| Revision as of 11:14, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 477023671 of page Cholesterol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 13:34, 1 October 2024 edit Marbletan (talk | contribs)Extended confirmed users5,666 editsNo edit summary |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 464397475 |
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| verifiedrevid = 477165736 |
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| ImageFile=Cholesterol.svg |
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| ImageFile = Prothioconazole 200.svg |
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| ImageSize= |
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| ImageSize = 280 |
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| ImageFile2=Cholesterol-3d.png |
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| ImageAlt = Chemical structure of prothioconazole |
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| IUPACName=(3β)-​cholest-​5-​en-​3-​ol |
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| ImageFile1 = Prothioconazole x.gif |
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| OtherNames=(10''R'',​13''R'')-​10,​13-​dimethyl-​17-​(6-​methylheptan-​2-​yl)-​2,​3,​4,​7,​8,​9,​11,​12,​14,​15,​16,​17-​dodecahydro-​1''H''-​cyclopenta​phenanthren-​3-​ol |
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| ImageSize1 = 280 |
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| Section1= {{Chembox Identifiers |
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| ImageAlt1 = 3D animation of prothioconazole molecular structure |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| IUPACName = 2--1H-1,2,4-triazole-3-thione |
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| UNII = 97C5T2UQ7J |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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| StdInChI=1S/C14H15Cl2N3OS/c15-11-4-2-1-3-10(11)7-14(20,13(16)5-6-13)8-19-12(21)17-9-18-19/h1-4,9,20H,5-8H2,(H,17,18,21) |
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| InChIKey = HVYWMOMLDIMFJA-DPAQBDIFBB |
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| StdInChIKey = MNHVNIJQQRJYDH-UHFFFAOYSA-N |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 112570 |
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| CASNo = 178928-70-6 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| StdInChI = 1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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| UNII = 27B9FV58IY |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEBI = 84008 |
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| StdInChIKey = HVYWMOMLDIMFJA-DPAQBDIFSA-N |
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| ChEMBL = 2251446 |
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| CASNo=57-88-5 |
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| ChemSpiderID = 4953623 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| EC_number = 605-841-2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5775 |
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| PubChem = 6451142 |
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| SMILES = C1CC1(C(CC2=CC=CC=C2Cl)(CN3C(=S)N=CN3)O)Cl |
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| PubChem=5997 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00040 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 16113 |
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| SMILES = C(CCCC(C)C)1CC21(CC32CC=C43(CC(C4)O)C)C |
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}} |
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}} |
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| Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>27</sub>H<sub>46</sub>O |
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| Formula =C<sub>14</sub>H<sub>15</sub>Cl<sub>2</sub>N<sub>3</sub>OS |
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| MolarMass=386.65 g/mol |
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| MolarMass = 344.2 g/mol |
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| Appearance= white crystalline powder<ref name=MSDS>{{cite web |url=http://physchem.ox.ac.uk/MSDS/CH/cholesterol.html |title=Safety (MSDS) data for cholesterol |accessdate=2007-10-20 |work=}}</ref> |
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| Appearance = white crystalline powder<ref name=MSDS>{{cite web |url= http://fs1.agrian.com/pdfs/Proline_480_SC_Fungicide1__NY__MSDS.pdf |title=Safety (MSDS) data for prothioconazole |accessdate=2007-10-20}}</ref> |
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| Density= 1.052 g/cm<sup>3</sup> |
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| Density = 1.36 g/cm<sup>3</sup><ref name="PubChem Summary"/> |
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| MeltingPtC = 139.1-144.5 |
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| MeltingPt=148–150 °C<ref name=MSDS/> |
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| MeltingPt_ref = <ref name="PubChem Summary"/> |
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| BoilingPt=360 °C (decomposes) |
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| BoilingPt = 437-537°C Decomposes at 222°C <ref name="PubChem Summary"/> |
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| Solubility=0.095 mg/L (30 °C) |
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| BoilingPt_notes = |
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| SolubleOther = soluble in ], ], ], ], ], ], ], ] |
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| Solubility = 300 mg/L at 20 °C<ref name="PubChem Summary">{{cite web |last1=PubChem |title=Compound Summary - Prothioconazole |url=https://pubchem.ncbi.nlm.nih.gov/compound/6451142 |accessdate=20 March 2020}}</ref> |
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}} |
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| SolubleOther = soluble in acetone, polyethylene glycol, esters <ref name="PubChem Summary"/> |
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| Section7= {{Chembox Hazards |
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| pKa = 6.9<ref name="PubChem Summary"/> |
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| MainHazards= |
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| VaporPressure = 3 × 10<sup>−7</sup> mm Hg<ref name="PubChem Summary"/> |
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| FlashPt= |
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| Autoignition= |
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| Section3 = {{Chembox Hazards |
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| Hazards_ref = <ref name="PubChem Summary" /> |
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<!-- (data page) --> |
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| ExternalSDS = |
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| GHSPictograms = {{GHS09}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|410}} |
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| PPhrases = {{P-phrases|273|391|501}} |
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| LD50 = 6200 mg/kg<ref name="Report08" /> |
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| LC50 = 4.9 mg/L<ref name="Report08" /> |
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}} |
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}} |
