Dichlorprop

Last updated
Dichlorprop
(RS)-Dichlorprop Structural Formula V.1a.svg
Names
IUPAC name
(R)-2-(2,4-dichlorophenoxy)propanoic acid
Other names
2,4-DP
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.991 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-390-5
KEGG
PubChem CID
RTECS number
  • UF1050000
UNII
UN number 3077 2765
  • InChI=1S/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13) Yes check.svgY
    Key: MZHCENGPTKEIGP-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13)
    Key: MZHCENGPTKEIGP-UHFFFAOYAD
  • Clc1cc(Cl)ccc1OC(C(=O)O)C
Properties
C9H8Cl2O3
Molar mass 235.064 g/mol
Appearancewhite solid
Melting point 116 to 120 °C (241 to 248 °F; 389 to 393 K) R-isomer
Boiling point 215 °C
720 mg/L at 20 °C (R-isomer)
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H312, H315, H318
P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P362, P363, P501
Flash point 204 °C (399 °F; 477 K)
Related compounds
Related compounds
2,4-D
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Dichlorprop is a chlorophenoxy herbicide similar in structure to 2,4-D that is used to kill annual and perennial broadleaf weeds. It is a component of many common weedkillers. About 4 million pounds of dichlorprop are used annually in the United States.

Contents

Chemistry

R-dichlorprop (dichlorprop-p) (R)-Dichlorprop Structural Formula V.1a.svg
R-dichlorprop (dichlorprop-p)

Dichlorprop possesses a single asymmetric carbon and is therefore a chiral molecule, however only the R-isomer is active as an herbicide. When dichlorprop was first marketed in the 1960s, it was sold as racemic mixture of stereoisomers, but since then advances in asymmetric synthesis have made possible the production of the enantiopure compound. Today, only R-dichlorprop (also called dichlorprop-p or 2,4-DP-p) and its derivatives are sold as pesticides in the United States.

Dichlorprop is a carboxylic acid, and like related herbicides with free acid groups, it is often sold as a salt or ester. Currently, the 2-ethylhexyl ester is used commercially. The butoxyethyl and isooctyl esters were once popular, but are no longer approved for agricultural use. For the salts, the dimethylamine salt is still available, while the diethanolamine salt is no longer used.

According to the United States Environmental Protection Agency (EPA), "2,4-DP-p is thought to increase cell wall plasticity, biosynthesis of proteins, and the production of ethylene. The abnormal increase in these processes result in abnormal and excessive cell division and growth, damaging vascular tissue. The most susceptible tissues are those that are undergoing active cell division and growth." [1]

Health effects

The EPA rates the oral acute toxicity of dichlorprop as "slight" based on a rat LD50 of 537 mg/kg, and its derivatives are even less toxic. It is, however, considered to be a severe eye irritant. [1] There has been concern that chlorophenoxy herbicides including dichlorprop may cause cancer, and in 1987 the International Agency for Research on Cancer (IARC) ranked this class of compounds as group 2B "possibly carcinogenic to humans". [2] The EPA classifies the R-isomer as “Not Likely to be Carcinogenic to Humans.” [1]

Related Research Articles

<span class="mw-page-title-main">Carcinogen</span> Substance, radionuclide, or radiation directly involved in causing cancer

A carcinogen is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruses and bacteria. Most carcinogens act by creating mutations in DNA that disrupt a cell's normal processes for regulating growth, leading to uncontrolled cellular proliferation. This occurs when the cell's DNA repair processes fail to identify DNA damage allowing the defect to be passed down to daughter cells. The damage accumulates over time. This is typically a multi-step process during which the regulatory mechanisms within the cell are gradually dismantled allowing for unchecked cellular division.

<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 kill plants indiscriminately. The combined effects of herbicides, nitrogen fertilizer, and improved cultivars has increased yields of major crops by three to six times from 1900 to 2000.

<span class="mw-page-title-main">Roundup (herbicide)</span> Glyphosate-based herbicide made by Monsanto

Roundup is a brand name of herbicide originally produced by Monsanto, which Bayer acquired in 2018. Prior to the late-2010s formulations, it used broad-spectrum glyphosate-based herbicides. As of 2009, sales of Roundup herbicides still represented about 10 percent of Monsanto's revenue despite competition from Chinese producers of other glyphosate-based herbicides. The overall Roundup line of products represented about half of Monsanto's yearly revenue in 2009. The product is marketed to consumers by Scotts Miracle-Gro Company. In the late-2010s other non-glyphosate containing herbicides were also sold under the Roundup brand.

