Dithiopyr

Dithiopyr
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarbothioate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.131.988 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H16F5NO2S2/c1-6(2)5-7-8(13(22)24-3)10(12(16)17)21-11(15(18,19)20)9(7)14(23)25-4/h6,12H,5H2,1-4H3 checkY
    Key: YUBJPYNSGLJZPQ-UHFFFAOYSA-N checkY
  • InChI=1/C15H16F5NO2S2/c1-6(2)5-7-8(13(22)24-3)10(12(16)17)21-11(15(18,19)20)9(7)14(23)25-4/h6,12H,5H2,1-4H3
    Key: YUBJPYNSGLJZPQ-UHFFFAOYAT
  • FC(F)(F)c1nc(c(c(c1C(=O)SC)CC(C)C)C(=O)SC)C(F)F
Properties
C15H16F5NO2S2
Molar mass 401.42 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dithiopyr is a preemergent herbicide for crabgrass control in turf and ornamental grasses. It is effective on 45 grassy and broadleaf weeds.[1] Dithiopyr inhibits root growth of susceptible weeds as well as turf grass and thus should be used only on established turf with a well-developed root system. Its duration of efficacy is approximately 4 months, so lawns should not be reseeded during this time frame following application of the chemical. Dithiopyr acts primarily as a preemergent herbicide but can also be used in early postemergent control of crabgrass.

It is an ingredient in many products including Dimension from Dow AgroSciences.[2]

Mode of action

[edit]

Dithiopyr acts as a root growth inhibitor, causing cessation of root elongation and inhibition of mitotic cell division. It inhibits formation of microtubules and spindle organizing centers. Dithiopyr may alter microtubule polymerization and stability by "interacting with microtubule associated proteins or microtubule organizing centers rather than interaction directly with tubulin."[3] Mitotic cells are arrested in late prometaphase. Cell entry into mitosis is unaffected.

Synthesis

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Dithiopyr can be obtained through a multi-step process starting from ethyl trifluoroacetoacetate and isovaleraldehyde.[4]

References

[edit]
  1. ^ "Dimension - Turf and Ornamental - Dow AgroSciences". www.dowagro.com. Archived from the original on 2016-04-16. Retrieved 2016-04-23.
  2. ^ Material Safety Data Sheet for Dimension
  3. ^ Barbara L. Armbruster; William T. Molin; M. Wayne Bugg (February 1, 1991). "Effects of the herbicide dithiopyr on cell division in wheat root tips". Pesticide Biochemistry and Physiology. 39 (2): 110–120. Bibcode:1991PBioP..39..110A. doi:10.1016/0048-3575(91)90131-5. The mode of action of dithiopyr may be to alter microtubule polymerization and stability by interacting with microtubule associated proteins and/or microtubule organizing centers rather than interaction directly with tubulin.
  4. ^ Thomas A. Unger (1996). Pesticide Synthesis Handbook. William Andrew Inc. p. 531. ISBN 0-81551853-6.
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