Mecoprop: Difference between revisions

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Revision as of 23:32, 26 November 2012 editReo On (talk \| contribs)Extended confirmed users2,021 edits removed Category:Herbicides; added Category:Auxinic herbicide using HotCat ← Previous edit		Latest revision as of 23:26, 25 October 2023 edit undoBenjah-bmm27 (talk \| contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers14,702 edits added a ball-and-stick model of the molecule based on crystallography
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	{{chembox		{{chembox
		⚫	\| Reference =<ref>''Merck Index'', 11th Edition, '''5666'''.</ref>
	\| verifiedrevid = 431632775
			\| ImageFile =Mecoprop.svg
⚫	\|Reference=<ref>''Merck Index'', 11th Edition, '''5666'''.</ref>
		⚫	\| ImageSize =
	\|ImageFile=(±)-Mecoprop Enantiomers Formulae.png
		⚫	\| ImageFile1 = Mecoprop-racemic-dimer-from-xtal-labelled-3D-balls.png
⚫	\|ImageSize=~~250px~~
		⚫	\| IUPACName =(''RS'')-2-(4-Chloro-2-methylphenoxy)propanoic acid
⚫	\|ImageFile1 = Mecoprop-racemic-dimer-from-xtal-labelled-3D-balls.png
		⚫	\| OtherNames =
	\|ImageSize1=250px
		⚫	\|Section1={{Chembox Identifiers
⚫	\|IUPACName=(''RS'')-2-(4-~~chloro~~-2-methylphenoxy)propanoic acid
		⚫	\| CASNo =93-65-2
⚫	\|OtherNames=
		⚫	\| CASNo_Ref = {{cascite\|correct\|CAS}}
⚫	\|Section1= {{Chembox Identifiers
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
⚫	\| CASNo=93-65-2
			\| UNII = 74N8TKR9P8
⚫	\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| PubChem=7153		\| PubChem =7153
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
⚫	\| SMILES=CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O
			\| ChEMBL = 2145254
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = C18742		\| KEGG = C18742
			\| EINECS = 230-386-8
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID = 6886
		⚫	\| SMILES = CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O
			\| InChI = 1/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)
			\| InChIKey = WNTGYJSOUMFZEP-UHFFFAOYAN
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
			\| StdInChI = 1S/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
			\| StdInChIKey = WNTGYJSOUMFZEP-UHFFFAOYSA-N
			\| RTECS =
			\| MeSHName =
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
			\| ChEBI = 75704
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=10 \| H=11 \| Cl=1 \| O=3
	\| Formula=C<sub>10</sub>H<sub>11</sub>ClO<sub>3</sub>
			\| Appearance =Solid
	\| MolarMass=214.646
			\| Density =
	\| Appearance=Solid
			\| MeltingPtC = 94 to 95
	\| Density=
	\| ~~MeltingPt~~= ~~94–95 °C~~ <ref name="GESTIS">{{GESTIS\|ZVG=510276\|Name=Mecoprop\|Date=8 September 2008}}</ref>		\| MeltingPt_ref = <ref name="GESTIS">{{GESTIS\|ZVG=510276\|Name=Mecoprop\|Date=8 September 2008}}</ref>
	\| BoilingPt= decomposes <ref name="GESTIS"/>		\| BoilingPt = decomposes <ref name="GESTIS"/>
	\| ~~Solubility~~= 900 mg/l (20 °C) <ref name="GESTIS"/>		\| Solubility = 900 mg/L (20 °C)<ref name="GESTIS"/>
⚫	}}
⚫	\|Section3= {{Chembox Hazards
⚫	\| MainHazards= Xn, N <ref name="GESTIS"/>
	\| FlashPt=
	\| Autoignition=
	}}		}}
		⚫	\|Section3={{Chembox Hazards
		⚫	\| MainHazards = Xn, N <ref name="GESTIS"/>
			\| FlashPt =
			\| AutoignitionPt =
		⚫	}}
	}}		}}

	'''Mecoprop''', or methylchlorophenoxypropionic acid (MCPP), is a common general use ] found in many household weed killers and "weed-and-feed" type lawn fertilizers.<ref>{{~~HPD~~\|~~2529~~}}</ref> It is primarily used to control broadleaf weeds.<ref name="EXTOXNET"> at EXTOXNET</ref> It is often used in combination with other chemically related herbicides such as ], ], and ].		'''Mecoprop''' (also known as '''methylchlorophenoxypropionic acid''' and '''MCPP''') is a common general use ] found in many household weed killers and "weed-and-feed" type lawn fertilizers.<ref>{{CPID\|id=2083\|name=2-(2-Methyl-4-chlorophenoxy)propionic acid}}</ref> It is primarily used to control ].<ref name="EXTOXNET"> at EXTOXNET</ref> It is often used in combination with other chemically related herbicides such as ], ], and ], which mimic the plant hormone ] (auxin) and kill most broadleaf weeds by causing uncontrolled growth.

