| Revision as of 02:45, 30 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk← Previous edit | Latest revision as of 20:23, 15 September 2024 edit undoCitation bot (talk | contribs)Bots5,429,581 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Thioesters | #UCB_Category 14/24 | ||
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| {{chembox | {{chembox | ||
| ⚫ | | verifiedrevid = 431687371 | ||
| | Verifiedfields = changed | |||
| ⚫ | | verifiedrevid = |
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| | ImageFile = Dithiopyr.png | | ImageFile = Dithiopyr.png | ||
| | ImageSize = 200px | | ImageSize = 200px | ||
| | ImageAlt = Skeletal formula | |||
| | ImageFile1 = Dithiopyr-3D-spacefill.png | |||
| | ImageAlt1 = Ball-and-stick model | |||
| | IUPACName = Dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarbothioate | | IUPACName = Dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarbothioate | ||
| | OtherNames = | | OtherNames = | ||
| | |
|Section1={{Chembox Identifiers | ||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| | ChemSpiderID = 82855 | | ChemSpiderID = 82855 | ||
| Line 17: | Line 19: | ||
| | CASNo_Ref = {{cascite|correct|CAS}} | | CASNo_Ref = {{cascite|correct|CAS}} | ||
| | CASNo = 97886-45-8 | | CASNo = 97886-45-8 | ||
| | UNII_Ref = {{fdacite|correct|FDA}} | |||
| | UNII = 2TXF17HAV1 | |||
| | PubChem = 91757 | | PubChem = 91757 | ||
| | KEGG_Ref = {{keggcite| |
| KEGG_Ref = {{keggcite|correct|kegg}} | ||
| | KEGG = C18826 | | KEGG = C18826 | ||
| | SMILES = FC(F)(F)c1nc(c(c(c1C(=O)SC)CC(C)C)C(=O)SC)C(F)F | | SMILES = FC(F)(F)c1nc(c(c(c1C(=O)SC)CC(C)C)C(=O)SC)C(F)F | ||
| }} | }} | ||
| | |
|Section2={{Chembox Properties | ||
| | Formula = C<sub>15</sub>H<sub>16</sub>F<sub>5</sub>NO<sub>2</sub>S<sub>2</sub> | | Formula = C<sub>15</sub>H<sub>16</sub>F<sub>5</sub>NO<sub>2</sub>S<sub>2</sub> | ||
| | MolarMass = 401.42 g/mol | | MolarMass = 401.42 g/mol | ||
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| | BoilingPt = | | BoilingPt = | ||
| | Solubility = }} | | Solubility = }} | ||
| | |
|Section3={{Chembox Hazards | ||
| | MainHazards = | | MainHazards = | ||
| | FlashPt = | | FlashPt = | ||
| | |
| AutoignitionPt = }} | ||
| }} | }} | ||
| '''Dithiopyr''' is a ] for ] control in turf and ornamental grasses. It is effective on 45 grassy and broadleaf weeds.<ref>{{Cite web|url=http://www.dowagro.com/turf/products/herbicides/dimension.htm|title=Dimension - Turf and Ornamental - Dow AgroSciences|website=www.dowagro.com|access-date=2016-04-23|archive-date=2016-04-16|archive-url=https://web.archive.org/web/20160416091948/http://www.dowagro.com/turf/products/herbicides/dimension.htm|url-status=dead}}</ref> 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 |
It is an ingredient in many products including ''Dimension'' from ].<ref> for Dimension</ref> | ||
| == Mode of action == | |||
| ⚫ | 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 ] polymerization and stability by "interacting with microtubule associated proteins or microtubule organizing centers rather than interaction directly with tubulin."<ref>{{cite journal |title=Effects of the herbicide dithiopyr on cell division in wheat root tips |author1=Barbara L. Armbruster |author2=William T. Molin |author3=M. Wayne Bugg | journal =Pesticide Biochemistry and Physiology | volume =39 | issue =2 | pages =110–120 |quote=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. |date=February 1, 1991 | doi=10.1016/0048-3575(91)90131-5|bibcode=1991PBioP..39..110A }}<!--|accessdate=2010-04-21 --></ref> Mitotic cells are arrested in late prometaphase. Cell entry into mitosis is unaffected. | ||
| == Synthesis == | |||
| Dithiopyr can be obtained through a multi-step process starting from ] and ].<ref name=unger>{{cite book| author = Thomas A. Unger | title = Pesticide Synthesis Handbook | publisher = William Andrew Inc. | isbn = 0-81551853-6 | date = 1996 | page = 531 }} </ref> | |||
| :]{{clear-left}} | |||
| ==References== | ==References== | ||
| {{reflist}} | {{reflist}} | ||
| {{Herbicides}} | {{Herbicides}} | ||
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| ] | ] | ||
| ] | ] | ||
| ] | |||
| ] | |||
| ] | |||
| {{Agriculture-stub}} | |||
| {{heterocyclic-stub}} | |||
Latest revision as of 20:23, 15 September 2024
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| Names | |
|---|---|
| IUPAC name Dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)pyridine-3,5-dicarbothioate | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.131.988 
|
| KEGG | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C15H16F5NO2S2 |
| Molar mass | 401.42 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
| |
Dithiopyr is a preemergent herbicide for crabgrass control in turf and ornamental grasses. It is effective on 45 grassy and broadleaf weeds. 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.
Mode of action
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." Mitotic cells are arrested in late prometaphase. Cell entry into mitosis is unaffected.
Synthesis
Dithiopyr can be obtained through a multi-step process starting from ethyl trifluoroacetoacetate and isovaleraldehyde.
References
- "Dimension - Turf and Ornamental - Dow AgroSciences". www.dowagro.com. Archived from the original on 2016-04-16. Retrieved 2016-04-23.
- Material Safety Data Sheet for Dimension
- 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.
- Thomas A. Unger (1996). Pesticide Synthesis Handbook. William Andrew Inc. p. 531. ISBN 0-81551853-6.