Thiophanate-methyl: Difference between revisions

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'''Thiophanate-methyl''' is a [[fungicide]] widely used in [[agriculture]] to control a broad spectrum of fungal diseases. It is a systemic fungicide, meaning it is absorbed by the plant and can move from the site of application to other parts of the plant. Thiophanate-methyl is a member of the [[benzimidazole]] class of fungicides and works by inhibiting cell division in the fungi.
{{DISPLAYTITLE:Thiophanate-methyl}}


==Chemical Structure and Properties==
== Overview ==
Thiophanate-methyl is a [[methyl ester]] of [[dimethyl 4,4'-(o-phenylene)bis(3-thioallophanate)]]. It is a white crystalline solid with a slight sulfurous odor. It is moderately soluble in water and readily soluble in most organic solvents. The [[chemical formula]] for thiophanate-methyl is C12H14N4O4S2.
[[File:Thiophanate_Methyl.png|thumb|right|Chemical structure of Thiophanate-methyl]]
'''Thiophanate-methyl''' is a [[systemic fungicide]] used in agriculture to control a wide range of fungal diseases. It belongs to the class of [[benzimidazole]] fungicides and is known for its broad-spectrum activity against various plant pathogens.


==Mode of Action==
== Chemical Properties ==
Thiophanate-methyl inhibits the process of [[mitosis]] in fungal cells by disrupting the formation of the [[mitotic spindle]], which is essential for cell division. This prevents the fungi from growing and reproducing, effectively controlling the disease.
Thiophanate-methyl is a [[thiophanate]] compound, characterized by its chemical structure that includes a [[benzimidazole]] moiety. It is a white crystalline solid with a molecular formula of C<sub>12</sub>H<sub>14</sub>N<sub>4</sub>O<sub>4</sub>S<sub>2</sub>. The compound is relatively stable under normal conditions but can degrade into other active metabolites, such as [[carbendazim]], which also possess fungicidal properties.


==Uses==
== Mode of Action ==
Thiophanate-methyl is used to control a wide range of fungal diseases in a variety of crops, including [[fruit]]s, [[vegetable]]s, [[ornamental plant|ornamentals]], and [[cereal]]s. It is effective against diseases such as [[powdery mildew]], [[gray mold]], and [[apple scab]].
Thiophanate-methyl acts by inhibiting the synthesis of [[tubulin]], a protein essential for the formation of [[microtubules]] in fungal cells. This disruption of microtubule formation interferes with cell division, ultimately leading to the death of the fungal organism. Its systemic nature allows it to be absorbed by plant tissues and translocated to various parts of the plant, providing protective and curative effects.


==Safety and Environmental Impact==
== Applications ==
Thiophanate-methyl is of low toxicity to humans and animals. However, it can cause irritation to the eyes and skin, and prolonged exposure can lead to allergic reactions. It is moderately toxic to fish and other aquatic organisms. Thiophanate-methyl is not persistent in the environment and is rapidly degraded by microbes in the soil.
Thiophanate-methyl is widely used in the agricultural industry to protect crops such as [[fruits]], [[vegetables]], [[ornamentals]], and [[turf]] from fungal infections. It is effective against diseases like [[powdery mildew]], [[leaf spot]], [[blight]], and [[root rot]]. The fungicide can be applied as a foliar spray, soil drench, or seed treatment, depending on the specific crop and disease.


==Regulation==
== Safety and Environmental Impact ==
In the [[European Union]], thiophanate-methyl has been classified as a potential [[endocrine disruptor]] and its use has been restricted since 2020. In the [[United States]], it is classified as a General Use Pesticide (GUP) by the [[Environmental Protection Agency]] (EPA).
While thiophanate-methyl is considered effective in controlling fungal diseases, it is important to use it responsibly to minimize potential risks to human health and the environment. Users should follow recommended application rates and safety guidelines to reduce exposure. The compound can persist in the environment and may pose risks to non-target organisms, including aquatic life, if not managed properly.
 
== Regulatory Status ==
Thiophanate-methyl is registered for use in many countries, subject to regulatory approvals and restrictions. It is important for users to comply with local regulations and guidelines when using this fungicide to ensure safe and effective application.
 
== Related Pages ==
* [[Fungicide]]
* [[Benzimidazole]]
* [[Carbendazim]]
* [[Systemic pesticide]]


[[Category:Fungicides]]
[[Category:Fungicides]]
[[Category:Agricultural chemicals]]
[[Category:Agricultural chemicals]]
[[Category:Endocrine disruptors]]
{{chemistry-stub}}
{{medicine-stub}}

Latest revision as of 11:19, 15 February 2025


Overview[edit]

Chemical structure of Thiophanate-methyl

Thiophanate-methyl is a systemic fungicide used in agriculture to control a wide range of fungal diseases. It belongs to the class of benzimidazole fungicides and is known for its broad-spectrum activity against various plant pathogens.

Chemical Properties[edit]

Thiophanate-methyl is a thiophanate compound, characterized by its chemical structure that includes a benzimidazole moiety. It is a white crystalline solid with a molecular formula of C12H14N4O4S2. The compound is relatively stable under normal conditions but can degrade into other active metabolites, such as carbendazim, which also possess fungicidal properties.

Mode of Action[edit]

Thiophanate-methyl acts by inhibiting the synthesis of tubulin, a protein essential for the formation of microtubules in fungal cells. This disruption of microtubule formation interferes with cell division, ultimately leading to the death of the fungal organism. Its systemic nature allows it to be absorbed by plant tissues and translocated to various parts of the plant, providing protective and curative effects.

Applications[edit]

Thiophanate-methyl is widely used in the agricultural industry to protect crops such as fruits, vegetables, ornamentals, and turf from fungal infections. It is effective against diseases like powdery mildew, leaf spot, blight, and root rot. The fungicide can be applied as a foliar spray, soil drench, or seed treatment, depending on the specific crop and disease.

Safety and Environmental Impact[edit]

While thiophanate-methyl is considered effective in controlling fungal diseases, it is important to use it responsibly to minimize potential risks to human health and the environment. Users should follow recommended application rates and safety guidelines to reduce exposure. The compound can persist in the environment and may pose risks to non-target organisms, including aquatic life, if not managed properly.

Regulatory Status[edit]

Thiophanate-methyl is registered for use in many countries, subject to regulatory approvals and restrictions. It is important for users to comply with local regulations and guidelines when using this fungicide to ensure safe and effective application.

Related Pages[edit]