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<!-- Adapted from the German Wikipedia article on dikegulac, accessed on 2017-01-07 at https://de.wikipedia.org/wiki/Diacetonketogulons%C3%A4ure-->

{{Chembox
{{Chembox
<!-- Images -->
<!-- Images -->
| ImageFile =
| ImageFile =
| ImageSize =
| ImageSize =
| ImageAlt =
| ImageAlt =
<!-- Names -->
<!-- Names -->
| IUPACName = sodium;(3aR,4aS,8aR,8bS)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxine-3a-carboxylate
| IUPACName = (E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol
| OtherNames =
| OtherNames = Sodium diprogulate
<!-- Sections -->
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo = 83657-22-1
| CASNo = 52508-35-7
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI = 38000
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| ChemSpiderID = 4941263
| PubChem = 6436604
| UNII = 3M4815901H
⚫
| ChemSpiderID = 58883
| SMILES = CC(C)(C)C(C(=CC1=CC=C(C=C1)Cl)N2C=NC=N2)O
| EC_number = 257-976-8
| PubChem = 23667639
| SMILES = CC1(OCC2C(O1)C3C(O2)(OC(O3)(C)C)C(=O)[O-])C.[Na+]
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| C=12 | H=17 | Na=1 | O=7
| Formula = C<sub>15</sub>H<sub>18</sub>C<sub>l<sub>N<sub>3O</sub>
| Appearance = white/colorless solid
| MolarMass = 291.779 g/mol
| Appearance =
| Density =
| Density =
| MeltingPtC =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility = 590 g/L
}}
}}
| Section3 = {{Chembox Hazards
| Section3 = {{Chembox Hazards
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'''Dikegulac sodium''', or '''sodium diprogulate''', is the [[Sodium salts|sodium salt]] of dikegulac (diprogulic acid), which is used as a [[Precursor (chemistry)|precursor]] in commercial [[Ascorbic Acid|ascorbic acid]] production.<ref>{{Cite book|title=The Dictionary of Drugs: Chemical Data, Structures and Bibliographies|last=Elks|first=J.|publisher=Springer|year=2014|isbn=978-1-4757-2085-3|pages=632|quote=|via=Google Books}}</ref> It a [[Plant growth regulator|plant growth regulator]], primarily used as a [[Plant growth regulator|branching agent]]. When it is taken up by a plant, dikegulac sodium is translocated to its [[Meristem#Apical meristems|apical meristems]], where it inhibits [[DNA]] synthesis.<ref name=":3">{{cite conference|title=Some Effects of Dikegulac on the Physiology of Whole Pants and Tissues; Interactions with Plant Hormones|first1=P.F.|last1=Bocion|first2=W.H.|last2=De Silva|year=1976|conference=International Conference on Plant Growth Substances, 9th|editor-first=Paul-Emile|editor-last=Pilet|book-title=Plant Growth Regulation (Proceedings in Life Sciences)|publisher=Springer Science & Business Media|archive-url=|pages=189-198|isbn=978-3-642-66589-9|language=en|via=Google Books}}</ref> This suppresses [[apical dominance]] in [[Plant|plants]] and can stimulate lateral branching.<ref name=":2">{{Cite journal|last=Arzee|first=Tova|last2=Langenauer|first2=Haviva|last3=Gressel|first3=J.|year=1977|title=Effects of Dikegulac, a New Growth Regulator, on Apical Growth and Development of Three Compositae|url=https://www.jstor.org/stable/2473627|journal=Botanical Gazette|volume=138|issue=1|pages=18-28|issn=0006-8071|via=JSTOR}}</ref> Dikegulac sodium is sometimes used to inhibit [[Fruit#Fruit development|fruiting]] and [[Flower#Organ development|flowering]].<ref>{{Cite journal|last1=Banko|first1=Thomas|last2=Stefani|first2=Marcia|year=1995|title=Growth Regulators for Management of Fruit Production on American Sweetgum|url=http://joa.isa-arbor.com/articles.asp?JournalID=1&VolumeID=21&IssueID=2|journal=Journal of Arboriculture|volume=21|issue=2|pages=88-89|issn=0278-5226|via=International Society of Arboriculture}}</ref>
'''Uniconazole''' is a commonly used [[Plant hormone|plant growth retardant]] and fungicide.

⚫
==Commercial formulations==
Commercial formulations available in the [[United States]] include Atrimmec,<ref>{{Cite web|url=http://www.gordonsprofessional.com/products.php?PRODUCT_CODE=6621076|title=Atrimmec Plant Growth Regulator|website=www.gordonsprofessional.com|access-date=2017-01-08}}</ref> Augeo,<ref name=":0">{{Cite web|url=http://www.ohp.com/Labels_MSDS/PDF/augeo_label.pdf|title=Augeo Plant Growth Regulator|last=|first=|date=|website=|publisher=OHP, Inc.|access-date=2017-01-07}}</ref> and Pinscher.<ref name=":1">{{Cite web|url=http://www.arborsystems.com/find-a-product/tree-care-2/plant-growth-regulators/pinscher/|title=Pinscher {{!}} ArborSystems|website=www.arborsystems.com|access-date=2017-01-08}}</ref>