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'''Prothioconazole''' is a ] chemical produced primarily for its ] properties. It is a member of the class of compounds ]s, and possesses a unique ] in this class of fungicides. Its effective fungicidal properties can be attributed to its ability to inhibit ]. This ] is required to biosynthesize ], a key component in the ] of ]. |
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Prothioconazole was first introduced into the market in 2004 by ] and quickly gained popularity due to its broad ] of activity against many fungal diseases of important cereal crops. It is used as a solo product under the trade name Proline, and in various mixtures in many other commercially produced fungicides. |
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== Synthesis == |
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The ] derivative of ] is added across the double bond of 1-chlorocyclopropyl-2-chloro-ethan-1-one. The ] within the ] is subsequently substituted by ]. Finally, to introduce the ] group at position 5 on the 1,2,4-triazole, the compound is first lithiated with ], followed by the addition of sulfur (S<sub>8</sub>).<ref name="Synthesis">{{cite news |last1=USEPA |title=Modern Crop Protection Compounds |date=6 May 2019 |publisher=John Wiley & Sons |isbn=9783527340897 |url=https://books.google.com/books?id=SECCDwAAQBAJ&q=Ulrich+Schirmer+Modern+Crop+Protection+Compounds |accessdate=20 March 2020}}</ref> This synthesis is not enantio-selective, resulting in a ].<ref name="Evaluation">{{cite news |last1=Ambrus |first1=Arpad |title=Prothioconazole |url=http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/JMPR/Evaluation08/Prothioconazole.pdf |accessdate=20 March 2020}}</ref> |
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== Chemical properties == |
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Prothioconazole does not dissolve well in water but can be dissolved in ], ]s and ].<ref name="Evaluation" /> |
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Photo-degeneration proceeds to completion, with the half life of photo degeneration being 47.7h.<ref name="Evaluation" /> |
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It does not readily undergo ], such that a pH of 4 and temperature of 50 °C results in half of the molecules being hydrolyzed after only 120 days. The primary degradation product is prothioconazole-desthio. This product possesses average mobility in the soil and its stability to hydrolysis consequently leads to its persistence in soil under ] conditions with total degradation in soil taking around 14.7 days.<ref name="Evaluation" /> It is also highly resistant to aqueous ] and degradation by both aerobic and ] ]s.<ref name="Pest" /> |
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== Toxicology == |
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=== Classification === |
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] of animal studies led to prothioconazole and its metabolites being classified as "Not likely to be Carcinogenic to Humans" by the ].<ref name="Pest">{{cite news |last1=USEPA |title=Pesticide Fact Sheet - Prothioconazole |url=https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-113961_14-Mar-07.pdf |accessdate=20 March 2020}}</ref> The ] assessed prothioconazole and deemed it to be very toxic to aquatic life with long lasting effects (H410).<ref>{{cite web |last1=PubChem |title=LABORATORY CHEMICAL SAFETY SUMMARY (LCSS) - Prothioconazole |url=https://pubchem.ncbi.nlm.nih.gov/compound/Prothioconazole#datasheet=LCSS |accessdate=20 March 2020}}</ref> |
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The ] (ADI) for prothioconazole amounts to 0.01 mg/kg body weight per day, whereas the ] (ARfD) was determined to be 0.01 mg/kg bw per day.<ref>European Commission "EU Pesticides database - Prothioconazole"</ref> |
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=== Toxicity === |
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Experiments were conducted on animals where the primary route of uptake was oral administration. Coupling the compound to a ] revealed ] of the compound.<ref name="PubMedRef">{{cite news |last1=USEPA |title=Human Health Risk Assessment - Prothioconazole |url=https://www.regulations.gov/document?D=EPA-HQ-OPP-2005-0312-0005 |accessdate=20 March 2020}}</ref> At the LOAEL, prothioconazole and its metabolites target the liver, kidneys and the bladder. The ] (LD<sub>50</sub>) is 6200 mg/kg bw in rats. The dermal LD<sub>50</sub> amounted to more than 2000 mg/kg bw, whereas a 4-hour inhalation LC<sub>50</sub> was determined to be over 4.9 mg/L. Short term studies assessed adverse hepatic effects, an increase in liver weight, increased activity of liver enzymes and microscopic lesions. Prothioconazole was reported to be irritating to rabbit eyes but not skin. Studies have shown that elimination via the feces is the main route of excretion with over 70% excreted within 24 hours.<ref name="Report08">{{cite news |last1=FAO/WHO |title=Pesticide residues in food 2008 - Prothioconazole |url=http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/JMPR/Report08/Prothioconazole.pdf |accessdate=20 March 2020}}</ref> The half-life of elimination was deduced to be 44.3 hours.<ref name="PubMedRef" /> |
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=== Metabolism in animals === |
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The biotransformation of prothioconazole proceeds by either ] or ] of the ] and subsequent conjugation with ]. The major metabolites maintain the ] moiety in all species investigated. The major metabolite was prothioconazole-''S''-glucuronide, which results from phase II reactions.<ref name="Evaluation" /> A linear dose-response relationship was observed for prothioconazole-desthio residues in liver and kidney at different feeding levels.<ref name="Report08" /> |
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=== Metabolism in plants === |
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Prothioconazole-desthio is the major ] found in all plant species investigated. Prothioconazole-desthio and prothioconazole share similar toxicological properties. Studies suggest that the plant takes up 1,2,4-triazole from the soil and directly metabolizes it, as the presence of free 1,2,4-triazole was undetectable.<ref name="Evaluation" /> |
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== Biochemical properties == |
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=== Interactions === |
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The primary mechanism of fungicidal action involves the inhibition of CYP51, a crucial component in the ] process of ] or 24-methyl dihydroano-sterol at position 14. Disruption of this process results in the impaired ] mechanism of ergosterol. ] is a precursor for vitamin D<sub>2</sub>, which is essential for the structure of the cell membrane in many fungal species.<ref name="Report08" /> |
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Studies also suggest that prothioconazole can also interact with and temporarily suppress ]. This enzyme is responsible for iodine (I<sub>2</sub>) formation from iodide (I<sup>−</sup>). Inhibition of this process results in decreased production of ] in humans, such as thyroxine or ].<ref name="PubMedRef" /> |
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== References == |
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{{reflist}} |
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