| Revision as of 11:57, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{chembox}} taken from revid 477053255 of page Metolachlor for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:00, 6 November 2024 edit OAbot (talk | contribs)Bots442,978 editsm Open access bot: pmc updated in citation with #oabot. |
| Line 1: |
Line 1: |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
|
| Watchedfields = changed |
|
| Watchedfields = changed |
|
| verifiedrevid = 444283352 |
|
| verifiedrevid = 477170024 |
|
| Reference = <ref>, Oregon State University</ref> |
|
| Reference = <ref>, Oregon State University</ref> |
|
| ImageFile = Metolachlor.png |
|
| ImageFile = Metolachlor.png |
|
| ImageSize = 200px |
|
| ImageSize = |
|
| IUPACName = (''RS'')-2-Chloro-''N''-(2-ethyl-6-methyl-phenyl)-''N''-(1-methoxypropan-2-yl)acetamide |
|
| IUPACName = (''RS'')-2-Chloro-''N''-(2-ethyl-6-methyl-phenyl)-''N''-(1-methoxypropan-2-yl)acetamide |
|
| OtherNames = Dual, Pimagram, Bicep, CGA-24705, Pennant. |
|
| OtherNames = Dual, Pimagram, Bicep, CGA-24705, Pennant. |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 4025 |
|
| ChemSpiderID = 4025 |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = C10953 |
|
| KEGG = C10953 |
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEBI = 6902 |
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEMBL = 1884974 |
|
| InChI = 1/C15H22ClNO2/c1-5-13-8-6-7-11(2)15(13)17(14(18)9-16)12(3)10-19-4/h6-8,12H,5,9-10H2,1-4H3 |
|
| InChI = 1/C15H22ClNO2/c1-5-13-8-6-7-11(2)15(13)17(14(18)9-16)12(3)10-19-4/h6-8,12H,5,9-10H2,1-4H3 |
|
| InChIKey = WVQBLGZPHOPPFO-UHFFFAOYAS |
|
| InChIKey = WVQBLGZPHOPPFO-UHFFFAOYAS |
| Line 21: |
Line 25: |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 51218-45-2 |
|
| CASNo = 51218-45-2 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| PubChem = 4169 |
|
|
|
| UNII = X0I01K05X2 |
| ⚫ |
| SMILES = CCc1cccc(c1N(C(C)COC)C(=O)CCl)C |
|
|
⚫ |
| PubChem = 4169 |
|
⚫ |
| SMILES = CCc1cccc(c1N(C(C)COC)C(=O)CCl)C |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C=15|H=22|Cl=1|N=1|O=2 |
|
| C=15 | H=22 | Cl=1 | N=1 | O=2 |
|
| Appearance = Off-white to colorless liquid |
|
| Appearance = Off-white to colorless liquid |
|
| Density = |
|
| Density = 1.1 g/mL |
|
| MeltingPt = |
|
| MeltingPt = |
|
| BoilingPt = 100 °C at 0.001 mmHg |
|
| BoilingPtC = 100 |
|
| Solubility = 530 ppm at 20 °C |
|
| BoilingPt_notes = at 0.001 mmHg |
|
|
| Solubility = 530 ppm at 20 °C |
| ⚫ |
}} |
|
| ⚫ |
| Section3 = {{Chembox Hazards |
|
| ⚫ |
| MainHazards = <ref> |
|
| ⚫ |
| FlashPt = |
|
|
| Autoignition = |
|
|
}} |
|
}} |
|
⚫ |
|Section3={{Chembox Hazards |
|
⚫ |
| MainHazards = <ref>{{cite web|url=http://extoxnet.orst.edu/pips/metolach.htm|title=EXTOXNET PIP - METOLACHLOR|work=orst.edu|accessdate=17 May 2015}}</ref> |
|
⚫ |
| FlashPt = |
|
|
| AutoignitionPt = |
|
⚫ |
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Metolachlor''' is an ] that is widely used as an ]. It is a derivative of ] and is a member of the chloroacetanilide family of herbicides. It is highly effective toward grasses. |
|
|
|
|
|
==Agricultural use== |
|
|
Metolachlor was developed by ]. Its acts by ] of ]s and of the ] (GGPP) cyclases, which are part of the ] pathway. It is used for grass and broadleaf weed control in corn, soybean, peanuts, sorghum, and cotton. It is also used in combination with other herbicides. |
|
|
|
|
|
Metolachlor is a popular herbicide in the United States.<ref>Kiely, T., D. Donaldson, and A. Grube. 2004. Pesticide industry sales and usage: 2000 and 2001 market estimates. US Environmental Protection Agency, Office of Pesticides Programs, Washington, DC</ref> As originally formulated metolachlor was applied as a ], a 1:1 mixture of the (''S'')- and (''R'')-stereoisomers. The (''R'')-enantiomer is less active, and modern production methods afford a higher concentration of S-metolachlor, thus current application rates are far lower than original formulations. |
