Triadimefon

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Triadimefon
Triadimefon.svg
Names
IUPAC name
1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one
Other names
Triadimeform, Strike, Miltek, Nurex, Reach.
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.050.986 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C14H16ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,13H,1-3H3
    Key: WURBVZBTWMNKQT-UHFFFAOYSA-N
  • InChI=1/C14H16ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,13H,1-3H3
    Key: WURBVZBTWMNKQT-UHFFFAOYAV
  • CC(C)(C)C(=O)C(N1C=NC=N1)OC2=CC=C(C=C2)Cl
Properties
C14H16ClN3O2
Molar mass 293.75 g·mol−1
Density 1.22 g/cm3 [1]
Melting point 82 °C (180 °F; 355 K) [1]
Boiling point decomposes
64 mg/L (20 °C) [1]
Hazards
Lethal dose or concentration (LD, LC):
363 mg/kg (oral, rat) [1]
> 5000 mg/kg (dermal, rat) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Triadimefon is a fungicide used in agriculture to control various fungal diseases. As a seed treatment, it is used on barley, corn, cotton, oats, rye, sorghum, and wheat. [2] In fruit it is used on pineapple and banana. [2] Non-food uses include pine seedlings, Christmas trees, turf, ornamental plants, and landscaping. [2]

Pharmacology

Estrogenic effect, inhibition of aromatase activity, decrease of estrogens production and increase androgens availability. [3]

Triadimefon potently inhibited rat’s neurosteroidogenic enzymes, 5α-Red1 and 3α-HSD. [4]

Dopamine as well as serotonergic pathways are involved. [5] [6]

Psychomotor stimulatory. [7] Anti-estrogen effect. [8]

References

  1. 1 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 "Triadimefon Reregistration Eligibility Decision (RED) and Triadimenol Tolerance Reassessment and Risk Management Decision (TRED) Fact Sheet". Environmental Protection Agency. Archived from the original on June 2, 2014.
  3. ↑ Okubo, T.; Yokoyama, Y.; Kano, K.; Soya, Y.; Kano, I. Estimation of estrogenic and antiestro-genic activities of selected pesticides by MCF-7 cell proliferation assay. Arch. Environ. Con-tam. Toxicol. 2004, 46, 445-453.
  4. ↑ Shen, Xiuwei; Chen, Fan; Chen, Lanlan; Su, Ying; Huang, Ping; Ge, Ren-Shan (2017). "Effects of Fungicides on Rat's Neurosteroid Synthetic Enzymes". BioMed Research Internation-al. 2017: 1–8. doi:10.1155/2017/5829756.
  5. ↑ Paredes-Zúñiga, Susana; Trost, Nils; De la Paz, Javiera F.; Alcayaga, Julio; Allende, Miguel L. (2019). "Behavioral effects of triadimefon in zebrafish are associated with alterations of the do-paminergic and serotonergic pathways". Progress in Neuro-Psychopharmacology and Biological Psychiatry. 92: 118–126. doi:10.1016/j.pnpbp.2018.12.012.
  6. ↑ Walker, Q.David; Mailman, Richard B. (1996). "Triadimefon and Triadimenol: Effects on Mono-amine Uptake and Release". Toxicology and Applied Pharmacology. 139 (2): 227–233. doi:10.1006/taap.1996.0161.
  7. ↑ Crofton, K. M.; Boncek, V. M.; MacPhail, R. C. (1989). "Evidence for monoaminergic involve-ment in triadimefon-induced hyperactivity". Psychopharmacology. 97 (3): 326–330. doi:10.1007/BF00439445
  8. ↑ Jiang, Jinhua; Hu, Gaojie; Zhang, Changpeng; Zhao, Xueping; Wang, Qiang; Chen, Liezhong (2017). "Toxicological analysis of triadimefon on endocrine disruption and oxidative stress dur-ing rare minnow (Gobiocypris rarus) larvae development". Environmental Science and Pollution Research. 24 (34): 26681–26691. doi:10.1007/s11356-017-0317-3.
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