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{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 399163352
| verifiedrevid = 477170024
| Reference = <ref>[http://extoxnet.orst.edu/pips/metolach.htm Extoxnet], Oregon State University</ref>
| Reference = <ref>[http://extoxnet.orst.edu/pips/metolach.htm Extoxnet], Oregon State University</ref>
| ImageFile = Metolachlor.png
| ImageFile = Metolachlor.png
| ImageSize = 200px
| ImageSize =
| IUPACName = 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|changed|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 20: 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>[http://extoxnet.orst.edu/pips/metolach.htm Extoxnet Pip - Metolachlor<!-- Bot generated title -->]</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 [[organic compound]] that is widely used as an [[herbicide]]. It is a derivative of [[aniline]] and is a member of the chloroacetanilide herbicides. It is highly effective toward grasses but its application is also controversial.
'''Metolachlor''' is an [[organic compound]] that is widely used as an [[herbicide]]. It is a derivative of [[aniline]] and is a member of the chloroacetanilide family of herbicides. It is highly effective toward grasses.


==Agricultural use==
==Agricultural use==
Metolachlor was developed by [[Ciba-Geigy]]. Its acts by [[enzyme inhibitor|inhibition]] of [[elongase]]s and of the [[geranylgeranyl pyrophosphate]] (GGPP) cyclases, which are part of the [[gibberellin]] 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 was developed by [[Ciba-Geigy]]. Its acts by [[enzyme inhibitor|inhibition]] of [[elongase]]s and of the [[geranylgeranyl pyrophosphate]] (GGPP) cyclases, which are part of the [[gibberellin]] 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> Metolachlor is becoming less and less common. As originally formulated metolachlor was applied as a [[racemate]], a 1:1 mixture of the (''S'')- and (''R'')-stereoisomers. The (''R'')-enantiomer is inactive, and modern production methods afford only (''S'')-metolachlor, thus current application rates are far lower than original formulations.
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 [[racemate]], 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==
==Production and basic structure==
Metolachlor is produced from 2-ethyl-6-methylaniline (MEA) via condensation with methoxy[[acetone]]. The resulting [[imine]] is [[hydrogenation|hydrogenated]] to give primarily the ''S''-stereoisomeric amine. This [[secondary amine]] is acetylated with chloroacetylchloride. Because of the [[steric effect]]s of the 2,6-disubstituted aniline, rotation about the aryl-C to N bond is restricted. Thus, for both the (''R'')- and the (''S'')-enantiomers exist as [[atropisomer]]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>
Metolachlor is produced from 2-ethyl-6-methylaniline (MEA) via condensation with methoxy[[acetone]]. The resulting [[imine]] is [[hydrogenation|hydrogenated]] to give primarily the ''S''-stereoisomeric amine. This [[secondary amine]] is acetylated with chloroacetylchloride. Because of the [[steric effect]]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 [[atropisomer]]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>
[[File:Metolachlor four stereoisomers V.1.svg|thumb|left|420px|The four stereoisomers of metolachlor]]{{clear left}}


==Safety and ecological effects ==
== Safety and ecological effects ==
Metolachlor has been detected in ground and surface waters and 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}}</ref> It is classified as a Category C pesticide by the [[United States Environmental Protection Agency]] (US EPA) which indicates limited evidence of carcinogenicity.<ref>USEPA,1987. Metolachlor Pesticide Registeration Standard. Springfield,IL: Natl. Tech. Info. Serv.</ref> Evidence of the bioaccumulation of metolachlor in edible species of fish as well as its adverse effect on the growth and development raise concerns on its effects on human health. There is no set maximum concentration ([[maximum contaminant level]], 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> It is classified as a Category C pesticide by the [[United States Environmental Protection Agency]] (US EPA), which indicates limited evidence of [[carcinogen]]icity.<ref>USEPA,1987. Metolachlor Pesticide Registration Standard. Springfield, IL: Natl. Tech. Info. Serv.</ref> Evidence of the [[bioaccumulation]] of metolachlor in edible species of fish as well as its adverse effect on the growth and development raise concerns on its effects on human health. Though there is no set maximum concentration ([[maximum contaminant level]], MCL) for metolachlor that is allowed in drinking water, the US EPA does have a health advisory level (HAL) of 0.525&nbsp;mg/L.


Metolachlor induces [[cytotoxic]] and [[genotoxic]] 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 = Mut. Res. Lett. | volume = 281 | pages = 295–298 | doi = 10.1016/0165-7992(92)90024-C | issue = 4}}</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}}</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>
Metolachlor induces [[cytotoxic]] and [[genotoxic]] 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 ===
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.
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.


