Jump to content

Aminocyclopyrachlor

From Wikipedia, the free encyclopedia
Aminocyclopyrachlor
Image
Names
IUPAC name
6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylic acid
Other names
  • KJM44[1]
  • DPX-KJM44
  • MAT-28[2]
  • 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.121.525 Edit this at Wikidata
EC Number
  • 617-769-9
UNII
  • InChI=1S/C8H8ClN3O2/c9-4-5(8(13)14)11-7(3-1-2-3)12-6(4)10/h3H,1-2H2,(H,13,14)(H2,10,11,12)
    Key: KWAIHLIXESXTJL-UHFFFAOYSA-N
  • C1CC1C2=NC(=C(C(=N2)N)Cl)C(=O)O
Properties
C8H8ClN3O2
Molar mass 213.62 g·mol−1
Appearance white amorphous solid[4]
Density 1.47 kg/L[4]
Melting point 140 °C (284 °F; 413 K) [4]
2.81 g/L[4]
Solubility in methanol 36.7g/L[4]
Vapor pressure 0.007 mPa[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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[5], and first used in Fall 2010,[6] though used experimentally since 2008 or before.[1] In 2014, DuPont settled with the United States Environmental Protection Agency (EPA) in response to reports of damage to trees after application of Imprelis.[7]

Chemical properties

[edit]

It has some solubility in water, 2.81 g/L, more so in methanol, 36.7 g/L, and is practically insoluble in acetone, 0.96 g/L, dichloromethane, 0.2 g/L, acetonitrile, 0.65 g/L and n-octanol, 1.9 g/L. The low vapor pressure and Henry's law constant suggest that it will not disperse through the air. A low octanol/water partition constant of -1.12 (Log Pow) indicates it be not bioaccumulative, and technical grade aminocyclopyrachor should be stable for at least 2 years in normal storage conditions.[4]

Aminocyclopyrachlor is not flammable, explosive or auto-flammable and except for photo-degradation, the pure aminocyclopyrachlor isn't chemically incompatible with oxidising or reducing agents and is essentially non-hazardous.[4]

Mechanism of action

[edit]

Aminocyclopyrachlor is a systemic herbicide and acts by disrupting gene expression. It belongs to the pyrimidine carboxylic acid chemical family and mimics auxin which is a growth-regulating hormone in dicots including broadleaf terrestrial plants.[8] This causes undifferentiated cell division and elongation, with resulting appearance characteristic of auxin herbicide damage such as leaf twisting and curling.[9][10]

This makes it a Group 4 herbicide, under the HRAC classification system.[4][11]

Use as an herbicide

[edit]

After the first introduction in 2010, aminocyclopyrachlor was registered as an active ingredient in Australia in September 2014, but no product containing it was registered until Bayer's "Method 240 SL" in 2022. Before this, aminocyclopyrachlor was registered in New Zealand. Method is a 240 g/L soluble concentrate (SL), with aminocyclopyrachlor present as its potassium salt.[4]

DuPont registered DuPont DPX-KJM44 0.02G Lawn Herbicide + Fertilizer, a formulation of 0.02% AMCP with fertilizer in 2010,[12] although they voluntarily withdrew the registration in 2014.[13]

It may be applied at 312 g/Ha (active ingredient) in 100-400 L/Ha of water.[4]

Imprelis

[edit]

Imprelis was the brand name of a formulation of aminocyclopyrachlor marketed by DuPont for use on lawn and turf applications in the United States. It was conditionally approved by the EPA in August 2010 [5] and was introduced to the market in October 2010.[14]

In August 2011, sales of Imprelis were suspended[15] as reports emerged of trees experiencing damage after application of Imprelis.[15] In the same month, the EPA issued a Stop Sale, Use or Removal Order[16][17] for Imprelis. In September 2011, its registration was amended[18] restricting its distribution and sale without the permission of the EPA.

The EPA registration for Imprelis expired in September 2014.[5]

Toxicology

[edit]

The human ADI is 2.8 mg/kg/day, (224 mg/day for an 80 kg adult) based on a NOEL of 297 mg/kg/d in a 2 year long study on rats.[4]

Non-target plant effects

[edit]

Although auxin-mimicking herbicides are selectively toxic to dicots, some angiosperms are also affected. Due to the emergence of damage to some conifer species, the United States Environmental Protection Agency and DuPont advised professional applicators and residential consumers to not use Imprelis where Norway spruce or white pine trees are present on or near the property being treated.[6]

Residue

[edit]

