| 词条 | Diprogulic acid |
| 释义 |
| ImageFile =Dikegulac.svg | ImageSize = 200px | ImageAlt = | IUPACName = (3aS,3bR,7aS,8aR)-2,2,5,5-Tetramethyltetrahydro-8aH-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine-8a-carboxylic acid | OtherNames = Dikegulac acid; Diacetone-2-ketogulonic acid; Oxogulonic acid diacetonide; Sodium dikegulac; Sodium diprogulate | Section1 = {{Chembox Identifiers | CASNo = 18467-77-1 | CASNo1 = 52508-35-7 | CASNo1_Comment = (sodium) | ChemSpiderID = 58884 | ChemSpiderID1 = 58883 | ChemSpiderID1_Comment = (sodium) | EC_number = 257-976-8 | PubChem = 65420 | PubChem1 = 23667639 | PubChem1_Comment = (sodium) | SMILES = CC1(OC[C@H]2[C@@H](O1)[C@H]3[C@@](O2)(OC(O3)(C)C)C(=O)O)C | StdInChI=1S/C12H18O7/c1-10(2)15-5-6-7(17-10)8-12(16-6,9(13)14)19-11(3,4)18-8/h6-8H,5H2,1-4H3,(H,13,14)/t6-,7+,8-,12+/m0/s1 | StdInChIKey=FWCBATIDXGJRMF-FLNNQWSLSA-N | Section2 = {{Chembox Properties | C=12 | H=18 | O=7 | Appearance = White/colorless solid | Density = | MeltingPtC = | BoilingPt = | Solubility = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}Diprogulic acid (also known as dikegulac) is a precursor used in commercial ascorbic acid production.[1] In agriculture, its sodium salt, dikegulac sodium, is used as 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 the plant and can stimulate lateral branching, resulting in a bushier growth habit.[3] Dikegulac sodium is sometimes used to inhibit fruiting and flowering.[4] Application methodsDikegulac sodium can be applied as a foliar spray[5] or a trunk injection.[6] PhytotoxicityDikegulac sodium application often causes phytotoxicity. Symptoms include chlorosis and stunted growth.[3][5] When higher concentrations are applied, there is a greater risk that these adverse effects will persist, leading to crop loss.[3] Reversing growth inhibitionGibberellins can be applied to fight undesired growth inhibition following dikegulac sodium application, but success can be limited.[2]RegulationsPlant protection products containing dikegulac were phased out in the European Union after the European Commission decided in 2002 not to include the chemical in Annex I to Directive 91/414/EEC.[6]Dikegulac sodium is approved for EPA registration in the United States.[7] Commercial formulationsCommercial formulations available in the United States include Atrimmec,[8] Augeo,[9] and Pinscher.[10] Ginkgo GateIn 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. Because the females are well known for their foul smelling fruit, the non-fruiting males are usually recommended for landscape use. However, these city trees were installed before Ginkgo saplings could easily be sexed, so many planted 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 was unsuccessful, the fruit matured and dropped from the trees. Some referred to the failure as "Ginkgo Gate".[11][12] References1. ^{{Cite book|title=The Dictionary of Drugs: Chemical Data, Structures and Bibliographies|last1=Elks|first1=J.|last2=Ganellin|first2=C.R.|publisher=Springer|year=2014|isbn=978-1-4757-2085-3|pages=632|via=Google Books}} 2. ^1 {{cite conference|title=Some Effects of Dikegulac on the Physiology of Whole Plants 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}} 3. ^1 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|jstor=2473627|journal=Botanical Gazette|volume=138|issue=1|pages=18–28|issn=0006-8071}} 4. ^{{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}} 5. ^{{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}} 6. ^{{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}} 7. ^{{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}} 8. ^{{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}} 9. ^1 {{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}} 10. ^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}} 11. ^{{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}} 12. ^{{Cite news|url=https://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}} 5 : Agricultural chemicals|Plant growth regulators|Carboxylic acids|Dioxanes|Dioxolanes |
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