Fluopicolide
[CAS# 239110-15-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: Fluopicolide
• Synonyms: 2,6-Dichloro-N-[[3-chloro-5-(trifluoro-methyl)-2-pyridinyl]methyl]benzamide
• Molecular Formula: C₁₄H₈Cl₃F₃N₂O
• Molecular Weight: 385.59
• CAS Registry Number: 239110-15-7
• EC Number: 607-285-6
• SMILES: C1=CC(=C(C(=C1)Cl)C(=O)NCC2=C(C=C(C=N2)C(F)(F)F)Cl)Cl

Properties

• Melting point: 150 ºC

Safety Data

• Hazard Symbols: GHS08;GHS09 Warning
• Hazard Statements: H361d-H400-H410
• Precautionary Statements: P203-P273-P280-P318-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Reproductive toxicity	Repr.	2	H361d
Reproductive toxicity	Repr.	2	H361d

Discovory and Applicatios

Fluopyram is a fungicide belonging to the carboxylic acid amide chemical class. Its chemical formula is C₁₆H₁₆F₃N₃O₄ and it is characterized by its ability to effectively control a wide range of plant pathogens. Fluopyram was developed through the collaborative efforts of scientists who were committed to enhancing the treatment of fungal diseases. Fluopyram was discovered during the search for novel compounds that could provide strong fungicidal activity with favorable environmental and safety profiles. The discovery of this compound involved a screening and optimization process to identify molecules with potent antifungal properties with minimal ecological impact.

The synthesis of fluopyram typically involves a multi-step organic chemistry process starting from basic chemical building blocks. The key steps include the introduction of fluorine atoms and the formation of amide bonds, which are essential for enhancing the stability, solubility, and biological activity of the compound. The goal of the final synthesis is to produce fluopyram with high purity and yield, suitable for commercial applications.

Fluopyram acts on fungal pathogens by inhibiting cellulose biosynthesis, which is essential for the structural integrity of the fungal cell wall. This disruption ultimately leads to cell wall brittleness and cell lysis, effectively halting fungal growth and preventing further infection of the plant. Its mode of action is different from traditional fungicides, offering a valuable alternative to disease management strategies.

Fluopyram is widely used in agriculture to protect a wide range of crops from fungal diseases. It is effective against a wide range of pathogens that threaten crop health and yield, such as downy mildew, wilts and molds. Depending on disease pressure and crop susceptibility, the fungicide can be used preventively or curatively, providing growers with a versatile disease management tool.

One of the significant advantages of fluopyram is its ability to break down quickly in the environment, minimizing residual issues. This property supports sustainable agricultural practices by reducing environmental impact and ensuring food safety compliance.

Fluopyram is recommended for rotation and combination with other fungicides to mitigate the development of resistance in fungal populations. Its unique mode of action forms an important component of resistance management programs designed to prolong fungicide efficacy and agricultural sustainability.

Fluopyram was designed with environmental stewardship in mind and has low toxicity to non-target organisms such as mammals, birds and beneficial insects when used according to label instructions. Regulatory agencies rigorously evaluate their safety to ensure that they pose minimal risks to human health and the environment over their life cycle.

References

2024. Fluopicolide is a selective inhibitor of V-ATPase in oomycetes. *Journal of Plant Diseases and Protection*, 131(4).
DOI: 10.1007/s41348-024-00908-y

2023. Within-Season Shift in Fungicide Sensitivity Profiles of Pseudoperonospora cubensis Populations in Response to Chemical Control. *Plant Disease*, 107(5).
DOI: 10.1094/pdis-09-22-2056-re

2011. Persistence and Dissipation of Fluopicolide in/on Grape Berries and Soil Under Semi Arid Tropical Climatic Conditions of India. *Bulletin of Environmental Contamination and Toxicology*, 86(2).
DOI: 10.1007/s00128-011-0193-3