Tomato plants are the preeminent bioassay platform for testing auxin herbicide damage because they are extremely sensitive to it.[19][20] In a controlled greenhouse test, tomato plants were mulched with the remains of Norway spruce and honey locust trees that were damaged from exposure to AMCP that had been applied to adjacent turf grass more than a year prior to the tomato tests. The mulch (i.e. shredded foliage and stems) contained 4.7 to 276 ppb of AMCP. All of the AMCP-exposed tomato plants sustained visible damage while the unexposed controls showed no damage. Residual AMCP in the exposed tomato plants ranged from 0.5 to 8.0 ppb.[21]

Environmental fate

[edit]

As with aminopyralid, AMCP-contaminated soil, mulch, or compost should be excluded from sensitive crops or gardens. Plant material that has been treated with AMCP may not be used for mulch or compost.[22] The dissipation half-life (DT50) time of AMCP has been measured at between 3 and >112 days in four soils from the Northern Great Plains.[23] More recently, the time required for 90% degradation (DT90) was found to be 622 to 921 days,[24] although an APVMA report cites a half-life in normal air of 42 hours, implying a wildly shorter DT90.[4]

Litigation

[edit]

In July 2011, a class action lawsuit was filed alleging that DuPont failed to provide adequate warnings about the effects of Imprelis on non-target plants.[25][26] A settlement in the class action suit was preliminarily approved in February 2013[27] and was approved in October 2013.[28]

In September 2014, the EPA filed a Consent Agreement and Final Order (CAFO) against DuPont alleging violations of the Federal Insecticide, Fungicide, and Rodenticide Act relating to Imprelis.[7] The order alleges that the Imprelis label "...did not contain directions for use and/or warning or caution statements which were adequate to protect non-target terrestrial plants when used in accordance with the approved label."[29] It also alleges that DuPont failed to report the results of 18 field studies that demonstrated adverse effects on non-target plants.[29] DuPont paid $1.85 million dollars to settle the order.[30]

Tradenames

[edit]

Aminocyclopyrachlor has been sold as "DPX-KJM44",[12] "Aptexor",[31] "Imprelis",[5] "Method", "Perspective", "Streamline", "Invora", "Viewpoint", "Plainview", "Navius", "TruVist" and "TruRange".[4] This list may be incomplete.

