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

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.

<span class="mw-page-title-main">Clopyralid</span> 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.

<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">Chlorpyrifos</span> 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 several 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.

<span class="mw-page-title-main">Agricultural wastewater treatment</span> 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.

<span class="mw-page-title-main">Syngenta</span> Global provider of agricultural science and technology

Syngenta is a global agricultural technology company headquartered in Basel, Switzerland. It primarily covers crop protection and seeds for farmers. Syngenta is part of the Syngenta Group, entirely owned by Sinochem, a Chinese state-owned enterprise.

<span class="mw-page-title-main">Diquat</span> 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.

<span class="mw-page-title-main">Picloram</span> 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.

Pesticide residue refers to the pesticides that may remain on or in food, after they are applied to food crops. The maximum allowable levels of these residues in foods are stipulated by regulatory bodies in many countries. Regulations such as pre-harvest intervals also prevent harvest of crop or livestock products if recently treated in order to allow residue concentrations to decrease over time to safe levels before harvest.

<span class="mw-page-title-main">Pioneer Hi Bred International</span> American producer of hybrid seeds for agriculture

Pioneer Hi-Bred International, Inc. is a U.S.-based producer of seeds for agriculture. They are a major producer of genetically modified crops with insect and herbicide resistance.

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

Iprodione is a hydantoin fungicide and nematicide.

Dow AgroSciences LLC was a wholly owned subsidiary of the Dow Chemical Company specializing in not only agricultural chemicals such as pesticides, but also seeds and biotechnology solutions. The company was based in Indianapolis, Indiana, in the United States. On 31 January 2006, Dow AgroSciences announced that it had received regulatory approval for the world's first plant-cell-produced vaccine against Newcastle disease virus from USDA Center for Veterinary Biologics. Dow AgroSciences operates brand names such as Sentricon, Vikane, Mycogen®, SmartStax®, Enlist™, Pfister Seed®, PhytoGen®, Prairie Brand Seed®, Alforex Seeds®, Profume, Dairyland Seed®, and Brodbeck Seed®.

<span class="mw-page-title-main">Environmental impact of pesticides</span> Environmental effect

The environmental effects of pesticides describe the broad series of consequences of using pesticides. The unintended consequences of pesticides is one of the main drivers of the negative impact of modern industrial agriculture on the environment. Pesticides, because they are toxic chemicals meant to kill pest species, can affect non-target species, such as plants, animals and humans. Over 98% of sprayed insecticides and 95% of herbicides reach a destination other than their target species, because they are sprayed or spread across entire agricultural fields. Other agrochemicals, such as fertilizers, can also have negative effects on the environment.

<span class="mw-page-title-main">Propachlor</span> 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.

Dimethyl tetrachloroterephthalate (DCPA, with the main trade name Dacthal) is an organic compound with the formula C6Cl4(CO2CH3)2. It is the dimethyl ester of tetrachloroterephthalic acid, used as a preemergent herbicide with the ISO common name chlorthal-dimethyl. It kills annual grasses and many common weeds without killing sensitive plants such as turf grasses, flowers, fruits, vegetables, and cotton.

<span class="mw-page-title-main">2,4-Dichlorophenoxyacetic acid</span> Herbicide

2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula Cl2C6H3OCH2CO2H. It is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide that kills most broadleaf weeds by causing uncontrolled growth, but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.

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

Bifenox is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis.

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.

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

Cyproconazole is an agricultural fungicide of the class of azoles, used on cereal crops, coffee, sugar beet, fruit trees and grapes, and peanuts, on sod farms and golf course turf and on wood as a preservative. It has been used against powdery mildew, rust on cereals and apple scab, and applied by air or on the ground or by chemigation.

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

Aclonifen is a diphenyl ether herbicide which has been used in agriculture since the 1980s. Its mode of action has been uncertain, with evidence suggesting it might interfere with carotenoid biosynthesis or inhibit the enzyme protoporphyrinogen oxidase (PPO). Both mechanisms could result in the observed whole-plant effect of bleaching and the compound includes chemical features that are known to result in PPO effects, as seen with acifluorfen, for example. In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting solanesyl diphosphate synthase which would also cause bleaching.

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?