Pendimethalin: Difference between revisions

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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII').
 
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{{chembox
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 431582962
| verifiedrevid = 444042332
| Reference = <ref>[http://pmep.cce.cornell.edu/profiles/extoxnet/metiram-propoxur/pendimethalin-ext.html EXTOXNET]</ref>
| Reference = <ref>[http://pmep.cce.cornell.edu/profiles/extoxnet/metiram-propoxur/pendimethalin-ext.html EXTOXNET]</ref>
| ImageFile = pendimethalin.png
| ImageFile = pendimethalin v2.svg
| ImageSize =
| ImageSize =
| IUPACName = 3,4-Dimethyl-2,6-dinitro-''N''-pentan-3-yl-aniline
| PIN = 3,4-Dimethyl-2,6-dinitro-''N''-(pentan-3-yl)aniline
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 40487-42-1
| CASNo = 40487-42-1
| PubChem = 38479
| PubChem = 38479
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11019
| KEGG = C11019
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫
| UNII = VL6L14C06U
| ChEBI = 83569
⚫
| SMILES = CCC(CC)NC1=C(C=C(C(=C1[N+](=O)[O-])C)C)[N+](=O)[O-]
| UNII_Ref = {{fdacite|correct|FDA}}
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}}
⚫
| UNII = VL6L14C06U
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| Section2 = {{Chembox Properties
| UNNumber = 3077 2588
⚫
| C=13|H=19|N=3|O=4
⚫
| SMILES = CCC(CC)Nc1c([N+](=O)[O-])cc(C)c(C)c1[N+](=O)[O-]
⚫
| Appearance =
| EINECS = 254-938-2
⚫
| Density = 1.17 g/cm³
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| MeltingPt = 47-58 °C
| BoilingPtC = 330
| ChemSpiderID = 35265
| InChI = 1/C13H19N3O4/c1-5-10(6-2)14-12-11(15(17)18)7-8(3)9(4)13(12)16(19)20/h7,10,14H,5-6H2,1-4H3
⚫
| Solubility = 0.275 ppm
| InChIKey = CHIFOSRWCNZCFN-UHFFFAOYAS
⚫
}}
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫
| Section3 = {{Chembox Hazards
| StdInChI = 1S/C13H19N3O4/c1-5-10(6-2)14-12-11(15(17)18)7-8(3)9(4)13(12)16(19)20/h7,10,14H,5-6H2,1-4H3
| MainHazards =
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫
| FlashPt =
| StdInChIKey = CHIFOSRWCNZCFN-UHFFFAOYSA-N
| Autoignition =
}}
}}
⚫
|Section2={{Chembox Properties
⚫
| C=13 | H=19 | N=3 | O=4
⚫
| Appearance =
⚫
| Density = 1.17 g/cm<sup>3</sup>
| MeltingPtC = 47 to 58
| MeltingPt_notes =
| BoilingPtC = 330
⚫
| Solubility = 0.275 ppm
⚫
}}
⚫
|Section7={{Chembox Hazards
| NFPA-H =
| NFPA-F =
| NFPA-R =
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|317|410}}
| PPhrases = {{P-phrases|261|272|273|280|302+352|321|333+313|363|391|501}}
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| FlashPt =
| AutoignitionPt =
⚫
}}
}}
}}


'''Pendimethalin''' is an [[herbicide]] used in premergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is listed in the K1-group according to the HRAC classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals (wheat, barley, rye, triticale), corn, soybeans, rice, potato, legumes, fruits, vegetables, nuts as well as lawns and ornamental plants.
'''Pendimethalin''' is an [[herbicide]] of the [[dinitroaniline]] class<ref name="Powles-Yu-2010">{{cite journal | last1=Powles | first1=Stephen B. | last2=Yu | first2=Qin | title=Evolution in Action: Plants Resistant to Herbicides | journal=[[Annual Review of Plant Biology]] | publisher=[[Annual Reviews (publisher)|Annual Reviews]] | volume=61 | issue=1 | date=2010-06-02 | issn=1543-5008 | doi=10.1146/annurev-arplant-042809-112119 | pages=317–347| pmid=20192743 }} p.{{nbs}}328</ref> used in premergence and postemergence applications to control annual grasses and certain [[broadleaf weeds]]. It inhibits cell division and cell elongation. Pendimethalin is listed in the K1-group according to the [[Herbicide Resistance Action Committee]] (HRAC) classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals (wheat, barley, rye, triticale), corn, soybeans, rice, potato, legumes, fruits, vegetables, nuts as well as lawns and ornamental plants.


