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 The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

Chemistry

Dichlorprop possesses a single

asymmetric carbon An asymmetric carbon atom (chiral carbon) is a carbon atom that is attached to four different types of atoms or groups of atoms. Le Bel-van't Hoff rule states that the number of stereoisomers of an organic compound is 2n, where n represents the num ...

and is therefore a

chiral Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from i ...

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

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

s, 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 Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

. 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 Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to aroun ...

salt is still available, while the

diethanolamine Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool meaning that it is often encoun ...

salt is no longer used. According to the

United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it ...

(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."Reregistration Eligibility Decision (RED) for Dichlorprop-p (2,4-DP-p)
US EPA, August 29, 2007]

Health effects

The EPA rates the oral

acute toxicity Acute toxicity describes the adverse effects of a substance that result either from a single exposure or from multiple exposures in a short period of time (usually less than 24 hours). To be described as ''acute'' toxicity, the adverse effect ...

of dichlorprop as "slight" based on a rat of 537 mg/kg, and its derivatives are even less toxic. It is, however, considered to be a severe eye irritant. There has been concern that chlorophenoxy herbicides including dichlorprop may cause cancer, and in 1987 the

International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; french: Centre International de Recherche sur le Cancer, CIRC) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and ...

(IARC) ranked this class of compounds as group 2B "possibly carcinogenic to humans".CHLOROPHENOXY HERBICIDES (Group 2B)
International Agency for Research on Cancer (IARC), 1987 The EPA classifies the ''R''-isomer as “Not Likely to be Carcinogenic to Humans.”

References

External links

{{Herbicides Carboxylic acids Organochlorides IARC Group 2B carcinogens Phenol ethers Auxinic herbicides