Pendimethalin
This article has an unclear citation style. (October 2024) |
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Preferred IUPAC name
3,4-Dimethyl-2,6-dinitro-N-(pentan-3-yl)aniline | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.049.927 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
UN number | 3077 2588 |
CompTox Dashboard (EPA)
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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: | |
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).
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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 (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, nuts as well as lawns and ornamental plants.
Use
[edit]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]
There is some control of Johnsongrass, but other dinitrolaniline herbicides, such as trifluralin and profluralin, showed much stronger effect.[8]
Mode of action
[edit]Pendimethalin acts both pre-emergence, that is before weed seedlings have emerged, and early post-emergence. Pendimethalin inhibits root and shoot growth, which 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, also called group D (Australia) or group 3 (numeric).
Risk factor for developing pancreatic cancer
[edit]A study in the International Journal of Cancer suggests that Pendimethalin exposure is associated with higher incidence of pancreatic cancer.[9] Mechanistic studies linking Pendimethalin to pancreatic cancer are lacking, warranting additional research.
Resistance
[edit]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.[10] Lolium rigidum has evolved resistance to pendimethalin, at least in part due to increased cytochrome P450 activity.[2]
Registrative status
[edit]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
[edit]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.[11]
Tradenames
[edit]Tradenames include Pendimethalin 440, Satellite, Halts, Prowl, PRE-M, Stomp, Stealth and Pendulum, Hilpendi etc.
References
[edit]- ^ EXTOXNET
- ^ 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
- ^ 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.
- ^ Little J.: EU´s pesticide regulation must be challenged. In: FarmBusiness. 2009 S. 26–27.
- ^ 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.
- ^ 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.
- ^ Gehring, K.: Ackerfuchschwanz und Windhalm – die zwei bedeutendsten Ungräser im Getreidebau. In: Getreide Magazin. Nr. 1, 2009, S. 20-25.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "4Farmers Pendimethalin 440 Safety Sheet" (PDF). 4farmers.com.au. 4Farmers Australia.
External links
[edit]- Pendimethalin in the Pesticide Properties DataBase (PPDB)