==Use==
==Use==
Pendimethalin protects crops like wheat, corn, soybeans potatoes, cabbage, peas, carrots and asparagus. It is used to control annual grasses and certain broadleaf weeds which interfere with growth, development, yield and quality of agricultural and horticultural crops by competing on nutrients, water and light.
Pendimethalin protects crops like wheat, corn, soybeans, potatoes, cabbage, peas, carrots, and asparagus. It is used to control annual grasses and certain broadleaf weeds which interfere with growth, development, yield and quality of agricultural and horticultural crops by competing on nutrients, water and light.


In areas where weed infestation is particularly high, yield losses can render wheat production economically unviable.<ref>Clarke, Wynn, Twinning, Berry, Cook, Ellis and Gladders Pesticide availability for cereals and oilseeds following revision of Directive 91/414/EEC; effects of losses and new research priorities.'' In: HGCA Research Review.'' Nr. 70, 2009.</ref> In addition to wheat, a large number of crops are grown in Europe that are a relatively small percentage of total agricultural output. Herbicide options are limited for these minor crops, with few effective herbicides available in the vegetable sector.<ref>Little J.: '' EU´s pesticide regulation must be challenged.'' In: '' FarmBusiness.'' 2009 S. 26–27.</ref> Long-term field studies performed in Germany by governmental research and advisory institutes together with farmers rank Pendimethalin as an efficient herbicide to control blackgrass, regarding to weed control efficacy, crop yield, treatment costs and environmental impact.<ref>Gehring, K. and S. Thyssen: ''Unkrautmanagement im Getreidebau – Herbizid-Leistungszahl – eine mehrfaktorielle Bewertung von Herbizidbehandlungen. LFL Pflanzenschutz. Institut für Pflanzenschutz der Bayerischen Landesanstalt für Landwirtschaft.'' In: '' Freising-Weihestephan, Deutschland.'' 2004.</ref><ref>Gehring, K. and S. Thyssen: ''Unkrautmanagement im Getreidebau – Herbizid-Leistungszahl – eine mehrfaktorielle Bewertung von Herbizidbehandlungen. LFL Pflanzenschutz. Institut für Pflanzenschutz der Bayerischen Landesanstalt für Landwirtschaft.'' In: '' Freising-Weihestephan, Deutschland.'' 2007.</ref><ref>Gehring, K.: '' Ackerfuchschwanz und Windhalm – die zwei bedeutendsten Ungräser im Getreidebau.'' In: '' Getreide Magazin.'' Nr. 1, 2009, S. 20-25.</ref>
In areas where weed infestation is particularly high, yield losses can render wheat production economically unviable.<ref>Clarke, Wynn, Twinning, Berry, Cook, Ellis and Gladders Pesticide availability for cereals and oilseeds following revision of Directive 91/414/EEC; effects of losses and new research priorities.'' In: HGCA Research Review.'' Nr. 70, 2009.</ref> In addition to wheat, a large number of crops are grown in Europe that are a relatively small percentage of total agricultural output. Herbicide options are limited for these minor crops, with few effective herbicides available in the vegetable sector.<ref>Little J.: '' EU´s pesticide regulation must be challenged.'' In: '' FarmBusiness.'' 2009 S. 26–27.</ref> Long-term field studies performed in Germany by governmental research and advisory institutes together with farmers rank Pendimethalin as an efficient herbicide to control blackgrass, regarding to weed control efficacy, crop yield, treatment costs and environmental impact.<ref>Gehring, K. and S. Thyssen: ''Unkrautmanagement im Getreidebau – Herbizid-Leistungszahl – eine mehrfaktorielle Bewertung von Herbizidbehandlungen. LFL Pflanzenschutz. Institut für Pflanzenschutz der Bayerischen Landesanstalt für Landwirtschaft.'' In: '' Freising-Weihestephan, Deutschland.'' 2004.</ref><ref>Gehring, K. and S. Thyssen: ''Unkrautmanagement im Getreidebau – Herbizid-Leistungszahl – eine mehrfaktorielle Bewertung von Herbizidbehandlungen. LFL Pflanzenschutz. Institut für Pflanzenschutz der Bayerischen Landesanstalt für Landwirtschaft.'' In: '' Freising-Weihestephan, Deutschland.'' 2007.</ref><ref>Gehring, K.: '' Ackerfuchschwanz und Windhalm – die zwei bedeutendsten Ungräser im Getreidebau.'' In: '' Getreide Magazin.'' Nr. 1, 2009, S. 20-25.</ref>


