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Aminocyclopyrachlor

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Aminocyclopyrachlor
Names
Preferred IUPAC name
6-Amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.121.525 Edit this at Wikidata
UNII
  • C1CC1C2=NC(=C(C(=N2)N)Cl)C(=O)O
Properties
C8H8ClN3O2
Molar mass 213.62 g·mol−1
Appearance Brown liquid[2]
Density 1.134 g/ml
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, and first used in Fall 2010.[3] 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.[4] This causes undifferentiated cell division and elongation, with resulting appearance characteristic of auxin herbicide damage such as leaf twisting and curling.[5][6]

Although auxin-mimicing 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.[3] [7]

Tomato plants are the preeminent bioassay platform for testing auxin herbicide damage because they are extremely sensitive to it.[8][9] 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.[10]

As with aminopyralid, AMCP-contaminated soil, mulch, or compost should be excluded from sensitive crops or gardens. 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.[11] More recently, the time required for 90% degradation (DT90) was found to be 622 to 921 days.[12] As a practical matter, all material in AMCP-treated areas should be regarded as permanently poisonous to tomatoes and other nightshades until proven safe.

References

[edit]
  1. ^ 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. doi:10.1614/ws-09-086.1. S2CID 28050305.
  2. ^ "MSDS" (PDF). Archived from the original (PDF) on May 10, 2011. Retrieved June 15, 2012.
  3. ^ a b United States EPA
  4. ^ AMINOCYCLOPYRACHLOR 3–42 JMPR 2014 https://apps.who.int/pesticide-residues-jmpr-database/Document/222
  5. ^ https://herbicidesymptoms.ipm.ucanr.edu/MOA/Synthetic_Auxins/
  6. ^ "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.
  7. ^ https://web.archive.org/web/20140108225248/https://www.epa.gov/pesticides/regulating/imprelis.html
  8. ^ 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
  9. ^ , 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
  10. ^ 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
  11. ^ 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
  12. ^ 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
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