Pendimethalin

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Pendimethalin[1]
Names
Preferred IUPAC name
3,4-Dimethyl-2,6-dinitro-N-(pentan-3-yl)aniline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.049.927 Edit this at Wikidata
EC Number
  • 254-938-2
KEGG
UNII
UN number 3077 2588
  • InChI=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 ☒N
    Key: CHIFOSRWCNZCFN-UHFFFAOYSA-N ☒N
  • 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
    Key: CHIFOSRWCNZCFN-UHFFFAOYAS
  • CCC(CC)Nc1c([N+](=O)[O-])cc(C)c(C)c1[N+](=O)[O-]
Properties
C13H19N3O4
Molar mass 281.312 g·mol−1
Density 1.17 g/cm3
Melting point 47 to 58 °C (117 to 136 °F; 320 to 331 K)
Boiling point 330 °C (626 °F; 603 K)
0.275 ppm
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H317, H410
P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, P501
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 ?)

Pendimethalin is an herbicide of the dinitroaniline class[2] 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

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.[3] 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.[4] 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.[5][6][7]

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.

Risk factor for developing pancreatic cancer

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.[8] Mechanistic studies linking Pendimethalin exposure to higher incidence of pancreatic cancer are however still lacking, warranting for additional studies.

Resistance

Herbicide 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.[9] Lolium rigidum has evolved resistance to pendimethalin, at least in part due to increased cytochrome P450 activity.[2]

Registrative status

Pendimethalin is registered globally for a wide range of crops, according to human and environmental safety standards by the European Commission, US-EPA, Canada-PMRA, Japan, Brazil-ANVISA and others.

Tradenames

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

References

  1. ^ EXTOXNET
  2. ^ a b Powles, Stephen B.; Yu, Qin (2010-06-02). "Evolution in Action: Plants Resistant to Herbicides". Annual Review of Plant Biology. 61 (1). Annual Reviews: 317–347. doi:10.1146/annurev-arplant-042809-112119. ISSN 1543-5008. PMID 20192743. p. 328
  3. ^ 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.
  4. ^ Little J.: EU´s pesticide regulation must be challenged. In: FarmBusiness. 2009 S. 26–27.
  5. ^ 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.
  6. ^ 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.
  7. ^ Gehring, K.: Ackerfuchschwanz und Windhalm – die zwei bedeutendsten Ungräser im Getreidebau. In: Getreide Magazin. Nr. 1, 2009, S. 20-25.
  8. ^ Andreotti, Gabriella; Freeman, Laura E. Beane; Hou, Lifang; Coble, Joseph; Rusiecki, Jennifer; Hoppin, Jane A.; Silverman, Debra T.; Alavanja, Michael C. R. (2009-05-15). "Agricultural pesticide use and pancreatic cancer risk in the Agricultural Health Study Cohort". International Journal of Cancer. 124 (10): 2495–2500. doi:10.1002/ijc.24185. ISSN 1097-0215. PMC 2674312. PMID 19142867.
  9. ^ 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.

External links

Retrieved from "https://mdwiki.org/wiki/Pendimethalin"