade (Moligand™); storage at −80 °C; shipped on dry ice + cold packs.
  • Not specified for this item; refer to CoA/Spec Sheet: exact purity %, residual solvent limits, water content, metal content, stabilizers, UV cutoff/blank, and chromatographic assay conditions.
• Practical implications:
  • For HTS/compound-library use, prepare DMSO stocks and filter if particulate is observed.
  • For quantitative assays (e.g., IC50/Ki), we recommend verifying purity and identity in-house (e.g., LC–MS and qNMR) and referencing the item’s CoA batch data.
• Documentation:
  • Always consult the batch-specific CoA and SDS packaged with your shipment for definitive analytical data and safety information.

Reaction & Applications

This compound is primarily used as a reference triazole fungicide scaffold and as a member of screening libraries. In synthetic and methodological contexts, it serves as a functionalized heteroaromatic building block.

• Reference compound roles (literature/general):
  • Tool molecule for studying azole-mediated inhibition of sterol 14α-demethylase (CYP51) in fungi.
  • Benchmark in agrochemical structure–activity studies comparing triazole pharmacophores.
• Transformations of the scaffold (synthetic):
  • Carbonyl reduction to triadimenol (known alcohol derivative) via hydride or catalytic hydrogenation.
  • Ether modifications via nucleophilic aromatic substitution on the p-chloro aryl (with appropriate activation) are limited; cross-coupling possible after halogen–metal exchange or via Pd-catalyzed C–O activation methods (advanced literature).
  • Triazole N-modification is constrained; N1 is bound in triadimefon, but electrophilic substitution on the aryl ring (SEAr) is feasible at positions ortho/para to substituents with suitable directing influences.
• Analytical applications:
  • Calibration/positive control for residue analysis workflows (GC–MS/LC–MS) in environmental matrices (method development and recovery studies).
• Practical tips:
  • For carbonyl reductions, control temperature to manage over-reduction; NaBH4 in MeOH/THF at 0–25 °C is effective (literature), with downstream diastereomer resolution for the alcohol product if needed.
  • For biological assay use, pre-dissolve in DMSO and confirm solubility at working concentrations to avoid precipitation in aqueous media.

Reaction Conditions

The following are literature/general conditions relevant to common manipulations of triadimefon; optimize for your substrate and scale. These are not specifications for this item.

• Carbonyl reduction to triadimenol (alcohol):
  • NaBH4 (1–2 equiv) in MeOH, EtOH, or THF/MeOH (0–25 °C, 0.5–2 h); quench with aqueous NH4Cl, extract with EtOAc/DCM. Diastereomeric alcohols may form; chromatographic separation or crystallization can resolve them.
  • Catalytic hydrogenation (H2, 1–3 bar) over Raney Ni or Pd/C in EtOH/THF at ambient temperature; monitor to avoid over-reduction of aryl chloride (literature).
• Oxime formation:
  • Hydroxylamine hydrochloride (1.2–2.0 equiv), pyridine or Et3N base, EtOH or MeOH, reflux 2–6 h; isolate oxime by standard workup.
• Cross-coupling on aryl chloride (if pursued):
  • Suzuki–Miyaura: Pd(dppf)Cl2 or Pd2(dba)3/XPhos, K2CO3 or Cs2CO3, dioxane/H2O or toluene/H2O, 60–100 °C, 4–16 h.
  • Buchwald–Hartwig amination: Pd2(dba)3/BINAP or XPhos, NaOtBu, toluene or dioxane, 80–110 °C, 8–20 h.
  • Note: The adjacent ether/triazole can influence reactivity; ligand screening is recommended.
• Analytical monitoring:
  • TLC (silica, hexanes/EtOAc 3:1 to 1:1) or RP-HPLC (C18, MeCN/H2O with 0.1% formic acid/base) with UV detection.
• Expected yields: Highly method- and substrate-dependent; reductions often provide good to excellent yields (literature), whereas cross-couplings require optimization.

Always employ inert atmosphere for air/moisture-sensitive steps and confirm identity/purity by NMR and LC–MS.