Line 61: Line 70:
*[[Acetochlor]]
*[[Acetochlor]]
*[[Alachlor]]
*[[Alachlor]]
*[[Josiphos ligands]]


== References ==
== References ==
{{reflist}}
{{reflist}}

==External links==
* {{PPDB|465}}


{{Herbicides}}
{{Herbicides}}


[[Category:Amides]]
[[Category:Herbicides]]
[[Category:Herbicides]]
[[Category:Acetanilides]]
[[Category:Acetanilides]]
[[Category:Ethers]]
[[Category:Ethers]]
[[Category:Organochlorides]]
[[Category:Organochlorides]]
[[Category:Alkyl-substituted benzenes]]

[[de:Metolachlor]]
[[Category:Preemergent herbicides|S-Metolachlor]]
[[fr:Métolachlore]]

Revision as of 03:43, 6 February 2024

Metolachlor[1]
Names
IUPAC name
(RS)-2-Chloro-N-(2-ethyl-6-methyl-phenyl)-N-(1-methoxypropan-2-yl)acetamide
Other names
Dual, Pimagram, Bicep, CGA-24705, Pennant.
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.051.856 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/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 checkY
    Key: WVQBLGZPHOPPFO-UHFFFAOYSA-N checkY
  • 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
    Key: WVQBLGZPHOPPFO-UHFFFAOYAS
  • CCc1cccc(c1N(C(C)COC)C(=O)CCl)C
Properties
C15H22ClNO2
Molar mass 283.80 g·mol−1
Appearance Off-white to colorless liquid
Density 1.1 g/mL
Boiling point 100 °C (212 °F; 373 K) at 0.001 mmHg
530 ppm at 20 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Metolachlor is an organic compound that is widely used as an herbicide. It is a derivative of aniline and is a member of the chloroacetanilide family of herbicides. It is highly effective toward grasses.

Agricultural use

Metolachlor was developed by Ciba-Geigy. Its acts by inhibition of elongases and of the geranylgeranyl pyrophosphate (GGPP) cyclases, which are part of the gibberellin 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.[3] As originally formulated metolachlor was applied as a racemate, 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 methoxyacetone. The resulting imine is hydrogenated to give primarily the S-stereoisomeric amine. This secondary amine is acetylated with chloroacetylchloride. Because of the steric effects 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 atropisomers. Both atropisomers of (S)-metolachlor exhibit the same biological activity.[4]

The four stereoisomers of metolachlor

Safety and ecological effects

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.[5] It is classified as a Category C pesticide by the United States Environmental Protection Agency (US EPA), which indicates limited evidence of carcinogenicity.[6] Evidence of the bioaccumulation of metolachlor in edible species of fish as well as its adverse effect on the growth and development raise concerns on its effects on human health. Though there is no set maximum concentration (maximum contaminant level, 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 induces cytotoxic and genotoxic effects in human lymphocytes.[7] Genotoxic effects have also been observed in tadpoles exposed to metolachlor.[8] Evidence also reveals that metolachlor affects cell growth. Cell division in yeast was reduced,[9] and chicken embryos exposed to metolchlor showed a significant decrease in the average body mass compared to the control.[10]

See also

References

  1. ^ Extoxnet, Oregon State University
  2. ^ "EXTOXNET PIP - METOLACHLOR". orst.edu. Retrieved 17 May 2015.
  3. ^ 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
  4. ^ H.U.-Blaser (2002). "The Chiral Switch of (S)-Metolachlor: A Personal Account of an Industrial Odyssey in Asymmetric Catalysis". Advanced Synthesis and Catalysis. 344: 17–31. doi:10.1002/1615-4169(200201)344:1<17::AID-ADSC17>3.0.CO;2-8.
  5. ^ Pothuluri, J.V., Evans, F.E., Doerge, D.R., Churchwell, M.I.,Cerniglia, C.E. (1997). "Metabolism of metolachlor by the fungus Cunninghamella elegans". Arch. Environ. Contam. Toxicol. 32 (2): 117–125. doi:10.1007/s002449900163. PMID 9069185. S2CID 20614148.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ USEPA,1987. Metolachlor Pesticide Registration Standard. Springfield, IL: Natl. Tech. Info. Serv.
  7. ^ Rollof, B., Belluck, D., Meiser, L. (1992). "Cytogenic effects of cyanazine and metolachlor on human lymphocytes exposed in vitro". Mutat. Res. Lett. 281 (4): 295–298. doi:10.1016/0165-7992(92)90024-C. PMID 1373225.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ Clements, C., Ralph, S.,Petras, M. (1997). "Genotoxicity of select herbicides on Rana catesbeiana tadpoles using alkaline single-cell gel DNA electrophoresis (Comet) assay". Env. Mol. Mut. 29 (3): 277–288. doi:10.1002/(SICI)1098-2280(1997)29:3<277::AID-EM8>3.0.CO;2-9. PMID 9142171. S2CID 27619855.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. ^ 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.
  10. ^ 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.
  • Metolachlor in the Pesticide Properties DataBase (PPDB)
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