⚫	Mecoprop is a mixture of two ]s, with the (R)-(+)-] ("Mecoprop-P", "Duplosan KV") possessing the herbicidal activity<ref>{{ cite journal \| journal = Acta ~~Cryst~~. \| volume = ~~B36~~ \| issue = 4 \| ~~month~~ = April ~~\| year =~~ 1980 \| pages = 992–994 \| doi = 10.1107/S0567740880005134 \| title = (+-)-2-(4-Chloro-2-methylphenoxy)propionic acid (mecoprop) \| ~~author~~ = G. Smith, C. H. L. Kennard, A. H. White ~~and~~ P. G. Hodgson }}</ref>.

	The ] has classified mecoprop as toxicity class III - slightly toxic.<ref name="EXTOXNET"/>		The ] has classified mecoprop as toxicity class III - slightly toxic.<ref name="EXTOXNET"/>

		⚫	Mecoprop is a mixture of two ]s, with the (''R'')-(+)-] ("Mecoprop-P", "Duplosan KV") possessing the herbicidal activity.<ref>{{ cite journal \| journal = Acta Crystallogr. B\| volume = 36 \| issue = 4 \|date=April 1980 \| pages = 992–994 \| doi = 10.1107/S0567740880005134 \| title = (±)-2-(4-Chloro-2-methylphenoxy)propionic acid (mecoprop) \|author1=G. Smith \|author2=C. H. L. Kennard \|author3=A. H. White \|author4=P. G. Hodgson }}</ref>

			]

	== See also ==		== See also ==
	* ]		* ]
	* ]		* ]

	== References ==		== References ==
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	== External links ==		== External links ==
	*		*
			* {{PPDB\|430\|Name=Mecoprop}}
	*
			* {{PPDB\|431\|Name=Mecoprop-P}}
	*
			{{Herbicides}}
	*
		⚫	]

	]		]
	]
	]		]
⚫	]

	]
	]
	]

Latest revision as of 23:26, 25 October 2023

Mecoprop
Names


IUPAC name (RS)-2-(4-Chloro-2-methylphenoxy)propanoic acid
Identifiers
CAS Number	93-65-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75704
ChEMBL	ChEMBL2145254
ChemSpider	6886
ECHA InfoCard	100.002.060
EC Number	230-386-8
KEGG	C18742
PubChem CID	7153
UNII	74N8TKR9P8
CompTox Dashboard (EPA)	DTXSID9024194
InChI InChI=1S/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)Key: WNTGYJSOUMFZEP-UHFFFAOYSA-N InChI=1/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)Key: WNTGYJSOUMFZEP-UHFFFAOYAN
SMILES CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O
Properties
Chemical formula	C₁₀H₁₁ClO₃
Molar mass	214.65 g·mol
Appearance	Solid
Melting point	94 to 95 °C (201 to 203 °F; 367 to 368 K)
Boiling point	decomposes
Solubility in water	900 mg/L (20 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Xn, N
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Mecoprop (also known as methylchlorophenoxypropionic acid and MCPP) is a common general use herbicide found in many household weed killers and "weed-and-feed" type lawn fertilizers. It is primarily used to control broadleaf weeds. It is often used in combination with other chemically related herbicides such as 2,4-D, dicamba, and MCPA, which mimic the plant hormone IAA (auxin) and kill most broadleaf weeds by causing uncontrolled growth.

The United States Environmental Protection Agency has classified mecoprop as toxicity class III - slightly toxic.

Mecoprop is a mixture of two stereoisomers, with the (R)-(+)-enantiomer ("Mecoprop-P", "Duplosan KV") possessing the herbicidal activity.

References

Merck Index, 11th Edition, 5666.
^ Record of Mecoprop in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 8 September 2008.
2-(2-Methyl-4-chlorophenoxy)propionic acid in the Consumer Product Information Database
^ Mecoprop at EXTOXNET
G. Smith; C. H. L. Kennard; A. H. White; P. G. Hodgson (April 1980). "(±)-2-(4-Chloro-2-methylphenoxy)propionic acid (mecoprop)". Acta Crystallogr. B. 36 (4): 992–994. doi:10.1107/S0567740880005134.

External links

Mecoprop Pesticide Information Profile - Extension Toxicology Network
Mecoprop in the Pesticide Properties DataBase (PPDB)
Mecoprop-P in the Pesticide Properties DataBase (PPDB)

Pest control: herbicides

FOP herbicides	chlorazifop cyhalofop diclofop fenoxaprop fluazifop haloxyfop quizalofop
DIM herbicides	sethoxydim

Protox inhibitors

Nitrophenyl ethers	acifluorfen bifenox fluorodifen fomesafen lactofen nitrofen oxyfluorfen
Pyrimidinediones	butafenacil saflufenacil
Triazolinones	carfentrazone sulfentrazone

Pyridines

Quaternary

Photosystem I inhibitors	cyperquat diquat paraquat

Triazines

Photosystem II inhibitors	ametryn atrazine cyanazine hexazinone prometon prometryn propazine simazine simetryn terbuthylazine terbutryn metamitron

Ureas

Photosystem II inhibitors	chlortoluron DCMU difenoxuron isoproturon linuron monuron monolinuron tebuthiuron
ALS inhibitors	chlorsulfuron flazasulfuron metsulfuron-methyl sulfometuron methyl tribenuron

Others

Categories:

Latest revision as of 23:26, 25 October 2023

See also

References

External links