Pendimethalin

Last updated
Pendimethalin [1]
Pendimethalin v2.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 254-938-2
KEGG
PubChem CID
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 X mark.svgN
    Key: CHIFOSRWCNZCFN-UHFFFAOYSA-N X mark.svgN
  • 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:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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.

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

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

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

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

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

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

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

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

Related Research Articles

<span class="mw-page-title-main">Herbicide</span> Type of chemical used to kill unwanted plants

Herbicides, also commonly known as weed killers, are substances used to control undesired plants, also known as weeds. Selective herbicides control specific weed species while leaving the desired crop relatively unharmed, while non-selective herbicides kill plants indiscriminately. The combined effects of herbicides, nitrogen fertilizer, and improved cultivars has increased yields of major crops by three to six times from 1900 to 2000.

<span class="mw-page-title-main">Glyphosate</span> Systemic herbicide and crop desiccant

Glyphosate is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSP). It is used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. Its herbicidal effectiveness was discovered by Monsanto chemist John E. Franz in 1970. Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup. Monsanto's last commercially relevant United States patent expired in 2000.

<span class="mw-page-title-main">Paraquat</span> Chemical compound used as an herbicide

Paraquat (trivial name; ), or N,N′-dimethyl-4,4′-bipyridinium dichloride (systematic name), also known as methyl viologen, is a toxic organic compound with the chemical formula [(C6H7N)2]Cl2. It is classified as a viologen, a family of redox-active heterocycles of similar structure. This salt is one of the most widely used herbicides worldwide. It is quick-acting and non-selective, killing green plant tissue on contact.

<span class="mw-page-title-main">Alachlor</span> Chemical compound; herbicide

Alachlor is an herbicide from the chloroacetanilide family. It is an odorless, white solid. The greatest use of alachlor is for control of annual grasses and broadleaf weeds in crops. Use of alachlor is illegal in the European Union and no products containing alachlor are currently registered in the United States.

<span class="mw-page-title-main">Chlortoluron</span> Chemical compound

Chlortoluron, chlorotoluron and CTU are the common names for an organic compound of the phenylurea class of herbicides used to control broadleaf and annual grass weeds in cereal crops.

<span class="mw-page-title-main">Dicamba</span> Chemical compound used as herbicide

Dicamba is a selective systemic herbicide first registered in 1967. Brand names for formulations of this herbicide include Dianat, Banvel, Diablo, Oracle and Vanquish. This chemical compound is a chlorinated derivative of o-anisic acid. It has been described as a "widely used, low-cost, environmentally friendly herbicide that does not persist in soils and shows little or no toxicity to wildlife and humans."

<span class="mw-page-title-main">Trifluralin</span> Weed control herbicide

Trifluralin is a common pre-emergent selective herbicide, a dinitroaniline. With about 14 million pounds (6,400 t) used in the United States in 2001, and 3–7 million pounds (1,400–3,200 t) in 2012, it is one of the most widely used herbicides. Trifluralin is also used in Australia, and New Zealand, previously in the EU. Introduced in 1964, Trifluralin was the first organofluorine compound used as an agrochemical.

<span class="mw-page-title-main">Mesotrione</span> Chemical compound used as an herbicide

Mesotrione is a selective herbicide used mainly in maize crops. It is a synthetic compound inspired by the natural substance leptospermone found in the bottlebrush tree Callistemon citrinus. It inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Callisto and Tenacity. It was first marketed by Syngenta in 2001.

<span class="mw-page-title-main">Benfluralin</span> Chemical compound

Benfluralin is an herbicide of the dinitroaniline class. The mechanism of action of benfluralin involves pre-emergent inhibition of mitosis, root and shoot development, same as trifluralin, from which benfluralin was developed in 1963.