==Application methods==
Dikegulac sodium can be applied as a foliar spray<ref name=":0" /> or a [[Tree injection|trunk injection.]]<ref name=":1" />

==Phytotoxicity==
Dikegulac sodium application often causes [[Phytotoxicity|phytotoxic]] symptoms such as [[chlorosis]] and stunted growth.<ref name=":2" /><ref>{{Cite journal|last=Sun|first=Youping|last2=Bi|first2=Guihong|last3=Niu|first3=Genhua|last4=Perez|first4=Christina|date=2015-06-01|title=Foliar Application of Dikegulac Sodium Increases Branching of ‘Merritt’s Supreme’ Bigleaf Hydrangea|url=http://horttech.ashspublications.org/content/25/3/306|journal=HortTechnology|language=en|volume=25|issue=3|pages=306–312|issn=1063-0198}}</ref> When higher concentrations are applied, there is a greater risk that these adverse effects will persist, leading to crop loss.<ref name=":2" />

==Reversing growth inhibition==
[[Gibberellin|Gibberellins]] can be applied to fight growth inhibition following dikegulac sodium application, but success can be limited.<ref name=":3" />

==Regulations==
[[Plant Protection Product (PPP)|Plant protection products]] containing dikegulac were phased out in the [[European Union]] after the [[European Commission]] decided in 2002 not to include it in Annex I to Directive 91/414/EEC.<ref>{{Cite web|url=http://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:32002R2076|title=Commission Regulation (EC) No 2076/2002|access-date=2017-01-09|website=eur-lex.europa.eu}}</ref>

Dikegulac sodium is approved for [[Pesticide regulation in the United States#Registration process|EPA registration]] in the [[United States]].<ref>{{Cite web|url=https://nepis.epa.gov/Exe/ZyNET.exe/P1003HNQ.TXT?ZyActionD=ZyDocument&Client=EPA&Index=2006+Thru+2010&Docs=&Query=&Time=&EndTime=&SearchMethod=1&TocRestrict=n&Toc=&TocEntry=&QField=&QFieldYear=&QFieldMonth=&QFieldDay=&IntQFieldOp=0&ExtQFieldOp=0&XmlQuery=&File=D:%5Czyfiles%5CIndex%20Data%5C06thru10%5CTxt%5C00000007%5CP1003HNQ.txt&User=ANONYMOUS&Password=anonymous&SortMethod=h%7C-&MaximumDocuments=1&FuzzyDegree=0&ImageQuality=r75g8/r75g8/x150y150g16/i425&Display=hpfr&DefSeekPage=x&SearchBack=ZyActionL&Back=ZyActionS&BackDesc=Results%20page&MaximumPages=1&ZyEntry=1&SeekPage=x&ZyPURL|title=Reregistration Eligibility Decision for Dikegulac sodium|website=nephis.epa.gov|language=en|access-date=2017-01-09}}</ref>

==Ginkgo Gate==
In Fall 2008, [[Washington, D.C.]]'s Urban Forestry Administration failed to suppress the fruiting of thousands of female ''[[Ginkgo biloba]]'' trees by [[Tree injection|injecting]] them with the dikegulac sodium product Pinscher.

''[[Ginkgo biloba]]'' is a [[Dioecious species|dioecious]] plant. The females are well known for their foul smelling fruit, so the non-fruiting males are recommended for landscape use. These city trees were installed before Gingko saplings could easily be sexed, however, so many were female.


The Urban Forestry Administration had previously sprayed the trees with [[chlorpropham]] to prevent fruiting, but their success had been limited. When the dikegulac sodium [[Tree injection|injection]] failed, the trees dropped their fruit, and some referred to the resulting uproar as "Ginkgo Gate".<ref>{{Cite news|url=https://cen.acs.org/articles/87/i50/Ginkgogate-Stench-Scandal.html|title=Ginkgogate: The Stench Of Scandal| date=2009-12-14|issn=0009-2347|volume=87|issue=50|page=48|newspaper=Chemical & Engineering News|last=Drahl|first=Carmen|access-date=2017-01-09|language=en}}</ref><ref>{{Cite news|url=http://www.washingtonpost.com/wp-dyn/content/article/2008/12/12/AR2008121204097.html|title=Ginkgo-Lined D.C., Capital of the U.S., and Now P.U.|last=Fahrenthold|first=David A.|date=2008-12-13|newspaper=The Washington Post|language=en-US|issn=0190-8286|access-date=2017-01-09}}</ref>
==Use as a Growth Retardant==
Uniconazole is applied to restrain the growth of plants. In ornamental plants this is usually to maintain a marketable size. It works by inhibiting the production of [[gibberellin]].