|
|
|
|
|
==Production and basic structure== |
|
|
Metolachlor is produced from 2-ethyl-6-methylaniline (MEA) via condensation with methoxy]. The resulting ] is ] to give primarily the ''S''-stereoisomeric amine. This ] is acetylated with chloroacetylchloride. Because of the ]s of the 2,6-disubstituted aniline, rotation about the aryl-C to N bond is restricted. Thus, both the (''R'')- and the (''S'')-enantiomers exist as ]s. Both atropisomers of (''S'')-metolachlor exhibit the same biological activity.<ref>{{cite journal | author = H.U.-Blaser | title = The Chiral Switch of (''S'')-Metolachlor: A Personal Account of an Industrial Odyssey in Asymmetric Catalysis | journal = Advanced Synthesis and Catalysis | year = 2002 | volume = 344 | pages = 17–31 | doi = 10.1002/1615-4169(200201)344:1<17::AID-ADSC17>3.0.CO;2-8}}</ref> |
|
|
]{{clear left}} |
|
|
|
|
|
== Safety and ecological effects == |
|
|
The European Chemicals Agency classified metolachlor as a suspected human carcinogen (Carcinogen category 2) in 2022.<ref>{{cite journal |last1=Alvarez |first1=Fernando |last2=Arena |first2=Maria |last3=Auteri |first3=Domenica |last4=Binaglia |first4=Marco |last5=Castoldi |first5=Anna Federica |last6=Chiusolo |first6=Arianna |last7=Colagiorgi |first7=Angelo |last8=Colas |first8=Mathilde |last9=Crivellente |first9=Federica |last10=De Lentdecker |first10=Chloe |last11=De Magistris |first11=Isabella |last12=Egsmose |first12=Mark |last13=Fait |first13=Gabriella |last14=Ferilli |first14=Franco |last15=Gouliarmou |first15=Varvara |last16=Nogareda |first16=Laia Herrero |last17=Ippolito |first17=Alessio |last18=Istace |first18=Frederique |last19=Jarrah |first19=Samira |last20=Kardassi |first20=Dimitra |last21=Kienzler |first21=Aude |last22=Lanzoni |first22=Anna |last23=Lava |first23=Roberto |last24=Leuschner |first24=Renata |last25=Linguadoca |first25=Alberto |last26=Lythgo |first26=Christopher |last27=Magrans |first27=Oriol |last28=Mangas |first28=Iris |last29=Miron |first29=Ileana |last30=Molnar |first30=Tunde |last31=Padovani |first31=Laura |last32=Panzarea |first32=Martina |last33=Parra Morte |first33=Juan Manuel |last34=Rizzuto |first34=Simone |last35=Serafimova |first35=Rositsa |last36=Sharp |first36=Rachel |last37=Szentes |first37=Csaba |last38=Szoradi |first38=Andras |last39=Terron |first39=Andrea |last40=Theobald |first40=Anne |last41=Tiramani |first41=Manuela |last42=Vianello |first42=Giorgia |last43=Villamar‐Bouza |first43=Laura |title=Peer review of the pesticide risk assessment of the active substance S‐metolachlor excluding the assessment of the endocrine disrupting properties |journal=EFSA Journal |date=February 2023 |volume=21 |issue=2 |doi=10.2903/j.efsa.2023.7852|pmc=9972551 }}</ref> The ] (US EPA) has classified Metolachlor as a Group C, possible human carcinogen, based on liver tumors in rats at the highest dose tested (HDT).<ref>{{cite web |title=S-metolachlor; Pesticide Tolerance |url=https://www.federalregister.gov/documents/2006/08/30/E6-14443/s-metolachlor-pesticide-tolerance |website=Federal Register |publisher=US EPA |access-date=15 October 2024 |date=August 30, 2006}}</ref><ref>USEPA,1987. Metolachlor Pesticide Registration Standard. Springfield, IL: Natl. Tech. Info. Serv.</ref> Evidence of the ] of metolachlor in edible species of fish as well as its adverse effect on the growth and development has raised concerns on its effects on human and environmental health. For example, products with this active ingredient are restricted to professional licensed applicators in the U.S. state of Massachusetts.