References

[edit]
  1. 1 2 "Aminocyclopyrachlor (KJM44) Combinations for Total Vegetation and Marestail (Conyza canadensis) Control" (PDF). University of Kentucky. 2009. Retrieved 20 March 2026.
  2. ↑ Sellers, B.A.; Ferrell, J.A. (2010). "WEED CONTROL AND FORAGE TOLERANCE WITH MAT-28" (PDF). Southern Weed Science Societ. 63. Gainesville: epartment of Agronomy, University of Florida.
  3. Bekir Bukun; R. Bradley Lindenmayer; Scott J. Nissen; Philip Westra; Dale L. Shaner; Galen Brunk (March–April 2010). "Absorption and Translocation of Aminocyclopyrachlor and Aminocyclopyrachlor-Methyl Ester in Canada Thistle (Cirsium arvense)". Weed Science. 58 (2): 96–102. Bibcode:2010WeedS..58...96B. doi:10.1614/ws-09-086.1. S2CID 28050305.
  4. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 "Public Release Summary on the evaluation of aminocyclopyrachlor in the product Method 240 SL Herbicide" (PDF). www.apvma.gov.au. Sydney, Australia: Australian Pesticides and Veterinary Medicines Authority. August 2022.
  5. 1 2 3 4 "Details for DUPONT IMPRELIS HERBICIDE". United States Environmental Protection Agency. July 3, 2026. Retrieved July 3, 2026.
  6. 1 2 EPA. "Imprelis and Investigation of Damage to Trees". Archived from the original on January 8, 2014.
  7. 1 2 US EPA, OECA (September 15, 2014). "E.I. du Pont de Nemours and Company FIFRA Settlement". www.epa.gov. Archived from the original on February 19, 2026. Retrieved 2026-07-03.
  8. ↑ AMINOCYCLOPYRACHLOR 3–42 JMPR 2014 https://apps.who.int/pesticide-residues-jmpr-database/Document/222
  9. ↑ University of California, Division of Agriculture and Natural Resources. "Synthetic Auxins". herbicidesymptoms.ipm.ucanr.edu. Archived from the original on 2024-09-08. Retrieved 2025-11-19.
  10. ↑ "Registration of the New Active Ingredient Aminocyclopyrachlor for Use on Non-Crop Areas, Sod Farms, Turf, and Residential Lawns". U.S. Environmental Protection Agency, Office of Pesticide Programs, Registration Division. August 24, 2010. p. 4. Retrieved January 6, 2013.
  11. ↑ "2026 HRAC Global Herbicide MoA Classification". Herbicide Resistance Action Committee. Retrieved 2026-07-03.
  12. 1 2 "LABEL AND E.P.A. LETTER | DuPont KJM44 O.02G Lawn Herbicide + Fertilizer" (PDF). E.P.A. 27 Sep 2010. Retrieved 21 March 2026.
  13. ↑ "Notice of Receipt of Requests To Voluntarily Cancel Certain Pesticide Registrations". Federal Register. 20 May 2014. Retrieved 21 March 2026.
  14. ↑ "DuPont introduces Imprelis herbicide". www.golfcourseindustry.com. October 3, 2010. Retrieved 2026-07-03.
  15. 1 2 Chappell, Bill (August 5, 2011). "DuPont Pulls Herbicide Blamed For Tree Deaths". NPR. Archived from the original on September 16, 2025. Retrieved 2026-07-03.
  16. ↑ Sullivan, Dan (September 19, 2011). "EPA Bans Imprelis Herbicide". BioCycle. Archived from the original on March 11, 2026. Retrieved 2026-07-03.
  17. ↑ US EPA, OECA (May 9, 2013). "E. I. du Pont de Nemours and Company Imprelis Order". www.epa.gov. Retrieved 2026-07-03.
  18. ↑ US EPA (September 8, 2011). "EPA Reg. No. 352-793" (PDF). Archived from the original (PDF) on December 12, 2025. Retrieved July 3, 2026.
  19. ↑ Israel, T.D., Rhodes, G.N. Jr., Wszelaki, A. Diagnosing Suspected Off-target Herbicide Damage to tomato, University of Tennessee Extension publication W 295-B, https://utia.tennessee.edu/publications/wp-content/uploads/sites/269/2023/10/W295-B.pdf
  20. ↑ , Ramda, K., Boyd, N., McAvoy, C., Suppress the weeds, not the crop, Vegetable and Specialty Crop News March 2019, https://swfrec.ifas.ufl.edu/docs/pdf/weed-science/2019-03-Herbicides%20phytotoxicity_VSC.pdf
  21. ↑ Patton et al.: AMCP in wood chips of damaged trees, Weed Technology 2013 27:803–809, https://oisc.purdue.edu/pesticide/pdf/wt-d-13-00066-1.pdf
  22. ↑ "Method 240SL US Product Label" (PDF). Envu US. Archived from the original (PDF) on January 14, 2026.
  23. ↑ Conklin KL, Lym RG. Effect of Temperature and Moisture on Aminocyclopyrachlor Soil Half-Life. Weed Technology. 2013;27(3):552–556. doi:10.1614/WT-D-12-00147.1
  24. ↑ Takeshita, V., Mendes, K.F., Junqueira, L.V. et al. Quantification of the Fate of Aminocyclopyrachlor in Soil Amended with Organic Residues from a Sugarcane System, Sugar Tech (May–June 2020) 22(3):428–436 https://doi.org/10.1007/s12355-019-00782-1
  25. ↑ "Golf course company files suit against DuPont". www.golfcourseindustry.com. July 19, 2011. Retrieved 2026-07-03.
  26. ↑ Foster, Joanna M. (July 19, 2011). "DuPont Is Sued Over New Herbicide". Green Blog. Retrieved 2026-07-04.
  27. ↑ "Judge approves DuPont settlement of herbicide lawsuits". Reuters. Retrieved 2026-07-04.
  28. ↑ In Re: Imprelis Herbicide Marketing, Sales Practices and Products Liability Litigation (PDF) (Court case). United States District Court for the Eastern District of Pennsylvania. October 17, 2023.
  29. 1 2 United States Environmental Protection Agency (September 15, 2014). "Consent Agreement and Final Order: E.I. du Pont de Nemours and Company" (PDF). Archived from the original (PDF) on February 16, 2026. Retrieved July 3, 2026.
  30. ↑ "EPA Settles with DuPont over Violations of Federal Pesticide Laws that Led to Widespread Tree Deaths and Damage/ DuPont to pay $1,853,000 penalty to resolve alleged violations of pesticide reporting and distribution laws". www.epa.gov. September 15, 2014. Archived from the original on February 19, 2026. Retrieved 2026-07-04.
  31. ↑ United States Environmental Protection Agency. "Details for DPX-MAT28 AMINOCYCLOPYRACHLOR TECHNICAL". US EPA. Retrieved July 3, 2026.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=Aminocyclopyrachlor&oldid=1379600657"