| Revision as of 17:05, 19 January 2012 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals...← Previous edit | Latest revision as of 04:40, 18 November 2024 edit undoRustyOldShip (talk | contribs)495 edits 1974 usage data | ||
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| {{redirect|Tordon|the Swedish ships|HSwMS Tordön}} | |||
| {{chembox | {{chembox | ||
| | Verifiedfields = changed | |||
| | Watchedfields = changed | |||
| | verifiedrevid = 472033103 | | verifiedrevid = 472033103 | ||
| | ImageFile = Picloram.png | | ImageFile = Picloram.png | ||
| | ImageSize = | | ImageSize = 160 | ||
| | ImageAlt = Skeletal formula | |||
| | IUPACName = 4-Amino-3,5,6-trichloro-2-pyridinecarboxylic acid | |||
| | ImageFile1 = Picloram-3D-spacefill.png | |||
| | ImageSize1 = 160 | |||
| | ImageAlt1 = Picloram molecule | |||
| | PIN = 4-Amino-3,5,6-trichloropyridine-2-carboxylic acid | |||
| | OtherNames = Picloram<br>Tordon<br>Grazon | | OtherNames = Picloram<br>Tordon<br>Grazon | ||
| | |
|Section1={{Chembox Identifiers | ||
| | |
| PubChem = 15965 | ||
| | |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| | ChemSpiderID = 15170 | | ChemSpiderID = 15170 | ||
| | |
| InChI = 1/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13) | ||
| | |
| InChIKey = NQQVFXUMIDALNH-UHFFFAOYAR | ||
| | |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| | StdInChI = 1S/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13) | | StdInChI = 1S/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13) | ||
| | |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | ||
| | StdInChIKey = NQQVFXUMIDALNH-UHFFFAOYSA-N | | StdInChIKey = NQQVFXUMIDALNH-UHFFFAOYSA-N | ||
| | Abbreviations = ATCP | | Abbreviations = ATCP | ||
| | CASNo_Ref = {{cascite|correct|CAS}} | | CASNo_Ref = {{cascite|correct|CAS}} | ||
| | CASNo = 1918-02-1 | | CASNo = 1918-02-1 | ||
| | UNII_Ref = {{fdacite|changed|FDA}} | |||
| | UNII = O7437X49DW | |||
| | EINECS = | | EINECS = | ||
| | ChEMBL_Ref = {{ebicite|correct|EBI}} | | ChEMBL_Ref = {{ebicite|correct|EBI}} | ||
| | ChEMBL = 461349 | | ChEMBL = 461349 | ||
| | SMILES = |
| SMILES = Nc1c(Cl)c(Cl)nc(C(=O)O)c1Cl | ||
| | RTECS = | | RTECS = | ||
| | MeSHName = | | MeSHName = | ||
| | ChEBI_Ref = {{ebicite|correct|EBI}} | | ChEBI_Ref = {{ebicite|correct|EBI}} | ||
| | ChEBI = | | ChEBI = 34922 | ||
| | KEGG_Ref = {{keggcite|correct|kegg}} | | KEGG_Ref = {{keggcite|correct|kegg}} | ||
| | KEGG = C14310 | | KEGG = C14310 | ||
| }} | |||
| | ATCCode_prefix = | |||
| ⚫ | |Section2={{Chembox Properties | ||
| | ATCCode_suffix = | |||
| | C=6 | H=3 | Cl=3 | N=2 | O=2 | |||
| | ATC_Supplemental =}} | |||
| | Appearance = colorless to white crystalline solid<ref name=PGCH/> | |||
| ⚫ | | |
||
| | Odor = chlorine-like<ref name=PGCH/> | |||
| | Formula = C<sub>6</sub>H<sub>3</sub>Cl<sub>3</sub>N<sub>2</sub>O<sub>2</sub> | |||
| | MolarMass = 241.46 | |||
| | Appearance = Crystalline solid | |||
| | Density = | | Density = | ||
| | |
| MeltingPtC = 218.5 | ||
| | MeltingPt_notes = decomposes | |||
| | Melting_notes = | |||
| | BoilingPt = | | BoilingPt = | ||
| | |
| BoilingPt_notes = | ||
| | Solubility = 0.04% (20°C)<ref name=PGCH/> 430 mg/L at 25 deg C<ref>{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/picloram#section=Solubility&fullscreen=true |title = Picloram}}</ref> | |||
| | Solubility = | |||
| | VaporPressure = 0.0000006 mmHg (35°C)<ref name=PGCH/> | |||
| | SolubleOther = | | SolubleOther = | ||
| | Solvent = | | Solvent = | ||
| | pKa = | | pKa = | ||
| | pKb = }} | | pKb = }} | ||
| | |
|Section7={{Chembox Hazards | ||
| | EUClass = | |||
| | EUIndex = | |||
| | MainHazards = | | MainHazards = | ||
| | NFPA-H = | | NFPA-H = | ||
| | NFPA-F = | | NFPA-F = | ||
| | NFPA-R = | | NFPA-R = | ||
| | NFPA- |
| NFPA-S = | ||
| | |
| HPhrases = | ||
| | |
| PPhrases = | ||
| | |
| GHS_ref = | ||
| | FlashPt = | | FlashPt = | ||
| | |
| AutoignitionPt = | ||
| | ExploLimits = | | ExploLimits = | ||
| | PEL = TWA 15 mg/m<sup>3</sup> (total) TWA 5 mg/m<sup>3</sup> (resp)<ref name=PGCH>{{PGCH|0514}}</ref> | |||
| | PEL = }} | |||
| | IDLH = N.D.<ref name=PGCH/> | |||
| | REL = none established<ref name=PGCH/> | |||
| }} | |||
| }} | }} | ||
| '''Picloram''' is a systemic herbicide used for general woody plant control |
