Triclopyr, also Trichlopyr, formally [(3,5,6-trichloropyridin-2-yl)oxy]acetic acid, is an organic compound in the pyridine family of herbicides that is used as a systemic foliar type of herbicide and, secondarily, as a fungicide. Triclopyr is an acetic acid derivative, and so a monocarboxylic acid, with a pyridyloxy substituent: specifically, a pyridin-2-yloxy group substituted by chloro groups at positions 3, 5, and 6. It functions as an herbicide by mimicking the action of the plant growth hormone auxin.
Structure and chemistry
Triclopyr is an acetic acid derivative, and so a monocarboxylic acid, with a pyridyloxy substiuent: specifically, a pyridin-2-yloxy group substituted by chloro groups at positions 3, 5, and 6. Triclopyr is commercially produced through a two-step process. First, sodium 3,5,6-trichloro-2-pyridinolate is reacted with methyl chloroacetate in a polar solvent to form methyl [3,5,6-trichloropyridin-2-yl)oxy]acetate:
CHNCl 3 O − Na + + CH 2 Cl − C ( O ) OCH 3 ⟶ CHNCl 3 − O − CH 2 C ( O ) OCH 3 + NaCl {\displaystyle {\ce {CHNCl3O- Na+ + CH2Cl-C(O)OCH3 -> CHNCl3-O-CH2C(O)OCH3 + NaCl}}}
In the second step, the methyl ester is hydrolysed under alkaline conditions, with an acidic work-up to afford the acid product. The yield obtained is improved by using a mineral acid like H2SO4 over acetic acid:
CHNCl 3 − O − CH 2 C ( O ) OCH 3 + NaOH ⟶ CHNCl 3 − O − CH 2 C ( O ) O − Na + + CH 3 OH {\displaystyle {\ce {CHNCl3-O-CH2C(O)OCH3 + NaOH -> CHNCl3-O-CH2C(O)O- Na+ + CH3OH}}}
CHNCl 3 − O − CH 2 C ( O ) O − Na + + H 2 SO 4 ⟶ CHNCl 3 − O − CH 2 C ( O ) OH + NaHSO 4 {\displaystyle {\ce {CHNCl3-O-CH2C(O)O- Na+ + H2SO4 -> CHNCl3-O-CH2C(O)OH + NaHSO4}}}
Once the product has cooled, a decolorising agent is often added, such as NaClO or 30% H2O2. Triclopyr is rapidly absorbed through plant leaves and roots. There, it mimics auxin, a plant hormone associated with plant growth regulation. Triclopyr is thought to acifdy the cell wall, stimulating the activity of a membrane-bound ATPase proton pump. This causes uncontrolled cell division and vascular tissue destruction.
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