<span class="mw-page-title-main">1,4-Dichlorobenzene</span> Chemical compound

1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.

<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">Nitrobenzene</span> Chemical compound

Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents. As confirmed by X-ray crystallography, nitrobenzene is a planar molecule.

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

Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which dissolves easily in water. It can be biodegraded by some bacteria, including Sphingobium chlorophenolicum.

IARC group 1 Carcinogens are substances, chemical mixtures, and exposure circumstances which have been classified as carcinogenic to humans by the International Agency for Research on Cancer (IARC). This category is used when there is sufficient evidence of carcinogenicity in humans. Exceptionally, an agent may be placed in this category when evidence of carcinogenicity in humans is less than sufficient, but when there is sufficient evidence of carcinogenicity in experimental animals and strong evidence in exposed humans that the agent (mixture) acts through a relevant mechanism of carcinogenicity.

IARC group 2B substances, mixtures and exposure circumstances are those that have been classified as "possibly carcinogenic to humans" by the International Agency for Research on Cancer (IARC) as This category is used when there is limited evidence of carcinogenicity in humans and less than sufficient evidence of carcinogenicity in experimental animals. It may also be used when there is insufficient evidence of carcinogenicity in humans but sufficient evidence in experimental animals. In some cases, an agent, mixture, or exposure circumstance with inadequate evidence of carcinogenicity in humans but limited evidence in experimental animals, combined with supporting evidence from other relevant data, may be included in this group.

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

Diethyl sulfate (DES) is an organosulfur compound with the formula (C2H5)2SO4. It occurs as a colorless, oily liquid with a faint peppermint odor. It is toxic, combustible, and likely carcinogenic chemical compound. Diethyl sulfate is used as an ethylating agent.

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

Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues. It is unrelated to caffeine.

<span class="mw-page-title-main">2,4,5-Trichlorophenoxyacetic acid</span> Chemical compound

2,4,5-Trichlorophenoxyacetic acid, a synthetic auxin, is a chlorophenoxy acetic acid herbicide used to defoliate broad-leafed plants. It was developed in the late 1940s, synthesized by reaction of 2,4,5-Trichlorophenol and chloroacetic acid. It was widely used in the agricultural industry until being phased out, starting in the late 1970s due to toxicity concerns. Agent Orange, a defoliant used by the British in the Malayan Emergency and the U.S. in the Vietnam War, was equal parts 2,4,5-T and 2,4-D. 2,4,5-T itself is toxic with a NOAEL of 3 mg/kg/day and a LOAEL of 10 mg/kg/day. Agent Pink contained 100% 2,4,5-T. Additionally, the manufacturing process for 2,4,5-T contaminates this chemical with trace amounts of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). TCDD is a carcinogenic persistent organic pollutant with long-term effects on the environment. With proper temperature control during production of 2,4,5-T, TCDD levels can be held to about .005 ppm. Before the TCDD risk was well understood, early production facilities lacked proper temperature controls and individual batches tested later were found to have as much as 60 ppm of TCDD.

<span class="mw-page-title-main">Phenoxy herbicide</span> Class of herbicide

Phenoxy herbicides are two families of chemicals that have been developed as commercially important herbicides, widely used in agriculture. They share the part structure of phenoxyacetic acid.

Hexachlorobenzene, or perchlorobenzene, is an aryl chloride and a six-substituted chlorobenzene with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the Stockholm Convention on Persistent Organic Pollutants.

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

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<i>o</i>-Toluidine Aryl amine

o-Toluidine (ortho-toluidine) is an organic compound with the chemical formula CH3C6H4NH2. It is the most important of the three isomeric toluidines. It is a colorless liquid although commercial samples are often yellowish. It is a precursor to the herbicides metolachlor and acetochlor.

<span class="mw-page-title-main">2,3,7,8-Tetrachlorodibenzodioxin</span> Polychlorinated dibenzo-p-dioxin, chemical compound

2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) is a polychlorinated dibenzo-p-dioxin (sometimes shortened, though inaccurately, to simply 'dioxin') with the chemical formula C12H4Cl4O2. Pure TCDD is a colorless solid with no distinguishable odor at room temperature. It is usually formed as an unwanted product in burning processes of organic materials or as a side product in organic synthesis.

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.

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. 1 2 3 Reregistration Eligibility Decision (RED) for Dichlorprop-p (2,4-DP-p), US EPA, August 29, 2007]
  2. CHLOROPHENOXY HERBICIDES (Group 2B), International Agency for Research on Cancer (IARC), 1987