'''Picloram''' is a systemic herbicide used for general woody plant control. It also controls a wide range of broad-leaved weeds, but most grasses are resistant.<ref name="PMEP">, Pesticide Management Education Program, ].</ref> A ] derivative of ], picloram is in the ] family of herbicides. | ||
| Picloram can be sprayed on foliage, injected into plants, applied to cut surfaces, or placed at the base of the plant where it will leach to the roots. Once absorbed by the foliage, stem, or roots, picloram is transported throughout the plant. | Picloram can be sprayed on foliage, injected into plants, applied to cut surfaces, or placed at the base of the plant where it will leach to the roots. Once absorbed by the foliage, stem, or roots, picloram is transported throughout the plant. | ||
| Herbicides containing picloram are sold under a variety of brand names. ] and now ] sell herbicides containing it under the brand name Tordon.<ref name="Greene2005">{{cite book|author=Stanley A. Greene|title=Sittig's Handbook of Pesticides and Agricultural Chemicals|url=https://books.google.com/books?id=hAoKEHpyu6wC&pg=PA717|year=2005|publisher=William Andrew|isbn=978-0-8155-1903-4|page=717}}</ref> | |||
| During the Vietnam War, a mixture of picloram and ], known as ], was sprayed on plants that survived treatment with ] (] and 2,4-D). | |||
| During the ], picloram and other herbicides were combined to make ] (commercially available as Tordon 101) and enhanced ], which was previously conducted by the British military during the ]. Large quantities of these herbicides were sprayed by U.S. forces in areas where they considered its long-term persistence desirable, such as inland forests.<ref name="HerbicidesMedicine1994">{{cite book|author1=Committee to Review the Health Effects in Vietnam Veterans of Exposure to Herbicides|author2=Institute of Medicine|title=Veterans and Agent Orange: Health Effects of Herbicides Used in Vietnam|url=https://books.google.com/books?id=RjCHcoUE3B8C&pg=PA89|year=1994|publisher=National Academies Press|isbn=978-0-309-55619-4|pages=89–90}}</ref> In 1974, {{convert|413000|lbs|t}} of picloram were used in the US, mainly by government and industry.<ref>{{cite web |title=Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974 |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=91012P4O.txt |website=epa.gov |publisher=EPA |date=1977}}</ref> | |||
| ⚫ | Picloram is of moderate toxicity to the eyes and only mildly toxic on the skin.<ref name="PMEP"/> |
||
| ==Safety== | |||
| ⚫ | Picloram is the most persistent of its family of herbicides.<ref>, U.S. ] |
||
| ⚫ | Picloram is of moderate toxicity to the eyes and only mildly toxic on the skin.<ref name="PMEP"/> No history of human intoxication by picloram has been documented, so symptoms of acute exposure are difficult to characterize. | ||
| ⚫ | Picloram is the most persistent of its family of herbicides.<ref>, U.S. ]</ref> It does not adhere to soil, so may leach to groundwater, and has in fact been detected there. It is degraded in soil and water mainly by microbes. Picloram has very little tendency to accumulate in aquatic life. | ||
| ⚫ | Gardeners who use dung as fertilizer should check to make certain that the animal source has not grazed on picloram |
||
| ⚫ | Gardeners who use dung as fertilizer should check to make certain that the animal source has not grazed on picloram-treated hay, as the dung still has broadleaf-killing potency.<ref> {{webarchive|url=https://web.archive.org/web/20100614011214/http://www.extension.umn.edu/distribution/livestocksystems/M1197.html |date=2010-06-14 }}, U. Minnesota Extension</ref> | ||
| In regards to occupational exposures, the U. S. ] has established a ] of 15 mg/m<sup>3</sup> total exposure and 5 mg/m<sup>3</sup> for respiratory exposure, over an eight-hour workshift.<ref>, Centers for Disease Control and Prevention</ref> | |||
| ==References== | ==References== | ||
| <references/> | <references/> | ||
| ==External links== | ==External links == | ||
| * {{PPDB|525}} | |||
| * , ] | |||
| {{Herbicides}} | {{Herbicides}} | ||
| ⚫ | ] | ||
| ] | |||
| ] | |||
| ] | |||
| ] | ] | ||
| ] | ] | ||
| ⚫ | ] | ||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
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| ] | |||
Latest revision as of 04:40, 18 November 2024
"Tordon" redirects here. For the Swedish ships, see HSwMS Tordön.
