Aminocyclopyrachlor

Last updated
Aminocyclopyrachlor
Aminocyclopyrachlor.svg
Names
Preferred IUPAC name
6-Amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.121.525 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • C1CC1C2=NC(=C(C(=N2)N)Cl)C(=O)O
Properties
C8H8ClN3O2
Molar mass 213.62 g·mol−1
AppearanceBrown 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 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. [3] The chemical is a systemic herbicide and acts by disrupting gene expression. This causes undifferentiated cell division and elongation. [4]

Due to the possibility of damage to specific 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]

The impacts of aminocyclopyrachlor on garden plants, when found as a residue in mulch is commonly reported. It is a highly toxic Persistent Herbicide that will kill a tomato plant at a concentration of one part per billion, and impact many other garden plants also. And is often used as a herbicide for hay and straw producers, which makes it increasingly likely that horse manure and bedding will be contaminated with it.

Persistent herbicides are a narrow range of herbicides used to kill broad leaf weeds and thistle that compete with grasses and grain crops. They are "persistent" because they will not decompose under the high temperatures in thermophilic composting and may take over 2 years or more to fully decay.

There are 4 persistent herbicides:

Picloram - Sold as Graslan™, Grazon®, Surmount®, and Tordon® Clopyralid - Sold as Stinger® Aminopyralid - Sold as Capstone™, Chaparral™, CleanWave®, Forefront®, GrazonNext®, Milestone®, Opensight®, PasturAll®, and Sendero.™ Aminocyclopyrachlor - Sold as Imprelis® These herbicides are extremely potent, with maximum application rates of only 7-12 liquid ounces....per acre.......per year.

Related Research Articles

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are used as plant protection products, which in general protect plants from weeds, fungi, or insects. In general, a pesticide is a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or are disease vectors. Along with these benefits, pesticides also have drawbacks, such as potential toxicity to humans and other species.

<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 (sometimes called total weed killers kill plants indiscriminately. Due to herbicide resistance – a major concern in agriculture – a number of products combine herbicides with different means of action. Integrated pest management may use herbicides alongside other pest control methods.

<span class="mw-page-title-main">Weed control</span> Botanical component of pest control for plants

Weed control is a type of pest control, which attempts to stop or reduce growth of weeds, especially noxious weeds, with the aim of reducing their competition with desired flora and fauna including domesticated plants and livestock, and in natural settings preventing non native species competing with native species.

<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">Lawn</span> Area of land planted with grasses and similar plants

A lawn is an area of soil-covered land planted with grasses and other durable plants such as clover which are maintained at a short height with a lawn mower and used for aesthetic and recreational purposes—it is also commonly referred to as part of a garden. Lawns are usually composed only of grass species, subject to weed and pest control, maintained in a green color, and are regularly mowed to ensure an acceptable length. Lawns are used around houses, apartments, commercial buildings and offices. Many city parks also have large lawn areas. In recreational contexts, the specialised names turf, pitch, field or green may be used, depending on the sport and the continent.

<span class="mw-page-title-main">Sod</span> Upper layer of soil and grass

Sod, also known as turf, is the upper layer of soil with the grass growing on it that is often harvested into rolls.

<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.

<span class="mw-page-title-main">Glufosinate</span> Broad-spectrum herbicide

Glufosinate is a naturally occurring broad-spectrum herbicide produced by several species of Streptomyces soil bacteria. Glufosinate is a non-selective, contact herbicide, with some systemic action. Plants may also metabolize bialaphos and phosalacine, other naturally occurring herbicides, directly into glufosinate. The compound irreversibly inhibits glutamine synthetase, an enzyme necessary for the production of glutamine and for ammonia detoxification, giving it antibacterial, antifungal and herbicidal properties. Application of glufosinate to plants leads to reduced glutamine and elevated ammonia levels in tissues, halting photosynthesis and resulting in plant death.

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

Pendimethalin is an herbicide of the dinitroaniline class used in premergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is listed in the K1-group 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, corn, soybeans, rice, potato, legumes, fruits, vegetables, nuts as well as lawns and ornamental plants.

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

Fenoprop, also called 2,4,5-TP, is the organic compound 2-(2,4,5-trichlorophenoxy)propionic acid. It is a phenoxy herbicide and a plant growth regulator, an analog of 2,4,5-T in which the latter's acetic acid sidechain is replaced with a propionate group (with an extra CH3). The addition of this extra methyl group creates a chiral centre in the molecule and useful biological activity is found only in the (2R)-isomer. The compound's mechanism of action is to mimic the auxin growth hormone indoleacetic acid (IAA). When sprayed on plants it induces rapid, uncontrolled growth. As with 2,4,5-T, fenoprop is toxic to shrubs and trees.

<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.

<span class="mw-page-title-main">Weed</span> Plant considered undesirable in a particular place or situation

A weed is a plant considered undesirable in a particular situation, growing where it conflicts with human preferences, needs, or goals. Plants with characteristics that make them hazardous, aesthetically unappealing, difficult to control in managed environments, or otherwise unwanted in farm land, orchards, gardens, lawns, parks, recreational spaces, residential and industrial areas, may all be considered weeds. The concept of weeds is particularly significant in agriculture, where the presence of weeds in fields used to grow crops may cause major losses in yields. Invasive species, plants introduced to an environment where their presence negatively impacts the overall functioning and biodiversity of the ecosystem, may also sometimes be considered weeds.

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

Bensulide is a selective organophosphate herbicide. It is one of a few organophosphate compounds that are used as an herbicide. Most of the others are used as insecticides. It is used on vegetable crops such as carrots, cucumbers, peppers, and melons and in cotton and turfgrass to control annual grasses such as bluegrass and crabgrass and broadleaf weeds. It is often applied before the weed seeds germinate (pre-emergence) in order to prevent them from germinating. It is available as granules or an emulsifiable concentrate. Estimates place the total use of bensulide in the United States at about 632,000 pounds annually. Application rates may be relatively heavy when it is used. The EPA classifies bensulide as a general use pesticide.

<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.

<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.

4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a class of herbicides that prevent growth in plants by blocking 4-Hydroxyphenylpyruvate dioxygenase, an enzyme in plants that breaks down the amino acid tyrosine into molecules that are then used by plants to create other molecules that plants need. This process of breakdown, or catabolism, and making new molecules from the results, or biosynthesis, is something all living things do. HPPD inhibitors were first brought to market in 1980, although their mechanism of action was not understood until the late 1990s. They were originally used primarily in Japan in rice production, but since the late 1990s have been used in Europe and North America for corn, soybeans, and cereals, and since the 2000s have become more important as weeds have become resistant to glyphosate and other herbicides. Genetically modified crops are under development that include resistance to HPPD inhibitors. There is a pharmaceutical drug on the market, nitisinone, that was originally under development as an herbicide as a member of this class, and is used to treat an orphan disease, type I tyrosinemia.

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

Bentazon is a chemical manufactured by BASF Chemicals for use in herbicides. It is categorized under the thiadiazine group of chemicals. Sodium bentazon is available commercially and appears slightly brown in colour.

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">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">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.

References

  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. 1 2 United States EPA
  4. "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.