<ref>{{cite web |author1=Massachusetts Department of Agricultural Resources |title=Groundwater Protection List |url=https://www.mass.gov/info-details/groundwater-protection-list |publisher=Commonwealth of Massachusetts |access-date=15 October 2024}}</ref> Though there is no set maximum concentration (], MCL) for metolachlor that is allowed in drinking water, the US EPA does have a health advisory level (HAL) of 0.525 mg/L. Metolachlor has been detected in ground and surface waters in concentrations ranging from 0.08 to 4.5 parts per billion (ppb) throughout the U.S.<ref>{{cite journal | author = Pothuluri, J.V., Evans, F.E., Doerge, D.R., Churchwell, M.I.,Cerniglia, C.E. | year = 1997 | title = Metabolism of metolachlor by the fungus ''Cunninghamella elegans'' | journal = Arch. Environ. Contam. Toxicol. | volume = 32 | pages = 117–125 | doi = 10.1007/s002449900163 | pmid = 9069185 | issue = 2| s2cid = 20614148 }}</ref> |
|
|
|
|
|
Metolachlor induces ] and ] effects in human lymphocytes.<ref>{{cite journal | author = Rollof, B., Belluck, D., Meiser, L. | year = 1992 | title = Cytogenic effects of cyanazine and metolachlor on human lymphocytes exposed in vitro | journal = Mutat. Res. Lett. | volume = 281 | pages = 295–298 | doi = 10.1016/0165-7992(92)90024-C | pmid = 1373225 | issue = 4| doi-access = free }}</ref> Genotoxic effects have also been observed in tadpoles exposed to metolachlor.<ref>{{cite journal | author = Clements, C., Ralph, S.,Petras, M. | year = 1997 | title = Genotoxicity of select herbicides on ''Rana catesbeiana'' tadpoles using alkaline single-cell gel DNA electrophoresis (Comet) assay | journal = Env. Mol. Mut. | volume = 29 | pages = 277–288 | doi = 10.1002/(SICI)1098-2280(1997)29:3<277::AID-EM8>3.0.CO;2-9 | issue = 3| pmid = 9142171 | s2cid = 27619855 }}</ref> Evidence also reveals that metolachlor affects cell growth. Cell division in yeast was reduced,<ref>Echeverrigaray,S., Gomes,L.H., Taveres, F.C.A.(1999). Isolation and characterization of metolachlor resistant mutants of ''Saccharomyces cerevisiae''. World Journal of Micro and Biotech. 15: 679–681.</ref> and chicken embryos exposed to metolchlor showed a significant decrease in the average body mass compared to the control.<ref>Varnargy,L., Budai, P., Fejes, S., Susan, M., Francsi, T., Keseru, M., Szabo, R.(2003). Toxicity and degradation of metolachlor (Dual 960EC) in chicken embryos. Commun. Agric. Appl. Biol. Sci.68:807–11.</ref> |
|
|
<!-- |
|
|
need a secondary citation: === Fate in the environment === |
|
|
Metabolites of metolachlor have been found in varying levels treated plants. Plants however, retain their metolachlor metabolites although animals that consume such plants are able to break down and eliminate the chemical rapidly. Some parts of plants, such as the leaves of cotton can retain much higher levels of metolachlor residues compared to other parts of the plants such as the seeds that can contain little. |
|
|
|
|
|
The breakdown of metolachlor in the soil is affected by a number of factors such as moisture, temperature, microbial activity, soil type , concentration of oxygen and nitrification and is mobile and easily leached through soil. The effect of changes in moisture content and temperature related to microbial activity also affects metolachlor breakdown.--> |
|
|
|
|
|
==See also== |
|
|
*] |
|
|
*] |
|
|
*] |
|
|
|
|
|
== References == |
|
|
{{reflist}} |
|
|
|
|
|
==External links== |
|
|
* {{PPDB|465}} |
|
|
|
|
|
{{Herbicides}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |