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Pendimethalin

Pendimethalin is an herbicide of the dinitroaniline class[2] used premergently and postemergently to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is a K1-group (in Australia group D, or numerically group 3) 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, and nuts, plus lawns and ornamental plants.

Pendimethalin[1]
Names
Preferred IUPAC name
3,4-Dimethyl-2,6-dinitro-N-(pentan-3-yl)aniline
Other names
  • penoxalin
  • phenoxalin
  • pendimethaline
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 ?)

Use

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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.

Where weed infestation is particularly bad, yield loss can render wheat production uneconomical.[3] Many other crops are grown in Europe that make a fraction of total agriculture. Herbicide options are limited for these minor crops, particularly in the vegetable sector.[4] Long-term field studies performed by the German government and institutions together with farmers call pendimethalin efficient for controlling blackgrass, regarding weed control efficacy, crop yield, treatment costs and environmental impact.[5][6][7]

There is some control of Johnsongrass, but other dinitrolaniline herbicides, such as trifluralin and profluralin, showed much stronger effect.[8]

In 2012, 6–12 million pounds (2,700–5,400 t) of pendimethalin was used in the US.[9]

Mode of action

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Pendimethalin acts in both pre-weed-emergence and early post-emergence. Pendimethalin is absorbed into roots and shoots, inhibits cell division and prevents growth,[10] to prevent weeds from emerging, particularly during the 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, also called group D (Australia) or group 3 (numeric).

Risk factor for developing pancreatic cancer

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A study in the International Journal of Cancer suggests that Pendimethalin exposure is associated with higher incidence of pancreatic cancer.[11] Mechanistic studies linking Pendimethalin to pancreatic cancer are lacking, warranting additional research. A French study found no association with lung cancer.[12]

Pendimethalin exposure can reduce apoptosis.[13]

Resistance

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Herbicide resistance increases production costs and limits herbicide options, cultivations and rotations. Up to 2009 pendimethalin did not show resistance. It is not cross-resistant with other grass weed herbicides. So pendimethalin supports other supplementary grass weed herbicides using other modes of action.[14] Lolium rigidum has evolved resistance to pendimethalin, at least in part due to increased cytochrome P450 activity.[2] This resistance mechanism in ryegrass (shared with other dinitroanilines like trifluralin, see for longer explanation) is by an opposing mutation to resistance to prosulfocarb, a thiocarbamate herbicide. By evolving resistance to one, the weed devolves its resistance to the other.[15]

Registrative status

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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.

Toxicology

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Pendimethalin is not toxic to mammals, though interestingly the oral LD50 for rats and mice is 1050-1620 mg/kg, yet for dogs and rabbits it is much less harmful, at over 5000 mg/kg. For comparison, table salt's LD50 is 3000 mg/kg. There may be chronic effects however; repeated or prolonged skin exposure may cause eczema, hives or Quincke's oedema. Prolonged exposure by other routes may affect changes to the liver.[16]

Soil behavior

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Pendimethalin is highly persistent in soil and water. It has high potential for bioaccumulation, and it is moderately mobile in soil,[17] despite it adsorbing strongly into soil.[18]

Tradenames

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Tradenames include Pendimethalin 440, Satellite, Halts, Prowl, PRE-M, Stomp, Stealth and Pendulum, Hilpendi etc.

References

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  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. ^ Jordan, T. N.; Baker, R. S.; Barrentine, W. L. (1978). "Comparative Toxicity of Several Dinitroaniline Herbicides". Weed Science. 26 (1): 72–75. doi:10.1017/S0043174500032707.
  9. ^ US EPA, OCSPP (29 October 2015). "Pesticides Industry Sales and Usage 2008 - 2012 Market Estimates". www.epa.gov.
  10. ^ "4Farmers Pendimethalin 440 EC Infosheet" (PDF). 4farmers.com.au. 4Farmers Australia Pty Ltd.
  11. ^ 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.
  12. ^ Boulanger, Mathilde; Tual, Séverine; Lemarchand, Clémentine; Baldi, Isabelle; Clin, Bénédicte; Lebailly, Pierre (August 2017). "0441 Exposure to dinitroanilines and risk of lung cancer (Lc) by subtypes: Results from the agrican cohort". Occupational & Environmental Medicine. 74 (Suppl 1): A140.1. doi:10.1136/oemed-2017-104636.365.
  13. ^ Sarıgöl Kılıç, Zehra; Ündeğer Bucurgat, Ülkü (2018). "The Apoptotic and Anti-Apoptotic Effects of Pendimethalin and Trifluralin on A549 Cells In Vitro". The Turkish Journal of Pharmaceutical Sciences. 15 (3): 364–369. doi:10.4274/tjps.94695. PMC 7227839. PMID 32454683.
  14. ^ 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.
  15. ^ Chen, Jinyi; Yu, Qin; Patterson, Eric; Sayer, Chad; Powles, Stephen (25 March 2021). "Dinitroaniline Herbicide Resistance and Mechanisms in Weeds". Frontiers in Plant Science. 12. doi:10.3389/fpls.2021.634018. PMC 8027333. PMID 33841462.
  16. ^ "4Farmers Pendimethalin 440 Safety Sheet" (PDF). 4farmers.com.au. 4Farmers Australia.
  17. ^ "4Farmers Pendimethalin 440 EC Leaflet" (PDF). 4farmers.com.au. 4Farmers Australia Pty Ltd.
  18. ^ "PRE-EMERGENT HERBICIDES FACT SHEET" (PDF). Grains Research and Development Corporation. 2022.
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