Aminopyralid

Last updated
Aminopyralid [1]
Aminopyralid.svg
Aminopyralid-3D-spacefill.png
Names
Preferred IUPAC name
4-Amino-3,6-dichloropyridine-2-carboxylic acid
Other names
4-Amino-3,6-dichloropicolinic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.110.366 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H4Cl2N2O2/c7-3-1-2(9)4(8)5(10-3)6(11)12/h1H,(H2,9,10)(H,11,12) Yes check.svgY
    Key: NIXXQNOQHKNPEJ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H4Cl2N2O2/c7-3-1-2(9)4(8)5(10-3)6(11)12/h1H,(H2,9,10)(H,11,12)
    Key: NIXXQNOQHKNPEJ-UHFFFAOYAN
  • Clc1c(nc(Cl)cc1N)C(=O)O
Properties
C6H4Cl2N2O2
Molar mass 207.01416 g/mole
AppearanceOff-white powder
Density 1.72 (20°C, relative to water at 4°C)
Melting point 161.75 to 165.23 °C (323.15 to 329.41 °F; 434.90 to 438.38 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Aminopyralid is a selective herbicide used for control of broadleaf weeds, especially thistles and clovers. It is in the picolinic acid family of herbicides, which also includes clopyralid, picloram, triclopyr, and several less common herbicides. [2] [3] It was first registered for use in 2005, in the USA under the brand name "Milestone" [4] and later under various names starting with "Grazon". [5] In the UK it is sold under the brand names Banish, Forefront, Halcyon, Pharaoh, Pro-Banish, Runway, Synero, and Upfront.

Aminopyralid is of concern to vegetable growers, as it can enter the food chain via manure, which contains long-lasting residues of the herbicide. It affects potatoes, tomatoes, and beans, causing deformed plants, and poor or non-existent yields. Problems with manure contaminated with aminopyralid residue surfaced in the UK in June and July 2008, and, at the end of July 2008, Dow AgroSciences implemented an immediate suspension of UK sales and use of herbicides containing aminopyralid. [6]

Tomato plant affected by aminopyralid herbicide residue from contaminated manure, grown July 2008, Cheshire, UK. Note tightly curled leaves, which is a symptom of aminopyralid contamination. Tomato plant affected by aminopyralid herbicide.jpg
Tomato plant affected by aminopyralid herbicide residue from contaminated manure, grown July 2008, Cheshire, UK. Note tightly curled leaves, which is a symptom of aminopyralid contamination.

Approval of aminopyralid was subsequently reinstated in the UK on October 6, 2009, as reported by the UK regulatory authority, the Advisory Committee on Pesticides. [7] The re-introduction was approved "with new recommendations and a stringent stewardship programme devised to prevent inadvertent movement of manure from farms". [8] :22

Despite restrictions, symptoms of aminopyralid damage were recorded on crops growing in allotments in Edinburgh, UK as recently as June 2010; enquiries traced the source of contamination to a farm supplying hay to the stables from where bags of manure had been obtained. Symptoms of aminopyralid injury to vegetable crops were reported by small farmers and gardeners in Britain in July 2011. [9]

Related Research Articles

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Good agricultural practice (GAP) is a certification system for agriculture, specifying procedures that must be implemented to create food for consumers or further processing that is safe and wholesome, using sustainable methods. While there are numerous competing definitions of what methods constitute good agricultural practice there are several broadly accepted schemes that producers can adhere too.

Clopyralid Chemical compound

Clopyralid is a selective herbicide used for control of broadleaf weeds, especially thistles and clovers. Clopyralid is in the picolinic acid family of herbicides, which also includes aminopyralid, picloram, triclopyr, and several less common herbicides. For control of creeping thistle, Cirsium arvense, a noxious, perennial weed, clopyralid is one of the few effective herbicides available. It is particularly damaging to peas, tomatoes, and sunflowers, and can render potatoes, lettuce, and spinach inedible. It does not affect grasses.

Chlorpyrifos Chemical compound

Chlorpyrifos (CPS), also known as Chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, and buildings, and in other settings, to kill a number of pests, including insects and worms. It acts on the nervous systems of insects by inhibiting the acetylcholinesterase enzyme. Chlorpyrifos was patented in 1966 by Dow Chemical Company.

Agrochemical Any chemical used in agriculture

An agrochemical or agrichemical, a contraction of agricultural chemical, is a chemical product used in agriculture. In most cases, agrichemical refers to pesticides including insecticides, herbicides, fungicides and nematicides. It may also include synthetic fertilizers, hormones and other chemical growth agents, and concentrated stores of raw animal manure.