==Mode of Action==
==Mode of action==
Pendimethalin acts both pre-emergence, that is before weed seedlings have emerged, and early post-emergence. Pendimethalin inhibits root and shoot growth. It controls the weed population and prevents weeds from emerging, particularly during the crucial development phase of the crop. Its primary [[mode of action]] is to prevent plant cell division and elongation in susceptible species. In the HRAC classification of herbicides according their mode of action, pendimethalin is listed in group K1.
Pendimethalin acts both pre-emergence, that is before weed seedlings have emerged, and early post-emergence. Pendimethalin inhibits root and shoot growth. It controls the weed population and prevents weeds from emerging, particularly during the crucial development phase of the crop. Its primary [[mode of action]] is to prevent plant cell division and elongation in susceptible species. In the [[Herbicide Resistance Action Committee|HRAC]] classification of herbicides according their mode of action, pendimethalin is listed in group K1.


== Risk factor for developing pancreatic cancer ==
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==Resistance==
In a study, published in the ''International Journal of Cancer'', it has been suggested that Pendimethalin exposure is associated with higher incidence of [[pancreatic cancer]].<ref name=":0">{{Cite journal |last1=Andreotti |first1=Gabriella |last2=Freeman |first2=Laura E. Beane |author-link2=Laura Beane Freeman |last3=Hou |first3=Lifang |last4=Coble |first4=Joseph |last5=Rusiecki |first5=Jennifer |last6=Hoppin |first6=Jane A. |last7=Silverman |first7=Debra T. |last8=Alavanja |first8=Michael C. R. |date=2009-05-15 |title=Agricultural pesticide use and pancreatic cancer risk in the Agricultural Health Study Cohort |journal=International Journal of Cancer |volume=124 |issue=10 |pages=2495–2500 |doi=10.1002/ijc.24185 |issn=1097-0215 |pmc=2674312 |pmid=19142867}}</ref> Mechanistic studies linking Pendimethalin exposure to higher incidence of pancreatic cancer are however still lacking, warranting for additional studies.
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Herbicide [[Pesticide resistance|resistance]] typically increases production costs and limits options for herbicide selection, cultivations and rotations. Up to now Pendimethalin does not show resistance. It is not cross-resistant with other grass weed herbicides. This means that Pendimethalin supports the effects of other supplementary grass weed herbicides that use a different mode of action.<ref>Moss, S. R. and R. Hull: '' The value of pre-emergence herbicides for combating herbicide-resistant Alopecurus myosuroides (blackgrass).'' In: '' Aspects of Applied Biology.'' Nr. 91, 2009.</ref>

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== Resistance ==
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Herbicide [[Pesticide resistance|resistance]] typically increases production costs and limits options for herbicide selection, cultivations and rotations. Up to 2009 Pendimethalin did not show resistance. It is not cross-resistant with other grass weed herbicides. This means that Pendimethalin supports the effects of other supplementary grass weed herbicides that use a different mode of action.<ref>Moss, S. R. and R. Hull: '' The value of pre-emergence herbicides for combating herbicide-resistant Alopecurus myosuroides (blackgrass).'' In: '' Aspects of Applied Biology.'' Nr. 91, 2009.</ref> ''[[Lolium rigidum]]'' has evolved [[herbicide resistance|resistance]] to pendimethalin, at least in part due to increased [[cytochrome P450]] activity.<ref name="Powles-Yu-2010" />


==Registrative status==
==Registrative status==
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==Tradenames==
==Tradenames==
Tradenames include Prowl, Stomp, and Pendulum.
Tradenames include Satellite, Halts, Prowl, PRE-M, Stomp, Stealth and Pendulum, Hilpendi etc.


==References==
==References==
{{Reflist}}
{{Reflist}}

==External links ==
* {{PPDB|511}}


{{Herbicides}}
{{Herbicides}}


[[Category:Anilines]]
[[Category:Anilines]]
[[Category:Nitrobenzenes]]
[[Category:Nitrobenzene derivatives]]
[[Category:Endocrine disruptors]]
[[Category:Endocrine disruptors]]
[[Category:Preemergent herbicides]]
[[Category:Preemergent herbicides]]
[[Category:Alkyl-substituted benzenes]]

[[Category:Secondary amines]]
[[fr:Pendiméthaline]]
[[nl:Pendimethalin]]
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