Safety & Handling

• Research use only: For laboratory research use; not for human or animal consumption, diagnostic, or clinical use.
• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the product SDS for authoritative hazard communication.
• Likely hazards (literature/general for triazole fungicides):
  • May be harmful if swallowed, inhaled, or in contact with skin; avoid exposure to dust or aerosols.
  • Irritation to eyes/skin possible; handle in a chemical fume hood.
• PPE recommendations (good laboratory practice):
  • Safety glasses or goggles compliant with ANSI/EN standards
  • Lab coat, nitrile gloves (change regularly), and closed-toe shoes
  • Use a dust mask/respirator if generating particulates outside a fume hood (consult SDS for permissible exposure limits).
• Handling guidance:
  • Avoid dust formation; use antistatic measures during weighing.
  • Prepare solutions in a fume hood; triadimefon dissolves readily in DMSO/DMF/acetone.
  • Prevent contamination of aqueous drains and the environment; collect waste as halogenated or mixed organic waste per institutional policy.
• Incompatibilities (general): Strong oxidizers; strong acids/bases may lead to decomposition or hydrolysis of the aryl ether/ketone under forcing conditions.
• Stability: Store frozen per item-specific instruction below; protect from moisture, heat, and direct light.
• First-aid overview (consult SDS for details):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation develops.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical attention immediately.

Solvent Selection

Triadimefon is a moderately lipophilic neutral heteroaromatic that dissolves well in common polar aprotic organic solvents. Selection depends on the intended use (screening stock vs. synthetic transformation).

• Stock solutions for screening/biology:
  • DMSO: Preferred; prepare 10–50 mM stocks (typical) for storage at −20 to −80 °C; dilute into assay buffers with ≤0.5–1% final DMSO (general practice).
  • DMF or NMP: Alternatives when higher solubility is required; consider potential assay interference.
• Synthetic/manipulation solvents (literature/general):
  • Chlorinated: DCM, chloroform – rapid dissolution, good for extractions and flash chromatography.
  • Ethers/esters: THF, EtOAc – workable but watch for limited solubility vs. DMSO/DMF.
  • Nitriles/ketones: MeCN, acetone – often provide clear solutions; acetone may be competitive in carbonyl chemistry.
• Aqueous media:
  • Water solubility is limited; for biological assays use cosolvent strategies (DMSO seed, surfactant at low % if validated) and pre-sonication.
• Comparison (general):
  • DMSO vs DMF: DMSO favored for biotesting due to lower volatility and established compatibility; DMF more hygroscopic and may need anhydrous handling.
  • MeCN vs DCM for purification: MeCN/H2O (with 0.1% acid/base) suits LC; DCM/hexanes/EtOAc suits normal-phase flash.
• Tip: Filter 0.22 µm if making long-term freezer stocks to minimize particulates; avoid high-pH aqueous solutions that could slowly degrade aryl–O–alkyl or carbonyl linkages under harsh conditions.

Storage & Reconstitution

• Storage conditions (item-specific): Store at −80 °C. Keep container tightly closed, desiccated, and protected from light. Avoid repeated freeze–thaw by aliquoting upon first opening.
• Shipping (item-specific): Shipped on dry ice packs + cold packs to maintain low temperature during transit.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/stock solution preparation (general):
  • Allow vial to warm in a desiccator to minimize condensation before opening.
  • Dissolve in anhydrous DMSO to prepare concentrated stocks (e.g., 10–50 mM). Gentle warming (≤40 °C) and brief sonication can aid dissolution; avoid prolonged heating.
  • For non-DMSO uses, triadimefon typically dissolves in DMF, acetone, MeCN, or chlorinated solvents; confirm compatibility with downstream applications.
• Stability (general guidance):
  • Solid: Stable when stored at −80 °C, dry and dark, for extended periods; monitor per CoA.
  • Solution: DMSO stocks are generally stable for weeks to months at −20 to −80 °C if protected from moisture and light; prepare single-use aliquots to avoid freeze–thaw cycles.
• Disposal: Collect and dispose of unused material and solutions as organic chemical waste in accordance with institutional and local regulations.