==References==
⚫
==Commercial Products==
The following commercial products include uniconzole as an active ingredient:
* Concise
* Sumagic

Latest revision as of 20:30, 29 May 2020


GreenAcres/sandbox
Names
IUPAC name
sodium;(3aR,4aS,8aR,8bS)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxine-3a-carboxylate
Other names
Sodium diprogulate
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 257-976-8
UNII
  • CC1(OCC2C(O1)C3C(O2)(OC(O3)(C)C)C(=O)[O-])C.[Na+]
Properties
C12H17NaO7
Molar mass 296.251 g·mol−1
Appearance white/colorless solid
590 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dikegulac sodium, or sodium diprogulate, is the sodium salt of dikegulac (diprogulic acid), which is used as a precursor in commercial ascorbic acid production.[1] It a plant growth regulator, primarily used as a branching agent. When it is taken up by a plant, dikegulac sodium is translocated to its apical meristems, where it inhibits DNA synthesis.[2] This suppresses apical dominance in plants and can stimulate lateral branching.[3] Dikegulac sodium is sometimes used to inhibit fruiting and flowering.[4]

Commercial formulations

[edit]

Commercial formulations available in the United States include Atrimmec,[5] Augeo,[6] and Pinscher.[7]

Application methods

[edit]

Dikegulac sodium can be applied as a foliar spray[6] or a trunk injection.[7]

Phytotoxicity

[edit]

Dikegulac sodium application often causes phytotoxic symptoms such as chlorosis and stunted growth.[3][8] When higher concentrations are applied, there is a greater risk that these adverse effects will persist, leading to crop loss.[3]

Reversing growth inhibition

[edit]

Gibberellins can be applied to fight growth inhibition following dikegulac sodium application, but success can be limited.[2]

Regulations

[edit]

Plant protection products containing dikegulac were phased out in the European Union after the European Commission decided in 2002 not to include it in Annex I to Directive 91/414/EEC.[9]

Dikegulac sodium is approved for EPA registration in the United States.[10]

Ginkgo Gate

[edit]

In Fall 2008, Washington, D.C.'s Urban Forestry Administration failed to suppress the fruiting of thousands of female Ginkgo biloba trees by injecting them with the dikegulac sodium product Pinscher.

Ginkgo biloba is a dioecious plant. The females are well known for their foul smelling fruit, so the non-fruiting males are recommended for landscape use. These city trees were installed before Gingko saplings could easily be sexed, however, so many were female.

The Urban Forestry Administration had previously sprayed the trees with chlorpropham to prevent fruiting, but their success had been limited. When the dikegulac sodium injection failed, the trees dropped their fruit, and some referred to the resulting uproar as "Ginkgo Gate".[11][12]

References

[edit]
  1. ^ Elks, J. (2014). The Dictionary of Drugs: Chemical Data, Structures and Bibliographies. Springer. p. 632. ISBN 978-1-4757-2085-3 – via Google Books.
  2. ^ a b Bocion, P.F.; De Silva, W.H. (1976). "Some Effects of Dikegulac on the Physiology of Whole Pants and Tissues; Interactions with Plant Hormones". In Pilet, Paul-Emile (ed.). Plant Growth Regulation (Proceedings in Life Sciences). International Conference on Plant Growth Substances, 9th. Springer Science & Business Media. pp. 189–198. ISBN 978-3-642-66589-9 – via Google Books.
  3. ^ a b c Arzee, Tova; Langenauer, Haviva; Gressel, J. (1977). "Effects of Dikegulac, a New Growth Regulator, on Apical Growth and Development of Three Compositae". Botanical Gazette. 138 (1): 18–28. ISSN 0006-8071 – via JSTOR.
  4. ^ Banko, Thomas; Stefani, Marcia (1995). "Growth Regulators for Management of Fruit Production on American Sweetgum". Journal of Arboriculture. 21 (2): 88–89. ISSN 0278-5226 – via International Society of Arboriculture.
  5. ^ "Atrimmec Plant Growth Regulator". www.gordonsprofessional.com. Retrieved 2017-01-08.
  6. ^ a b "Augeo Plant Growth Regulator" (PDF). OHP, Inc. Retrieved 2017-01-07.
  7. ^ a b "Pinscher | ArborSystems". www.arborsystems.com. Retrieved 2017-01-08.
  8. ^ Sun, Youping; Bi, Guihong; Niu, Genhua; Perez, Christina (2015-06-01). "Foliar Application of Dikegulac Sodium Increases Branching of 'Merritt's Supreme' Bigleaf Hydrangea". HortTechnology. 25 (3): 306–312. ISSN 1063-0198.
  9. ^ "Commission Regulation (EC) No 2076/2002". eur-lex.europa.eu. Retrieved 2017-01-09.
  10. ^ "Reregistration Eligibility Decision for Dikegulac sodium". nephis.epa.gov. Retrieved 2017-01-09.
  11. ^ Drahl, Carmen (2009-12-14). "Ginkgogate: The Stench Of Scandal". Chemical & Engineering News. Vol. 87, no. 50. p. 48. ISSN 0009-2347. Retrieved 2017-01-09.
  12. ^ Fahrenthold, David A. (2008-12-13). "Ginkgo-Lined D.C., Capital of the U.S., and Now P.U." The Washington Post. ISSN 0190-8286. Retrieved 2017-01-09.
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