Fenoprop, also called 2,4,5-TP, is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

2-(2,4,5-trichlorophenoxy)propionic acid. It is a

phenoxy herbicide Phenoxy herbicides (or "phenoxies") 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. Auxins The first group to be discove ...

and a

plant growth regulator Plant hormones (or phytohormones) are signal molecules, produced within plants, that occur in extremely low concentrations. Plant hormones control all aspects of plant growth and development, including embryogenesis, the regulation of organ si ...

, an

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

2,4,5-T 2,4,5-Trichlorophenoxyacetic acid (also known as 2,4,5-T), 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 ...

in which the latter's

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

sidechain is replaced with a

propionate Propionic acid (, from the Greek words πρῶτος : ''prōtos'', meaning "first", and πίων : ''píōn'', meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula . It is a liquid with a p ...

group (with an extra CH₃). The addition of this extra

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...

creates a

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

centre in the molecule and useful

biological activity In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or ...

is found only in the (2R)-isomer. The compound's mechanism of action is to mimic the auxin growth hormone

indoleacetic acid Indole-3-acetic acid (IAA, 3-IAA) is the most common naturally occurring plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists. IAA is a derivative of indole, con ...

(IAA). When sprayed on plants it induces rapid, uncontrolled growth. As with 2,4,5-T, fenoprop is toxic to shrubs and trees. The name Silvex was used in the USA but it has been banned from use there since 1985. According to the

Environmental Protection Agency Environmental Protection Agency may refer to the following government organizations: * Environmental Protection Agency (Queensland), Australia * Environmental Protection Agency (Ghana) * Environmental Protection Agency (Ireland) * Environmenta ...

its greatest use was as a postemergence herbicide for control of woody plants, and broadleaf herbaceous weeds in rice and bluegrass turf, in sugarcane, in rangeland improvement programs and on lawns. Fenoprop and some of its

esters In chemistry, an ester is a chemical compound, compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds c ...

were in use from 1945 but are now obsolete.

References

{{Herbicides Auxinic herbicides Carboxylic acids Chlorobenzene derivatives Phenol ethers Group 4 herbicides

See also

References