For batch-specific shelf life, assay purity, and any stabilizers, consult the accompanying CoA and SDS.

Structure & Identity

Triadimefon is a triazole-containing aryl ether ketone widely used in agrochemical research and as a reference scaffold in small-molecule libraries.

• Item-specific identifiers (this product):
  • SKU: T1495489
  • CAS: 43121-43-3
  • Grade: Moligand™
  • Category: Small molecules and compound libraries (research use only)
• Structure (general/literature):
  • Core features: a 1,2,4-triazole ring N-linked to a tertiary-butyl-like dimethylcarbinyl ketone, aryl-ether linked to a p-chlorophenyl ring.
  • Functional groups: 1,2,4-triazole (azole heteroaromatic), aryl chloride (para), aryl–O–alkyl ether, aryl ketone (benzoyl ether motif), tert-alkyl (gem-dimethyl) center.
  • Ring systems: one 1,2,4-triazole (five-membered) and one para-chloro phenyl (six-membered) ring.
  • Stereochemistry: none specified in the parent compound (triadimefon is achiral); note that reduction to triadimenol introduces stereocenters (literature).
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature commonly reports a formula consistent with an aryl ether triazole ketone.)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature reports a single-component MW in the ~290–295 g/mol range.)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• 2D description: para-chlorophenyl ring connected via oxygen to a carbonyl-bearing tert-alkyl chain whose carbonyl α-carbon is N-substituted with a 1,2,4-triazolyl moiety.

Synthetic Utility

Triadimefon combines a triazole heteroaromatic, an aryl chloride, an aryl–O–alkyl ether, and a tertiary ketone, providing several vectors for derivatization and SAR expansion.

• Reactive handles and typical transformations (literature/general):
  • Carbonyl chemistry: Reduction to the corresponding tertiary alcohol (triadimenol) via NaBH4, LiAlH4, or catalytic hydrogenation; formation of oximes/hydrazones with hydroxylamine/hydrazines; acylation at the adjacent nitrogen is not applicable (N already bound), but enolization under strong base is limited due to tert-alkyl substitution.
  • Aryl chloride: Cross-coupling (Suzuki, Buchwald–Hartwig after amination, or Negishi) is possible with suitable catalysts/ligands; electron-withdrawing/triazole–ether environment may influence oxidative addition rates.
  • Ether linkage: Generally robust; advanced C–O activation (e.g., Ni-catalyzed) can enable cross-coupling in expert hands.
  • Triazole ring: Electrophilic substitution is low; N1 is substituted; N2/N4 tautomerism is constrained by substitution pattern; metalation at C-5 under strong base may allow further functionalization in specialized conditions.
• Utility in synthesis:
  • Serves as a late-stage diversification platform for generating focused libraries around an azole fungicide core.
  • Useful standard for validating analytical and purification methods for related azoles.
• Retrosynthetic note: The scaffold arises from coupling a p-chlorophenoxy benzoyl equivalent with a triazolyl-tert-alkyl ketone fragment; modular routes allow independent optimization of aryl and azole fragments.

Target Specificity

This product is a small molecule, not an antibody or protein reagent. Target information below is provided as literature context for users employing triadimefon in biochemical studies.

• Primary biochemical target (literature): Fungal sterol 14α-demethylase (CYP51), a cytochrome P450 enzyme in ergosterol biosynthesis. The triazole coordinates to the heme iron, inhibiting catalytic activity.
• Selectivity notes: Relative potency and selectivity vary across fungal species and CYP51 isoforms. Off-target interactions with other P450s are possible at higher concentrations; empirical profiling is recommended for each system.
• Assay modalities:
  • Enzyme kinetics with purified CYP51 (spectral binding and activity assays).
  • Yeast/fungal growth inhibition assays as phenotypic proxies for CYP51 inhibition.
• No clone/isotype/species reactivity data apply to this product type.

For definitive target engagement in your system, consider orthogonal readouts (e.g., spectral binding, sterol profiling by GC–MS, and genetic rescue experiments).