| |
| |
| Names | |
|---|---|
| Preferred IUPAC name 4-Amino-3,5,6-trichloropyridine-2-carboxylic acid | |
| Other names
Picloram Tordon Grazon | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| Abbreviations | ATCP |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.016.034 
|
| KEGG | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C6H3Cl3N2O2 |
| Molar mass | 241.45 g·mol |
| Appearance | colorless to white crystalline solid |
| Odor | chlorine-like |
| Melting point | 218.5 °C (425.3 °F; 491.6 K) decomposes |
| Solubility in water | 0.04% (20°C) 430 mg/L at 25 deg C |
| Vapor pressure | 0.0000006 mmHg (35°C) |
| Hazards | |
| NIOSH (US health exposure limits): | |
| PEL (Permissible) | TWA 15 mg/m (total) TWA 5 mg/m (resp) |
| REL (Recommended) | none established |
| IDLH (Immediate danger) | N.D. |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 N verify (what is ?)
Infobox references
| |
Picloram is a systemic herbicide used for general woody plant control. It also controls a wide range of broad-leaved weeds, but most grasses are resistant. A chlorinated derivative of picolinic acid, picloram is in the pyridine family of herbicides.
Picloram can be sprayed on foliage, injected into plants, applied to cut surfaces, or placed at the base of the plant where it will leach to the roots. Once absorbed by the foliage, stem, or roots, picloram is transported throughout the plant.
Herbicides containing picloram are sold under a variety of brand names. Dow Chemicals and now Dow AgroSciences sell herbicides containing it under the brand name Tordon.
During the Vietnam War, picloram and other herbicides were combined to make Agent White (commercially available as Tordon 101) and enhanced Agent Orange, which was previously conducted by the British military during the Malayan Emergency. Large quantities of these herbicides were sprayed by U.S. forces in areas where they considered its long-term persistence desirable, such as inland forests. In 1974, 413,000 pounds (187 t) of picloram were used in the US, mainly by government and industry.
Safety
Picloram is of moderate toxicity to the eyes and only mildly toxic on the skin. No history of human intoxication by picloram has been documented, so symptoms of acute exposure are difficult to characterize.
Picloram is the most persistent of its family of herbicides. It does not adhere to soil, so may leach to groundwater, and has in fact been detected there. It is degraded in soil and water mainly by microbes. Picloram has very little tendency to accumulate in aquatic life.
Gardeners who use dung as fertilizer should check to make certain that the animal source has not grazed on picloram-treated hay, as the dung still has broadleaf-killing potency.
In regards to occupational exposures, the U. S. Occupational Safety and Health Administration has established a permissible exposure limit of 15 mg/m total exposure and 5 mg/m for respiratory exposure, over an eight-hour workshift.
References
- ^ NIOSH Pocket Guide to Chemical Hazards. "#0514". National Institute for Occupational Safety and Health (NIOSH).
- "Picloram".
- ^ Picloram Pesticide Information Profile, Pesticide Management Education Program, Cornell University.
- Stanley A. Greene (2005). Sittig's Handbook of Pesticides and Agricultural Chemicals. William Andrew. p. 717. ISBN 978-0-8155-1903-4.
- Committee to Review the Health Effects in Vietnam Veterans of Exposure to Herbicides; Institute of Medicine (1994). Veterans and Agent Orange: Health Effects of Herbicides Used in Vietnam. National Academies Press. pp. 89–90. ISBN 978-0-309-55619-4.
- "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
- Consumer Factsheet on: PICLORAM, U.S. Environmental Protection Agency
- Use Caution When Harvesting and Feeding Ditch Hay Archived 2010-06-14 at the Wayback Machine, U. Minnesota Extension
- NIOSH Pocket Guide to Chemical Hazards, Centers for Disease Control and Prevention
External links
- Picloram in the Pesticide Properties DataBase (PPDB)