<span class="mw-page-title-main">Aminocyclopyrachlor</span> Chemical compound

Aminocyclopyrachlor (AMCP) is a selective, low-toxicity, auxin-mimicking herbicide that provides pre- and post-emergent control of broadleaf weeds on several non-food use sites including rights of way, wildlife management areas, recreational areas, turf/lawns, golf courses and sod farms. It was conditionally registered as Imprelis by DuPont in August 2010, and first used in Fall 2010. The chemical is a systemic herbicide and acts by disrupting gene expression. Aminocyclopyrachlor belongs to the pyrimidine carboxylic acid chemical family and mimics auxin which is a growth-regulating hormone in dicots including broadleaf terrestrial plants. This causes undifferentiated cell division and elongation, with resulting appearance characteristic of auxin herbicide damage such as leaf twisting and curling.

<span class="mw-page-title-main">Fluazifop</span> ACCase herbicide, fop, anti-grass

Fluazifop is the common name used by the ISO for an organic compound that is used as a selective herbicide. The active ingredient is the 2R enantiomer at its chiral centre and this material is known as fluazifop-P when used in that form. More commonly, it is sold as its butyl ester, fluazifop-P butyl with the brand name Fusilade.

<span class="mw-page-title-main">Indaziflam</span> Preemergent herbicide discovered in 2009

Indaziflam is a preemergent herbicide especially for grass control in tree and bush crops.

<span class="mw-page-title-main">Tribenuron</span> Chemical compound

Tribenuron in the form of tribenuron-methyl is a sulfonylurea herbicide. Its mode of action is the inhibition of acetolactate synthase, group 2 of the Herbicide Resistance Action Committee's classification scheme.

<span class="mw-page-title-main">Chlorsulfuron</span> ALS inhibitor herbicide

Chlorsulfuron is an ALS inhibitor herbicide, and is a sulfonylurea compound. It was discovered by George Levitt in February 1976 while working at DuPont, which was the patent assignee.

<span class="mw-page-title-main">Prosulfocarb</span> Weed control herbicide

Prosulfocarb is a pre-emergent herbicide used agriculturally in Australia, the EU, Japan, New Zealand,, Morocco and Iran, for control of annual ryegrass and toad rush in wheat and barley crops. It was introduced to the EU in 1988 and is rapidly growing in use, with sales increasing by over 500% in France since 2008.

The Herbicide Resistance Action Committee (HRAC) classifies herbicides by their mode of action (MoA) to provide a uniform way for farmers and growers to identify the agents they use and better manage pesticide resistance around the world. It is run by CropLife International in conjunction with the Weed Science Society of America (WSSA).

<span class="mw-page-title-main">Nitralin</span> Weed control herbicide

Nitralin is a selective pre-emergent dinitroaniline herbicide that is closely related to trifluralin, and released two years later in 1966. Today it is largely obsolete. It was used in the USA, France and Australia to control annual grasses and broad-leaved weeds, and was applied on vines, crops and turf.

<span class="mw-page-title-main">Profluralin</span> Chemical compound

Profluralin is a dinitroaniline herbicide used preëmergently to control annual grasses and broadleaf weeds, in cotton, soybeans, peanuts, sunflower, cabbage, cauliflower, tomato and others. Profluralin has largely fallen out of use. It rose out of the related, still in common use, trifluralin.

<span class="mw-page-title-main">Ethalfluralin</span> Weed control herbicide

Ethalfluralin is a herbicide. It is a preëmergent dinitroaniline developed from trifluralin, used to control annual grasses and broad-leaved weeds. It was synthesised in 1971, first sold in Turkey in 1975, the United States in 1983. It is used on soybeans, peanuts, potatoes, and as of 2023, is the first conventional herbicide the EPA permits on hemp, as ethalfluralin leaves no residue in the plant. Ethalfluralin is not used domestically.

<span class="mw-page-title-main">Dinitramine</span> Weed control herbicide

Dinitramine is a preëmergent dinitroaniline herbicide incorporated into soil to control weeds for months after. It is no longer approved in the U.S.A., and is not in the European Union, though in Iran it has been used to control annual grasses and broadleaf weeds in cotton and soybeans, as it was in the U.S. as of 1975, where it was also used on sunflower.

References

  1. EXTOXNET
  2. 1 2 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.
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  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.
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  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.
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