Agricultural wastewater treatment Farm management for controlling pollution from confined animal operations and surface runoff

Agricultural wastewater treatment is a farm management agenda for controlling pollution from confined animal operations and from surface runoff that may be contaminated by chemicals in fertilizer, pesticides, animal slurry, crop residues or irrigation water. Agricultural wastewater treatment is required for continuous confined animal operations like milk and egg production. It may be performed in plants using mechanized treatment units similar to those used for industrial wastewater. Where land is available for ponds, settling basins and facultative lagoons may have lower operational costs for seasonal use conditions from breeding or harvest cycles. Animal slurries are usually treated by containment in anaerobic lagoons before disposal by spray or trickle application to grassland. Constructed wetlands are sometimes used to facilitate treatment of animal wastes.

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Diquat Chemical compound

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

Picloram Chemical compound

Picloram is a systemic herbicide used for general woody plant control. It also controls a wide range of broad-leaved weeds, but most grasses are resistant. A chlorinated derivative of picolinic acid, picloram is in the pyridine family of herbicides.

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Iprodione Chemical compound

Iprodione is a hydantoin fungicide and nematicide.

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A milestone is a marker of distance along roads.

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Propachlor Chemical compound

Propachlor (2-chloro-N-isopropylacetanilide) is an herbicide first marketed by Monsanto. It was registered for use in the United States during 1965.

Mesotrione Chemical compound used as an herbicide

Mesotrione is the ISO common name for an organic compound that is used as a selective herbicide, especially in maize. A synthetic inspired by the natural substance leptospermone, 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.

2,4-Dichlorophenoxyacetic acid Herbicide

2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula C8H6Cl2O3 which is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide which kills most broadleaf weeds by causing uncontrolled growth in them but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.

Aminocyclopyrachlor Chemical compound

Aminocyclopyrachlor is a selective, low-toxicity herbicide that provides pre- and post-emergent control of broadleaf weeds, woody species, vines and grasses on several non-food use sites, such as 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. This causes undifferentiated cell division and elongation.

The Enlist Weed Control System is an agricultural system that includes seeds for genetically modified crops that are resistant to Enlist and the Enlist herbicide; spraying the herbicide will kill weeds but not the resulting crop. The system was developed by Dow AgroSciences, part of Dow Chemical Company. In October 2014 the system was registered for restricted use in Illinois, Indiana, Iowa, Ohio, South Dakota and Wisconsin by the US Environmental Protection Agency. In 2013, the system was approved by Canada for the same uses.

Glyphosate-based herbicides are usually made of a glyphosate salt that is combined with other ingredients that are needed to stabilize the herbicide formula and allow penetration into plants. The glyphosate-based herbicide Roundup was first developed by Monsanto in the 1970s. It is used most heavily on corn, soy, and cotton crops that have been genetically modified to be resistant to the herbicide. Some products include two active ingredients, such as Enlist Duo which includes 2,4-D as well as glyphosate. As of 2010, more than 750 glyphosate products were on the market. The names of inert ingredients used in glyphosate formulations are usually not listed on the product labels.

References

  1. Aminopyralid - Compound Summary, PubChem.
  2. Staff, Virginia Tech Cooperative Extension. Revised May 14, 2012 Pyridine Herbicide Carryover: Causes and Precautions Archived 2016-11-30 at the Wayback Machine Accessed May 27, 2013
  3. Bob Hartzler, extension weed management specialist, Department of Agronomy, Iowa State University. February 21, 2006 Aminopyralid - New herbicide for pastures, roadsides, etc. Archived 2014-11-03 at the Wayback Machine Accessed May 27, 2013
  4. Milestone FAQ
  5. GrazonNext HL Herbicide Accessed 20190203 -- for other name variations, do a google search on Grazon and Aminopyralid.
  6. Statement from Dow AgroSciences regarding suspension of Aminopyralid products in the UK Archived September 8, 2008, at the Wayback Machine
  7. Staff, Advisory Committee on Pesticides Aminopyralid - New Approvals Accessed May 27, 2013
  8. Staff, FarmBusiness. October 23, 2009 AMINOPYRALID Aminopyralid Reapproved for Grassland Archived 2016-03-05 at the Wayback Machine
  9. 'George Monbiot for The Guardian. July 15, 2011. Have you spotted a strange curling disease in your home-grown veg?